MedKoo Cat#: 556353 | Name: Pam2Cys HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pam2Cys is a novel TLR2 agonist as potential adjuvant for cancer vaccines. Pam2Cys is a synthetic lipopeptide that mimics bacterial lipoproteins and is often used in immunological research. Here's a bit more detail: It has two palmitic acid chains and is part of the Toll-like receptor (TLR) ligand family. Pam2Cys primarily activates TLR2/6 heterodimers on immune cells, leading to the production of pro-inflammatory cytokines. This makes it a potent tool for studying innate immunity, vaccine adjuvants, and inflammatory signaling pathways. Pam2Cys enhances immune responses to co-administered antigen.

Chemical Structure

Pam2Cys HCl
Pam2Cys HCl
CAS#Pam2Cys HCl

Theoretical Analysis

MedKoo Cat#: 556353

Name: Pam2Cys HCl

CAS#: Pam2Cys HCl

Chemical Formula: C38H73NO6S

Exact Mass: 671.5159

Molecular Weight: 672.06

Elemental Analysis: C, 67.91; H, 10.95; N, 2.08; O, 14.28; S, 4.77

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Pam2Cys; Pam2 Cys; Pam2-Cys; Pam2Cys; dipalmitoyl-S-glyceryl cysteine.
IUPAC/Chemical Name
S-(2,3-bis(palmitoyloxy)propyl)-L-cysteine
InChi Key
UPAQRWMRKQCLSD-HTIIIDOHSA-N
InChi Code
InChI=1S/C38H73NO6S/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)44-31-34(32-46-33-35(39)38(42)43)45-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35H,3-33,39H2,1-2H3,(H,42,43)/t34?,35-/m0/s1
SMILES Code
CCCCCCCCCCCCCCCC(=O)OCC(CSC[C@@H](C(=O)O)N)OC(=O)CCCCCCCCCCCCCCC
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 672.06 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Franzoni G, Anfossi A, De Ciucis CG, Mecocci S, Carta T, Dei Giudici S, Fruscione F, Zinellu S, Vito G, Graham SP, Oggiano A, Chessa B, Razzuoli E. Targeting Toll-Like Receptor 2: Polarization of Porcine Macrophages by a Mycoplasma-Derived Pam2cys Lipopeptide. Vaccines (Basel). 2021 Jun 23;9(7):692. doi: 10.3390/vaccines9070692. PMID: 34201691; PMCID: PMC8310132. 2: Mifsud EJ, Tan AC, Reading PC, Jackson DC. Mapping the pulmonary environment of animals protected from virulent H1N1 influenza infection using the TLR-2 agonist Pam₂Cys. Immunol Cell Biol. 2016 Feb;94(2):169-76. doi: 10.1038/icb.2015.81. Epub 2015 Aug 14. PMID: 26272554. 3: Mifsud EJ, Tan AC, Brown LE, Chua BY, Jackson DC. Generation of Adaptive Immune Responses Following Influenza Virus Challenge is Not Compromised by Pre- Treatment with the TLR-2 Agonist Pam2Cys. Front Immunol. 2015 Jun 5;6:290. doi: 10.3389/fimmu.2015.00290. PMID: 26097481; PMCID: PMC4457020. 4: Tan AC, Mifsud EJ, Zeng W, Edenborough K, McVernon J, Brown LE, Jackson DC. Intranasal administration of the TLR2 agonist Pam2Cys provides rapid protection against influenza in mice. Mol Pharm. 2012 Sep 4;9(9):2710-8. doi: 10.1021/mp300257x. Epub 2012 Aug 3. PMID: 22823162. 5: Thomann JS, Monneaux F, Creusat G, Spanedda MV, Heurtault B, Habermacher C, Schuber F, Bourel-Bonnet L, Frisch B. Novel glycolipid TLR2 ligands of the type Pam2Cys-α-Gal: synthesis and biological properties. Eur J Med Chem. 2012 May;51:174-83. doi: 10.1016/j.ejmech.2012.02.039. Epub 2012 Mar 21. PMID: 22483966. 6: Gowthaman U, Singh V, Zeng W, Jain S, Siddiqui KF, Chodisetti SB, Gurram RK, Parihar P, Gupta P, Gupta UD, Jackson DC, Agrewala JN. Promiscuous peptide of 16 kDa antigen linked to Pam2Cys protects against Mycobacterium tuberculosis by evoking enduring memory T-cell response. J Infect Dis. 2011 Nov;204(9):1328-38. doi: 10.1093/infdis/jir548. Epub 2011 Sep 20. PMID: 21933875. 7: Zeng W, Eriksson E, Chua B, Grollo L, Jackson DC. Structural requirement for the agonist activity of the TLR2 ligand Pam2Cys. Amino Acids. 2010 Jul;39(2):471-80. doi: 10.1007/s00726-009-0463-0. Epub 2010 Jan 21. PMID: 20091415.