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SML1594

Sigma-Aldrich

Cilengitide trifluoroacetic acid salt

≥95% (HPLC)

Synonym(s):

2,2,2-trifluoroacetate, Cyclo(L-arginylglycyl-L-a-aspartyl-D-phenylalanyl-N-methyl-L-valyl), 2,2,2-trifluoroacetate, EMD 121974, NSC 707544, c(RGDF(NMe)V)

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About This Item

Empirical Formula (Hill Notation):
C27H40N8O7 · xC2HF3O2
CAS Number:
188968-51-6
Molecular Weight:
588.66 (free base basis)
UNSPSC Code:
12352106
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

H2O: 20 mg/mL, clear

storage temp.

−20°C

InChI

1S/C27H40N8O7/c1-15(2)22-25(41)33-17(10-7-11-30-27(28)29)23(39)31-14-20(36)32-18(13-21(37)38)24(40)34-19(26(42)35(22)3)12-16-8-5-4-6-9-16/h4-6,8-9,15,17-19,22H,7,10-14H2,1-3H3,(H,31,39)(H,32,36)(H,33,41)(H,34,40)(H,37,38)(H4,28,29,30)/t17-,18-,19+,22-/m0/s1

InChI key

AMLYAMJWYAIXIA-VWNVYAMZSA-N

Application

Cilengitide trifluoroacetic acid salt has been used as an inhibitor of integrin αvβ5.

Biochem/physiol Actions

Cilengitide is a vascular targeting agent (VTA) that acts as an integrin antagonist. Cilengitide is a cyclized Arg-Gly-Glu(RGD)-containing pentapeptide that selectively blocks activation of the αvβ3 and αvβ5 integrins.
It exhibits antitumor activity in glioblastoma multiforme tumors. Integrins are heterodimers of α and β chain. They are transmembrane receptors which are responsible for cell-to-cell and cell-extracellular matrix interactions. They control tumor angiogenesis, invasion and migration.

WGK

WGK 3

Regulatory Information

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David A Reardon et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 26(34), 5610-5617 (2008-11-05)
Cilengitide, an inhibitor of alphavbeta3 and alphavbeta5 integrin receptors, demonstrated minimal toxicity and durable activity across a wide range of doses administered to adults with recurrent glioblastoma multiforme (GBM) in a prior phase I study. The current multicenter phase II
Marco A Alfonzo-Méndez et al.
Nature communications, 13(1), 905-905 (2022-02-18)
The crosstalk between growth factor and adhesion receptors is key for cell growth and migration. In pathological settings, these receptors are drivers of cancer. Yet, how growth and adhesion signals are spatially organized and integrated is poorly understood. Here we
David A Reardon et al.
Expert opinion on investigational drugs, 17(8), 1225-1235 (2008-07-12)
Glioblastoma multiforme (GBM), a highly invasive and vascular cancer, responds poorly to conventional cytotoxic therapy. Integrins, widely expressed in GBM and tumor vasculature, mediate cell survival, migration and angiogenesis. Cilengitide is a potent alphavbeta3 and alphavbeta5 integrin inhibitor. To summarize
Activation of Hepatic Stellate Cells During Liver Carcinogenesis Requires Fibrinogen/Integrin αvβ5 in Zebrafish.
Yan C, et al.
Neoplasia, 20(5), 533-542 (2018)
Caroline Decourt et al.
Endocrinology, 164(2) (2022-12-13)
Timing of puberty requires exquisite coordination of genes, hormones, and brain circuitry. An increasing level of body adiposity, signaled to the brain via the fat-derived hormone leptin, is recognized as a major factor controlling puberty onset. However, it is clear
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