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2. Topical, immunomodulatory epoxy-tiglianes induce biofilm disruption and healing in acute and chronic skin wounds

Author

Powell, Lydia C., primary, Cullen, Jason K., additional, Boyle, Glen M., additional, De Ridder, Tom, additional, Yap, Pei-Yi, additional, Xue, Wenya, additional, Pierce, Carly J., additional, Pritchard, Manon F., additional, Menzies, Georgina E., additional, Abdulkarim, Muthanna, additional, Adams, Jennifer Y. M., additional, Stokniene, Joana, additional, Francis, Lewis W., additional, Gumbleton, Mark, additional, Johns, Jenny, additional, Hill, Katja E., additional, Jones, Adam V., additional, Parsons, Peter G., additional, Reddell, Paul, additional, and Thomas, David W., additional

Published
2022
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4. EBC‐232 and 323: A Structural Conundrum Necessitating Unification of Five In Silico Prediction and Elucidation Methods**

Author

Maslovskaya, Lidia A., primary, Savchenko, Andrei I., additional, Krenske, Elizabeth H., additional, Chow, Sharon, additional, Holt, Tina, additional, Gordon, Victoria A., additional, Reddell, Paul W., additional, Pierce, Carly J., additional, Parsons, Peter G., additional, Boyle, Glen M., additional, Kutateladze, Andrei G., additional, and Williams, Craig M., additional

Published
2020
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8. Berichtigung: Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere

Author

Chalmers, Benjamin A., primary, Xing, Hui, additional, Houston, Sevan, additional, Clark, Charlotte, additional, Ghassabian, Sussan, additional, Kuo, Andy, additional, Cao, Benjamin, additional, Reitsma, Andrea, additional, Murray, Cody‐Ellen P., additional, Stok, Jeanette E., additional, Boyle, Glen M., additional, Pierce, Carly J., additional, Littler, Stuart W., additional, Winkler, David A., additional, Bernhardt, Paul V., additional, Pasay, Cielo, additional, De Voss, James J., additional, McCarthy, James, additional, Parsons, Peter G., additional, Walter, Gimme H., additional, Smith, Maree T., additional, Cooper, Helen M., additional, Nilsson, Susan K., additional, Tsanaktsidis, John, additional, Savage, G. Paul, additional, and Williams, Craig M., additional

Published
2018
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9. Corrigendum: Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere

Author

Chalmers, Benjamin A., primary, Xing, Hui, additional, Houston, Sevan, additional, Clark, Charlotte, additional, Ghassabian, Sussan, additional, Kuo, Andy, additional, Cao, Benjamin, additional, Reitsma, Andrea, additional, Murray, Cody‐Ellen P., additional, Stok, Jeanette E., additional, Boyle, Glen M., additional, Pierce, Carly J., additional, Littler, Stuart W., additional, Winkler, David A., additional, Bernhardt, Paul V., additional, Pasay, Cielo, additional, De Voss, James J., additional, McCarthy, James, additional, Parsons, Peter G., additional, Walter, Gimme H., additional, Smith, Maree T., additional, Cooper, Helen M., additional, Nilsson, Susan K., additional, Tsanaktsidis, John, additional, Savage, G. Paul, additional, and Williams, Craig M., additional

Published
2018
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12. Intra-Lesional Injection of the Novel PKC Activator EBC-46 Rapidly Ablates Tumors in Mouse Models

Author

Pierce, Carly J. and Boyle, Glen M.

Abstract

Intra-lesional chemotherapy for treatment of cutaneous malignancies has been used for many decades, allowing higher local drug concentrations and less toxicity than systemic agents. Here we describe a novel diterpene ester, EBC-46, and provide preclinical data supporting its use as an intra-lesional treatment. A single injection of EBC-46 caused rapid inflammation and influx of blood, followed by eschar formation and rapid tumor ablation in a range of syngeneic and xenograft models. EBC-46 induced oxidative burst from purified human polymorphonuclear cells, which was prevented by the Protein Kinase C inhibitor bisindolylmaleimide-1. EBC-46 activated a more specific subset of PKC isoforms (PKC-βI, -βII, -α and -γ) compared to the structurally related phorbol 12-myristate 13-acetate (PMA). Although EBC-46 showed threefold less potency for inhibiting cell growth than PMA in vitro, it was more effective for cure of tumors in vivo. No viable tumor cells were evident four hours after injection by ex vivo culture. Pharmacokinetic profiles from treated mice indicated that EBC-46 was retained preferentially within the tumor, and resulted in significantly greater local responses (erythema, oedema) following intra-lesional injection compared with injection into normal skin. The efficacy of EBC-46 was reduced by co-injection with bisindolylmaleimide-1. Loss of vascular integrity following treatment was demonstrated by an increased permeability of endothelial cell monolayers in vitro and by CD31 immunostaining of treated tumors in vivo. Our results demonstrate that a single intra-lesional injection of EBC-46 causes PKC-dependent hemorrhagic necrosis, rapid tumor cell death and ultimate cure of solid tumors in pre-clinical models of cancer.

Published
2014

13. Expression profiling of cutaneous squamous cell carcinoma with perineural invasion implicates the p53 pathway in the process

Author

Warren, Timothy A., primary, Broit, Natasa, additional, Simmons, Jacinta L., additional, Pierce, Carly J., additional, Chawla, Sharad, additional, Lambie, Duncan L. J., additional, Quagliotto, Gary, additional, Brown, Ian S., additional, Parsons, Peter G., additional, Panizza, Benedict J., additional, and Boyle, Glen M., additional

Published
2016
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17. Frontispiece: Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere

Author

Chalmers, Benjamin A., primary, Xing, Hui, additional, Houston, Sevan, additional, Clark, Charlotte, additional, Ghassabian, Sussan, additional, Kuo, Andy, additional, Cao, Benjamin, additional, Reitsma, Andrea, additional, Murray, Cody-Ellen P., additional, Stok, Jeanette E., additional, Boyle, Glen M., additional, Pierce, Carly J., additional, Littler, Stuart W., additional, Winkler, David A., additional, Bernhardt, Paul V., additional, Pasay, Cielo, additional, De Voss, James J., additional, McCarthy, James, additional, Parsons, Peter G., additional, Walter, Gimme H., additional, Smith, Maree T., additional, Cooper, Helen M., additional, Nilsson, Susan K., additional, Tsanaktsidis, John, additional, Savage, G. Paul, additional, and Williams, Craig M., additional

Published
2016
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18. Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere

Author

Chalmers, Benjamin A., primary, Xing, Hui, additional, Houston, Sevan, additional, Clark, Charlotte, additional, Ghassabian, Sussan, additional, Kuo, Andy, additional, Cao, Benjamin, additional, Reitsma, Andrea, additional, Murray, Cody‐Ellen P., additional, Stok, Jeanette E., additional, Boyle, Glen M., additional, Pierce, Carly J., additional, Littler, Stuart W., additional, Winkler, David A., additional, Bernhardt, Paul V., additional, Pasay, Cielo, additional, De Voss, James J., additional, McCarthy, James, additional, Parsons, Peter G., additional, Walter, Gimme H., additional, Smith, Maree T., additional, Cooper, Helen M., additional, Nilsson, Susan K., additional, Tsanaktsidis, John, additional, Savage, G. Paul, additional, and Williams, Craig M., additional

Published
2016
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23. The First Casbane Hydroperoxides EBC-304 and EBC-320 from the Australian Rainforest.

Author

Maslovskaya, Lidiya A., Savchenko, Andrei I., Gordon, Victoria A., Reddell, Paul W., Pierce, Carly J., Parsons, Peter G., and Williams, Craig M.

Subjects
HYDROPEROXIDES, AUSTRALIAN rainforests, DENSITY functional theory, EUPHORBIACEAE, NUCLEAR magnetic resonance spectroscopy
Abstract

Investigation of the Australian rainforest plant Croton insularis led to isolation of the first casbane hydroperoxide diterpenes EBC-304 and EBC-320. Extensive DFT and electronic circular dichroism (ECD) calculations in combination with 2D NMR spectroscopy determined the absolute configurations. EBC-304 and EBC-320 both display significant cytotoxicity. [ABSTRACT FROM AUTHOR]

Published
2017
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30. Unprecedented 1,14- seco-Crotofolanes from Croton insularis: Oxidative Cleavage of Crotofolin C by a Putative Homo-Baeyer-Villiger Rearrangement.

Author

Maslovskaya, Lidiya A., Savchenko, Andrei I., Pierce, Carly J., Gordon, Victoria A., Reddell, Paul W., Parsons, Peter G., and Williams, Craig M.

Subjects
CROTON (Genus), INTERMEDIATES (Chemistry), BIOSYNTHESIS, DITERPENES, ANTINEOPLASTIC agents, CHEMICAL decomposition
Abstract

EBC-162 isolated from Croton insularis, obtained from the northern rainforest of Australia, was structurally affirmed as crotofolin C ( 4). Novel oxidative degradation products, EBC-233 and EBC-300, which are the first crotofolane endoperoxides, were also isolated. Both endoperoxides were found to be stable intermediates, which are proposed to undergo an unprecedented homo-Baeyer-Villiger biosynthetic rearrangement to give a new class of 1,14- seco-crotofolane diterpenes. Prolonged storage of all isolates assisted in authenticating their natural product status. Anticancer activities of reported compounds are presented. [ABSTRACT FROM AUTHOR]

Published
2014
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32. EBC-232 and 323: A Structural Conundrum Necessitating Unification of Five In Silico Prediction and Elucidation Methods.

Author

Maslovskaya LA, Savchenko AI, Krenske EH, Chow S, Holt T, Gordon VA, Reddell PW, Pierce CJ, Parsons PG, Boyle GM, Kutateladze AG, and Williams CM

Abstract

Structurally unique halimanes EBC-232 and EBC-323, isolated from the Australian rainforest plant Croton insularis, proved considerably difficult to elucidate. The two diastereomers, which consist an unusual oxo-6,7-spiro ring system fused to a dihydrofuran, were solved by unification and consultation of five in silico NMR elucidation and prediction methods [i.e., ACDLabs, olefin strain energy (OSE), DP4, DU8+ and TD DFT CD]. Structure elucidation challenges of this nature are prime test case examples for empowering future AI learning in structure elucidation., (© 2020 Wiley-VCH GmbH.)

Published
2020
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33. New Casbanes and the First trans-Cyclopropane seco-Casbane from the Australian Rainforest Plant Croton insularis.

Author

Maslovskaya LA, Savchenko AI, Pierce CJ, Boyle GM, Gordon VA, Reddell PW, Parsons PG, and Williams CM

Abstract

Investigation of the Australian rainforest plant Croton insularis revealed seven new cis-, two new trans-cyclopropane casbanes, and the first trans-cyclopropane seco-casbane. The relative configuration of the cyclopropane moiety for all compounds (EBC-182, 217, 218, 220, 343, 357, 358, 361, 365, 373; EBC=EcoBiotics Compound) was assigned using 13 C NMR data. Comparison of the experimental electronic circular dichroism (ECD) spectra with the theoretical curves, calculated by TD-DFT at the B3LYP/6-31+G**//B3LYP/6-31+G** level, in conjunction with NOE data afforded the absolute configuration. EBC-180, 181 and 220 displayed potent activity against cervical carcinoma (HeLa cells)., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2019
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35. The First Casbane Hydroperoxides EBC-304 and EBC-320 from the Australian Rainforest.

Author

Maslovskaya LA, Savchenko AI, Gordon VA, Reddell PW, Pierce CJ, Parsons PG, and Williams CM

Subjects
Australia, Cell Line, Tumor, Cell Proliferation drug effects, Circular Dichroism, Croton metabolism, Diterpenes isolation & purification, Diterpenes toxicity, Humans, Magnetic Resonance Spectroscopy, Molecular Conformation, Peroxides isolation & purification, Peroxides toxicity, Rainforest, Croton chemistry, Diterpenes chemistry, Peroxides chemistry
Abstract

Investigation of the Australian rainforest plant Croton insularis led to isolation of the first casbane hydroperoxide diterpenes EBC-304 and EBC-320. Extensive DFT and electronic circular dichroism (ECD) calculations in combination with 2D NMR spectroscopy determined the absolute configurations. EBC-304 and EBC-320 both display significant cytotoxicity., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2017
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36. Ectopic expression of protein kinase C-β sensitizes head and neck squamous cell carcinoma to diterpene esters.

Author

Adams RA, D'Souza MM, Pierce CJ, Korica N, Wallwork B, Parsons PG, Panizza B, and Boyle GM

Subjects
Carcinoma, Squamous Cell enzymology, Carcinoma, Squamous Cell pathology, Cell Survival drug effects, Head and Neck Neoplasms enzymology, Head and Neck Neoplasms pathology, Humans, Isoenzymes analysis, Protein Kinase C beta analysis, Squamous Cell Carcinoma of Head and Neck, Tetradecanoylphorbol Acetate pharmacology, Tumor Cells, Cultured, Carcinoma, Squamous Cell drug therapy, Diterpenes pharmacology, Head and Neck Neoplasms drug therapy, Protein Kinase C beta physiology
Abstract

Background: The objective of this study was to examine the effect of specific Protein kinase C (PKC) isoform re-expression in solid malignancies, particularly head and neck squamous cell carcinoma cell lines, and the impact this may have on treatment with known activators of PKC., Materials and Methods: The constitutive expression of PKC isoforms were determined in six head and neck squamous cell carcinoma (SCC) cell lines. Cytotoxicity of the prototypic phorbol ester, 12-O-tetradecanoylphorbol-13-acetate (TPA) and the novel diterpene ester PEP005 was established. Viral transduction to re-express PKCβ isoforms in two of these cell lines was performed, and its effect on the sensitivity to the compounds was quantified., Results: Tongue and hypopharyngeal SCC cell lines were resistant to both TPA and PEP005, with the concentration required to inhibit growth by 50% (IC50) being >1,000 ng/ml. CAL-27 (tongue SCC) and FaDu (hypopharyngeal SCC) cell lines re-expressing PKCβI and -βII isoforms demonstrated IC50 of 1-5 ng/ml with TPA or PEP005., Conclusion: Re-expression of PKCβ in head and neck SCC cell lines leads to cells one thousand-times more sensitive to the cytotoxic effects of phorbol or diterpene esters in culture. This highlights the importance of the isoform in tumor progression and presents the potential benefit of these compounds in malignancies expressing the protein, and in combination therapy., (Copyright© 2015 International Institute of Anticancer Research (Dr. John G. Delinassios), All rights reserved.)

Published
2015

37. Unprecedented 1,14-seco-crotofolanes from Croton insularis: oxidative cleavage of crotofolin C by a putative homo-Baeyer-Villiger rearrangement.

Author

Maslovskaya LA, Savchenko AI, Pierce CJ, Gordon VA, Reddell PW, Parsons PG, and Williams CM

Subjects
Diterpenes isolation & purification, Magnetic Resonance Spectroscopy, Models, Molecular, Oxidation-Reduction, Plant Extracts chemistry, Plant Extracts isolation & purification, Croton chemistry, Diterpenes chemistry
Abstract

EBC-162 isolated from Croton insularis, obtained from the northern rainforest of Australia, was structurally affirmed as crotofolin C (4). Novel oxidative degradation products, EBC-233 and EBC-300, which are the first crotofolane endoperoxides, were also isolated. Both endoperoxides were found to be stable intermediates, which are proposed to undergo an unprecedented homo-Baeyer-Villiger biosynthetic rearrangement to give a new class of 1,14-seco-crotofolane diterpenes. Prolonged storage of all isolates assisted in authenticating their natural product status. Anticancer activities of reported compounds are presented., (© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2014
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38. EBC-219: a new diterpene skeleton, crotinsulidane, from the Australian rainforest containing a bridgehead double bond.

Author

Maslovskaya LA, Savchenko AI, Krenske EH, Pierce CJ, Gordon VA, Reddell PW, Parsons PG, and Williams CM

Subjects
Australia, Biological Products isolation & purification, Biological Products toxicity, Cell Line, Cell Survival drug effects, Diterpenes toxicity, HT29 Cells, HeLa Cells, Humans, K562 Cells, MCF-7 Cells, Magnetic Resonance Spectroscopy, Molecular Conformation, Biological Products chemistry, Diterpenes chemistry
Abstract

EBC-219 (4), isolated from Croton insularis (Baill), was established by spectroscopic and DFT methods as the first member of a new diterpene skeletal class, uniquely defined by the presence of a bicyclo[10.2.1] bridgehead olefin. The proposed biogenetic pathway to 4 from the co-isolated natural products EBC-131 (1), EBC-180 (2) and EBC-181 (3) is highly likely. EBC-180 (2) and EBC-181 (3) showed moderate to strong cytotoxic activity against various cancer cell lines., (© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2014
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