Halenaquinone

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 407360

CAS#: 86690-14-4

Description: 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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Halenaquinone is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 407360
Name: Halenaquinone
CAS#: 86690-14-4
Chemical Formula: C20H12O5
Exact Mass: 332.0685
Molecular Weight: 332.311
Elemental Analysis: C, 72.29; H, 3.64; O, 24.07


Synonym: Halenaquinone

IUPAC/Chemical Name: (S)-12b-methyl-1H-tetrapheno[5,4-bc]furan-3,6,8,11(2H,12bH)-tetraone

InChi Key: SMGBXXZKAPMTBB-FQEVSTJZSA-N

InChi Code: 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

SMILES Code: O=C1CC[C@@]2(C)C3=CC4=C(C(C=CC4=O)=O)C=C3C(C5=C2C1=CO5)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

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.

11: Wakefield B, Halter RJ, Wipf P. Synthesis of (+/-)-thiohalenaquinone by iterative metalations of thiophene. Org Lett. 2007 Aug 2;9(16):3121-4. PubMed PMID: 17630756.

12: Nakamura M, Kakuda T, Qi J, Hirata M, Shintani T, Yoshioka Y, Okamoto T, Oba Y, Nakamura H, Ojika M. Novel relationship between the antifungal activity and cytotoxicity of marine-derived metabolite xestoquinone and its family. Biosci Biotechnol Biochem. 2005 Sep;69(9):1749-52. PubMed PMID: 16195594.

13: Lee RH, Slate DL, Moretti R, Alvi KA, Crews P. Marine sponge polyketide inhibitors of protein tyrosine kinase. Biochem Biophys Res Commun. 1992 Apr 30;184(2):765-72. PubMed PMID: 1315532.