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SML1594

Sigma-Aldrich

Cilengitide trifluoroacetic acid salt

≥95% (HPLC)

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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)
Empirical Formula (Hill Notation):
C27H40N8O7 · xC2HF3O2
CAS Number:
Molecular Weight:
588.66 (free base basis)

Quality Level

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

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Show Differences

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This Item
E3285SML2408SML1051
EIINFEKL trifluoroacetate salt ≥95% (HPLC)

E3285

EIINFEKL trifluoroacetate salt

UNC3866 trifluoroacetate salt ≥98% (HPLC)

SML2408

UNC3866 trifluoroacetate salt

Sigma-Aldrich

SML1051

Bivalirudin trifluoroacetate salt

form

powder

form

powder

form

lyophilized powder (white)

form

powder

Quality Level

100

Quality Level

-

Quality Level

-

Quality Level

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

H2O: 20 mg/mL, clear

solubility

acetonitrile: water: ~1 mg/mL (60/40)

solubility

-

solubility

-

color

white to beige

color

white

color

white to off-white

color

white to off-white

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3


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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)
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
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
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
Nikolina Stojanović et al.
Molecular pharmacology, 94(6), 1334-1351 (2018-09-29)
Low survival rates of patients with metastatic triple-negative breast cancer (TNBC) and melanoma, in which current therapies are ineffective, emphasize the need for new therapeutic approaches. Integrin β1 appears to be a promising target when combined with chemotherapy, but recent

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