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SML2869

Sigma-Aldrich

Ispinesib

≥98% (HPLC)

Synonyme(s) :

(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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About This Item

Formule empirique (notation de Hill):
C30H33ClN4O2
Numéro CAS:
336113-53-2
Poids moléculaire :
517.06
Numéro MDL:
MFCD22628831
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

powder

Activité optique

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

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

QJZRFPJCWMNVAV-HHHXNRCGSA-N

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H300 + H330,H341

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

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Certificats d'analyse (COA)

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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
James W Purcell et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 16(2), 566-576 (2010-01-14)
Ispinesib (SB-715992) is a potent inhibitor of kinesin spindle protein, a kinesin motor protein essential for the formation of a bipolar mitotic spindle and cell cycle progression through mitosis. Clinical studies of ispinesib have shown a 9% response rate in
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
Lusong Luo et al.
Nature chemical biology, 3(11), 722-726 (2007-10-09)
The mitotic kinesin KSP (kinesin spindle protein, or Eg5) has an essential role in centrosome separation and formation of the bipolar mitotic spindle. Its exclusive involvement in the mitotic spindle of proliferating cells presents an opportunity for developing new anticancer
JiaRui Zhang et al.
Redox biology, 21, 101112-101112 (2019-01-28)
Intracellular tension activity plays a crucial role in cytotoxic brain edema and astrocyte swelling. Here, a few genetically encoded FRET-based tension probes were designed to detect cytoskeletal structural tension optically, including their magnitude and vectors. The astrocyte swelling resulted in

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