Cilengitide free base

Cilengitide is a cyclic Arg-Gly-Asp peptide with potential antineoplastic activity. Cilengitide binds to and inhibits the activities of the alpha(v)beta(3) and alpha(v)beta(5) integrins, thereby inhibiting endothelial cell-cell interactions, endothelial cell-matrix interactions, and angiogenesis.

Product information

CAS Number: 188968-51-6

Molecular Weight: 588.66

Formula: C27H40N8O7

Synonym:

EMD-85189

EMD-121974

NSC-707544

Cilengitide

EMD 85189

EMD85189

EMD121974

EMD 121974

D03497

Cyclo(L-arginylglycyl-L-aspartyl-D-phenylalanyl-N-methyl-L-valyl)

Chemical Name: 2-((2S,5R,8S,11S)-5-benzyl-11-(3-((diaminomethylene)amino)propyl)-8-isopropyl-7-methyl-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaazacyclopentadecan-2-yl)acetic acid

Smiles: CC(C)[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](CC2C=CC=CC=2)C(=O)N1C

InChiKey: AMLYAMJWYAIXIA-VWNVYAMZSA-N

InChi: 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

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

Cilengitide is a cyclized RGD (Arg-Gly-Asp motif)-containing pentapeptide. Cilengitide blocks integrin ανβ3- and ανβ5-mediated endothelial cell attachment and migration. Cilengitide inhibits integrin-mediated binding to Vitronectin with IC50's of 0.4 and 0.4 μM in cell adhesion studies assessing the human melanoma M21 or UCLA-P3 human lung carcinoma cell lines . Cilengitide inhibits the attachment of human umbilical vein endothelial cells to Vitronectin with an IC50 of 2 μM .

In Vivo:

Cilengitide (i.p. at 10, 50, and 250 μg three times per week) inhibits M21-L melanoma tumors growth in nude mice.

References:

1. Zhang L, Gülses A, Purcz N, Weimer J, Wiltfang J, Açil Y. A comparative assessment of the effects of integrin inhibitor cilengitide on primary culture of head and neck squamous cell carcinoma (HNSCC) and HNSCC cell lines. Clin Transl Oncol. 2019 Jan 10. doi: 10.1007/s12094-018-02025-3. [Epub ahead of print] PubMed PMID: 30632010.
2. Garciarena CD, McHale TM, Martin-Loeches I, Kerrigan SW. Pre-emptive and therapeutic value of blocking bacterial attachment to the endothelial alphaVbeta3 integrin with cilengitide in sepsis. Crit Care. 2017 Sep 26;21(1):246. doi: 10.1186/s13054-017-1838-3. PubMed PMID: 28946901; PubMed Central PMCID: PMC5613315.

Products are for research use only. Not for human use.