| Source: |
Nocardiopsis sp |
| Synonyms |
Antibiotic K-252a
Antibiotic SF 2370systematic name:
9,12-Epoxy-1H-diindolo(1,2,3-fg:3',2',1'-kl)pyrrolo(3,4-i)(1,6)benzodiazocine-10-carboxylic
acid, 2,3,9,10,11,12-hexahydro-10-
hydroxy-9-methyl-1-oxo-, methyl ester, (9alpha,10beta,12alpha)- |
| Description: |
K252a: Cell permeable protein kinase inhibitor |
| CAS number: |
99533-80-9
; 97161-97-2 |
| Merck index: |
Not listed |
| Molecular weight: |
467.5 |
| Structure: |
 |
| Molecular Formula: |
C27H21N3O5 |
Solubility
information: |
Readily soluble in chloroform, acetonitrile, acetone, dioxane, tetrahydrofuran, pyridine;
soluble in ethanol, methanol, 1-propanol, ethyl acetate and n-butanol;
insoluble in water, 2-propanol |
| Specifications |
|
| Appearance: |
White to pale yellow powder |
| Purity: |
At least 97% by TLC |
| λmax: |
205, 250, 289, 334, 367 |
| Melting point |
255oC-270oC
;
Melting point in informational only and is not a part of release
specifications for this product. |
| Solubility |
Clear colorless solution at 5mg/ml of Dichloromethane |
| Storage |
-20oC. Protect from light. Hygroscopic. Protect from moisture |
| Applications |
K252a is a highly potent cell permeable inhibitor of CaM kinase and phosphorylase kinase . At high concentrations it also inhibitors of serine/threonine protein kinases K252a inhibits tyrosine phosphorylation of Trk A induced by NGF K252a is reported to promote myogenic differentiation in C2 mouse myoblasts |
| Classification |
indolocarbazole alkaloid
PK inhibitor |
| Warnings |
|
| Related products |
KT5853 , KT5720 , Staurosporine , PKC412
K252a , K252B K252c
|
| | For Research use only. Not for Human or Drug use
GMP/API grade available on request
No genetically modified organisms are used. |
| Publications | |
| |
Raychaudhuri SP, Sanyal M, Weltman H, Kundu-Raychaudhuri S.
K252a, a high-affinity nerve growth factor receptor blocker, improves psoriasis: an in vivo study using the severe combined immunodeficient mouse-human skin model.
J Invest Dermatol. 2004 Mar;122(3):812-9. |
| |
Winston JH, Toma H, Shenoy M, He ZJ, Zou L, Xiao SY, Micci MA, Pasricha PJ.
Acute pancreatitis results in referred mechanical hypersensitivity and neuropeptide up-regulation that can be suppressed by the protein kinase inhibitor k252a.
J Pain. 2003 Aug;4(6):329-37. |
| |
Roux PP, Dorval G, Boudreau M, Angers-Loustau A, Morris SJ, Makkerh J, Barker PA.
K252a and CEP1347 are neuroprotective compounds that inhibit mixed-lineage kinase-3 and induce activation of Akt and ERK.
J Biol Chem. 2002 Dec 20;277(51):49473-80. Epub 2002 Oct 17 |
| |
Nheu TV, He H, Hirokawa Y, Tamaki K, Florin L, Schmitz ML, Suzuki-Takahashi I, Jorissen RN, Burgess AW, Nishimura S, Wood J, Maruta H.
The K252a derivatives, inhibitors for the PAK/MLK kinase family selectively block the growth of RAS transformants.
Cancer J. 2002 Jul-Aug;8(4):328-36. |
| |
Morotti A, Mila S, Accornero P, Tagliabue E, Ponzetto C.
K252a inhibits the oncogenic properties of Met, the HGF receptor.
Oncogene. 2002 Jul 25;21(32):4885-93. |
| |
Hirayama E, Sasao N, Yoshimasu S, Kim J.
K252a, an indrocarbazole derivative, causes the membrane of myoblasts to enter a fusion-capable state.
Biochem Biophys Res Commun. 2001 Aug 3;285(5):1237-43. |
| |
Tamaki K, Shotwell JB, White RD, Drutu I, Petsch DT, Nheu TV, He H, Hirokawa Y, Maruta H, Wood JL.
Efficient syntheses of novel C2'-alkylated (+/-)-K252a analogues.
Org Lett. 2001 May 31;3(11):1689-92. |
| |
Lee KH, Lee SH, Kim D, Rhee S, Kim C, Chung CH, Kwon H, Kang MS.
Promotion of skeletal muscle differentiation by K252a with tyrosine phosphorylation of focal adhesion: a possible involvement of small GTPase Rho.
Exp Cell Res. 1999 Nov 1;252(2):401-15. |
| |
Chin LS, Murray SF, Doherty PF, Singh SK.
K252a induces cell cycle arrest and apoptosis by inhibiting Cdc2 and Cdc25c.
Cancer Invest. 1999;17(6):391-5. |
| |
Mohri T, Kameshita I, Suzuki S, Hioki K, Tokunaga R, Takatani S.
Rapid adhesion and spread of non-adherent colon cancer Colo201 cells induced by the protein kinase inhibitors, K252a and KT5720 and suppression of the adhesion by the immunosuppressants FK506 and cyclosporin A.
Cell Struct Funct. 1998 Oct;23(5):255-64. |
| |
Applications of KT 5720, K252a and
K525b from Fermentek in methods for quantitative analysis of
captured kinases and proteases, see United States Patent
Application 20090253156 |
|
K252A on Wikipedia
|
 |
| Disambiguation
K252a was discovered twice, and was given two CAS numbers.
The first publication is
J Antibiot (Tokyo). 1985 Oct;38(10):1437-9.
A new antibiotic
SF-2370 produced by Actinomadura.
Sezaki M, Sasaki T, Nakazawa T, Takeda U, Iwata M, Watanabe
T, Koyama M, Kai F, Shomura T, Kojima M.
This compound was given [CAS]
99533-80-9
A year later, Kase and al
published the following report:
J Antibiot (Tokyo). 1986
Aug;39(8):1059-65.
K-252a, a potent inhibitor of protein kinase C from
microbial origin.
Kase H, Iwahashi K, Matsuda Y.
"K-252a,
a metabolite isolated from the culture broth of Nocardiopsis
sp. K-252a, was found to exhibit an extremely potent
inhibitory activity on protein kinase C.
"
This time, [CAS] 97161-97-2
was given to the compound.
These two compounds have peen
proved identical
Because Kase
was the first to note the PKC related properties of
K252a, the name K252a
and the CAS number
97161-97-2
became much more popular than the other ones. However,
recently more and more vendors tend to use the CAS number
99533-80-9 in conjunction
with the name K252a. Therefore we decided to display here both
CAS numbers.
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