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Merck
CN

SML2869

Sigma-Aldrich

Ispinesib

≥98% (HPLC)

别名:

(R)-N-(3-Aminopropyl)-N-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropyl]-4-methylbenzamide, CK0238273, N-(3-Aminopropyl)-N-[(1R)-1-[7-chloro-3,4-dihydro-4-oxo-3-(phenylmethyl)-2-quinazolinyl]-2-methylpropyl]-4-methylbenzamide, SB 715992, SB-715992, SB715992

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关于此项目

经验公式（希尔记法）:
C30H33ClN4O2
化学文摘社编号:
336113-53-2
分子量:
517.06
MDL编号:
MFCD22628831
UNSPSC代码:
12352200
NACRES:
NA.77

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质量水平

100

方案

≥98% (HPLC)

表单

powder

旋光性

[α]/D +315 to +375°, c = 0.5 in chloroform-d

颜色

white to beige

溶解性

DMSO: 2 mg/mL, clear

储存温度

2-8°C

SMILES字符串

Clc1cc2nc([n]([c](c2cc1)=O)Cc4ccccc4)[C@H](N(CCCN)C(=O)c3ccc(cc3)C)C(C)C

InChI

1S/C30H33ClN4O2/c1-20(2)27(34(17-7-16-32)29(36)23-12-10-21(3)11-13-23)28-33-26-18-24(31)14-15-25(26)30(37)35(28)19-22-8-5-4-6-9-22/h4-6,8-15,18,20,27H,7,16-17,19,32H2,1-3H3/t27-/m1/s1

InChI key

QJZRFPJCWMNVAV-HHHXNRCGSA-N

相关类别

生化/生理作用

Ispinesib (SB-715992) is a potent and highly selective kinesin spindle protein (KSP, KIF11, EG5) allosteric inhibtor that specifically inhibits microtubule (MT)-stimulated ATPase activity of KSP (Ki = 1.7 nM; 5 μM MT, 500 μM ATP, 0.75 nM human KSP), but not ubiquitous kinesin heavy chain KHC, neuronal kinesin KIF1A, or mitotic kinesins CENP-E, RabK6, MCAK, MKLP1. Ispinesib exhibits anti-cancer efficacy in cultures (GI50 = 45 nM/BT-474 & 19 nM/MDA-MB-468) and in cancer xenograft models in vivo (8 or 10 mg/kg q4d×3 ip. mice with MCF-7, HCC-1954, KPL4, BT-474 xenografts).
Potent and highly selective kinesin spindle protein (KSP, KIF11, EG5) allosteric inhibtor with in vitro and in vivo anti-cancer efficacy.

象形图

Skull and crossbonesHealth hazard
GHS06,GHS08

警示用语：

Danger

危险声明

H300 + H330,H341

危险分类

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Muta. 2

储存分类代码

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000471378
0000471378
0000174291
0000174291
0000105541

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Hung Yi Kristal Kaan et al.
The Journal of biological chemistry, 288(25), 18588-18598 (2013-05-10)
Kinesins comprise a superfamily of molecular motors that drive a wide variety of cellular physiologies, from cytoplasmic transport to formation of the bipolar spindle in mitosis. These differing roles are reflected in corresponding polymorphisms in key kinesin structural elements. One
Jasper Edgar Neggers et al.
Nature communications, 9(1), 502-502 (2018-02-07)
Unraveling the mechanism of action and molecular target of small molecules remains a major challenge in drug discovery. While many cancer drugs target genetic vulnerabilities, loss-of-function screens fail to identify essential genes in drug mechanism of action. Here, we report
Sandeep K Talapatra et al.
Journal of medicinal chemistry, 56(16), 6317-6329 (2013-07-24)
Development of drug resistance during cancer chemotherapy is one of the major causes of chemotherapeutic failure for the majority of clinical agents. The aim of this study was to investigate the underlying molecular mechanism of resistance developed by the mitotic
Geng-Yuan Chen et al.
ACS chemical biology, 12(4), 1038-1046 (2017-02-07)
To uncover their contrasting mechanisms, antimitotic drugs that inhibit Eg5 (kinesin-5) were analyzed in mixed-motor gliding assays of kinesin-1 and Eg5 motors in which Eg5 "braking" dominates motility. Loop-5 inhibitors (monastrol, STLC, ispinesib, and filanesib) increased gliding speeds, consistent with
David A Davis et al.
BMC cancer, 6, 22-22 (2006-01-26)
Kinesin spindle proteins (KSP) are motor proteins that play an essential role in mitotic spindle formation. HsEg5, a KSP, is responsible for the formation of the bipolar spindle, which is critical for proper cell division during mitosis. The function of
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