K252a

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IUPACName= (9S-(9α,10β,12α))-2,3,9,10,11,12-hexahydro-10-hydroxy-10-(methoxycarbonyl)-9-methyl-9,12-epoxy-1H-diindolo [1,2,3-fg:3',2',1'-kl] pyrrolo [3,4-i] [1,6] benzodiazocin-1-one
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C=27|H=21|N=3|O=5
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K252a is an alkaloid isolated from "Nocardiopisis" sp. soil fungi. 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). [Ruegg, U.T. "et al." (1989) Tips 10, 218.] [Eliot, L.H. "et al." (1990) B.B.R.C. 171, 148.] [Simpson, D.l. "et al." (1991) J. Neurosci. Res, 28, 148.] [Chin, L.S. "et al." (1999) Cancer Invest. 17, 391.] [Tapley, P. "et al." (1992) Oncogene 7, 371.] [Hashimoto, S. (1998) J. Cell Biol. 107, 1531.] [Kase, H. "et al." (1987) B.B.R.C. 142, 436.] [Hirayama E. "et al." (2001) B.B.R.C. 285, 1237.]

K252a is reported to promote myogenic differentiation in C2 mouse myoblasts [Tapley, P. "et al." (1992) Oncogene 7, 371.] and has been shown to block the neuronal differentiation of rat pheochromocytoma PC12 cells by inhibition of trk tyrosine kinase activity. [Borasio, G.D. Neurosci. Lett. (1990) 108, 207.] Paradoxically, K252a exerts neurotrophic effects on primary sensory neurons, neuroblastoma cells, PC12 cells, and central neurons. [Hashimoto, S. "et al." (1989) Exp. Cell Res. 184, 351.] [Tischler, A.S. "et al." (1991) J. Biol. Chem. 266, 1141.]

K252a inhibits tyrosine phosphorylation of Trk A induced by NGF. PC12 cells were incubated in the presence or absence of 10 ng/ml NGF with or without various concentrations of K252a.

Physical and chemical data [*A vendor product page about K252A: [http://www.fermentek.co.il/K252a.htm K252a] from Fermentek.]

UV spectrum: 205, 250, 289, 334, 367 nm

Solubility: DMSO, dichloromethane, methanol

CAS number : 97161-97-2

Molecular weight: 467.5

Molecular formula: C₂₇H₂₁N₃O₅

References

Further reading

*cite journal | title = Total synthesis of (+)- and (−)-K252a
author = Wood JL, Stoltz BM, Dietrich H-J | journal = | year = 1995 | volume = 117 | issue = 41 | pages = 10413–4 |doi=10.1021/ja00146a039