Published November 30, 2020
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Synthesis of bilocularin A carbamate derivatives and their evaluation as leucine transport inhibitors in prostate cancer cells
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- 1. * & Griffith Institute for Drug Discovery, School of Environment and Science, Griffith University, Brisbane, QLD 4111, Australia
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Huxley, Cohan, Wibowo, Mario, Lum, Kah Yean, Gordon, Shelly, D'Hyon, Sebastian, Guan, Hanyu, Wang, Xueyi, Chen, Yuxi, Si, Mingran, Wang, Mengchao, White, Jonathan M., Wahi, Kanu, Wang, Qian, Holst, Jeff, Davis, Rohan A. (2020): Synthesis of bilocularin A carbamate derivatives and their evaluation as leucine transport inhibitors in prostate cancer cells. Phytochemistry (112478) 179: 1-7, DOI: 10.1016/j.phytochem.2020.112478, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112478
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- urn:lsid:plazi.org:pub:FFBF733D8B79FFC2E53AFFD0D92A032F
References
- Askin, S., Bond, T.E.H., Sorenson, A.E., Moreau, M.J.J., Antony, H., Davis, R.A., Schaeffer, P.M., 2018. Selective protein unfolding: a universal mechanism of action for the development of irreversible inhibitors. Chem. Commun. 54, 1738-1741. https://doi.org/10.1039/C8CC00090E.
- Barnes, E.C., Choomuenwai, V., Andrews, K.T., Quinn, R.J., Davis, R.A., 2012. Design and synthesis of screening libraries based on the muurolane natural product scaffold. Org. Biomol. Chem. 10, 4015-4023. https://doi.org/10.1039/c2ob00029f.
- Barnes, E.C., Kumar, R., Davis, R.A., 2016. The use of isolated natural products as scaffolds for the generation of chemically diverse screening libraries for drug discovery. Nat. Prod. Rep. 33, 372-381. https://doi.org/10.1039/C5NP00121H.
- Callies, O., S´anchez-Canete t, M.P., Gamarro, F., Jim´enez, I.A., Castanys, S., Bazzocchi, I. L., 2015. Restoration of chemosensitivity in P-glycoprotein-dependent multidrugresistant cells by dihydro- β -agarofuran sesquiterpenes from Celastrus vulcanicola. J. Nat. Prod. 78, 736-745. https://doi.org/10.1021/np500903a.
- Choomuenwai, V., Andrews, K.T., Davis, R.A., 2012. Synthesis and antimalarial evaluation of a screening library based on a tetrahydroanthraquinone natural product scaffold. Bioorg. Med. Chem. 20, 7167-7174. https://doi.org/10.1016/j. bmc.2012.09.052.
- Davis, R.A., Pierens, G.K., Parsons, P.G., 2007. Synthesis and spectroscopic characterisation of a combinatorial library based on the fungal natural product 3- chloro-4-hydroxyphenylacetamide. Magn. Reson. Chem. 45, 442-445. https://doi. org/10.1002/mrc.1984.
- Delebecq, E., Pascault, J.-P., Boutevin, B., Ganachaud, F., 2013. On the versatility of urethane/urea bonds: reversibility, blocked isocyanate, and non-isocyanate polyurethane. Chem. Rev. 113, 80-118. https://doi.org/10.1021/cr300195n.
- Dilrukshi Herath, H.M.P., Preston, S., Hofmann, A., Davis, R.A., Koehler, A.V., Chang, B. C.H., Jabbar, A., Gasser, R.B., 2017. Screening of a small, well-curated natural product-based library identifies two rotenoids with potent nematocidal activity against Haemonchus contortus. Vet. Parasitol. 244, 172-175. https://doi.org/ 10.1016/j.vetpar.2017.07.005.
- Egbewande, F.A., Coster, M.J., Jenkins, I.D., Davis, R.A., 2019. Reaction of papaverine with Baran diversinatesTM. Molecules 24, 3938. https://doi.org/10.3390/ molecules24213938.
- Egbewande, F.A., Nilsson, N., White, J.M., Coster, M.J., Davis, R.A., 2017. The design, synthesis, and anti-inflammatory evaluation of a drug-like library based on the natural product valerenic acid. Bioorg. Med. Chem. Lett 27, 3185-3189. https://doi. org/10.1016/j.bmcl.2017.05.021.
- Egbewande, F.A., Sadowski, M.C., Levrier, C., Tousignant, K.D., White, J.M., Coster, M. J., Nelson, C.C., Davis, R.A., 2018. Identification of gibberellic acid derivatives that deregulate cholesterol metabolism in prostate cancer cells. J. Nat. Prod. 81, 838-845. https://doi.org/10.1021/acs.jnatprod.7b00929.
- Farrugia, L.J., 1999. WinGX suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr. 32, 837-838. https://doi.org/10.1107/S0021889899006020.
- Feher, M., Schmidt, J.M., 2003. Property distributions: differences between drugs, natural products, and molecules from combinatorial chemistry. J. Chem. Inf. Comput. Sci. 43, 218-227. https://doi.org/10.1021/ci0200467.
- Flack, H.D., 1983. On enantiomorph-polarity estimation. Acta Crystallogr. A 39, 876-881. https://doi.org/10.1107/S0108767383001762.
- Fu, Y., Wang, W., Gong, Q., Zhang, H., Zhao, W., 2019. Neuroprotective dihydroβ -agarofuran-type sesquiterpenes from the seeds of Euonymus maackii. J. Nat. Prod. 82, 3096-3103. https://doi.org/10.1021/acs.jnatprod.9b00701.
- Gao, J.-M., Wu, W.-J., Zhang, J.-W., Konishi, Y., 2007. The dihydro- β -agarofuran sesquiterpenoids. Nat. Prod. Rep. 24, 1153-1189. https://doi.org/10.1039/ B601473A.
- Gierasch, T.M., Shi, Z., Verdine, G.L., 2003. Extensively stereodiversified scaffolds for use in diversity-oriented library synthesis. Org. Lett. 5, 621-624. https://doi.org/ 10.1021/ol027116f.
- Gordon, S., Wibowo, M., Wang, Q., Holst, J., Davis, R.A., 2019. Dihydro- β -agarofurans from the Australian rainforest plant Denhamia celastroides that inhibit leucine transport in prostate cancer cells. Magn. Reson. Chem. 57, 101-109. https://doi.org/ 10.1002/mrc.4801.
- Grabowski, K., Baringhaus, K.-H., Schneider, G., 2008. Scaffold diversity of natural products: inspiration for combinatorial library design. Nat. Prod. Rep. 25, 892-904. https://doi.org/10.1039/B715668P.
- Kumar, R., Sadowski, M.C., Levrier, C., Nelson, C.C., Jones, A.J., Holleran, J.P., Avery, V. M., Healy, P.C., Davis, R.A., 2015. Design and synthesis of a screening library using the natural product scaffold 3-chloro-4-hydroxyphenylacetic acid. J. Nat. Prod. 78, 914-918. https://doi.org/10.1021/np500856u.
- Leenders, R.G.G., Ruytenbeek, R., Damen, E.W.P., Scheeren, H.W., 1996. Highly Diastereoselective Synthesis of Anomeric β- O -glycopyranosyl Carbamates from Isocyanates. Synthesis (Stuttg), pp. 1309-1312. https://doi.org/10.1055/s-1996- 4377, 1996.
- Levrier, C., Sadowski, M.C., Nelson, C.C., Healy, P.C., Davis, R.A., 2015. Denhaminols A-H, dihydro- β -agarofurans from the endemic Australian rainforest plant Denhamia celastroides. J. Nat. Prod. 78, 111-119. https://doi.org/10.1021/np500740f.
- Macrae, C.F., Bruno, I.J., Chisholm, J.A., Edgington, P.R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., Wood, P.A., 2008. Mercury CSD 2.0 - new features for the visualization and investigation of crystal structures. J. Appl. Crystallogr. 41, 466-470. https://doi.org/10.1107/S0021889807067908.
- Perestelo, N.R., Jim´enez, I.A., Tokuda, H., V´azquez, J.T., Ichiishi, E., Bazzocchi, I.L., 2016. Absolute configuration of dihydro- β -agarofuran sesquiterpenes from Maytenus jelskii and their potential antitumor-promoting effects. J. Nat. Prod. 79, 2324-2331. https://doi.org/10.1021/acs.jnatprod.6b00469.
- Sasikumar, P., Sharathna, P., Prabha, B., Varughese, S., Kumar, A.N., Sivan, V.V., Sherin, D.R., Suresh, E., Manojkumar, T.K., Radhakrishnan, K.V., 2018. Dihydroβ -agarofuran sesquiterpenoids from the seeds of Celastrus paniculatus Willd. and their α -glucosidase inhibitory activity. Phytochem. Lett. 26, 1-8. https://doi.org/ 10.1016/j.phytol.2018.04.011.
- Schwetlick, K., Noack, R., 1995. Kinetics and catalysis of consecutive isocyanate reactions. Formation of carbamates, allophanates and isocyanurates. J. Chem. Soc. Perkin Trans. 2, 395-402. https://doi.org/10.1039/P29950000395.
- Sheldrick, G.M., 2015. Crystal structure refinement with SHELXL. Acta Crystallogr. C 71, 3-8. https://doi.org/10.1107/S2053229614024218.
- Sheldrick, G.M., 2008. A short history of SHELX. Acta Crystallogr. A 64, 112-122. https://doi.org/10.1107/S0108767307043930.
- Spivey, A.C., Weston, M., Woodhead, S., 2002. Celastraceae sesquiterpenoids: biological activity and synthesis. Chem. Soc. Rev. 31, 43-59. https://doi.org/10.1039/ b000678p.
- Wang, Q., Bailey, C.G., Ng, C., Tiffen, J., Thoeng, A., Minhas, V., Lehman, M.L., Hendy, S. C., Buchanan, G., Nelson, C.C., Rasko, J.E.J., Holst, J., 2011. Androgenreceptor and nutrient signaling pathways coordinate the demand for increased amino acid transport during prostate cancer progression. Canc. Res. 71, 7525-7536. https://doi. org/10.1158/0008-5472.CAN-11-1821.
- Wibowo, M., Forster, P.I., Guymer, G.P., Hofmann, A., Davis, R.A., 2019. Using UHPLC- MS profiling for the discovery of new dihydro- β -agarofurans from Australian Celastraceae plant extracts. Molecules 24, 859. https://doi.org/10.3390/ molecules24050859.
- Wibowo, M., Levrier, C., Sadowski, M.C., Nelson, C.C., Wang, Q., Holst, J., Healy, P.C., Hofmann, A., Davis, R.A., 2016a. Bioactive dihydro- β -agarofuran sesquiterpenoids from the Australian rainforest plant Maytenus bilocularis. J. Nat. Prod. 79, 1445-1453. https://doi.org/10.1021/acs.jnatprod.6b00190.
- Wibowo, M., Wang, Q., Holst, J., White, J.M., Hofmann, A., Davis, R.A., 2018. Dihydroβ -agarofurans from the roots of the Australian endemic rainforest tree Maytenus bilocularis act as leucine transport inhibitors. Phytochemistry 148, 71-77. https:// doi.org/10.1016/j.phytochem.2018.01.009.
- Wibowo, M., Wang, Q., Holst, J., White, J.M., Hofmann, A., Davis, R.A., 2017. Celastrofurans A-G: dihydro- β -agarofurans from the Australian rainforest vine Celastrus subspicata and their inhibitory effect on leucine transport in prostate cancer cells. J. Nat. Prod. 80, 1918-1925. https://doi.org/10.1021/acs.jnatprod.7b00220.
- Wibowo, M., Wang, Q., Holst, J., White, J.M., Hofmann, A., Davis, R.A., 2016b. Dihydroβ -agarofurans from the Australian endemic rainforest plant Denhamia pittosporoides inhibit leucine transport in prostate cancer cells. Asian J. Org. Chem. 5, 1461-1466. https://doi.org/10.1002/ajoc.201600462.
- Zhao, X., Xu, S., Yin, M., Wang, X., Wang, Q., Shan, Y., Chen, Y., Liu, F., Guo, S., Feng, X., 2018. Six new dihydro- β -agarofuran sesquiterpenes from the stems and leaves of Monimopetalum chinense and their antimicrobial activities. Phytochem. Lett. 27, 160-166. https://doi.org/10.1016/j.phytol.2018.07.024.
- Zhou, L., He, Q.-J., Lu, L.-W., Zhao, F., Zhang, Y., Huang, X.-X., Lin, B., Song, S.-J., 2019. Tripterfordins A-O, dihydro- β -agarofuran sesquiterpenoids from the leaves of Tripterygium wilfordii. J. Nat. Prod. 82, 2696-2706. https://doi.org/10.1021/acs. jnatprod.9b00089.
- Zulfiqar, B., Jones, A.J., Sykes, M.L., Shelper, T.B., Davis, R.A., Avery, V.M., 2017. Screening a natural product-based library against kinetoplastid parasites. Molecules 22, 1715. https://doi.org/10.3390/molecules22101715.