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Halenaquinone

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names：
(S)-12b-methyl-1H-tetrapheno[5,4-bc]furan-3,6,8,11(2H,12bH)-tetraone
CAS號：
86690-14-4
MDL Number：
MF(分子式)： C20H12O5 MW(分子量)： 332.311
EINECS: Reaxys Number:
Pubchem ID: Brand:BIOFOUNT

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中文別名	Halenaquinone
英文別名	Halenaquinone
CAS號	86690-14-4
Inchi	InChI=1S/C20H12O5/c1-20-5-4-16(23)12-8-25-19(17(12)20)18(24)11-6-9-10(7-13(11)20)15(22)3-2-14(9)21/h2-3,6-8H,4-5H2,1H3/t20-/m0/s1
InchiKey	SMGBXXZKAPMTBB-FQEVSTJZSA-N
分子式 Formula	C20H12O5
分子量 Molecular Weight	332.311
溶解度Solubility
性狀	Solid powder
儲藏條件 Storage conditions	Dry, dark and store at 0-4℃ for short term (days to weeks) or -20℃ for long term (Store correctly 2-3years).

產品說明	Halenaquinone(CAS:86690-14-4):僅限應用于工業或者科學研究過程中非醫療目的，不應用于人類或動物的臨床診斷以及治過程療，該產品非藥用，非食用。
Introduction	Halenaquinone is a phosphatidylinositol 3-kinase inhibitor, was isolated from the marine sponge Petrosia alfiani. Halenaquinone inhibits RANKL-induced osteoclastogenesis. Halenaquinone specifically inhibits the secondary DNA binding of RAD51. Halenaquinone induces apoptosis in PC12 cells.
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[1]Tsukamoto S, Takeuchi T, Kawabata T, Kato H, Yamakuma M, Matsuo K, El-Desoky AH, Losung F, Mangindaan RE, de Voogd NJ, Arata Y, Yokosawa H. Halenaquinone inhibits RANKL-induced osteoclastogenesis. Bioorg Med Chem Lett. 2014 Nov 15;24(22):5315-7. doi: 10.1016/j.bmcl.2014.09.043. PubMed PMID: 25278237.

[2]Takaku M, Kainuma T, Ishida-Takaku T, Ishigami S, Suzuki H, Tashiro S, van Soest RW, Nakao Y, Kurumizaka H. Halenaquinone, a chemical compound that specifically inhibits the secondary DNA binding of RAD51. Genes Cells. 2011 Apr;16(4):427-36. doi: 10.1111/j.1365-2443.2011.01494.x. PubMed PMID: 21375680.

[3] Shih SP, Lee MG, El-Shazly M, Juan YS, Wen ZH, Du YC, Su JH, Sung PJ, Chen YC, Yang JC, Wu YC, Lu MC. Tackling the Cytotoxic Effect of a Marine Polycyclic Quinone-Type Metabolite: Halenaquinone Induces Molt 4 Cells Apoptosis via Oxidative Stress Combined with the Inhibition of HDAC and Topoisomerase Activities. Mar Drugs. 2015 May 20;13(5):3132-53. doi: 10.3390/md13053132. PubMed PMID: 26006712; PubMed Central PMCID: PMC4446623.

[4] Wang J, Bourguet-Kondracki ML, Longeon A, Dubois J, Valentin A, Copp BR. Chemical and biological explorations of the electrophilic reactivity of the bioactive marine natural product halenaquinone with biomimetic nucleophiles. Bioorg Med Chem Lett. 2011 Feb 15;21(4):1261-4. doi: 10.1016/j.bmcl.2010.12.056. PubMed PMID: 21256013.

[5] Longeon A, Copp BR, Roué M, Dubois J, Valentin A, Petek S, Debitus C, Bourguet-Kondracki ML. New bioactive halenaquinone derivatives from South Pacific marine sponges of the genus Xestospongia. Bioorg Med Chem. 2010 Aug 15;18(16):6006-11. doi: 10.1016/j.bmc.2010.06.066. PubMed PMID: 20634081.

6: Kienzler MA, Suseno S, Trauner D. Vinyl quinones as Diels-Alder dienes: concise synthesis of (-)-halenaquinone. J Am Chem Soc. 2008 Jul 9;130(27):8604-5. doi: 10.1021/ja8035042. PubMed PMID: 18549215.7: Fujiwara H, Matsunaga K, Saito M, Hagiya S, Furukawa K, Nakamura H, Ohizumi Y. Halenaquinone, a novel phosphatidylinositol 3-kinase inhibitor from a marine sponge, induces apoptosis in PC12 cells. Eur J Pharmacol. 2001 Feb 9;413(1):37-45. PubMed PMID: 11173061.8: Cao S, Foster C, Brisson M, Lazo JS, Kingston DG. Halenaquinone and xestoquinone derivatives, inhibitors of Cdc25B phosphatase from a Xestospongia sp. Bioorg Med Chem. 2005 Feb 15;13(4):999-1003. PubMed PMID: 15670907.9: Sutherland HS, Souza FE, Rodrigo RG. A short synthesis of (+/-)-halenaquinone. J Org Chem. 2001 May 18;66(10):3639-41. PubMed PMID: 11348164.10: Bae MA, Tsuji T, Kondo K, Hirase T, Ishibashi M, Shigemori H, Kobayashi J. Inhibition of Mammalian Topoisomerase I by Xestoquinone and Halenaquinone. Biosci Biotechnol Biochem. 1993 Jan;57(2):330-1. doi: 10.1271/bbb.57.330. PubMed PMID: 27314795.1

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