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SML1594

Cilengitide trifluoroacetic acid salt

Name: Cilengitide trifluoroacetic acid salt
Brand: SIGMA

≥95% (HPLC), vascular targeting agent, powder

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

Assay:

≥95% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

Cilengitide trifluoroacetic acid salt, ≥95% (HPLC)

Quality Level

100

assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

H₂O: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

N1([C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@@H](C1=O)Cc2ccccc2)CC(=O)O)CCCN\C(=N\[H])\N)C(C)C)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

Description

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 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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

Regulatory Information

常规特殊物品

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Certificates of Analysis (COA)

Lot/Batch Number

046M4747V

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Activation of Hepatic Stellate Cells During Liver Carcinogenesis Requires Fibrinogen/Integrin αvβ5 in Zebrafish.

Yan C, et al.

Neoplasia, 20(5), 533-542 (2018)

Cilengitide: an integrin-targeting arginine-glycine-aspartic acid peptide with promising activity for glioblastoma multiforme.

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

Randomized phase II study of cilengitide, an integrin-targeting arginine-glycine-aspartic acid peptide, in recurrent glioblastoma multiforme.