LL-37 amide (trifluoroacetate salt)

LL-37 is a cationic and alpha-helical antimicrobial peptide expressed in human bone marrow, testis, granulocytes, and gingival epithelium and is upregulated in psoriatic lesions. It inhibits growth of Gram-positive E. coli D21 and Gram-negative B. megatarium in a concentration-dependent manner and LL-37 expression is induced in A549 epithelial cells, alveolar macrophages, neutrophils, and monocyte-derived macrophages following M. tuberculosis infection. LL-37 binds sheep erythrocytes coated with S. minnesota Re-LPS and induces agglutination with a minimal agglutinating concentration (MAC) of 12.1 µg/ml. It is a chemoattractant for, and can induce calcium mobilization in, human monocytes, neutrophils, and T cells that naturally express formyl peptide receptor-like 1 (FPRL1) and FPRL1-transfected HEK293 cells. LL-37 (10-15 µM) pretreatment of dengue virus type 2 (DENV-2) reduces its infectivity as well as levels of viral genomic RNA and NS1 antigen. In vivo, LL-37 inhibits cecal ligation and puncture-induced caspase-1 activation and pyroptosis of peritoneal macrophages, reduces levels of the inflammatory cytokines IL-1beta, IL-6, and TNF-alpha, and improves survival in polybacterial septic mice.Formal Name: L-leucyl-L-leucylglycyl-L-alpha-aspartyl-L-phenylalanyl-L-phenylalanyl-L-arginyl-L-lysyl-L-seryl-L-lysyl-L-alpha-glutamyl-L-lysyl-L-isoleucylglycyl-L-lysyl-L-alpha-glutamyl-L-phenylalanyl-L-lysyl-L-arginyl-L-isoleucyl-L-valyl-L-glutaminyl-L-arginyl-L-isoleucyl-L-lysyl-L-alpha-aspartyl-L-phenylalanyl-L-leucyl-L-arginyl-L-asparaginyl-L-leucyl-L-valyl-L-prolyl-L-arginyl-L-threonyl-L-alpha-glutamyl-L-serinamide, trifluoroacetate salt. Synonyms: CAP-18, hCAP-18, Cathelicidin, FALL-39. Molecular Formula: C205H341N61O52 . XCF3COOH. Formula Weight: 4492.3. Purity: >95%. Formulation: (Request formulation change), A lyophilized powder. Peptide Sequence: LLGDFFRKSKEKIGKEFKRIVQRIKDFLRNLVPRTES-NH2. Solubility: Water: 1 mg/ml. SMILES: NC([C@H](CO)NC([C@H](CCC(O)=O)NC([C@@]([C@@H](C)O)([H])NC([C@H](CCCNC(N)=N)NC([C@@H]1CCCN1C([C@H](C(C)C)NC([C@H](CC(C)C)NC([C@H](CC(N)=O)NC([C@H](CCCNC(N)=N)NC([C@H](CC(C)C)NC([C@@H](NC([C@@H](NC([C@H](CCCCN)NC([C@@]([C@H](CC)C)([H])NC([C@H](CCCNC(N)=N)NC([C@H](CCC(N)=O)NC([C@H](C(C)C)NC([C@@]([C@H](CC)C)([H])NC([C@H](CCCNC(N)=N)NC([C@H](CCCCN)NC([C@@H](NC([C@H](CCC(O)=O)NC([C@H](CCCCN)NC(CNC([C@@]([C@H](CC)C)([H])NC([C@H](CCCCN)NC([C@H](CCC(O)=O)NC([C@H](CCCCN)NC([C@H](CO)NC([C@H](CCCCN)NC([C@H](CCCNC(N)=N)NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@H](CC(C)C)NC([C@H](CC(C)C)N[H])=O)=O)=O)CC(O)=O)=O)CC2=CC=CC=C2)=O)CC3=CC=CC=C3)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)CC4=CC=CC=C4)=O)=O)=O)=O)=O)=O)=O)=O)=O)CC(O)=O)=O)CC5=CC=CC=C5)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O.FC(F)(C(O)=O)F. InChi Code: InChI=1S/C205H341N61O52.C2HF3O2/c1-20-114(16)162(262-180(298)128(66-40-46-86-211)236-177(295)135(74-78-155(274)275)244-171(289)125(63-37-43-83-208)242-193(311)149(107-268)259-175(293)126(64-38-44-84-209)235-172(290)129(67-47-87-226-201(216)217)241-186(304)142(98-119-55-29-24-30-56-119)253-188(306)144(100-121-59-33-26-34-60-121)254-190(308)146(102-158(280)281)234-154(273)104-231-168(286)138(94-109(6)7)249-167(285)122(212)93-108(4)5)195(313)232-105-153(272)233-123(61-35-41-81-206)169(287)243-136(75-79-156(276)277)178(296)252-141(97-118-53-27-23-28-54-118)185(303)239-124(62-36-42-82-207)170(288)237-131(69-49-89-228-203(220)221)182(300)264-164(116(18)22-3)198(316)260-160(112(12)13)196(314)247-134(73-77-151(213)270)176(294)238-132(70-50-90-229-204(222)223)181(299)263-163(115(17)21-2)197(315)246-127(65-39-45-85-210)173(291)257-147(103-159(282)283)191(309)255-143(99-120-57-31-25-32-58-120)187(305)250-139(95-110(8)9)184(302)240-130(68-48-88-227-202(218)219)174(292)256-145(101-152(214)271)189(307)251-140(96-111(10)11)192(310)261-161(113(14)15)200(318)266-92-52-72-150(266)194(312)245-133(71-51-91-230-205(224)225)183(301)265-165(117(19)269)199(317)248-137(76-80-157(278)279)179(297)258-148(106-267)166(215)284,3-2(4,5)1(6)7/h23-34,53-60,108-117,122-150,160-165,267-269H,20-22,35-52,61-107,206-212H2,1-19H3,(H2,213,270)(H2,214,271)(H2,215,284)(H,231,286)(H,232,313)(H,233,272)(H,234,273)(H,235,290)(H,236,295)(H,237,288)(H,238,294)(H,239,303)(H,240,302)(H,241,304)(H,242,311)(H,243,287)(H,244,289)(H,245,312)(H,246,315)(H,247,314)(H,248,317)(H,249,285)(H,250,305)(H,251,307)(H,252,296)(H,253,306)(H,254,308)(H,255,309)(H,256,292)(H,257,291)(H,258,297)(H,259,293)(H,260,316)(H,261,310)(H,262,298)(H,263,299)(H,264,300)(H,265,301)(H,274,275)(H,276,277)(H,278,279)(H,280,281)(H,282,283)(H4,216,217,226)(H4,218,219,227)(H4,220,221,228)(H4,222,223,229)(H4,224,225,230),(H,6,7)/t114-,115-,116-,117+,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,1. InChi Key: YCAOMMPDUJYSPT-YLLLKHBJSA-N.