(R)-Macrophage-activating Lipopeptide 2 (trifluoroacetate salt)

(R)-Macrophage-activating lipopeptide 2 ((R)-MALP-2) is an agonist of toll-like receptor 2 (TLR2) and TLR6 and a synthetic lipopeptide derivative of M. fermentans MALP-2 that contains palmitic acid (Cay-10006627, Cay-43561) at both acyl chain positions on the glycerol moiety. It is selective for TLR2/6 over TLR2/1 (EC50s = <1 and 10 ng/ml, respectively, in reporter assays). (R)-MALP-2 induces nitric oxide (NO), TNF-alpha, and IL-6 production in C3H/HeJ macrophages and protects galactosamine-sensitized C57BL/10ScCr mice, which lack functional TLR4, against lethal doses of TNF-alpha. It induces wound leukocyte infiltration and accelerates wound closure in obese diabetic mice.. SMILES: NCCCC[C@@H](C(O)=O)NC([C@H](CCC(O)=O)NC([C@H](CCCCN)NC([C@@H](NC([C@H](CO)NC([C@H]([C@@H](C)CC)NC([C@H](CC(N)=O)NC([C@H](CO)NC([C@H](CCC(O)=O)NC([C@H](CC(O)=O)NC([C@H](CC(N)=O)NC([C@H](CC(N)=O)NC(CNC([C@@H](N)CSC[C@H](OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)CC1=CC=CC=C1)=O)=O)=O.O=C(O)C(F)(F)F. InChi Code: InChI=1S/C99H167N19O30S.C2HF3O2/c1-5-8-10-12-14-16-18-20-22-24-26-28-33-43-84(131)147-59-64(148-85(132)44-34-29-27-25-23-21-19-17-15-13-11-9-6-2)60-149-61-65(102)87(133)106-56-80(124)107-71(52-77(103)121)92(138)113-72(53-78(104)122)93(139)115-74(55-83(129)130)94(140)110-68(46-48-82(127)128)90(136)116-75(57-119)96(142)114-73(54-79(105)123)95(141)118-86(62(4)7-3)98(144)117-76(58-120)97(143)112-70(51-63-39-31-30-32-40-63)91(137)108-66(41-35-37-49-100)88(134)109-67(45-47-81(125)126)89(135)111-69(99(145)146)42-36-38-50-101,3-2(4,5)1(6)7/h30-32,39-40,62,64-76,86,119-120H,5-29,33-38,41-61,100-102H2,1-4H3,(H2,103,121)(H2,104,122)(H2,105,123)(H,106,133)(H,107,124)(H,108,137)(H,109,134)(H,110,140)(H,111,135)(H,112,143)(H,113,138)(H,114,142)(H,115,139)(H,116,136)(H,117,144)(H,118,141)(H,125,126)(H,127,128)(H,129,130)(H,145,146),(H,6,7)/t62-,64+,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,86-,/m0./s1. InChi Key: PUMSXJLPBHUQDA-PRRXSRCGSA-N