Gap19 TFA

• CAT Number: I045999
• Molecular Formula: C57H97F3N14O15
• Molecular Weight: 1275.46
• Purity: ≥95%
• Synonyms: (2S)-6-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-5-amino-2-[[(2S)-2,6-diaminohexanoyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]hexanoyl]amino]-3-phenylpropanoyl]amino]hexanoic acid;2,2,2-trifluoroacetic acid
• InChI: InChI=1S/C55H96N14O13.C2HF3O2/c1-5-33(3)45(69-51(77)40(25-27-44(71)72)65-54(80)46(34(4)6-2)68-50(76)39(24-26-43(61)70)62-47(73)36(60)20-10-14-28-56)53(79)64-38(22-12-16-30-58)48(74)63-37(21-11-15-29-57)49(75)67-42(32-35-18-8-7-9-19-35)52(78)66-41(55(81)82)23-13-17-31-59;3-2(4,5)1(6)7/h7-9,18-19,33-34,36-42,45-46H,5-6,10-17,20-32,56-60H2,1-4H3,(H2,61,70)(H,62,73)(H,63,74)(H,64,79)(H,65,80)(H,66,78)(H,67,75)(H,68,76)(H,69,77)(H,71,72)(H,81,82);(H,6,7)/t33-,34-,36-,37-,38-,39-,40-,41-,42-,45-,46-;/m0./s1
• InChIKey: UBIXVFFLYALTSN-TWIANDLUSA-N
• SMILES: CCC(C)C(C(=O)NC(CCC(=O)O)C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCCCN)C(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)N.C(=O)(C(F)(F)F)O

Gap19 TFA, a peptide derived from nine amino acids of the Cx43 cytoplasmic loop (CL), is a potent and selective connexin 43 (Cx43) hemichannel blocker. Gap19 TFA inhibits hemichannels caused by preventing intramolecular interactions of the C-terminus (CT) with the CL. Gap19 TFA is not blocking GJ channels or Cx40/pannexin-1 hemichannels. Gap19 TFA has protective effects against myocardial[1][2].
Gap19 TFA (250 μM; for 30 min ) decreases mitochondrial potassium uptake[1].
Gap19 TFA (400 μM) inhibits unitary hemichannel currents in HeLa-Cx43 cells[2].
Gap19 TFA (100 μM) inhibits hemichannel unitary currents in ventricular cardiomyocytes[2].
Gap19 TFA (250 μM, 30 min) protects against myocardial ischemia/reperfusion injury in vitro and in vivo[2].
Gap19 TFA (iv; 25 mg/kg; 10 min before ligation) significantly reduces the infarct size by approximately one-fifth[2].

Reference

[1]. Boengler K, et al. Connexin 43 impacts on mitochondrial potassium uptake. Front Pharmacol. 2013 Jun 6;4:73.
 [Content Brief]

[2]. Wang N, et al. Selective inhibition of Cx43 hemichannels by Gap19 and its impact on myocardial ischemia/reperfusion injury. Basic Res Cardiol. 2013 Jan;108(1):309.
 [Content Brief]