7-Oxo-staurosporine

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MedKoo CAT#: 463268

CAS#: 141196-69-2

Description: 7-Oxo-staurosporine is a potent dual PKCθ/δ inhibitor, efficiently inhibiting tumor growth in pancreatic cancer (PC) by inducing cellular apoptosis and suppressing the NF-κB/p-P65 pathway.


Chemical Structure

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7-Oxo-staurosporine
CAS# 141196-69-2

Theoretical Analysis

MedKoo Cat#: 463268
Name: 7-Oxo-staurosporine
CAS#: 141196-69-2
Chemical Formula: C28H24N4O4
Exact Mass: 480.1798
Molecular Weight: 480.524
Elemental Analysis: C, 69.99; H, 5.03; N, 11.66; O, 13.32

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: 7-Oxo-staurosporine; 7 Oxo-staurosporine; 7-Oxostaurosporine; 7-Oxo staurosporine;

IUPAC/Chemical Name: (5S,6R,7R,9R)-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9-tetrahydro-5H,14H-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacene-14,16(15H)-dione

InChi Key: POTTVLREWUNNRO-UGZRAAABSA-N

InChi Code: InChI=1S/C28H24N4O4/c1-28-25(35-3)15(29-2)12-18(36-28)31-16-10-6-4-8-13(16)19-21-22(27(34)30-26(21)33)20-14-9-5-7-11-17(14)32(28)24(20)23(19)31/h4-11,15,18,25,29H,12H2,1-3H3,(H,30,33,34)/t15-,18-,25-,28+/m1/s1

SMILES Code: O=C1NC(C(C2=C3N([C@]4(C)[C@H](OC)[C@H](NC)C[C@@]5([H])O4)C6=CC=CC=C62)=C1C7=C3N5C8=CC=CC=C78)=O

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: >3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 480.524 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

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1: Wang J, Jin W, Zhou X, Li J, Xu C, Ma Z, Wang J, Qin L, Zhou B, Ding W, Gao T, Yao H, Chen Z. Identification, Structure-Activity Relationships of Marine- Derived Indolocarbazoles, and a Dual PKCθ/δ Inhibitor with Potent Antipancreatic Cancer Efficacy. J Med Chem. 2020 Oct 25. doi: 10.1021/acs.jmedchem.0c01271. Epub ahead of print. PMID: 33100009.

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3: Cartuche L, Sifaoui I, López-Arencibia A, Bethencourt-Estrella CJ, San Nicolás-Hernández D, Lorenzo-Morales J, Piñero JE, Díaz-Marrero AR, Fernández JJ. Antikinetoplastid Activity of Indolocarbazoles from Streptomyces sanyensis. Biomolecules. 2020 Apr 24;10(4):657. doi: 10.3390/biom10040657. PMID: 32344693; PMCID: PMC7226613.

4: Cartuche L, Reyes-Batlle M, Sifaoui I, Arberas-Jiménez I, Piñero JE, Fernández JJ, Lorenzo-Morales J, Díaz-Marrero AR. Antiamoebic Activities of Indolocarbazole Metabolites Isolated from Streptomyces sanyensis Cultures. Mar Drugs. 2019 Oct 17;17(10):588. doi: 10.3390/md17100588. PMID: 31627366; PMCID: PMC6836125.

5: Cho KJ, Park JH, Hancock JF. Staurosporine: A new tool for studying phosphatidylserine trafficking. Commun Integr Biol. 2013 Jul 1;6(4):e24746. doi: 10.4161/cib.24746. Epub 2013 May 10. PMID: 23986809; PMCID: PMC3737755.

6: Jimenez PC, Wilke DV, Ferreira EG, Takeara R, de Moraes MO, da Silveira ER, da Cruz Lotufo TM, Lopes NP, Costa-Lotufo LV. Structure elucidation and anticancer activity of 7-oxostaurosporine derivatives from the Brazilian endemic tunicate Eudistoma vannamei. Mar Drugs. 2012 May;10(5):1092-102. doi: 10.3390/md10051092. Epub 2012 May 21. PMID: 22822359; PMCID: PMC3397465.

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9: Miyamoto K, Takeda K, Koga K, Ohshima T, Wakusawa S. Antitumour effects and pharmacokinetics of combination of vinblastine with a staurosporine derivative, NA-382, in P388/ADR-bearing mice. J Pharm Pharmacol. 1995 Jun;47(6):524-9. doi: 10.1111/j.2042-7158.1995.tb05843.x. PMID: 7674138.

10: Miyamoto K, Inoko K, Wakusawa S, Kajita S, Hasegawa T, Takagi K, Koyama M. Inhibition of multidrug resistance by a new staurosporine derivative, NA-382, in vitro and in vivo. Cancer Res. 1993 Apr 1;53(7):1555-9. PMID: 8095855.

11: Miyamoto K, Inoko K, Ikeda K, Wakusawa S, Kajita S, Hasegawa T, Takagi K, Koyama M. Effect of staurosporine derivatives on protein kinase activity and vinblastine accumulation in mouse leukaemia P388/ADR cells. J Pharm Pharmacol. 1993 Jan;45(1):43-7. doi: 10.1111/j.2042-7158.1993.tb03677.x. PMID: 8094445.

12: Miyamoto K, Wakusawa S, Inoko K, Takagi K, Koyama M. Reversal of vinblastine resistance by a new staurosporine derivative, NA-382, in P388/ADR cells. Cancer Lett. 1992 Jun 15;64(2):177-83. doi: 10.1016/0304-3835(92)90079-b. PMID: 1351792.

13: Koshino H, Osada H, Isono K. A new inhibitor of protein kinase C, RK-1409 (7-oxostaurosporine). II. Fermentation, isolation, physico-chemical properties and structure. J Antibiot (Tokyo). 1992 Feb;45(2):195-8. doi: 10.7164/antibiotics.45.195. PMID: 1556010.

14: Osada H, Koshino H, Kudo T, Onose R, Isono K. A new inhibitor of protein kinase C, RK-1409 (7-oxostaurosporine). I. Taxonomy and biological activity. J Antibiot (Tokyo). 1992 Feb;45(2):189-94. doi: 10.7164/antibiotics.45.189. PMID: 1556009.