TAT-cyclo-CLLFVY is a cyclic peptide inhibitor of HIF-1 heterodimerization that inhibits hypoxia signaling in cancer cells. TAT-cyclo-CLLFVY disrupts HIF-1α/HIF-1β protein-protein interaction with an IC50 of 1.3 μM.

Product information

CAS Number: 1446322-66-2

Molecular Weight: 2559.08

Formula: C111H188N42O24S2

Chemical Name: (2S)-5-amino-2-[[(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[2-[[(2R)-2-amino-3-[[(2R, 5S, 8S, 11S, 14S, 17S)-11-benzyl-17-[(4-hydroxyphenyl)methyl]-5, 8-bis(2-methylpropyl)-3, 6, 9, 12, 15, 18-hexaoxo-14-propan-2-yl-1, 4, 7, 10, 13, 16-hexazacyclooctadec-2-yl]methyldisulfanyl]propanoyl]amino]acetyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]hexanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoic acid

Smiles: CC(C)C1NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CSSCC(N)C(=O)NCC(=O)NC(CCCNC(N)=N)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCNC(N)=N)C(=O)NC(CCCNC(N)=N)C(=O)NC(CCC(N)=O)C(=O)NC(CCCNC(N)=N)C(=O)NC(CCCNC(N)=N)C(=O)NC(CCCNC(N)=N)C(=O)N2CCCC2C(=O)N2CCCC2C(=O)NC(CCC(N)=O)C(O)=O)NC(=O)C(CC2=CC=C(O)C=C2)NC1=O

InChiKey: AWUUHEHYNQGEFC-UHFFFAOYSA-N

InChi: InChI=1S/C111H188N42O24S2/c1-59(2)52-76-97(168)148-79(54-62-22-8-7-9-23-62)99(170)151-86(61(5)6)102(173)149-78(55-63-34-36-64(154)37-35-63)98(169)150-80(100(171)147-77(53-60(3)4)96(167)146-76)58-179-178-57-65(114)87(158)135-56-85(157)136-66(26-14-44-129-106(117)118)88(159)137-67(24-10-12-42-112)89(160)138-68(25-11-13-43-113)90(161)139-69(27-15-45-130-107(119)120)91(162)140-71(29-17-47-132-109(123)124)93(164)143-73(38-40-83(115)155)95(166)142-70(28-16-46-131-108(121)122)92(163)141-72(30-18-48-133-110(125)126)94(165)144-74(31-19-49-134-111(127)128)103(174)153-51-21-33-82(153)104(175)152-50-20-32-81(152)101(172)145-75(105(176)177)39-41-84(116)156/h7-9,22-23,34-37,59-61,65-82,86,154H,10-21,24-33,38-58,112-114H2,1-6H3,(H2,115,155)(H2,116,156)(H,135,158)(H,136,157)(H,137,159)(H,138,160)(H,139,161)(H,140,162)(H,141,163)(H,142,166)(H,143,164)(H,144,165)(H,145,172)(H,146,167)(H,147,171)(H,148,168)(H,149,173)(H,150,169)(H,151,170)(H,176,177)(H4,117,118,129)(H4,119,120,130)(H4,121,122,131)(H4,123,124,132)(H4,125,126,133)(H4,127,128,134)

Technical Data

Appearance: Solid Power

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

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:

TAT-cyclo-CLLFVY inhibits HIF-1 activity in a mammalian cell luciferase reporter assay. Hypoxia (1% O2) results in a ~12-fold increase in the luciferase signal, which is inhibited in a dose-dependent manner by TAT-cyclo-CLLFVY (IC50 of 19±2 μM). To assess the cell-specificity of TAT-cyclo-CLLFVY, the experiment is repeated in MCF-7 breast cancer cells with similar results (TAT-cyclo-CLLFVY IC50 of 16±1 μM).

References:

1. Elena Miranda, et al. A cyclic peptide inhibitor of HIF-1 heterodimerization that inhibits hypoxia signaling in cancer cells. J Am Chem Soc. 2013 Jul 17;135(28):10418-25.

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