A bacterial lipopeptide and TLR2 agonist
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Pam2CSK4 (trifluoroacetate salt)

Item No. 33338

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
S-[(2R)-2,3-bis[(1-oxohexadecyl)oxy]propyl]-L-cysteinyl-L-seryl-L-lysyl-L-lysyl-L-lysyl-L-lysine, trifluoroacetate salt
Synonyms
  • Pam2Cys-Ser-(Lys)4
Molecular Formula
C65H126N10O12S • XCF3COOH
Formula Weight
1271.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetic Acid (0.25%): 1 mg/ml
SMILES
CCCCCCCCCCCCCCCC(OC[C@@H](OC(CCCCCCCCCCCCCCC)=O)CSC[C@H](N)C(N[C@@H](CO)C(N[C@@H](CCCCN)C(N[C@@H](CCCCN)C(N[C@@H](CCCCN)C(N[C@H](C(O)=O)CCCCN)=O)=O)=O)=O)=O)=O.OC(C(F)(F)F)=O
InChi Code
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
InChi Key
WUCKUXUWRPCGSL-WJRQQJDCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Pam2CSK4 is a synthetic bacterial lipopeptide and an agonist of the toll-like receptor 2 (TLR2).1 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.2 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.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Irvine, K.L., Hopkins, L.J., Gangloff, M., et al. The molecular basis for recognition of bacterial ligands at equine TLR2, TLR1 and TLR6. Vet. Res. 44(1), 50 (2013).

    2. Kulsantiwong, P., Pudla, M., Srisaowakarn, C., et al. Pam2CSK4 and Pam3CSK4 induce iNOS expression via TBK1 and MyD88 molecules in mouse macrophage cell line RAW264.7. Inflamm. Res. 66(10), 843-853 (2017).

    3. de Souza, J.A.C., Magalháes, F.A.C., de Oliveira, G.J.P.L., et al. Pam2CSK4 (TLR2 agonist) induces periodontal destruction in mice. Braz. Oral. Res. 34, e012 (2020).

    4. Halliday, A., Turner, J.D., Guimarães, A., et al. The TLR2/6 ligand PAM2CSK4 is a Th2 polarizing adjuvant in Leishmania major and Brugia malayi murine vaccine models. Parasit. Vectors 9, 96 (2016).