Cilengitide free base


Catalog No. size PriceQuantity
M7059-2 2mg solid $112
M7059-10 10mg solid $458

Description

Cas:188968-51-6 (free base)

Product Information

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.

 

Chemical Formula: C27H40N8O7

 

Exact Mass: 588.302

 

Molecular Weight: 588.666

 

Elemental Analysis: C, 55.09; H, 6.85; N, 19.04; O, 19.02

 

Synonym: 

 

EMD-85189

EMD 85189

EMD85189

EMD-121974

EMD121974

EMD 121974

NSC-707544

D03497

Cilengitide

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

 

InChi Key:

AMLYAMJWYAIXIA-VWNVYAMZSA-N

 

InChi Code: 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

 

Smiles Code:

O=C(O)C[C@@H](C(N[C@H](CC1=CC=CC=C1)C(N(C)[C@@H](C(C)C)C(N[C@@H](CCC/N=C(N)\N)C(NC2)=O)=O)=O)=O)NC2=O

 

 

Technical Data:

 

Appearance: Solid powder

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

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

 

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. Xu HL, Yang JJ, ZhuGe DL, Lin MT, Zhu QY, Jin BH, Tong MQ, Shen BX, Xiao J, Zhao YZ. Glioma-Targeted Delivery of a Theranostic Liposome Integrated with Quantum Dots, Superparamagnetic Iron Oxide, and Cilengitide for Dual-Imaging Guiding Cancer Surgery. Adv Healthc Mater. 2018 May;7(9):e1701130. doi: 10.1002/adhm.201701130. Epub 2018 Jan 19. PubMed PMID: 29350498.

 

  1. Massabeau C, Khalifa J, Filleron T, Modesto A, Bigay-Gamé L, Plat G, Dierickx L, Aziza R, Rouquette I, Gomez-Roca C, Mounier M, Delord JP, Toulas C, Olivier P, Chatelut E, Mazières J, Cohen-Jonathan Moyal E. Continuous Infusion of Cilengitide Plus Chemoradiotherapy for Patients With Stage III Non-Small-cell Lung Cancer: A Phase I Study. Clin Lung Cancer. 2018 May;19(3):e277-e285. doi: 10.1016/j.cllc.2017.11.002. Epub 2017 Nov 21. PubMed PMID: 29221762.

 

  1. 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.

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