K-252a | 99533-80-9

MedKoo Cat#: 407890 | Name: K-252a

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Description:

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

K-252a, also known as SF 2370, is an alkaloid isolated from Nocardiopisis bacteria. This staurosporine analog is a highly potent cell permeable inhibitor of CaM kinase and phosphorylase kinase (IC50 = 1.8 and 1.7 nmol/L, respectively). At higher concentrations it is also an efficient inhibitor of serine/threonine protein kinases (IC50 of 10 to 30 nmol/L).

Chemical Structure

K-252a

CAS#99533-80-9

Theoretical Analysis

MedKoo Cat#: 407890

Name: K-252a

CAS#: 99533-80-9

Chemical Formula: C27H21N3O5

Exact Mass: 467.1481

Molecular Weight: 467.48

Elemental Analysis: C, 69.37; H, 4.53; N, 8.99; O, 17.11

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 250.00	2 Weeks
5mg	USD 650.00	2 Weeks

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Related CAS #

99533-80-9 97161-97-2

Synonym

Antibiotic K 252a; Antibiotic SF 2370; SF2370; SF-2370; K252a; K 252 a; K-252-a;

IUPAC/Chemical Name

methyl (5S,6R,8R)-6-hydroxy-5-methyl-13-oxo-5,6,7,8,14,15-hexahydro-13H-16-oxa-4b,8a,14-triaza-5,8-methanodibenzo[b,h]cycloocta[jkl]cyclopenta[e]-as-indacene-6-carboxylate

InChi Key

KOZFSFOOLUUIGY-SOLYNIJKSA-N

InChi Code

InChI=1S/C27H21N3O5/c1-26-27(33,25(32)34-2)11-18(35-26)29-16-9-5-3-7-13(16)20-21-15(12-28-24(21)31)19-14-8-4-6-10-17(14)30(26)23(19)22(20)29/h3-10,18,33H,11-12H2,1-2H3,(H,28,31)/t18-,26+,27+/m1/s1

SMILES Code

[H][C@](C[C@]8(O)[C@@](OC)=O)(O[C@]78C)N5C3=C2N7C1=CC=CC=C1C2=C(CNC6=O)C6=C3C4=CC=CC=C45

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 467.48 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.

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: Chiu HT, Lin YC, Lee MN, Chen YL, Wang MS, Lai CC. Biochemical characterization and substrate specificity of the gene cluster for biosyntheses of K-252a and its analogs by in vitro heterologous expression system of Escherichia coli. Mol Biosyst. 2009 Oct;5(10):1192-203. doi: 10.1039/b912395b. Epub 2009 Aug 4. PubMed PMID: 19756309. 2: Chiu HT, Chen YL, Chen CY, Jin C, Lee MN, Lin YC. Molecular cloning, sequence analysis and functional characterization of the gene cluster for biosynthesis of K-252a and its analogs. Mol Biosyst. 2009 Oct;5(10):1180-91. doi: 10.1039/b905293c. Epub 2009 Aug 4. PubMed PMID: 19756308. 3: Delarue-Cochin S, McCort-Tranchepain I. Synthesis of new aza-analogs of staurosporine, K-252a and rebeccamycin by nucleophilic opening of C2-symmetric bis-aziridines. Org Biomol Chem. 2009 Feb 21;7(4):706-16. doi: 10.1039/b815737e. Epub 2008 Dec 17. PubMed PMID: 19194586. 4: Fujikawa-Yamamoto K, Miyagoshi M, Yamagishi H. Polyploidization of 2nH1 (ES) cells by K-252a and staurosporine. Hum Cell. 2007 Nov;20(4):91-9. PubMed PMID: 17949348. 5: Kim SY, Park JS, Chae CS, Hyun CG, Choi BW, Shin J, Oh KB. Genetic organization of the biosynthetic gene cluster for the indolocarbazole K-252a in Nonomuraea longicatena JCM 11136. Appl Microbiol Biotechnol. 2007 Jul;75(5):1119-26. Epub 2007 Mar 30. PubMed PMID: 17396254. 6: Hudkins RL, Johnson NW, Angeles TS, Gessner GW, Mallamo JP. Synthesis and mixed lineage kinase activity of pyrrolocarbazole and isoindolone analogs of (+)K-252a. J Med Chem. 2007 Feb 8;50(3):433-41. PubMed PMID: 17266195. 7: Moffat D, Nichols CJ, Riley DA, Simpkins NS. The synthesis of bioactive indolocarbazoles related to K-252a. Org Biomol Chem. 2005 Aug 21;3(16):2953-75. Epub 2005 Jun 30. PubMed PMID: 16186927. 8: Gingrich DE, Yang SX, Gessner GW, Angeles TS, Hudkins RL. Synthesis, modeling, and in vitro activity of (3'S)-epi-K-252a analogues. Elucidating the stereochemical requirements of the 3'-sugar alcohol on trkA tyrosine kinase activity. J Med Chem. 2005 Jun 2;48(11):3776-83. PubMed PMID: 15916429. 9: Shen H, Ligaba A, Yamaguchi M, Osawa H, Shibata K, Yan X, Matsumoto H. Effect of K-252a and abscisic acid on the efflux of citrate from soybean roots. J Exp Bot. 2004 Mar;55(397):663-71. Epub 2004 Jan 30. PubMed PMID: 14754917. 10: Schiering N, Knapp S, Marconi M, Flocco MM, Cui J, Perego R, Rusconi L, Cristiani C. Crystal structure of the tyrosine kinase domain of the hepatocyte growth factor receptor c-Met and its complex with the microbial alkaloid K-252a. Proc Natl Acad Sci U S A. 2003 Oct 28;100(22):12654-9. Epub 2003 Oct 14. PubMed PMID: 14559966; PubMed Central PMCID: PMC240673. 11: Fujikawa-Yamamoto K, Yamagishi H, Miyagoshi M. Establishment of a triploid V79 cell line from tetraploid cells obtained through polyploidization using K-252a. Cell Prolif. 2002 Dec;35(6):369-79. PubMed PMID: 12427255. 12: Gingrich DE, Hudkins RL. Synthesis and kinase inhibitory activity of 3'-(S)-epi-K-252a. Bioorg Med Chem Lett. 2002 Oct 21;12(20):2829-31. PubMed PMID: 12270156. 13: Fujikawa-Yamamoto K, Wang S, Yamagishi H, Ohdoi C, Murano H, Ikeda T. Establishment of a tetraploid Meth-A cell line through polyploidization by demecolcine but not by staurosporine, K-252A and paclitaxel. Cell Prolif. 2001 Aug;34(4):211-22. PubMed PMID: 11529879. 14: Fujikawa-Yamamoto K, Yamagishi H, Zong ZP, Ohdoi C, Wang SY. Different responses of polyploidized V79 cells after removal of two drugs, demecolcine and K-252a. Cell Struct Funct. 2000 Feb;25(1):41-6. PubMed PMID: 10791893. 15: Quentmeier H, Zaborski M, Drexler HG. Effects of thrombopoietin, interleukin-3 and the kinase inhibitor K-252a on growth and polyploidization of the megakaryocytic cell line M-07e. Leukemia. 1998 Oct;12(10):1603-11. PubMed PMID: 9766506. 16: Iwabe K, Teramura M, Yoshinaga K, Kobayashi S, Hoshikawa Y, Maeda T, Hatakeyama M, Mizoguchi H. K-252a-induced polyploidization and differentiation of a human megakaryocytic cell line, Meg-J: transient elevation and subsequent suppression of cyclin B1 and cdc2 expression in the process of polyploidization. Br J Haematol. 1998 Aug;102(3):812-9. PubMed PMID: 9722312. 17: Kim YS, Kawai A. Studies on the antiviral mechanisms of protein kinase inhibitors K-252a and KT5926 against the replication of vesicular stomatitis virus. Biol Pharm Bull. 1998 May;21(5):498-505. PubMed PMID: 9635507. 18: Angeles TS, Yang SX, Steffler C, Dionne CA. Kinetics of trkA tyrosine kinase activity and inhibition by K-252a. Arch Biochem Biophys. 1998 Jan 15;349(2):267-74. PubMed PMID: 9448714. 19: Kino M, Shono K, Nishimura T, Nagamura S. Practical Preparation of K-252a from a Fermentation Solution. Biosci Biotechnol Biochem. 1998;62(8):1627-9. doi: 10.1271/bbb.62.1627. PubMed PMID: 27388849. 20: Oberstar JV, Challacombe JF, Roche FK, Letourneau PC. Concentration-dependent stimulation and inhibition of growth cone behavior and neurite elongation by protein kinase inhibitors KT5926 and K-252a. J Neurobiol. 1997 Aug;33(2):161-71. PubMed PMID: 9240372.