22 results on '"Swamynayaka A"'
Search Results
2. Oxazine drug-seed induces paraptosis and apoptosis through reactive oxygen species/JNK pathway in human breast cancer cells
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Na Young Kim, Dukanya Dukanya, Gautam Sethi, Swamy S Girimanchanaika, Jirui Yang, Omantheswara Nagaraja, Ananda Swamynayaka, Divakar Vishwanath, Keerthikumara Venkantesha, Shreeja Basappa, Arunachalam Chinnathambi, Sulaiman Ali Alharbi, Mahendra Madegowda, Alexey Sukhorukov, Vijay Pandey, Peter E. Lobie, Basappa Basappa, and Kwang Seok Ahn more...
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Oxazine ,Apoptosis ,Paraptosis ,ROS ,JNK ,Breast cancer ,Neoplasms. Tumors. Oncology. Including cancer and carcinogens ,RC254-282 - Abstract
Small molecule-driven JNK activation has been found to induce apoptosis and paraptosis in cancer cells. Herein pharmacological effects of synthetic oxazine (4aS, 7aS)-3-((4-(4‑chloro-2-fluorophenyl)piperazin-1-yl)methyl)-4-phenyl-4, 4a, 5, 6, 7, 7a-hexahydrocyclopenta[e] [1,2]oxazine (FPPO; BSO-07) on JNK-driven apoptosis and paraptosis has been demonstrated in human breast cancer (BC) MDA-MB231 and MCF-7 cells respectively. BSO-07 imparted significant cytotoxicity in BC cells, induced activation of JNK, and increased intracellular reactive oxygen species (ROS) levels. It also enhanced the expression of apoptosis-associated proteins like PARP, Bax, and phosphorylated p53, while decreasing the levels of Bcl-2, Bcl-xL, and Survivin. Furthermore, the drug altered the expression of proteins linked to paraptosis, such as ATF4 and CHOP. Treatment with N-acetyl-cysteine (antioxidant) or SP600125 (JNK inhibitor) partly reversed the effects of BSO-07 on apoptosis and paraptosis. Advanced in silico bioinformatics, cheminformatics, density Fourier transform and molecular electrostatic potential analysis further demonstrated that BSO-07 induced apoptosis and paraptosis via the ROS/JNK pathway in human BC cells. more...
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- 2024
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Catalog
3. Eco-friendly mercury ion detection and removal in water using anthocyanins: Mechanistic insights through DFT studies
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Mane, Padmaja V., Mahishi, Anusha, Bhat, Mahesh P., Lee, Kyeong-Hwan, Swamynayaka, Ananda, Madegowda, Mahendra, Isloor, Arun M., and Kurkuri, Mahaveer
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- 2025
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4. Optical limiting and third-order nonlinear optical properties of thiazole-based chalcone derivative: Insights from experimental and theoretical approaches
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Venkatesha, Keerthikumara, Srinivas, Mahesh Sankanahalli, Swamynayaka, Ananda, Madegowda, Mahendra, Krishna, Ravi Singh, Hegde, Tejaswi Ashok, and Sadashiva, Maralinganadoddi P.
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- 2024
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5. A simple fluorescent “Turn-Off” Schiff base sensor for Cu2+ and Fe2+ ions and its applications in real water sample analysis and logic gate construction
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Jyothi Priya, M., Revanasiddappa, H.D., Jayalakshmi, B., Swamynayaka, Ananda, Madegowda, Mahendra, Iqbal, Muzaffar, Shivamallu, Chandan, and Prasad Kollur, Shiva
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- 2024
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6. Third-order nonlinear response of a novel organic acetohydrazide derivative: Experimental and theoretical approach
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Swamynayaka, Ananda, Venkatesha, Keerthikumara, Harish, Keshav Kumar, Revanna, Bhavya Nelligere, Venkatesh, Chethan, Madegowda, Mahendra, and Hegde, Tejaswi Ashok
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- 2023
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7. Third-order nonlinear optical studies of Bis(4-methylbenzylammonium) tetrachloridocuprate metal-organic crystal with optical limiting behavior: Experimental and theoretical investigations
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Swamynayaka, Ananda, Srinivas, Mahesh Sankanahalli, M, Vindu Vahini, Khamees, Hussien Ahmed, Madegowda, Mahendra, Hegde, Vinayakprasanna N., Hegde, Tejaswi Ashok, and Vinitha, G.
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- 2022
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8. Methyl-Thiol-Bridged Oxadiazole and Triazole Heterocycles as Inhibitors of NF-κB in Chronic Myelogenous Leukemia Cells
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Basappa Basappa, Young Yun Jung, Akshay Ravish, Zhang Xi, Ananda Swamynayaka, Mahendra Madegowda, Vijay Pandey, Peter E. Lobie, Gautam Sethi, and Kwang Seok Ahn
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chronic myelogenous leukemia cells ,NF-κB ,triazole ,oxadiazole ,click chemistry ,Biology (General) ,QH301-705.5 - Abstract
Nuclear factor kappa beta (NF-κB) is a transcriptional factor that plays a crucial role in regulating cancer cell proliferation. Therefore, the inhibition of NF-κB activity by small molecules may be beneficial in cancer therapy. In this report, methyl-thiol-bridged oxadiazole and triazole heterocycles were synthesized via click chemistry and it was observed that the lead structure, 2-(((1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-5-(4-methoxybenzyl)-1,3,4-oxadiazole (4c), reduced the viability of MCF-7 cells with an IC50 value of 7.4 µM. Compound 4c also caused concentration-dependent loss of cell viability in chronic myelogenous leukemia (CML) cells. Furthermore, compound 4c inhibited the activation of NF-κB in human CML cells as observed by nuclear translocation and DNA binding assays. Functionally, compound 4c produced PARP cleavage and also suppressed expression of Bcl-2/xl, MMP-9, COX-2, survivin, as well as VEGF, resulting in apoptosis of CML cells. Moreover, ChIP assay showed that compound 4c decreased the binding of COX-2 to the p65 gene promoter. Detailed in silico analysis also indicated that compound 4c targeted NF-κB in CML cells. In conclusion, a novel structure bearing both triazole and oxadiazole moieties has been identified that can target NF-κB in CML cells and may constitute a potential novel drug candidate. more...
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- 2023
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9. Discovery of Pyrimidine- and Coumarin-Linked Hybrid Molecules as Inducers of JNK Phosphorylation through ROS Generation in Breast Cancer Cells
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Na Young Kim, Divakar Vishwanath, Zhang Xi, Omantheswara Nagaraja, Ananda Swamynayaka, Keshav Kumar Harish, Shreeja Basappa, Mahendra Madegowda, Vijay Pandey, Gautam Sethi, Peter E. Lobie, Kwang Seok Ahn, and Basappa Basappa more...
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JNK signaling ,pyrimidine ,coumarin ,HER-2 positive breast cancer ,apoptosis ,Organic chemistry ,QD241-441 - Abstract
Human epidermal growth factor receptor 2 (HER2)-positive breast cancer exhibits early relapses, poor prognoses, and high recurrence rates. Herein, a JNK-targeting compound has been developed that may be of utility in HER2-positive mammary carcinoma. The design of a pyrimidine-and coumarin-linked structure targeting JNK was explored and the lead structure PC-12 [4-(3-((2-((4-chlorobenzyl)thio) pyrimidin-4-yl)oxy)propoxy)-6-fluoro-2H-chromen-2-one (5d)] was observed to selectively inhibit the proliferation of HER2-positive BC cells. The compound PC-12 exerted DNA damage and induced apoptosis in HER-2 positive BC cells more significantly compared to HER-2 negative BC cells. PC-12 induced PARP cleavage and down-regulated the expression of IAP-1, BCL-2, SURVIVIN, and CYCLIN D1 in BC cells. In silico and theoretical calculations showed that PC-12 could interact with JNK, and in vitro studies demonstrated that it enhanced JNK phosphorylation through ROS generation. Overall, these findings will assist the discovery of new compounds targeting JNK for use in HER2-positive BC cells. more...
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- 2023
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10. De Novo Design of Imidazopyridine-Tethered Pyrazolines That Target Phosphorylation of STAT3 in Human Breast Cancer Cells
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Akshay Ravish, Rashmi Shivakumar, Zhang Xi, Min Hee Yang, Ji-Rui Yang, Ananda Swamynayaka, Omantheswara Nagaraja, Mahendra Madegowda, Arunachalam Chinnathambi, Sulaiman Ali Alharbi, Vijay Pandey, Gautam Sethi, Kwang Seok Ahn, Peter E. Lobie, and Basappa Basappa more...
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human breast cancer ,STAT3 ,imidazopyridine ,pyrazolines ,DFT ,de novo design ,Technology ,Biology (General) ,QH301-705.5 - Abstract
In breast cancer (BC), STAT3 is hyperactivated. This study explored the design of imidazopyridine-tethered pyrazolines as a de novo drug strategy for inhibiting STAT3 phosphorylation in human BC cells. This involved the synthesis and characterization of two series of compounds namely, 1-(3-(2,6-dimethylimidazo [1,2-a]pyridin-3-yl)-5-(3-nitrophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-(4-(substituted)piperazin-1-yl)ethanone and N-substituted-3-(2,6-dimethylimidazo[1,2-a]pyridin-3-yl)-5-(3-nitrophenyl)-4,5-dihydro-1H-pyrazoline-1-carbothioamides. Compound 3f with 2,3-dichlorophenyl substitution was recognized among the tested series as a lead structure that inhibited the viability of MCF-7 cells with an IC50 value of 9.2 μM. A dose- and time-dependent inhibition of STAT3 phosphorylation at Tyr705 and Ser727 was observed in MCF-7 and T47D cells when compound 3f was added in vitro. Calculations using density functional theory showed that the title compounds HOMOs and LUMOs are situated on imidazopyridine-pyrazoline and nitrophenyl rings, respectively. Hence, compound 3f effectively inhibited STAT3 phosphorylation in MCF-7 and T47D cells, indicating that these structures may be an alternative synthon to target STAT3 signaling in BC. more...
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- 2023
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11. Nano-Zirconium Dioxide Catalyzed Multicomponent Synthesis of Bioactive Pyranopyrazoles That Target Cyclin Dependent Kinase 1 in Human Breast Cancer Cells
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Basappa Basappa, Lisha K. Poonacha, Zhang Xi, Divakar Vishwanath, Ji-Rui Yang, Omantheswara Nagaraja, Ananda Swamynayaka, Mahendra Madegowda, Arunachalam Chinnathambi, Sulaiman Ali Alharbi, Doddahosuru Mahadevappa Gurudatt, Vijay Pandey, Nanjundaswamy Shivananju, Kwang Seok Ahn, Gautam Sethi, Peter E. Lobie, and Priya Babu Shubha more...
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pyranopyrazoles ,CDK1 ,Gibbs free energy ,CHEMBL ,nano-zirconium dioxide ,Biology (General) ,QH301-705.5 - Abstract
Small molecules are being used to inhibit cyclin dependent kinase (CDK) enzymes in cancer treatment. There is evidence that CDK is a drug-target for cancer therapy across many tumor types because it catalyzes the transfer of the terminal phosphate of ATP to a protein that acts as a substrate. Herein, the identification of pyranopyrazoles that were CDK inhibitors was attempted, whose synthesis was catalyzed by nano-zirconium dioxide via multicomponent reaction. Additionally, we performed an in-situ analysis of the intermediates of multicomponent reactions, for the first-time, which revealed that nano-zirconium dioxide stimulated the reaction, as estimated by Gibbs free energy calculations of spontaneity. Functionally, the novel pyranopyrazoles were tested for a loss of cell viability using human breast cancer cells (MCF-7). It was observed that compounds 5b and 5f effectively produced loss of viability of MCF-7 cells with IC50 values of 17.83 and 23.79 µM, respectively. In vitro and in silico mode-of-action studies showed that pyranopyrazoles target CDK1 in human breast cancer cells, with lead compounds 5b and 5f having potent IC50 values of 960 nM and 7.16 μM, respectively. Hence, the newly synthesized bioactive pyranopyrazoles could serve as better structures to develop CDK1 inhibitors against human breast cancer cells. more...
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- 2023
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12. Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine
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Hussien Ahmed Khamees, Kumara Chaluvaiah, Nasseem Ahmed El-khatatneh, Ananda Swamynayaka, Kwong Huey Chong, Jagadeesh Prasad Dasappa, and Mahendra Madegowda
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crystal structure ,imidazole-pyridine derivative ,π–π interactions ,dft calculation ,hirshfeld surface analysis ,energy framework ,frontier molecular orbitals ,Crystallography ,QD901-999 - Abstract
The title imidazo[1,2-a] pyridine derivative, C13H8Br2N2, was synthesized via a single-step reaction method. The title molecule is planar, showing a dihedral angle of 0.62 (17)° between the phenyl and the imidazo[1,2-a] pyridine rings. An intramolecular C—H...N hydrogen bond with an S(5) ring motif is present. In the crystal, a short H...H contact links adjacent molecules into inversion-related dimers. The dimers are linked in turn by weak C—H...π and slipped π–π stacking interactions, forming layers parallel to (110). The layers are connected into a three-dimensional network by short Br...H contacts. Two-dimensional fingerprint plots and three-dimensional Hirshfeld surface analysis of the intermolecular contacts reveal that the most important contributions for the crystal packing are from H...Br/Br...H (26.1%), H...H (21.7%), H...C/C...H (21.3%) and C...C (6.5%) interactions. Energy framework calculations suggest that the contacts formed between molecules are largely dispersive in nature. Analysis of HOMO–LUMO energies from a DFT calculation reveals the pure π character of the aromatic rings with the highest electron density on the phenyl ring, and σ character of the electron density on the Br atoms. The HOMO–LUMO gap was found to be 4.343 eV. more...
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- 2019
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13. Development of 1-(4-(Substituted)piperazin-1-yl)-2-((2-((4-methoxybenzyl)thio)pyrimidin-4-yl)oxy)ethanones That Target Poly (ADP-Ribose) Polymerase in Human Breast Cancer Cells
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Suresha N. Deveshegowda, Prashant K. Metri, Rashmi Shivakumar, Ji-Rui Yang, Shobith Rangappa, Ananda Swamynayaka, Muthu K. Shanmugam, Omantheswara Nagaraja, Mahendra Madegowda, Priya Babu Shubha, Arunachalam Chinnathambi, Sulaiman Ali Alharbi, Vijay Pandey, Kwang Seok Ahn, Peter E. Lobie, and Basappa Basappa more...
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PARPi ,breast cancer ,thiouracil amides ,apoptosis ,Organic chemistry ,QD241-441 - Abstract
A number of uracil amides cleave poly (ADP-ribose) polymerase and therefore novel thiouracil amide compounds were synthesized and screened for the loss of cell viability in a human-estrogen-receptor-positive breast cancer cell line. The synthesized compounds exhibited moderate to significant efficacy against human breast cancer cells, where the compound 5e IC50 value was found to be 18 μM. Thouracil amide compounds 5a and 5e inhibited the catalytical activity of PARP1, enhanced cleavage of PARP1, enhanced phosphorylation of H2AX, and increased CASPASE 3/7 activity. Finally, in silico analysis demonstrated that compound 5e interacted with PARP1. Hence, specific thiouracil amides may serve as new drug-seeds for the development of PARP inhibitors for use in oncology. more...
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- 2022
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14. Discovery of Pyrimidine- and Coumarin-Linked Hybrid Molecules as Inducers of JNK Phosphorylation through ROS Generation in Breast Cancer Cells.
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Kim, Na Young, Vishwanath, Divakar, Xi, Zhang, Nagaraja, Omantheswara, Swamynayaka, Ananda, Kumar Harish, Keshav, Basappa, Shreeja, Madegowda, Mahendra, Pandey, Vijay, Sethi, Gautam, Lobie, Peter E., Ahn, Kwang Seok, and Basappa, Basappa more...
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CANCER cells ,BREAST cancer ,HER2 positive breast cancer ,BREAST ,PHOSPHORYLATION ,MOLECULES ,EPIDERMAL growth factor receptors - Abstract
Human epidermal growth factor receptor 2 (HER2)-positive breast cancer exhibits early relapses, poor prognoses, and high recurrence rates. Herein, a JNK-targeting compound has been developed that may be of utility in HER2-positive mammary carcinoma. The design of a pyrimidine-and coumarin-linked structure targeting JNK was explored and the lead structure PC-12 [4-(3-((2-((4-chlorobenzyl)thio) pyrimidin-4-yl)oxy)propoxy)-6-fluoro-2H-chromen-2-one (5d)] was observed to selectively inhibit the proliferation of HER2-positive BC cells. The compound PC-12 exerted DNA damage and induced apoptosis in HER-2 positive BC cells more significantly compared to HER-2 negative BC cells. PC-12 induced PARP cleavage and down-regulated the expression of IAP-1, BCL-2, SURVIVIN, and CYCLIN D1 in BC cells. In silico and theoretical calculations showed that PC-12 could interact with JNK, and in vitro studies demonstrated that it enhanced JNK phosphorylation through ROS generation. Overall, these findings will assist the discovery of new compounds targeting JNK for use in HER2-positive BC cells. [ABSTRACT FROM AUTHOR] more...
- Published
- 2023
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15. Investigation of NPB Analogs That Target Phosphorylation of BAD-Ser99 in Human Mammary Carcinoma Cells
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Divya Maldepalli Govindachar, Peter E. Lobie, Swamy Savvemala Girimanchanaika, Kanchugarakoppal S. Rangappa, Ananda Swamynayaka, Basappa Basappa, Mahendra Madegowda, Vijay Pandey, Dukanya Dukanya, and Ganga Periyasamy more...
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human mammary carcinoma ,Stereochemistry ,QH301-705.5 ,drug design ,Petasis reaction ,Molecular Conformation ,Breast Neoplasms ,Crystallography, X-Ray ,lead optimization ,Catalysis ,Article ,Inorganic Chemistry ,Mammary carcinoma ,Benzaldehyde ,chemistry.chemical_compound ,Serine ,Phenol ,Humans ,Viability assay ,Physical and Theoretical Chemistry ,Phosphorylation ,Biology (General) ,Molecular Biology ,QD1-999 ,Spectroscopy ,Density Functional Theory ,Nitrobenzenes ,Organic Chemistry ,General Medicine ,Small molecule ,Computer Science Applications ,BAD phosphorylation ,Chemistry ,chemistry ,Cancer cell ,MCF-7 Cells ,Female ,bcl-Associated Death Protein - Abstract
The design and development of a small molecule named NPB [3-{(4(2,3-dichlorophenyl)piperazin-1-yl}{2-hydroxyphenyl)methyl}-N-cyclopentylbenzamide], which specifically inhibited the phosphorylation of BAD at Ser99 in human carcinoma cells has been previously reported. Herein, the synthesis, characterization, and effect on cancer cell viability of NPB analogs, and the single-crystal X-ray crystallographic studies of an example compound (4r), which was grown via slow-solvent evaporation technique is reported. Screening for loss of viability in mammary carcinoma cells revealed that compounds such as 2[(4(2,3-dichlorophenyl)piperazin-1-yl][naphthalen-1-yl]methyl)phenol (4e), 5[(4(2,3-dichlorophenyl)piperazin-1-yl][2-hydroxyphenyl)methyl)uran-2-carbaldehyde (4f), 3[(2-hydroxyphenyl][4(p-tolyl)piperazin-1-yl)methyl)benzaldehyde (4i), and NPB inhibited the viability of MCF-7 cells with IC50 values of 5.90, 3.11, 7.68, and 6.5 µM, respectively. The loss of cell viability was enhanced by the NPB analogs synthesized by adding newer rings such as naphthalene and furan-2-carbaldehyde in place of N-cyclopentyl-benzamide of NPB. Furthermore, these compounds decreased Ser99 phosphorylation of hBAD. Additional in silico density functional theory calculations suggested possibilities for other analogs of NPB that may be more suitable for further development. more...
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- 2021
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16. Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine
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Ananda Swamynayaka, Kumara Chaluvaiah, Kwong Huey Chong, Jagadeesh Prasad Dasappa, Mahendra Madegowda, Nasseem Ahmed El-khatatneh, and Hussien Ahmed Khamees
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crystal structure ,frontier molecular orbitals ,Stacking ,π–π interactions ,Crystal structure ,Dihedral angle ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Research Communications ,chemistry.chemical_compound ,dft calculation ,Pyridine ,hirshfeld surface analysis ,General Materials Science ,imidazole-pyridine derivative ,Crystallography ,010405 organic chemistry ,Hydrogen bond ,Aromaticity ,General Chemistry ,Condensed Matter Physics ,0104 chemical sciences ,chemistry ,QD901-999 ,π–π interactions ,frontier molecular orbitals ,Derivative (chemistry) ,energy framework - Abstract
The molecular system displays a planar conformation between the phenyl and imidazo[1,2-a] pyridine rings. Weak C—H⋯π and π–π interactions as well as short contacts consolidate the three-dimensional network structure., The title imidazo[1,2-a] pyridine derivative, C13H8Br2N2, was synthesized via a single-step reaction method. The title molecule is planar, showing a dihedral angle of 0.62 (17)° between the phenyl and the imidazo[1,2-a] pyridine rings. An intramolecular C—H⋯N hydrogen bond with an S(5) ring motif is present. In the crystal, a short H⋯H contact links adjacent molecules into inversion-related dimers. The dimers are linked in turn by weak C—H⋯π and slipped π–π stacking interactions, forming layers parallel to (110). The layers are connected into a three-dimensional network by short Br⋯H contacts. Two-dimensional fingerprint plots and three-dimensional Hirshfeld surface analysis of the intermolecular contacts reveal that the most important contributions for the crystal packing are from H⋯Br/Br⋯H (26.1%), H⋯H (21.7%), H⋯C/C⋯H (21.3%) and C⋯C (6.5%) interactions. Energy framework calculations suggest that the contacts formed between molecules are largely dispersive in nature. Analysis of HOMO–LUMO energies from a DFT calculation reveals the pure π character of the aromatic rings with the highest electron density on the phenyl ring, and σ character of the electron density on the Br atoms. The HOMO–LUMO gap was found to be 4.343 eV. more...
- Published
- 2019
17. De Novo Design of Imidazopyridine-Tethered Pyrazolines That Target Phosphorylation of STAT3 in Human Breast Cancer Cells.
- Author
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Ravish, Akshay, Shivakumar, Rashmi, Xi, Zhang, Yang, Min Hee, Yang, Ji-Rui, Swamynayaka, Ananda, Nagaraja, Omantheswara, Madegowda, Mahendra, Chinnathambi, Arunachalam, Alharbi, Sulaiman Ali, Pandey, Vijay, Sethi, Gautam, Ahn, Kwang Seok, Lobie, Peter E., and Basappa, Basappa more...
- Subjects
STAT proteins ,BREAST cancer ,CANCER cells ,PHOSPHORYLATION ,DENSITY functional theory ,LIGANDS (Biochemistry) - Abstract
In breast cancer (BC), STAT3 is hyperactivated. This study explored the design of imidazopyridine-tethered pyrazolines as a de novo drug strategy for inhibiting STAT3 phosphorylation in human BC cells. This involved the synthesis and characterization of two series of compounds namely, 1-(3-(2,6-dimethylimidazo [1,2-a]pyridin-3-yl)-5-(3-nitrophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-(4-(substituted)piperazin-1-yl)ethanone and N-substituted-3-(2,6-dimethylimidazo[1,2-a]pyridin-3-yl)-5-(3-nitrophenyl)-4,5-dihydro-1H-pyrazoline-1-carbothioamides. Compound 3f with 2,3-dichlorophenyl substitution was recognized among the tested series as a lead structure that inhibited the viability of MCF-7 cells with an IC
50 value of 9.2 μM. A dose- and time-dependent inhibition of STAT3 phosphorylation at Tyr705 and Ser727 was observed in MCF-7 and T47D cells when compound 3f was added in vitro. Calculations using density functional theory showed that the title compounds HOMOs and LUMOs are situated on imidazopyridine-pyrazoline and nitrophenyl rings, respectively. Hence, compound 3f effectively inhibited STAT3 phosphorylation in MCF-7 and T47D cells, indicating that these structures may be an alternative synthon to target STAT3 signaling in BC. [ABSTRACT FROM AUTHOR] more...- Published
- 2023
- Full Text
- View/download PDF
18. Development of 1-(4-(Substituted)piperazin-1-yl)-2-((2-((4-methoxybenzyl)thio)pyrimidin-4-yl)oxy)ethanones That Target Poly (ADP-Ribose) Polymerase in Human Breast Cancer Cells.
- Author
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Deveshegowda, Suresha N., Metri, Prashant K., Shivakumar, Rashmi, Yang, Ji-Rui, Rangappa, Shobith, Swamynayaka, Ananda, Shanmugam, Muthu K., Nagaraja, Omantheswara, Madegowda, Mahendra, Babu Shubha, Priya, Chinnathambi, Arunachalam, Alharbi, Sulaiman Ali, Pandey, Vijay, Ahn, Kwang Seok, Lobie, Peter E., and Basappa, Basappa more...
- Subjects
POLY ADP ribose ,BREAST cancer ,THIOURACIL ,CHEMICAL synthesis ,AMIDES ,URACIL ,ADP-ribosylation ,CANCER cells - Abstract
A number of uracil amides cleave poly (ADP-ribose) polymerase and therefore novel thiouracil amide compounds were synthesized and screened for the loss of cell viability in a human-estrogen-receptor-positive breast cancer cell line. The synthesized compounds exhibited moderate to significant efficacy against human breast cancer cells, where the compound 5e IC
50 value was found to be 18 μM. Thouracil amide compounds 5a and 5e inhibited the catalytical activity of PARP1, enhanced cleavage of PARP1, enhanced phosphorylation of H2AX, and increased CASPASE 3/7 activity. Finally, in silico analysis demonstrated that compound 5e interacted with PARP1. Hence, specific thiouracil amides may serve as new drug-seeds for the development of PARP inhibitors for use in oncology. [ABSTRACT FROM AUTHOR] more...- Published
- 2022
- Full Text
- View/download PDF
19. Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine.
- Author
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Khamees, Hussien Ahmed, Chaluvaiah, Kumara, El-khatatneh, Nasseem Ahmed, Swamynayaka, Ananda, Chong, Kwong Huey, Dasappa, Jagadeesh Prasad, and Madegowda, Mahendra
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SURFACE analysis ,IMIDAZOPYRIDINES ,SURFACE energy ,CRYSTAL structure ,DIHEDRAL angles ,FRONTIER orbitals ,ELECTRON density - Abstract
The title imidazo[1,2-a] pyridine derivative, C
13 H8 Br2 N2 , was synthesized via a single-step reaction method. The title molecule is planar, showing a dihedral angle of 0.62 (17)° between the phenyl and the imidazo[1,2-a] pyridine rings. An intramolecular C—H∙∙∙N hydrogen bond with an S(5) ring motif is present. In the crystal, a short H∙∙∙H contact links adjacent molecules into inversion-related dimers. The dimers are linked in turn by weak C—H∙∙∙π and slipped π–π stacking interactions, forming layers parallel to (110). The layers are connected into a three-dimensional network by short Br∙∙∙H contacts. Two-dimensional fingerprint plots and three-dimensional Hirshfeld surface analysis of the intermolecular contacts reveal that the most important contributions for the crystal packing are from H∙∙∙Br/Br∙∙∙H (26.1%), H∙∙∙H (21.7%), H∙∙∙C/C∙∙∙H (21.3%) and CC (6.5%) interactions. Energy framework calculations suggest that the contacts formed between molecules are largely dispersive in nature. Analysis of HOMO–LUMO energies from a DFT calculation reveals the pure π character of the aromatic rings with the highest electron density on the phenyl ring, and σ character of the electron density on the Br atoms. The HOMO–LUMO gap was found to be 4.343 eV. [ABSTRACT FROM AUTHOR] more...- Published
- 2019
- Full Text
- View/download PDF
20. Molecular Structure, DFT, Vibrational Spectra with Fluorescence Effect, Hirshfeld Surface, Docking Simulation and Antioxidant Activity of Thiazole Derivative.
- Author
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Khamees, Hussien A., Mohammed, Yasser H. E., Swamynayaka, Ananda, Al‐Ostoot, Fares H., Sert, Yusuf, Alghamdi, Saad, Khanum, Shaukath A., and Madegowda, Mahendra
- Subjects
THIAZOLE derivatives ,ANTIOXIDANTS ,DENSITY functional theory - Abstract
2‐(4‐methylphenoxy)‐N‐(4‐(4‐bromophenyl) thiazol‐2‐yl) acetamide compound was obtained via a multistep synthesis sequence processes, which is characterized by 1H NMR, 13C NMR and its three‐dimensional structure has been confirmed by single crystal X‐ray diffraction method. The supramolecular structure of the molecule revealed the stability of crystal packing with diverse intermolecular interactions. Density functional theory calculations (DFT) at B3LYP 6–311++G(d,p) level has been used to predict the molecular geometry and were in good agreement with the experimental data. Moreover, the theoretical calculations were carried out to appraise the electronic structure, vibrational spectra, natural bond orbital analysis, molecular electrostatic potential, frontier molecular orbitals and global reactivity descriptors. Raman spectra with fluorescence effect was examined with visible and near IR excitation wavelengths. Hirshfeld surface and energy framework analysis revealed the important intermolecular contacts and interaction energies. The antioxidant activity of this synthesized compound was predicted by in silico docking study on human peroxiredoxin 5 protein. The potential antioxidant activity was investigated by 1,1‐diphenyl‐1‐picrylhydrazyl (DPPH) free radical screening and compared with standard drug ascorbic acid. [ABSTRACT FROM AUTHOR] more...
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- 2019
- Full Text
- View/download PDF
21. Investigation of NPB Analogs That Target Phosphorylation of BAD-Ser99 in Human Mammary Carcinoma Cells.
- Author
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Girimanchanaika, Swamy Savvemala, Dukanya, Dukanya, Swamynayaka, Ananda, Govindachar, Divya Maldepalli, Madegowda, Mahendra, Periyasamy, Ganga, Rangappa, Kanchugarakoppal Subbegowda, Pandey, Vijay, Lobie, Peter E., and Basappa, Basappa more...
- Subjects
CARCINOMA ,SMALL molecules ,DENSITY functional theory ,PHOSPHORYLATION ,CELL survival - Abstract
The design and development of a small molecule named NPB [3-{(4(2,3-dichlorophenyl)piperazin-1-yl}{2-hydroxyphenyl)methyl}-N-cyclopentylbenzamide], which specifically inhibited the phosphorylation of BAD at Ser99 in human carcinoma cells has been previously reported. Herein, the synthesis, characterization, and effect on cancer cell viability of NPB analogs, and the single-crystal X-ray crystallographic studies of an example compound (4r), which was grown via slow-solvent evaporation technique is reported. Screening for loss of viability in mammary carcinoma cells revealed that compounds such as 2[(4(2,3-dichlorophenyl)piperazin-1-yl][naphthalen-1-yl]methyl)phenol (4e), 5[(4(2,3-dichlorophenyl)piperazin-1-yl][2-hydroxyphenyl)methyl)uran-2-carbaldehyde (4f), 3[(2-hydroxyphenyl][4(p-tolyl)piperazin-1-yl)methyl)benzaldehyde (4i), and NPB inhibited the viability of MCF-7 cells with IC
50 values of 5.90, 3.11, 7.68, and 6.5 µM, respectively. The loss of cell viability was enhanced by the NPB analogs synthesized by adding newer rings such as naphthalene and furan-2-carbaldehyde in place of N-cyclopentyl-benzamide of NPB. Furthermore, these compounds decreased Ser99 phosphorylation of hBAD. Additional in silico density functional theory calculations suggested possibilities for other analogs of NPB that may be more suitable for further development. [ABSTRACT FROM AUTHOR] more...- Published
- 2021
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22. Chalcone-based Turn-Off Chemosensor for Selective and Susceptible Detection of Fe2+ Ions: Spectroscopic and DFT Investigations.
- Author
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Revanna, Bhavya Nelligere, Kamat, Vinuta, Swamynayaka, Ananda, Harish, Keshav Kumar, Venkatesha, Keerthikumara, Madegowda, Mahendra, Poojary, Boja, Majani, Sanjay S., and Kollur, Shiva Prasad
- Abstract
Herein, in this report we are introducing newly synthesized chalcone derivative, “(E)-1-phenyl-3-(4-((5-(((Z)-thiophen-2-ylmethylene)amino)-1,3,4-thiadiazol-2-yl)thio)phenyl)prop-2-en-1-one” (5), as a chemosensor to detect Fe2+ metal ions in HEPES buffer solution of pH 7.5. Spectroscopic techniques were used to confirm the synthesized sensor. To determine the chemical reactivity and molecular stability of the probe, a frontier molecular orbitals investigation was carried out. A molecular electrostatic potential map was investigated to know the binding site of 5 for metal ion coordination. The theoretical absorption and fluorescence emission properties were estimated and correlated with the experimental observations. The sensor showed excellent selectivity for Fe2+ compared to all other studied metal ions. The fluorescence binding studies were carried out by adding different amounts of Fe2+ ions for a fixed concentration of probe 5. The inclusion of Fe2+ ions resulted in a decrease in fluorescence intensity with a bathochromic shift of emission wavelength of 5 due to the 5-Fe2+ complexation. The binding affinity value for the probe was found to be 576.2 M−1 with the help of the Stern–Volmer plot. The Job's plot and mass spectra supported the 2:1 (5: Fe2+) stoichiometry of complex formation. The detection limit and limit of quantification of 5 for Fe2+ were calculated to be 4.79 × 10–5 M and 14.54 × 10–5 M. Further, in addition to this, the photophysical parameters such as fluorescence lifetime of 5 and 5-Fe2+ complex measured to be 0.1439 and 0.1574 ns. The quantum yield of 5 and 5-Fe2+ was found to be 0.0398 and 0.0376. All these experimental findings revealed that probe 5 has excellent selectivity and sensitivity for Fe2+ ions. [ABSTRACT FROM AUTHOR] more...
- Published
- 2024
- Full Text
- View/download PDF
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