Cortistatins

This article is about the class of alkaloids. For the neuropeptide, see cortistatin (neuropeptide).

Cortistatin A
Names

IUPAC name (1R,2R,3S,5R,8β,17β)-3-(Dimethylamino)-17-(isoquinolin-7-yl)-5,8-epoxy-9,19-cyclo-9,10-secoandrosta-9(11),10-diene-1,2-diol
Other names Cortistatine A
Identifiers
CAS Registry Number	882976-95-6^Y
ChEBI	CHEBI:67171^Y
ChemSpider	9736681
InChI InChI=1S/C30H36N2O3/c1-28-10-8-21-15-23-26(33)27(34)24(32(2)3)16-29(23)11-12-30(21,35-29)25(28)7-6-22(28)19-5-4-18-9-13-31-17-20(18)14-19/h4-5,8-9,13-15,17,22,24-27,33-34H,6-7,10-12,16H2,1-3H3/t22-,24+,25-,26-,27-,28-,29-,30-/m1/s1 Key: KSGZCKSNTAJOJS-DZBMUNJRSA-N InChI=1/C30H36N2O3/c1-28-10-8-21-15-23-26(33)27(34)24(32(2)3)16-29(23)11-12-30(21,35-29)25(28)7-6-22(28)19-5-4-18-9-13-31-17-20(18)14-19/h4-5,8-9,13-15,17,22,24-27,33-34H,6-7,10-12,16H2,1-3H3/t22-,24+,25-,26-,27-,28-,29-,30-/m1/s1 Key: KSGZCKSNTAJOJS-DZBMUNJRBJ
Jmol-3D images	Image
PubChem	11561907
SMILES C[C@]12CC=C3C=C4[C@H]([C@@H]([C@H](C[C@]45CC[C@@]3([C@@H]1CC[C@@H]2c6ccc7ccncc7c6)O5)N(C)C)O)O
Properties
Molecular formula	C₃₀H₃₆N₂O₃
Molar mass	472.62 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

The cortistatins are a group of steroidal alkaloids first isolated in 2006 from the marine sponge Corticium simplex.^[1] The cortistatins inhibit proliferation of human umbilical vein endothelial cells (HUVECs) with high selectivity, with cortistatin A being the most potent compound in the class.^[2] Cortistatin A represses viral replication in cells infected with HIV via binding to the Tat protein. ^[3]

The unique chemical structure and potent biological activity of these compounds have stimulated interest in their total synthesis and further biological evaluation.^[4]^[5]

Chemical structures

Cortistatin A
Cortistatin B
Cortistatin C
Cortistatin D
Cortistatin E
Cortistatin F
Cortistatin G
Cortistatin H
Cortistatin J
Cortistatin K
Cortistatin L

References

↑ Aoki, S; Watanabe, Y; Sanagawa, M; Setiawan, A; Kotoku, N; Kobayashi, M (2006). "Cortistatins A, B, C, and D, anti-angiogenic steroidal alkaloids, from the marine sponge Corticium simplex". Journal of the American Chemical Society 128 (10): 3148–9. doi:10.1021/ja057404h. PMID 16522087.
↑ Aoki, S; Watanabe, Y; Tanabe, D; Arai, M; Suna, H; Miyamoto, K; Tsujibo, H; Tsujikawa, K; Yamamoto, H (2007). "Structure-activity relationship and biological property of cortistatins, anti-angiogenic spongean steroidal alkaloids". Bioorganic & Medicinal Chemistry 15 (21): 6758–62. doi:10.1016/j.bmc.2007.08.017. PMID 17765550.
↑ Mousseau, G.; Clementz, M. A.; Bakeman, W. N.; Nagarsheth, N.; Cameron, M.; Shi, J.; Baran, P.; Fromentin, R. M.; Chomont, N.; Valente, S. T. (2012). "An Analog of the Natural Steroidal Alkaloid Cortistatin a Potently Suppresses Tat-Dependent HIV Transcription". Cell Host & Microbe 12 (1): 97–108. doi:10.1016/j.chom.2012.05.016. PMC 3403716. PMID 22817991.
↑ Chen, David Yu-Kai; Tseng, Chih-Chung (2010). "Chemistry of the cortistatins–a novel class of anti-angiogenic agents". Organic & Biomolecular Chemistry 8 (13): 2900. doi:10.1039/C003935G.
↑ Hardin Narayan, Alison R.; Simmons, Eric M.; Sarpong, Richmond (2010). "Synthetic Strategies Directed Towards the Cortistatin Family of Natural Products". European Journal of Organic Chemistry 2010 (19): 3553. doi:10.1002/ejoc.201000247.