K252a

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K252a
Names
Preferred IUPAC name
Methyl (13S,14R,16R)-14-hydroxy-13-methyl-5-oxo-6,7,13,14,15,16-hexahydro-5H-13,16-epoxydiindolo[1,2,3-fg:3′,2′,1′-kl]pyrrolo[3,4-i][1,6]benzodiazocine-14-carboxylate
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard 100.167.781 Edit this at Wikidata
UNII
  • 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 checkY
    Key: KOZFSFOOLUUIGY-CYBHFKQVSA-N checkY
Properties[1]
C27H21N3O5
Molar mass 467.481 g·mol−1
Solubility in other solvents Soluble in DMSO, dichloromethane, and methanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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K252a is an alkaloid isolated from Nocardiopsis 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).[2][3][4][5][6][7][8][9]

K252a is reported to promote myogenic differentiation in C2 mouse myoblasts[6] and has been shown to block the neuronal differentiation of rat pheochromocytoma PC12 cells by inhibition of trk tyrosine kinase activity.[10]

K252a has been reported in preclinical research as a potential treatment for psoriasis[11]

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.

See also[edit]

References[edit]

  1. ^ K252a from Fermentek
  2. ^ Ruegg, U.T. et al. (1989) Tips 10, 218.
  3. ^ Eliot, L.H. et al. (1990) B.B.R.C. 171, 148.
  4. ^ Simpson, D.l. et al. (1991) J. Neurosci. Res, 28, 148.
  5. ^ Chin, L.S. et al. (1999) Cancer Invest. 17, 391.
  6. ^ a b Tapley, P. et al. (1992) Oncogene 7, 371.
  7. ^ Hashimoto, S. (1998) J. Cell Biol. 107, 1531.
  8. ^ Kase, H. et al. (1987) B.B.R.C. 142, 436.
  9. ^ Hirayama E. et al. (2001) B.B.R.C. 285, 1237.
  10. ^ Borasio, G.D. Neurosci. Lett. (1990) 108, 207.
  11. ^ Promising New Treatments for Psoriasis,

    Sarah Dubois Declercq and Roxane Pouliot >.

    The Scientific World Journal; Volume 2013, Article ID 980419; https://dx.doi.org/10.1155/2013/980419

Further reading[edit]

  • Wood JL, Stoltz BM, Dietrich HJ (1995). "Total synthesis of (+)- and (−)-K252a". J Am Chem Soc. 117 (41): 10413–4. doi:10.1021/ja00146a039.


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