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BACKGROUND Curcumin has become increasingly popular in functional foods and beverages field as a result of its high biological activity. Nevertheless, the application of curcumin is usually limited by its poor water solubility, low absorption, rapid metabolism and instability. Accordingly, the development of an appropriate wall material is crucial for its effective use. In the present study, curcumin-octenyl succinic anhydride modified pullulan (Cur-OSAP) micelles were successfully prepared by an anti-solvent co-precipitation method. RESULTS Octenyl succinic anhydride modified pullulan (OSAP) micelles exhibited the highest encapsulation efficiency (57.31%) and loading capacity (5.73%) of curcumin when the mass ratio of OSAP to curcumin was 10:1 and the degree of substitution of OSAP was 0.0469, at which point Cur-OSAP micelles formed via hydrogen binding and hydrophobic interactions, as confirmed by Fourier transform infrared and fluorescence techniques. The transmission electron microscopy results showed that the Cur-OSAP micelles were roughly spherical in shape with diameters in the approximate range 30-60 nm. CONCLUSION The encapsulation of OSAP greatly improved photostability and sustained release properties of curcumin in Cur-OSAP micelles. These findings suggest that OSAP can be used as a carrier to encapsulate and protect hydrophobic food ingredients. © 2021 Society of Chemical Industry.

Background Previous studies have demonstrated the preclinical pharmacological and toxicological consistency, and clinical pharmacokinetic equivalence of bevacizumab biosimilar LY01008 with reference bevacizumab (Avastin). This randomized controlled trial aimed to compare the efficacy and safety of LY01008 with Avastin in first‐line treatment of Chinese patients with advanced or recurrent non‐squamous non‐small cell lung cancer (NSCLC). Methods Stage IIIB‐IV NSCLC patients with evaluable lesions, good physical status, and adequate organ functions from 67 centers across China were randomized in a ratio of 1:1 to receive LY01008 or Avastin 15 mg/kg intravenously in combination with paclitaxel/carboplatin (combined treatment) for 4‐6 cycles, followed by maintenance monotherapy with LY01008 until disease progression, intolerable toxicity, or death. The primary endpoint was objective response rate (ORR) in accordance with Response Evaluation Criteria in Solid Tumors (RECIST) version 1.1 confirmed by independent radiological review committees (IRRC). Secondary endpoints included disease control rate (DCR), duration of response (DoR), progression‐free survival (PFS), overall survival (OS), and safety. This study was registered in ClinicalTrials.gov (NCT03533127). Results Between December 15th, 2017, and May 15th, 2019, a total of 649 patients were randomized to the LY01008 (n = 324) or Avastin (n = 325) group. As of September 25th, 2019 for primary endpoint analysis, 589 patients received ORR evaluation, with a median number of combined treatment cycles of 5 (range 1‐6) and median duration of treatment of 3.0 (range 0.0‐5.1) months. ORR of response‐evaluable patients in the LY01008 and Avastin groups were 48.5% and 53.0%, respectively. The stratified ORR ratio was 0.91 (90% CI 0.80‐1.04, within the prespecified equivalence margin of 0.75‐1.33). Up to May 15th, 2020, with a median follow‐up of 13.6 (range 0.8‐28.4) months, no notable differences in DCR, median DoR, median PFS, median OS, and 1‐year OS rate were observed between the LY01008 and Avastin groups. There were no clinically meaningful differences in safety and immunogenicity across treatment groups. Conclusions LY01008 demonstrated similarity to Avastin in terms of efficacy and safety in Chinese patients with advanced or recurrent non‐squamous NSCLC. LY01008 combined with paclitaxel/carboplatin is expected to become a new treatment option for unresectable, metastatic, or recurrent non‐squamous NSCLC patients in the first‐line setting., This study demonstrated similarity between LY01008 and reference bevacizumab (Avastin) in terms of efficacy, safety, and immunogenicity in combination with paclitaxel and carboplatin as first‐line treatment in Chinese patients with advanced non‐squamous NSCLC.

We report herein the asymmetric total synthesis of norzoanthamine using radical reactions as key steps for rapid access to the congested carbocyclic core, which is the major synthetic challenge for most zoanthamine alkaloids. (1) The Ueno-Stork radical cyclization was applied to construct the adjacent quaternary centers at the C-9 and C-22 positions; (2) a Co-catalyzed HAT radical reaction was successfully applied to construct the quaternary center at C-12 via Csp3 -Csp2 bond formation; (3) a Mn-catalyzed HAT radical reaction was used to stereospecifically reduce the tetra-substituted olefin (C13=C18) and install the contiguous stereocenters in proximity to the quaternary center. A one-pot bio-inspired cyclization step was finally applied to forge the unstable bis-amino acetal skeleton. Our approach can precisely control the stereochemistry of seven vicinal stereocenters and effectively construct the highly congested heptacyclic skeleton.

Mammalian carboxylesterases (CES) are key enzymes that participate in the hydrolytic metabolism of various endogenous and exogenous substrates. Human carboxylesterase 2A (hCES2A), mainly distributed in the small intestine and colon, plays a significant role in the hydrolysis of many drugs. In this study, 3-arylisoquinolones 3 h [3-(4-(benzyloxy)-3-methoxyphenyl)-7,8-dimethoxyisoquinolin-1(2H)-one] and 4 a [3-(4-(benzyloxy)-3-methoxyphenyl)-4-bromo-7,8-dimethoxyisoquinolin-1(2H)-one] were found to have potent inhibitory effects on hCES2A (IC50 =0.68 μΜ, Ki =0.36 μΜ) and excellent specificity (more than 147.05-fold over hCES1 A). Moreover, 4 a exhibited threefold improved inhibition on intracellular hCES2A in living HepG2 cells relative to 3 h, with an IC50 value of 0.41 μΜ. Results of inhibition kinetics studies and molecular docking simulations demonstrate that both 3 h and 4 a can bind to multiple sites on hCES2A, functioning as mixed inhibitors. Structure-activity relationship analysis revealed that the lactam moiety on the B ring is crucial for specificity towards hCES2A, while a benzyloxy group is optimal for hCES2A inhibitory potency; the introduction of a bromine atom may enhance cell permeability, thereby increasing the intracellular hCES2A inhibitory activity.

QF-036 is an HIV-1 maturation inhibitor in pre-clinical development, and its antiviral activity against a laboratory HIV-1 strain and two drug-resistant strains was determined in the C8166 line. QF-036 was also subjected to absorption, distribution and metabolism (ADM) assessment in vitro, and pharmacokinetic profiles were evaluated in rats and monkeys. The 50% effective concentrations (EC50 ) of QF-036 against the three strains were 20.36 nM, 0.39 μM and 2.11 nM, respectively, demonstrating better antiviral potential than the first-generation antiviral maturation inhibitor bevirimat. QF-036 demonstrated moderate cell permeability, high plasma protein binding ability and good metabolic stability in vitro. After oral QF-036 administration to rats and monkeys, both species exhibited moderate bioavailability, and the plasma drug exposure increased in an approximately dose-proportional manner. When administered orally (30 mg/kg) to monkeys, the QF-036 plasma concentration (Cmax ) peaked at 3671 ng/mL (4.82 μM), 12 to 2410 times higher than the EC50 of laboratory or resistant HIV-1 strains. Moreover, the plasma concentration of QF-036 at 12 hours after administration was 263 ng/mL (0.35 μM), which approximately matched the highest EC50 value of the three test strains. The favourable viral inhibitory activity and pharmacokinetic properties provide critical support for QF-036 as a promising anti-HIV therapeutic candidate.

TANK-binding kinase 1 (TBK1) belongs to the noncanonical IκB kinase (IKK) family. The ubiquitously expressed protein is well known to play a pivotal role in innate immune response and inflammation. Although excessive inflammatory activities have been shown to affect osteoclast (OC) differentiation and function, direct relevance of TBK1 in bone turnover is not known. In this work, we specifically altered the TBK1 protein level by knocking down or overexpressing it without affecting its homologous protein IKKε expression, and demonstrated the effect of TBK1 on OC differentiation in bone marrow macrophages (BMMs) and RAW264.7 cells upon induction by receptor activator of nuclear factor-κB (NF-κB) ligand (RANKL). TBK1 knockdown was found to markedly inhibit the OC differentiation and function, while TBK1 overexpression enhanced OC formation. Downregulation of TBK1 greatly suppressed RANKL-induced gene expression of Mmp9, Atp6v0d2, Acp5, Ctsk andNfatc1 involved in the regulation of OC formation and function in both BMM and RAW264.7 cells. Mechanistic studies indicated that TBK1 affected the NF-κB signaling pathway as well as mitogen-activated protein kinases (MAPKs) and protein kinase B (Akt) activation during OC differentiation. Moreover, the protein level of TNF receptor-associated factor 6 (TRAF6) was increased, and the interaction of TRAF6 with TBK1 was potentiated, by RANKL. Collectively, we provide direct evidence showing that TBK1 effectively mediates OC differentiation and function by regulating NF-κB, MAPKs and Akt signals. A TBK1-targeted therapeutic strategy may be useful for the treatment of bone-related disorders.

A new TiIII -mediated reductive epoxide-opening/ Beckwith-Dowd rearrangement process efficiently assembles the bicyclo[3.2.1]octane framework of highly oxidized grayanane diterpenoids. By incorporation of a Cu(tbs)2 -catalyzed (tbs=N-tert-butylsalicylaldiminato) intramolecular cyclopropanation, a diastereoselective oxidative dearomatization-induced Diels-Alder cycloaddition and a MeReO3 -catalyzed Rubottom oxidation, this approach has enabled the first total syntheses of rhodomolleins XX and XXII in 23 and 22 steps, respectively.

5-methoxycanthin-6-one, a major canthinone alkaloid isolated from Picrasma quassioides, exhibited significant pharmacological activities. In this study, a rapid and sensitive LC-MS/MS method was established and validated for the determination of 5-hydroxy-4-methoxycanthin-6-one in rat plasma. Small quantities (20 μL) of plasma sample were used for sample preparation. 5-Hydroxy-4-methoxycanthin-6-one and an internal standard (IS, caffeine) were separated using an ACQUITY HSS T3 column (50 × 2.1 mm, 1.7 μm; Waters, Milford, MA, USA). The mobile phase was composed of 0.1% formic acid in water and acetonitrile. Precursor-to-product ion transitions were m/z 267.0 → 168.2 and m/z 195.0 → 138.1 for quantitative monitoring of 5-hydroxy-4-methoxycanthin-6-one and IS, respectively. The assay was linear over the concentration range of 0.5-500 ng/mL (r > 0.99) with the lower limit of quantification 0.5 ng/mL. Other parameters, including intra- and inter-day precision and accuracy, carryover, stability, extraction recovery, matrix effect, and dilution effect, were within acceptable limits. The validated method was successfully applied to pharmacokinetic study in rats after intravenous (5 mg/kg) and oral (10, 25, 50 mg/kg) administration of 5-hydroxy-4-methoxycanthin-6-one. The result indicated that 5-hydroxy-4-methoxycanthin-6-one was quickly absorbed into the blood and reached the highest concentration at ~33.0-42.0 min, with moderate elimination half-life (0.85-2.11 h) and low bioavailability (16.62-24.42%) after oral administration. The study provided valuable information that can be used as a reference for studying other canthinone alkaloids.

Background Human BarH-like homeobox 2 (Barx2), a homeodomain factor of the Bar family, plays a critical role in cell adhesion and cytoskeleton remodeling, and has been reported in an increasing array of tumor types except non-small cell lung carcinoma (NSCLC). The purpose of the current study was to characterize the expression of Barx2 and assess the clinical significance of Barx2 in NSCLC. Methods Quantitative real-time polymerase chain reaction, immunohistochemistry and western blot analysis were used to examine mRNA and protein expression, respectively. The relationships between Barx2 expression and clinicopathological variables were analyzed. Cell Counting Kit-8 and plate colony formation assay were used to detect cell proliferation. Transwell assay was used to examine cell migration ability. Glucose uptake, lactate, adenosine triphosphate, and lactate dehydrogenase assays were used to detect aerobic glycolysis. Results Barx2 is downregulated in NSCLC tissues compared with para-carcinoma. Furthermore, Barx2 expression shows a negative correlation with advanced TNM stage and a high level of Ki-67. Survival analysis reveals that Barx2 level is an independent prognostic factor for NSCLC patients. The Barx2 (low) Ki-67 (high) group had the worst prognosis. Furthermore, the data indicate that downregulation of Barx2 expression promotes cell proliferation, migration, and aerobic glycolysis, including increased lactate dehydrogenase activity, glucose utilization, lactate production, and decreased intracellular adenosine triphospahte level. Furthermore, Barx2 acts as a negative regulator of the canonical Wnt/β-catenin pathway. Reactivation of Wnt/β-catenin pathway by LiCl can reverse the inhibiting effect of Barx2. Conclusions These findings reveal that Barx2 serving as a tumor suppressor gene could decrease cell proliferation, migration, and aerobic glycolysis through inhibiting the Wnt/β-catenin signaling pathway, and predicts a good prognosis in NSCLC.

A hydrophobic cobalt catalyst was synthesized and proved to be effective in the alcohol oxidation under the assistance of hydrocarbon solvent with oxygen as the terminal oxidant. A series of catalyst with different water contact angles was applied to investigate the hydrophobic effect. Further insight in to the reaction process was researched by reaction kinetics, isotopic effect, etc. It showed that thehydrocarbon solvent participated in the alcohol oxidation, andwith the aid of the in-situ generated free radicals, the α-C-H bond was smoothly activated and the alcohol was converted to carbonyl compounds. The hydrophobic effect promoted the alcohol oxidation through affecting the solvent oxidation.

BACKGROUND Lettuce is a significant source of antioxidants and bioactive compounds. Nitrate is a cardinal fertilizer in horticulture and influences vegetable yield and quality; however, the negative effects of nitrate on the biosynthesis of flavonoids require further study. It is expected that using fertilizers containing organic N could promote the synthesis of health-promoting compounds. RESULTS Lettuces were hydroponically cultured in media containing 9 mM nitrate or 9 mM glycine for 4 weeks. Primary and secondary metabolites were analyzed using gas chromatography-mass spectrometer (GC-MS) and ultra-performance liquid chromatography-ion mobility spectrometry-quadrupole time-of-flight-mass spectrometer (UPLC-IMS-QTOF-MS). Data analysis revealed 29 metabolites were significantly altered between nitrate and glycine treatment. Metabolites were tentatively identified by comparison with online databases, literature and standards, and using collision cross section values. Significant differences in flavonoid biosynthesis, phenolic biosynthesis and the tricarboxylic acid cycle (TCA cycle) response were observed between N sources. Compared to nitrate, glycine promoted accumulation of glycosylated flavonoids (quercetin 3-glucoside, quercetin 3-(6''-malonyl-glucoside), luteolin 7-glucuronide, luteolin 7-glucoside), ascorbic acid and amino acids (L-valine, L-leucine, L-glutamine, asparagine, L-serine, L-ornithine, 4-aminobutanoic acid, L-phenylalanine), but reduced phenolic acids (dihydroxybenzoic acid hexose isomer 1 and isomer 2, chicoric acid and isomer) and TCA intermediates (fumaric, malic, citric and succinic acid). CONCLUSION The novel methodology applied in this study can be used to characterize metabolites in lettuce. Accumulation of glycosylated flavonoids, amino acids and ascorbic acid in response to glycine supply provides strong evidence supporting the idea that using amino acids as an N source alters the nutritional value of vegetable crops.

Pillar[5]arene–Py–Cu gel, a supramolecular metallo(organo)gel, was made from an A1/A2-bipyridyl-functionalized pillar[5]arene ligand (L) through metal–ligand complexation. The xerogel obtained from pillar[5]arene–Py–Cu gel has a hydrangea-flower-like rugate layered structure, and a sheet-like structured gel-precipitate was formed from pillar[5]arene–Py–Cu gel under shaking or sonication. Both the xerogel and the gel-precipitate can extract Sudan III from its ethanol solution.

7-epi-Taxane has been achieved efficiently in gram scale from natural taxane via inversion of the 7-hydroxyl group simply using Ag2O as catalyst and DMF as solvent. The catalyst could be quantitatively recovered by filtration without loss of catalytic activity. This condition is also applicable to the direct epimerization of taxane derivatives (e.g., docetaxel and paclitaxel) to 7-epi-taxane derivatives (e.g., 7-epi-docetaxel and 7-epi-paclitaxel). Furthermore, 33 ester derivatives of 7-epi-taxane with different amino acid moieties at the position of C-13 were successfully synthesized via esterification without protecting C-7-OH. Bioassay results revealed that compounds 13 and 18 have good selectivity against prostatic cancer cell line DU145, with IC50 value as low as 15.9 nmol/L for 18.

Imatinib (IM), a tyrosine-kinase inhibitor, is used in treatment of multiple cancers, most notably Philadelphia chromosome-positive (Ph+ ) chronic myelogenous leukemia (CML). However, the majority of patients continue to present with minimal residual disease occurred in the bone marrow (BM) microenvironment. One of the key factors that contribute to leukemia cell drug resistance is chemokine CXCL12. In the current study, co-culturing CML cell K562 and KU812 with BM stromal cell M2-10B4 attenuated IM-induced apoptosis. CXCL12/CXCR7 pathway was activated in co-culture models, which was further proved to be related to drug resistance by silencing CXCR7. ERK phosphorylation and downstream apoptosis related proteins' activation were also observed in co-culture group after the activation of CXCR7. Moreover, oroxylin A, a bioactive flavonoid isolated from the root of Scutellaria baicalensis Georgi, was found to be effective in reversing BM stroma induced CML resistance to IM. After cells were treated with weakly toxic concentration of oroxylin A, cell apoptosis induced by IM in co-culture model was enhanced. And the activated CXCL12/CXCR7 pathway, the expression of p-ERK and downstream apoptosis related proteins were suppressed. The in vivo study also showed that oroxylin A increased apoptosis of CML cells with low systemic toxicity, and the mechanism was consistent with the in vitro study. In conclusion, oroxylin A improved sensitivity of CML cells to IM treatment in BM microenvironment through regulating CXCL12/CXCR7 pathway. © 2016 Wiley Periodicals, Inc.

Oroxylin A is one of the main active components extracted from Scutellariae radix. It has been proved that oroxylin A possesses a broad spectrum of pharmacological functions, including anti-cancer, antiinflammation, neuroprotective, anti-coagulation and so on. The pharmacological activity of oroxylin A has been studied in vitro and on animal models, which reflected its promising potency in disease treatment. This review aims to recapitulate the pharmacological function and the molecular mechanisms of oroxylin A, as well as its sources, extraction, synthesis and toxicity study. These data confirmed the therapeutic potential of oroxylin A and provided reference for further development. Copyright © 2016 John Wiley & Sons, Ltd.

We have recently identified that phosphorylation at tyrosine (Y)406 is critical for the tumor suppressor functions of the thyroid hormone receptor β1 (TRβ) in a breast cancer line. However, still unclear is whether the critical tumor suppressor role of phosphorylated Y406 of TRβ is limited to only breast cancer cells or could be extended to other cell types. In the present studies, we addressed this question by stably expressing TRβ, a mutated TRβ oncogene (PV), or a TRβ mutated at Y406 (TRβY406F) in rat PCCL3 thyroid follicular cells and evaluated their tumor characteristics in athymic mice with elevated thyroid stimulating hormone. PCCL3 cells stably expressing PV (PCCL3-PV), TRβY406F (PCCL3-TRβY406F), or vector only (PCCL3-Neo) developed tumors with sizes in the rank order of TRβY406F>PV = Neo, whereas PCCL3 cells expressing TRβ (PCCL3-TRβ) barely developed tumors. As evidenced by markedly elevated Ki67, cyclin D1, and p-Rb protein abundance, proliferative activity was high in PV and TRβY406F tumors, but low in TRβ tumors. These results indicate that TRβ acted as a tumor suppressor in PCCL3 cells, whereas TRβY406F and PV had lost tumor suppressor activity. Interestingly, TRβY406F tumors had very low necrotic areas with decreased TNFα-NFκB signaling to lower apoptotic activity. In contrast, PV tumors had prominent large necrotic areas, with no apparent changes in TNFα-NFκB signaling, indicating distinct oncogenic activities of mutant PV and TRβY406F. Thus, the present studies uncovered a novel mechanism by which TRβ could function as a tumor suppressor through modulation of the TNFα-NFκB signaling. © 2016 Wiley Periodicals, Inc.

Plasma is generated by ionizing gas molecules. Helium (He)‐based cold atmospheric plasma (CAP) was generated using a high‐voltage power supply with low‐frequency excitation (60 Hz at 7 kV) and He flow at 2 l/min. Platinum nanoparticles (Pt‐NPs) are potent antioxidants due to their unique ability to scavenge superoxides and peroxides. These features make them useful for the protection against oxidative stress‐associated pathologies. Here, the effects of Pt‐NPs on He‐CAP‐induced apoptosis and the underlying mechanism were examined in human lymphoma U937 cells. Apoptosis was measured after cells were exposed to He‐CAP in the presence or absence of Pt‐NPs. The effects of combined treatment were determined by observing the changes in intracellular reactive oxygen species (ROS) and both mitochondrial and Fas dependent pathway. The results indicate that Pt‐NPs substantially scavenge He‐CAP‐induced superoxides and peroxides and inhibit all the pathways involved in apoptosis execution. This might be because of the SOD/catalase mimetic effects of Pt‐NPs. These results showed that the Pt‐NPs can induce He‐CAP desensitization in human lymphoma U937 cells.

Introduction Gentianaceae species which widely occur all over the world are used as folk medicine and raw food material with bitter properties. Although comparative analysis on metabolites in several Gentianaceae species has been reported, metabolic similarities used for chemotaxonomic studies are not yet clear. Objective To systematically characterise the variations of holistic metabolome and characteristic metabolites (iridoid glycosides and phenols) in nine Gentianaceae species from western China. Methodology Fourier transform infrared (FT-IR) spectroscopy was applied to determine the variations of holistic metabolome. A targeted metabolic profiling using liquid chromatography with tandem mass spectrometry (LC–MS/MS) was established for determination of seven characteristic metabolites and identification of their derivatives. Both FT-IR and LC–MS/MS data were subjected to chemometrics analysis for exploring variations in iridoid glycosides and phenols within these species. Results Holistic metabolome in genera Gentiana and Swertia was largely different. Diversity of the biosynthetic pathway of iridoid glycosides was also observed in these species. Principal component analysis (PCA) showed a clear separation according to infrageneric classifications of genus Gentiana. Some secondary metabolites, such as mangiferin, rhodenthoside A-C, isoorientin, isovitexin, amarogentin, and swertianolin would serve as potential chemotaxonomic markers to differentiate Gentianaceae species. Furthermore, the accumulation of the six major metabolites seems to depend on geographical regions in Sect. Monopodiae and Sect. Cruciata. Conclusions The combination of LC–MS/MS and FT-IR would provide some potential evidence on chemotaxonomic studies of Gentianaceae. Copyright © 2016 John Wiley & Sons, Ltd.

Snail is closely linked to tumor invasion, metastasis, and recurrence and indicates prognosis of patients suffering from cancer. Overexpression of Snail increases motility and invasiveness of cancer cells, which has become target for anti-metastatic treatment. Oroxylin A, a natural compound extracted from Scutellaria radix, has been reported to inhibit invasion and migration in breast cancer. In this study, we investigated the anti-invasive effect of oroxylin A on lung cells and uncovered its underlying mechanism. The results suggested that oroxylin A could inhibit migration and invasion in Snail-expressing 95-D, and A549 cells whereas it had little effect on non-expressing GLC-82 cells. Furthermore, enhanced Snail expression after transfection of Snail vector in GLC-82 cells is decreased by oroxylin A. Snail can also induce epithelial-mesenchymal transition. We found oroxylin A could reverse TGFβ1-induced epithelial-mesenchymal transition by inhibiting Snail expression. As a result, oroxylin A up-regulated E-cadherin expression and down-regulated vimentin, MMP-9, and CD44v6 expression, which could lead to the inhibition of tumor migration and invasion. Mechanically, we demonstrated that oroxylin A suppressed activation of ERK instead of AKT pathway and then promoted activation of GSK-3β to reduce Snail protein content. Finally, we established transplanted, metastatic, and orthotopic models of A549 cells, and found that oroxylin A inhibited the growth and lung metastasis of A549 cells in vivo. Taken together, we proposed that oroxylin A might be a promising candidate targeting tumor metastasis. © 2016 Wiley Periodicals, Inc.

A family of trigonal starburst conjugated molecules (TrFPy, TrFPy, and TrF2Py) composed of a truxene core and pyrene cappers with various bridge lengths is synthesized and characterized. The incorporation of pyrene cappers successfully depress the crystallization tendency, resulting in enhanced glassy temperature and improved morphological stability of the thin films. The high photoluminescence yield in neat films and excellent thermal stability render these pyrene-capped starbursts promising lasing optical gain media. Low amplified spontaneous emission (ASE) thresholds (EthASE) of 180 nJ pulse-1 and 101 nJ pulse–1 were recorded for TrFPy and TrF2Py, respectively. One dimensional distributed feedback (1D DFB) lasers demonstrated lasing threshold of 9.3 kW/cm2 and 7.3 kW/cm2 for TrFPy (at 457 nm) and TrF2Py lasers (at 451 nm), respectively. The ASE performance of TrFPy and TrF2Py in an ambient condition was recorded with various annealing temperature (from 80 to 250 °C, 10 min). Surprisingly, TrFPy exhibited excellent ASE stability in an ambient condition, which is still detectable even after annealing at 250 °C for 10 min. The results suggest the pyrene-capped molecular design strategy is positive on improving the optical gain stability and meanwhile maintaining excellent lasing properties.

Tobacco smoke (TS) has been shown to cause gastric cancer. Epithelial–mesenchymal transition (EMT) is a crucial pathophysiological process in cancer development. Mitogen-activated protein kinase (MAPK) pathways play central roles in tumorigenesis including EMT process. Curcumin is a promising chemopreventive agent for several types of cancers. In the present study, we investigated the effects of TS on MAPK pathway activation and EMT alterations in the stomach of mice, and the preventive effect of curcumin was further examined. Results showed that exposure of mice to TS for 12 weeks resulted in activation of extracellular regulated protein kinases 1 and 2 (ERK1/2), the Jun N-terminal kinase (JNK), p38, and ERK5 MAPK pathways as well as activator protein 1 (AP-1) proteins in stomach. TS reduced the mRNA and protein expression levels of the epithelial markers E-cadherin and ZO-1, while the mRNA and protein expression levels of the mesenchymal markers vimentin and N-cadherin were increased. Treatment of curcumin effectively abrogated TS-triggered gastric activation of ERK1/2 and JNK MAPK pathways, AP-1 proteins, and EMT alterations. These results suggest for the first time the protective effects of curcumin in long-term TS exposure-induced gastric MAPK activation and EMT, thus providing new insights into the pathogenesis and chemoprevention of TS-associated gastric cancer. Copyright © 2015 John Wiley & Sons, Ltd.

A trinuclear AuI complex (3A) was synthesized and fully characterized relative to mononuclear (1A) and dinuclear (2A) complexes. The single-crystal X-ray diffraction analyses show that the AuI-centered vectors in each of the AuI complexes (1A–3A) are all in a slightly distorted linear configuration, in which the AuI center is diagonally coordinated by one Cl– and one phosphine ligand. In 3A each P–Au–Cl vector is radially attached to the core of 1-(thiazol-2′-yl)imidazolyl, which does not allow the short contact between the Au atoms to develop an aurophilic AuI–AuI interaction. Every P–Au–Cl moiety in 3A is different to each other in terms of Au–P and Au–Cl bond lengths, P–Au–Cl bond angles, and P–Au–Cl configurable orientation owing to the different coordinating ability of the involved phosphines. When 1A–3A were employed as the precatalysts for the hydration of phenylacetylene in aqueous methanol media without the involvement of any auxiliary additive, and at the same benchmark Au concentration, the reaction over 3A proceeded selectively according to Markovnikov's rule with the highest yield of acetophenone relative to those over 2A and 1A. This indicates that the catalytic performance of 3A is the outcome of the synergetic effect of the three different R3P–Au centers, in which each R3P–Au site plays an individual role in activating the substrate molecule.

Graphene oxide (GO) with different oxidation degrees were synthesized by harsh oxidation of graphite using the improved Hummers method. The GO/polyimide (PI) mixed matrix membrane was successfully fabricated by in situ polymerization of PI monomers (3,3′,4,4′-biphenyltetracarboxylic dianhydride and 4,4′-diaminodiphenyl ether) with GO. The structure of GO was characterized by Fourier transform infrared, transmission electron microscopy, atomic force microscopy, X-ray diffraction, and thermal gravimetric analysis–differential thermal analysis. The performance of different GO/PI mixed matrix membranes was evaluated by permeation experiments of CO2/N2 gas mixture (volume ratio, 1:9). Results showed that more polar functional groups were introduced to GO with the increase in oxidation degree of GO in the preparation process, producing fewer layers and more translucent structures. GO with higher oxidation degree has significant effect on its dispersion in the N,N-dimethylacetamide solvent and polymer matrix materials. The permeability of GO/PI hybrid membranes for CO2 and N2 increased. The CO2/N2 permeation selectivity of membranes exhibited a trend of initial increase, followed by a decrease, with the increase in oxidation degree, when the same amount of GO was added. For GO with the same oxidation degree, the permeability and permeation selectivity of hybrid membrane initially increased, and then decreased with the addition content of GO. In the case of hybrid membrane containing 1 wt% monolayer GO, the maximum permeability and permeation selectivity of hybrid membranes for CO2 were 14.3 and 4.2 times more than that of PI membrane without GO, respectively. Copyright © 2015 John Wiley & Sons, Ltd.

The present study aimed to test the hypothesis that berberine, a plant-derived anti-oxidant, attenuates adverse left ventricular remodelling and improves cardiac function in a rat model of myocardial infarction (MI). Furthermore, the potential mechanisms that mediated the cardioprotective actions of berberine, in particular the effect on autophagy, were also investigated. Acute MI was induced by ligating the left anterior descending coronary artery of Sprague-Dawley rats. Cardiac function was assessed by transthoracic echocardiography. The protein activity/levels of autophagy related to signalling pathways (e.g. LC-3B, Beclin-1) were measured in myocardial tissue by immunohistochemical staining and western blot. Four weeks after MI, berberine significantly prevented cardiac dysfunction and adverse cardiac remodelling. MI rats treated with low dose berberine (10 mg/kg per day) showed higher left ventricular ejection fraction and fractional shortening than those treated with high-dose berberine (50 mg/kg per day). Both doses reduced interstitial fibrosis and post-MI adverse cardiac remodelling. The cardioprotective action of berberine was associated with increased LC-3B II and Beclin-1 expressions. Furthermore, cardioprotection with berberine was potentially related to p38 MAPK inhibition and phospho-Akt activation. The present in vivo study showed that berberine is effective in promoting autophagy, and subsequently attenuating left ventricular remodelling and cardiac dysfunction after MI. The potential underlying mechanism is augmentation of autophagy through inhibition of p38 MAPK and activation of phospho-Akt signalling pathways.

The peroxisome proliferator-activated receptor alpha (PPAR-α), a member of the family of ligand-activated nuclear hormone receptors, plays a relevant role in the development of Alzheimer's disease (AD). To better understand the role of PPAR-α in AD, we examined the ability of fenofibrate (a PPAR-α agonist) to regulate amyloid precursor protein (APP) processing in APP/PS1 transgenic mice. After intragastric administration of fenofibrate into 3-month-old APP/PS1 transgenic mice for 6 months, and the levels of relative proteins were quantified by quantitative reverse transcription-PCR, Western blotting and ELISA. We found that fenofibrate increased the expression of PPAR-α, and decreased beta-site amyloid precursor protein cleaving enzyme 1 (BACE-1) mRNA and protein levels, and also reduced soluble APPβ (sAPPβ) and amyloid-β 42 (Aβ42) releases. However. fenofibrate did not modify the levels of APP and presenilin 1 (PS1). Furthermore, LY294002, the phosphoinositide 3-kinase (PI3-K) inhibitor, suppressed the effects of fenofibrate on BACE-1, sAPPβ, and Aβ42, but not PPAR-α. Our data suggest that fenofibrate may reduce the amyloidogenic processing of APP in APP/PS1 transgenic mice via PPAR-α/PI3-K pathway.

Acute lung injury (ALI) from a variety of clinical disorders, characterized by diffuse inflammation, is a cause of acute respiratory failure that develops in patients of all ages. Previous studies reported that wogonin, a flavonoid-like chemical compound which was found in Scutellaria baicalensis, has anti-inflammatory effects in several inflammation models, but not in ALI. Here, the in vivo protective effect of wogonin in the amelioration of lipopolysaccharide (LPS) -induced lung injury and inflammation was assessed. In addition, the in vitro effects and mechanisms of wogonin were studied in the mouse macrophage cell lines Ana-1 and RAW264.7. In vivo results indicated that wogonin attenuated LPS-induced histological alterations. Peripheral blood leucocytes decreased in the LPS-induced group, which was ameliorated by wogonin. In addition, wogonin inhibited the production of several inflammatory cytokines, including tumour necrosis factor-α, interleukin-1β (IL-1β) and IL-6, in the bronchoalveolar lavage fluid and lung tissues after LPS challenge, while the peroxisome proliferator-activated receptor γ (PPARγ) inhibitor GW9662 reversed these effects. In vitro results indicated that wogonin significantly decreased the secretion of IL-6, IL-1β and tumour necrosis factor-α in Ana-1 and RAW264.7 cells, which was suppressed by transfection of PPARγ small interfering RNA and GW9662 treatment. Moreover, wogonin activated PPARγ, induced PPARγ-mediated attenuation of the nuclear translocation and the DNA-binding activity of nuclear factor-κB in vivo and in vitro. In conclusion, all of these results showed that wogonin may serve as a promising agent for the attenuation of ALI-associated inflammation and pathology by regulating the PPARγ-involved nuclear factor-κB pathway.

The endocannabinoid ligand 2-arachidonoylglycerol (2-AG) is inactivated primarily by monoacylglycerol lipase (MAGL). We have shown recently that chronic treatments with MAGL inhibitor JZL184 produce antidepressant- and anxiolytic-like effects in a chronic unpredictable stress (CUS) model of depression in mice. However, the underlying mechanisms remain poorly understood. Adult hippocampal neurogenesis has been implicated in animal models of anxiety and depression and behavioral effects of antidepressants. We tested whether CUS and chronic JZL184 treatments affected adult neurogenesis and synaptic plasticity in the dentate gyrus (DG) of mouse hippocampus. We report that CUS induced depressive-like behaviors and decreased the number of bromodeoxyuridine-labeled neural progenitor cells and doublecortin-positive immature neurons in the DG, while chronic JZL184 treatments prevented these behavioral and cellular deficits. We also investigated the effects of CUS and chronic JZL184 on a form long-term potentiation (LTP) in the DG known to be neurogenesis-dependent. CUS impaired LTP induction, whereas chronic JZL184 treatments restored LTP in CUS-exposed mice. These results suggest that enhanced adult neurogenesis and long-term synaptic plasticity in the DG of the hippocampus might contribute to antidepressant- and anxiolytic-like behavioral effects of JZL184.

Objective To isolate, purify, and cultivate primary retinal microvascular pericytes (RMPs) from rats to facilitate the study of their properties in vitro. Methods Primary RMPs were isolated from weanling rats by mechanical morcel and collagenase digestion, and purified by a step-wise combination of selective medium with different glucose concentrations, medium exchange, and partial enzymatic digestion. Morphology of RMPs was assessed by phase contrast microscopy. Further characterization was analyzed by immunofluorescence. Functional assay was evaluated by the pericytes- endothelial cells (ECs) coculture system. Results Retinal microvascular pericytes migrated out of microvascular fragments after 24-48 hours of plating and reached subconfluence on days 14-16. The cells showed typical pericyte morphology with large irregular triangular cell bodies and multiple long processes, and uniformly expressed the cellular markers α-SMA, PDGFR-β, NG2 and desmin, but were negative for vWF, GS, GFAP and SMMHC. Ninety-nine percent of the cell population had double positive staining for α-SMA and PDGFR-β. In the coculture system, RMPs can directly contact ECs and move together to form the capillary-like cords. Conclusions Retinal microvascular pericytes can be readily obtained by our method. We report the first cultivation of primary RMPs from rats and establish a simple method for their isolation and purification.

Increasing evidence from various clinical and experimental studies has demonstrated that the inflammatory microenvironment facilitates tumor metastasis. Clinically, it will be a promising choice to suppress tumor metastasis by targeting inflammatory microenvironment. Our previous studies have demonstrated that wogonin (a bioflavonoid isolated from the traditional Chinese medicine of Huang-Qin) possesses the anti-metastatic and anti-inflammatory activity, but we have little idea about its efficacy on inflammatory-induced tumor metastasis and the mechanism underlying it. In this study, we focused on epithelial mesenchymal transition (EMT), the first step of tumor metastasis, to evaluate the effects of wogonin on tumor metastasis in inflammatory microenvironment. We found that wogonin inhibited THP-1 conditioned-medium- (CM-) and IL-6-induced EMT by inactivating STAT3 signal. And in wogonin-treated A549 cells which pretreated with THP-1 CM or IL-6, the expression level of E-cadherin, an EMT negative biomarker, increased while that of N-cadherin, Vimentin, and EMT-related transcription factors including Snail and Twist decreased. Moreover, wogonin inhibited IL-6-induced phosphorylation of STAT3, prevented p-STAT3 dimer translocation into the nucleus, and suppressed the DNA-binding activity of p-STAT3. Interestingly, similar results were obtained in the tumor xenografts mice, including downregulation of p-STAT3, N-cadherin, and Vimentin while up-regulation of E-cadherin. Wogonin also inhibit the metastasis of A549 cells in vivo. Taken all data together, we concluded that wogonin suppresses tumor cells migration in inflammatory microenvironment by inactivating STAT3 signal. © 2014 Wiley Periodicals, Inc.

Many species from genus Gentiana (Gentianaceae) have a long history of applications as folk medicines in the world. A simple rapid UPLC-UV-MS/MS method has been developed and validated for the simultaneous determination of six index constituents (gentiopicroside, swertiamarin, loganic acid, sweroside, mangiferin and ferulic acid) from the four ethnomedicines (G. rigescens Franch. ex Hemsl., G. rhodantha Franch. ex Hemsl., G. scabra Bunge and G. farreri Balf. f.). The UPLC analysis was performed on Shim-Pack XR-ODS III (150×2.0mm, 2.2 μm). The mobile phase was consisted of acetoni- trile-0.1% formic acid water using gradient elution. The wavelength 242nm was chose for the four iridoids as well as mangiferin and 320nm was set for ferulic acid. Mass spectrometry was applied for identification and quantification for analytes with low concentration. All the regression equations revealed a good linear relationship (R 2 >0.9993). Accuracy and precision were all within the required limits. The chromatogram fingerprints analysis combined with principal compo- nent analysis showed the similarity values of the four species were 0.993, which provided reasonable foundation for utilization and clinical application of the four ethnomedicines. This developed method appears to be a useful tool for quality control of the four ethnomedicines. Copyright © 2014 John Wiley & Sons, Ltd.

An efficient multicomponent reaction of 3-indolyl-3-oxopropanenitriles with dialkyl acetylenedicarboxylates and isocyanides under mild conditions leading to highly functionalized 6-(indol-3-yl)-4H-pyrans in moderate to good yields has been developed.

A simple, new type of chiral sulfinamide monophosphines, the so-called Ming-Phos ligands, is reported; these ligands could be easily prepared from inexpensive and commercially available starting materials. The Ming-Phos ligands performed well in the enantioselective gold-catalyzed cycloaddition reaction of 2-(1-alkynyl)-alk-2-en-1-ones with nitrones. Both enantiomers of the products could be obtained in good yields and with excellent diastereo- and enantioselectivity through transformations that were catalyzed by gold complexes derived from two diastereomers of Ming-Phos ligand M5 (Ar=1-naphthyl).

Hybrid membranes containing multi-walled carbon nanotubes (MWCNTs) were initially prepared to separate benzene/cyclohexane mixtures. Subsequently, MWCNT surfaces were chemically modified using two methods to change the surface polarity of the MWCNTs and improve the distribution thereof in Poly(methylmethacrylate) (PMMA). This change consequently enhanced the separation performance of hybrid membranes with MWCNTs. Raman spectroscopy was used to characterize the structure of the pristine MWCNTs and the modified MWCNTs. The morphology and distribution of the MWCNTs in PMMA were investigated by transmission electron microscopy. The results showed that the addition of MWCNTs clearly improved the separation performance of the hybrid membranes. Surface modification introduced polar groups onto the MWCNT surface, which significantly improved the distribution of MWCNTs in the PMMA membranes and the performance of hybrid membranes. MWCNTs with higher surface polarity also increased the amount of MWCNTs distributed homogeneously in PMMA. Aminated MWCNTs (MWCNT-NH2) showed the highest surface polarity. Thus, the content of MWCNT-NH2 well distributed in PMMA was the highest among the three types of MWCNTs. The highest separation factor for the hybrid membranes with 1.0 wt% MWCNT-NH2 was about seven times that of membranes containing pristine MWCNTs. Copyright © 2013 John Wiley & Sons, Ltd.

Highly efficient diastereo- and enantioselective Michael addition reactions between 3-substituted oxindoles and trifluoromethylated nitro olefins catalyzed by a quinine-derived squaramide have been investigated. The corresponding adducts, each bearing a chiral tertiary carbon center attached to a trifluoromethyl group and adjacent to a quaternary stereocenter at the C3 position of the oxindole, were obtained in good to excellent yields (up to 99 %) and with high diastereoselectivities (up to >20:1 dr) and excellent enantioselectivities (up to 99 % ee).

Summary Medium- and long-chain triacylglycerols (MLCTs)–enriched structured lipid (SL) was synthesised through enzymatic interesterification from Cinnamomum camphora seed oil (CCSO) and camellia oil (CO) using Lipozyme RM IM from Rhizomucor miehei as a biocatalyst. Effects of different reaction conditions including substrate molar ratio, reaction time and reaction temperature were investigated. Results showed that 55.81% of total MLCT species (CCO/LaCL, LaCO/LCL, COO/OCO and LaOO/OLaO) was obtained in the interesterified product under the optimal conditions of substrate molar ratio of 1:1.5 (CCSO/CO) at 60 °C for 3 h. Thereafter, fatty acid profiles, tocopherol contents and physiochemical characteristics of the interesterified product and physical blend were comparatively investigated. The fatty acid composition of the interesterified product consisted of capric acid (26.33%), lauric acid (21.29%) and oleic acid (42.33%). It should be mentioned that the interesterified product contained predominantly oleic acid (88.69%) at Sn-2 position, while MCFAs (68.05%) at Sn-1,3 positions. Compared with physical blend, the reduction in tocopherol contents and changes of physiochemical characteristics occurred in SL. The smoke point of the interesterified product was much higher than that of the physical blend, which meant that such MLCTs-enriched SL could be better for cooking purpose.

Infection is still a major concern in bone implants, especially in the implants with porous structures. As silver shows superior and broad-spectrum antibacterial activity, porous silver-doped β-tricalcium phosphate (β-TCP) bioceramics are prepared with 5% and 10% nanometer silver. The bioceramics show similar porous macrostructure with pure β-TCP bioceramic, except slightly color change. They have almost identical microstructure to its pure β-TCP counterpart under field emission scanning electron microscope. Their physical, chemical, and mechanical properties were investigated with X-ray diffraction, Fourier transforming infrared spectrometer, and AG-5kN, and no significant difference has been found between silver-doped β-TCP bioceramics and pure β-TCP bioceramic. Bactericidal concentration of silver ions was detected in the solution soaked with the bioceramics. They can efficiently inhibit the growth of Staphylococcus epidermidis and Styphylococcus aureus, but show no cytotoxicity to L929 cells. It suggests that silver-doped β-TCP bioceramics can be developed into new type of bone substitutes with anti-infection properties.

Hypoxia induced drug resistance is a major obstacle in the development of effective cancer therapy. In the present study, the reversal abilities of wogonin on the hypoxia resistance and the underlying mechanisms were discovered. MTT assay revealed that hypoxia increased maximal 1.71-, 2.08-, and 2.15-fold of IC50 toward paclitaxel, ADM, and DDP in human colon cancer cell lines HCT116, respectively. Furthermore, wogonin showed strong reversal potency in HCT116 cells in hypoxia and the RF reached 2.05. hypoxia-inducible factor-1α (HIF-1α) can activate the expression of target genes involved in glycolysis. Wogonin decreased the expression of glycolysis-related proteins (HKII, PDHK1, LDHA), glucose uptake, and lactate generation in a dose-dependent manner. Further, Western blot experiments exhibited that wogonin could down regulate HIF-1α expression and glycolysis through inhibiting PI3K/Akt signaling pathway, which might be the mechanism of reversal resistance of wogonin. Also, wogonin could inhibit the growth of transplantable tumors and the expression of HIF-1α, glycolysis-related proteins and PI3K/Akt in vivo. In summary, wogonin could be a good candidate for the development of new multidrug resistance (MDR) reversal agent and its reversal mechanism probably is due to the suppression of HIF-1α expression via inhibiting PI3K/Akt signaling pathway.

Tetraamido-oxacalix[4]arene derivatives have been synthesized via the reactions of tetraamino-oxacalix[4]arene with excess butyryl chloride, octanoyl chloride, benzoyl chloride and p-toluenesulfonyl chloride, respectively. 1H NMR results suggest that these oxacalix[4]arene derivatives preferentially adopt the 1,3-alternate (saddle-like) conformation in solution, which were also the case in the solid state as demonstrated by single crystal X-ray analysis. A dimerized slipped capsule could be formed by tetra-butyramido-oxacalix[4]arene in the solid state via intermolecular hydrogen bond interactions under the assistance of two encapsulated methanol molecules. On the other hand, a molecular cavity was formed by tetra-p-toluenesulfonamido-oxacalix[4]arene which can encapsulate a solvent molecule of ethyl acetate.

The development of high amylose corn (Zea mays L.) in the public sector has been hindered by the lack of high amylose germplasm available to breeders and difficulties in accurate and efficient amylose content measurement. GEMS-0067 is the first public germplasm that possesses recessive amylose-extender (ae) gene and a modifier gene or genes that raises amylose level to over 70%. Several lines of evidences suggested that SbeI is one of the major modifier genes for high amylose corn, and our work for the first time showed that SbeI explained 49% of the total amylose variance in the amylose extender background. We developed and validated functional codominant molecular markers of SbeI and SbeIIb for GEMS-0067 that were able to distinguish AeAe, Aeae, and aeae genotypes. These simple, sequence-specific, polymerase chain reaction-based, low-cost markers amenable to larger numbers of plant samples make them potentially viable for marker-assisted selection in practical high amylose corn breeding programs. GEMS-0067 was of mixed heterotic derivation. Our result clearly showed that GEMS-0067 was genetically more similar to Mo17 and was clustered into non-Stiff Stalk heterotic group based on 25 simple sequence repeat profiles. The information provided here would facilitate the development of high amylose corn.

Osthole, a major component isolated from the fruit of Cnidium monnieri (L.) Cusson, has been widely used in traditional Chinese medicine. We developed and validated a rapid and sensitive LC-MS/MS method for the quantification of osthole in rat plasma. Sample preparation involved simple liquid-liquid extraction by ethyl acetate after addition of imperatorin as internal standard (IS). The analyte was separated using a C(18) column with the mobile phase of methanol-0.1% formic acid (80:20, v/v) at a flow rate of 0.4 mL/min. The elutes were detected under positive electrospray ionization in multiple reaction monitoring mode. The method was sensitive with 0.5 ng/mL as the lower limit of detection. Good linearity was obtained over the range of 1.0-500.0 ng/mL. The intra and inter-batch accuracy for osthole in rat plasma samples ranged from 99.5 to 108.1% and the variation was

In metal–organic framework (MOF) chemistry, polar functionalities greatly affect the gas adsorption properties. However, synthesis of MOFs with desired functionality is very challenging because many chemical functionalities cannot be achieved under the conditions for MOF assembly. Herein, a facile synthesis of new functionalized two-dimensional MOFs with preferential CO2 capture is presented, which uses two successive synthesis steps: 1) rational design and template-free synthesis of the parent MOF with designated pendant amino groups and 2) postsynthetic modification of the active amino groups with acetic acid and trimesoyl chloride functionalities. The only variation in structure arises from the functional groups of these materials. Experimental results demonstrate that the three 2D layered MOFs have remarkable thermal stability and moisture resistance, which are particularly advantageous for practical CO2 capture. Although their surface areas are moderate (270–340 m2 g−1), they still have excellent CO2 adsorption capacity (up to 2.9 mmol g−1 at 1 bar and 273 K) comparable to that of previously reported MOFs with much higher surface areas. Based on first-principles calculations, it is shown that the acidic carbonyl functionalities in addition to the amino groups are also favorable to bind CO2 molecules. The adsorption sites generated from polar functionalities are key factors leading to high CO2 uptake.

Two coordination polymers (CPs), {[Zn2(BMB)(5-AIPA)2]·2H2O}n(1) and [Zn(BMB)(5-NIPA)]n(2) {BMB = 1, 4-bis[(2-methyl-imidazol-1-yl)methyl]benzene, 5-AIPA = 5-aminoisophthalic acid, 5-NIPA = 5-nitroisophthalic acid}, were synthesized under hydrothermal conditions. Compound 1 displays a 2D double-layer structure, which is packed into a 3D supramolecule by interlayer hydrogen bonds and π–π stacking interactions. Compound 2 displays a threefold interpenetrating 3D network, which is composed of left-handed helical chains and two types of meso-helical chains along different directions.