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MedKoo Cat#: 341429 | Name: Xestoquinone

Description:

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

Xestoquinone is a biochemical.

Chemical Structure

Xestoquinone
Xestoquinone
CAS#97743-96-9

Theoretical Analysis

MedKoo Cat#: 341429

Name: Xestoquinone

CAS#: 97743-96-9

Chemical Formula: C20H14O4

Exact Mass: 318.0892

Molecular Weight: 318.33

Elemental Analysis: C, 75.46; H, 4.43; O, 20.10

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Xestoquinone;
IUPAC/Chemical Name
1H-Benzo(6,7)phenanthro(10,1-bc)furan-6,8,11(12bH)-trione, 2,3-dihydro-12b-methyl-, (S)-
InChi Key
HDONDRKCXFRHQQ-FQEVSTJZSA-N
InChi Code
InChI=1S/C20H14O4/c1-20-6-2-3-10-9-24-19(17(10)20)18(23)13-7-11-12(8-14(13)20)16(22)5-4-15(11)21/h4-5,7-9H,2-3,6H2,1H3/t20-/m0/s1
SMILES Code
O=C1C2=C(C=C3C(C(C=CC3=O)=O)=C2)[C@]4(C)CCCC5=COC1=C54
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 318.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Du L, Mahdi F, Datta S, Jekabsons MB, Zhou YD, Nagle DG. Structures and mechanisms of antitumor agents: xestoquinones uncouple cellular respiration and disrupt HIF signaling in human breast tumor cells. J Nat Prod. 2012 Sep 28;75(9):1553-9. Epub 2012 Aug 31. PubMed PMID: 22938093; PubMed Central PMCID: PMC3482980. 2: Winder PL, Baker HL, Linley P, Guzmán EA, Pomponi SA, Diaz MC, Reed JK, Wright AE. Neopetrosiquinones A and B, sesquiterpene benzoquinones isolated from the deep-water sponge Neopetrosia cf. proxima. Bioorg Med Chem. 2011 Nov 15;19(22):6599-603. doi: 10.1016/j.bmc.2011.09.026. Epub 2011 Sep 21. PubMed PMID: 22014756; PubMed Central PMCID: PMC3268459. 3: Gademann K, Kobylinska J. Antimalarial natural products of marine and freshwater origin. Chem Rec. 2009;9(3):187-98. doi: 10.1002/tcr.200900001. Review. PubMed PMID: 19424997. 4: Desoubzdanne D, Marcourt L, Raux R, Chevalley S, Dorin D, Doerig C, Valentin A, Ausseil F, Debitus C. Alisiaquinones and alisiaquinol, dual inhibitors of Plasmodium falciparum enzyme targets from a New Caledonian deep water sponge. J Nat Prod. 2008 Jul;71(7):1189-92. doi: 10.1021/np8000909. Epub 2008 May 31. PubMed PMID: 18512987. 5: Laurent D, Jullian V, Parenty A, Knibiehler M, Dorin D, Schmitt S, Lozach O, Lebouvier N, Frostin M, Alby F, Maurel S, Doerig C, Meijer L, Sauvain M. Antimalarial potential of xestoquinone, a protein kinase inhibitor isolated from a Vanuatu marine sponge Xestospongia sp. Bioorg Med Chem. 2006 Jul 1;14(13):4477-82. Epub 2006 Mar 2. PubMed PMID: 16513357. 6: 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. 7: 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. 8: Nakamura M, Kakuda T, Oba Y, Ojika M, Nakamura H. Synthesis of biotinylated xestoquinone that retains inhibitory activity against Ca2+ ATPase of skeletal muscle myosin. Bioorg Med Chem. 2003 Jul 17;11(14):3077-82. PubMed PMID: 12818670. 9: 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. 10: Ito M, Hirata Y, Nakamura H, Ohizumi Y. Xestoquinone, isolated from sea sponge, causes Ca(2+) release through sulfhydryl modification from skeletal muscle sarcoplasmic reticulum. J Pharmacol Exp Ther. 1999 Dec;291(3):976-81. PubMed PMID: 10565813. 11: Carlini R, Higgs K, Older C, Randhawa S, Rodrigo R. Intramolecular Diels-Alder and Cope Reactions of o-Quinonoid Monoketals and Their Adducts: Efficient Syntheses of (+/-)-Xestoquinone and Heterocycles Related to Viridin. J Org Chem. 1997 Apr 18;62(8):2330-2331. PubMed PMID: 11671562. 12: Concepción GP, Foderaro TA, Eldredge GS, Lobkovsky E, Clardy J, Barrows LR, Ireland CM. Topoisomerase II-mediated DNA cleavage by adocia- and xestoquinones from the Philippine sponge Xestospongia sp. J Med Chem. 1995 Oct 27;38(22):4503-7. PubMed PMID: 7473578. 13: Sakamoto H, Furukawa K, Matsunaga K, Nakamura H, Ohizumi Y. Xestoquinone activates skeletal muscle actomyosin ATPase by modification of the specific sulfhydryl group in the myosin head probably distinct from sulfhydryl groups SH1 and SH2. Biochemistry. 1995 Oct 3;34(39):12570-5. PubMed PMID: 7548005. 14: Ohizumi Y. [Tendency of development on novel type of cardiotonic drugs]. Nihon Rinsho. 1993 May;51(5):1299-304. Review. Japanese. PubMed PMID: 8101238. 15: 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. 16: Ohizumi Y. [Novel types of cardiotonic drugs]. Nihon Yakurigaku Zasshi. 1992 Sep;100(3):259-69. Review. Japanese. PubMed PMID: 1398336. 17: 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. 18: Ohizumi Y. [Useful natural products for the biochemical study on muscle contractile systems]. Seikagaku. 1992 Mar;64(3):177-81. Review. Japanese. PubMed PMID: 1320082. 19: Kobayashi M, Nakamura H, Kobayashi J, Ohizumi Y. Mechanism of inotropic action of xestoquinone, a novel cardiotonic agent isolated from a sea sponge. J Pharmacol Exp Ther. 1991 Apr;257(1):82-9. PubMed PMID: 1850480. 20: Kobayashi M, Muroyama A, Nakamura H, Kobayashi J, Ohizumi Y. Xestoquinone, a novel cardiotonic agent activates actomyosin ATPase to enhance contractility of skinned cardiac or skeletal muscle fibers. J Pharmacol Exp Ther. 1991 Apr;257(1):90-4. PubMed PMID: 1826930.