Pam2CSK4 TFA salt

• CAT Number: I034185
• Molecular Formula: C67H127F3N10O14S
• Molecular Weight: 1385.8642
• Purity: 98%
• Synonyms: Pam2CSK4 TFA salt; Pam2-CSK4 TFA salt; Pam2 CSK4 TFA salt; Pam2Cys-Ser-(Lys)4
• Solubility: To be determined
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: S-((R)-2,3-bis(palmitoyloxy)propyl)-L-cysteinyl-L-seryl-L-lysyl-L-lysyl-L-lysyl-L-lysine compound with 2,2,2-trifluoroacetic acid (1:1)
• InChI: InChI=1S/C65H126N10O12S.C2HF3O2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-41-58(77)86-48-51(87-59(78)42-28-26-24-22-20-18-16-14-12-10-8-6-4-2)49-88-50-52(70)60(79)75-57(47-76)64(83)73-54(38-30-34-44-67)62(81)71-53(37-29-33-43-66)61(80)72-55(39-31-35-45-68)63(82)74-56(65(84)85)40-32-36-46-69;3-2(4,5)1(6)7/h51-57,76H,3-50,66-70H2,1-2H3,(H,71,81)(H,72,80)(H,73,83)(H,74,82)(H,75,79)(H,84,85);(H,6,7)/t51-,52+,53+,54+,55+,56+,57+;/m1./s1
• InChIKey: WUCKUXUWRPCGSL-WJRQQJDCSA-N
• SMILES: CCCCCCCCCCCCCCCC(OC[C@H](CSC[C@@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](CCCCN)C(O)=O)=O)CCCCN)=O)CCCCN)=O)CCCCN)=O)CO)=O)N)OC(CCCCCCCCCCCCCCC)=O)=O.OC(C(F)(F)F)=O

Pam2CSK4 is a synthetic bacterial lipopeptide and an agonist of the toll-like receptor 2 (TLR2). It is selective for the TLR2/TLR6 heterodimer over TLR2/TLR1 (EC50s = 0.015 and 4.12 ng/ml, respectively, in reporter assays using human receptors). Pam2CSK4 increases the levels of inducible nitric oxide synthase (iNOS) and the production of nitric oxide (NO) in RAW 264.7 macrophages when used at a concentration of 100 ng/ml. It stimulates osteoclast formation, induces gingival inflammation, and decreases alveolar bone mass in a mouse model of periodontitis when administered at a dose of 5 µg/animal.3 Pam2CSK4 (10 µg/vaccine), when used as an adjuvant, reduces parasite burden and enhances the response to antigen, as measured by IgG levels, in a mouse model of lymphatic filariasis induced by B. malayi.

Reference

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