In vitro and in silico studies of holothurin A on androgen receptor in prostate cancer

References

• Bahrami, Y., & Franco, C. M. M. (2016). Acetylated triterpene glycosides and their biological activity from holothuroidea reported in the past six decades. Marine Drugs, 14, 147. https://doi.org/10.3390/md14080147
   PubMed Web of Science ®Google Scholar
• Ban, F., Leblanc, E., Li, H., Munuganti, R. S. N., Frewin, K., Rennie, P. S., & Cherkasov, A. (2014). Discovery of 1H-Indole-2-carboxamides as Novel Inhibitors of the Androgen Receptor Binding Function 3 (BF3). Journal of Medicinal Chemistry, 57(15), 6867–6872. https://doi.org/10.1021/jm500684r
   PubMed Web of Science ®Google Scholar
• Bhuiyan, M. M. R., Li, Y., Banerjee, S., Ahmed, F., Wang, Z., Ali, S., & Sarkar, F. H. (2006). Down-regulation of Androgen Receptor by 3,3'-diindolylmethane contributes to inhibition of cell proliferation and induction of apoptosis in both hormone-sensitive LNCaP and insensitive C4-2B prostate cancer cells. Cancer Research, 66(20), 10064–10072. https://doi.org/10.1158/0008-5472.CAN-06-2011
   PubMed Web of Science ®Google Scholar
• Buchanan, G., Yang, M., Harris, J. M., Nahm, H. S., Han, G., Moore, N., Bentel, J. M., Matusik, R. J., Horsfall, D. J., Marshall, V. R., Greenberg, N. M., & Tilley, W. D. (2001). Mutations at the boundary of the hinge and ligand binding domain of the androgen receptor confer increased transactivation function. Molecular Endocrinology (Baltimore, Md.), 15(1), 46–56. https://doi.org/10.1210/mend.15.1.0581
   PubMedGoogle Scholar
• Buzón, V., Carbó, L. R., Estruch, S. B., Fletterick, R. J., & Estébanez-Perpiñá, E. (2012). A conserved surface on the ligand binding domain of nuclear receptors for allosteric control. Molecular and Cellular Endocrinology, 348(2), 394–402. https://doi.org/10.1016/j.mce.2011.08.012
   PubMed Web of Science ®Google Scholar
• Cairns, S. D., & Olmstead, C. A. (1973). Effect of holothurin on sarcoma 180 and B-16 melanoma tumors in mice gulf. Gulf Research Reports, 4, 205–213. https://doi.org/10.18785/grr.0402.07
   Google Scholar
• De Groof, R. C., & Narahashi, T. (1976). The effects of holothurin A on the resting membrane potential and conductance of squid axon. European Journal of Pharmacology, 36(2), 337–346. https://doi.org/10.1016/0014-2999(76)90087-x
   PubMed Web of Science ®Google Scholar
• De Leon, J. T., Iwai, A., Feau, C., Garcia, Y., Balsiger, H. A., Storer, C. L., Suro, R. M., Garza, K. M., Lee, S., Kim, Y. S., Chen, Y., Ning, Y.-M., Riggs, D. L., Fletterick, R. J., Guy, R. K., Trepel, J. B., Neckers, L. M., & Cox, M. B. (2011). Targeting the regulation of androgen receptor signaling by the heat shock protein 90 cochaperone FKBP52 in prostate cancer cells. Proceedings of the National Academy of Sciences of the United States of America, 108(29), 11878–11883. https://doi.org/10.1073/pnas.1105160108
   PubMed Web of Science ®Google Scholar
• Estébanez-Perpiñá, E., Arnold, L. A., Arnold, A. A., Nguyen, P., Rodrigues, E. D., Mar, E., Bateman, R., Pallai, P., Shokat, K. M., Baxter, J. D., Guy, R. K., Webb, P., & Fletterick, R. J. (2007). A surface on the androgen receptor that allosterically regulates coactivator binding. Proceedings of the National Academy of Sciences of the United States of America, 104(41), 16074–16079. https://doi.org/10.1073/pnas.0708036104
   PubMed Web of Science ®Google Scholar
• Götz, A. W., Williamson, M. J., Xu, D., Poole, D., Le Grand, S., & Walker, R. C. (2012). Routine microsecond molecular dynamics simulations with AMBER on GPUs. 1. Generalized born. Journal of Chemical Theory and Computation, 8(5), 1542–1555. https://doi.org/10.1021/ct200909j
   PubMed Web of Science ®Google Scholar
• Halgren, T. A. (1996). Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. Journal of Computational Chemistry, 17(5-6), 490–519. https://doi.org/10.1002/(SICI)1096-987X(199604)17:5/6<490::AID-JCC1>3.0.CO;2-P
   Web of Science ®Google Scholar
• Han, H., Li, L., Yi, Y-h., & Wang X-h, Pan, M-x. (2012). Triterpene glycosides from sea cucumber Holothuria scabra with cytotoxic activity. Chinese Herbal Medicines, 4, 183–188. https://doi.org/10.3969/j.issn.1674-6384.2012.03.002
   Google Scholar
• Jehle, K., Cato, L., Neeb, A., Muhle-Goll, C., Jung, N., Smith, E. W., Buzon, V., Carbó, L. R., Estébanez-Perpiñá, E., Schmitz, K., Fruk, L., Luy, B., Chen, Y., Cox, M. B., Bräse, S., Brown, M., & Cato, A. C. B. (2014). Coregulator control of androgen receptor action by a novel nuclear receptor-binding motif. The Journal of Biological Chemistry, 289(13), 8839–8851. https://doi.org/10.1074/jbc.M113.534859
   PubMed Web of Science ®Google Scholar
• Jin, Y., Duan, M., Wang, X., Kong, X., Zhou, W., Sun, H., Liu, H., Li, D., Yu, H., Li, Y., & Hou, T. (2019). Communication between the ligand-binding pocket and the activation function-2 domain of androgen receptor revealed by molecular dynamics simulations. Journal of Chemical Information and Modeling, 59(2), 842–857. https://doi.org/10.1021/acs.jcim.8b00796
   PubMed Web of Science ®Google Scholar
• Khattab, R. A., Elbandy, M., Lawrence, A., Paget, T., Rae-Rho, J., Binnaser, Y. S., & Ali, I. (2018). Extraction, identification and biological activities of saponins in sea cucumber Pearsonothuria graeffei. Combinatorial Chemistry & High Throughput Screening, 21(3), 222–231. https://doi.org/10.2174/1386207321666180212165448
   PubMed Web of Science ®Google Scholar
• Kitagawa, I., Nishino, T., & Kyogoku, Y. (1979). Structure of holothurin A biologically active triterpene-oligoglycoside from the sea cucumber holothuria leucospilota brandt. Tetrahedron Letters, 20(16), 1419–1422. https://doi.org/10.1016/S0040-4039(01)86166-9
   Google Scholar
• Lallous, N., Dalal, K., Cherkasov, A., & Rennie, P. S. (2013). Targeting alternative sites on the androgen receptor to treat castration-resistant prostate cancer. International Journal of Molecular Sciences, 14(6), 12496–12519. https://doi.org/10.3390/ijms140612496
   PubMed Web of Science ®Google Scholar
• Lallous, N., Leblanc, E., Munuganti, R. S. N., Hassona, M. D. H., Nakouzi, N. A., Awrey, S., Morin, H., Roshan-Moniri, M., Singh, K., Lawn, S., Yamazaki, T., Adomat, H. H., Andre, C., Daugaard, M., Young, R. N., Guns, E. S. T., Rennie, P. S., & Cherkasov, A. (2016). Targeting binding function-3 of the androgen receptor blocks its co-chaperone interactions, nuclear translocation, and activation. Molecular Cancer Therapeutics, 15(12), 2936–2945. https://doi.org/10.1158/1535-7163.MCT-16-0354
   PubMed Web of Science ®Google Scholar
• Martinez-Ariza, G., & Hulme, C. (2015). Recent advances in allosteric androgen receptor inhibitors for the potential treatment of castration-resistant prostate cancer. Pharmaceutical Patent Analyst, 4(5), 387–402. https://doi.org/10.4155/ppa.15.20
   PubMed Web of Science ®Google Scholar
• Miller, B. R., McGee, T. D., Swails, J. M., Homeyer, N., Gohlke, H., & Roitberg, A. E. (2012). MMPBSA.py: an efficient program for end-state free energy calculations. Journal of Chemical Theory and Computation, 8(9), 3314–3321. https://doi.org/10.1021/ct300418h
   PubMed Web of Science ®Google Scholar
• Munuganti, R. S. N., Hassona, M. D. H., Leblanc, E., Frewin, K., Singh, K., Ma, D., Ban, F., Hsing, M., Adomat, H., Lallous, N., Andre, C., Jonadass, J. P. S., Zoubeidi, A., Young, R. N., Guns, E. T., Rennie, P. S., & Cherkasov, A. (2014). Identification of a potent antiandrogen that targets the BF3 site of the androgen receptor and inhibits enzalutamide-resistant prostate cancer. Chemistry & Biology, 21(11), 1476–1485. https://doi.org/10.1016/j.chembiol.2014.09.012
   PubMedGoogle Scholar
• Munuganti, R. S. N., Leblanc, E., Axerio-Cilies, P., Labriere, C., Frewin, K., Singh, K., Hassona, M. D. H., Lack, N. A., Li, H., Ban, F., Tomlinson Guns, E., Young, R., Rennie, P. S., & Cherkasov, A. (2013). Targeting the binding function 3 (BF3) site of the androgen receptor through virtual screening. 2. development of 2-((2-phenoxyethyl) thio)-1H-benzimidazole derivatives. Journal of Medicinal Chemistry, 56(3), 1136–1148. https://doi.org/10.1021/jm3015712
   PubMed Web of Science ®Google Scholar
• Osguthorpe, D. J., & Hagler, A. T. (2011). Mechanism of androgen receptor antagonism by bicalutamide in the treatment of prostate cancer. Biochemistry, 50(19), 4105–4113. https://doi.org/10.1021/bi102059z
   PubMed Web of Science ®Google Scholar
• Roe, D. R., & Cheatham, T. E. (2013). PTRAJ and CPPTRAJ: Software for processing and analysis of molecular dynamics trajectory data. Journal of Chemical Theory and Computation, 9(7), 3084–3095. https://doi.org/10.1021/ct400341p
   PubMed Web of Science ®Google Scholar
• Siegel, R. L., Miller, K. D., & Jemal, A. (2019). Cancer statistics, 2019. CA: A Cancer Journal for Clinicians, 69(1), 7–34. https://doi.org/10.3322/caac.21551
   PubMed Web of Science ®Google Scholar
• Tan, M. H., Li, J., Xu, H. E., Melcher, K., & Yong, E. L. (2015). Androgen receptor: Structure, role in prostate cancer and drug discovery. Acta Pharmacologica Sinica, 36(1), 3–23. https://doi.org/10.1038/aps.2014.18
   PubMed Web of Science ®Google Scholar
• Wang, J., Wang, W., Kollman, P., & Case, D. (2000). ANTECHAMBER: An accessory software package for molecular mechanical calculations. Journal of Chemical Information and Computer Sciences - JCISD, 222, U403. https://doi.org/10.1016/j.jmgm.2005.12.005.
   Google Scholar
• Wargasetia, T. L., Permana, S. & Widodo, (2018). The role of sea cucumber active compound and its derivative as an anti-cancer agent. Current Pharmacology Reports, 4, 27–32. https://doi.org/10.1007/s40495-018-0121-x
   Google Scholar
• Wargasetia, T. L. & Widodo, (2017). Mechanisms of cancer cell killing by sea cucumber-derived compounds. Invest New Drugs, 35, 820–826. https://doi.org/10.1007/s10637-017-0505-5
   PubMed Web of Science ®Google Scholar
• Wolber, G., & Langer, T. (2005). LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters. Journal of Chemical Information and Modeling, 45(1), 160–169. https://doi.org/10.1021/ci049885e
   PubMed Web of Science ®Google Scholar