AdipoGen Life Sciences

Pam3Cys-Ser-(Lys)4 . 3HCl

CHF 480.00
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AG-CP3-0003-M0022 mgCHF 480.00
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Product Details
Synonyms Pam3Cys-Ser-(Lys)4 trihydrochloride; Pam3CSK4; Pam3Cys-SKKKK; (S)-[2,3-Bis(palmitoyloxy)-(2- RS)-propyl]-N-palmitoyl-(R)-Cys-(S)-Ser-(S)-Lys4-OH
Product Type Chemical
Properties
Formula

C81H156N10O13S . 3HCl

MW 1510.3 . 109.4
CAS 112208-04-5
Source/Host Chemicals Synthetic.
Purity Chemicals Absence of detectable protein or DNA contaminants with agonistic TLR activity.
Appearance Colorless powder.
Solubility Soluble in water, saline or aqueous buffers at pH <7.5.
Reconstitution Reconstitute in 2ml endotoxin-free water to get a 1mg/ml stock solution. Use a homogeniser or sonicator to prepare a homogenous solution.
Formulation Lyophilized.
Concentration 1mg/ml after reconstitution.
InChi Key ZRKOETJPZDQIFB-OQOFFOABSA-N
Smiles CCCCCCCCCCCCCCCC(=O)NC(CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)N[C@@H](CO)C(=O)C(=O)[C@H](CCCCN)NN[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(O)=O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice After reconstitution, prepare aliquots and store at -20°C.
Avoid freeze/thaw cycles.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Selective agonist of TLR1/TLR2 complex.
  • Cell permeable, water soluble synthetic cationic lipohexapeptide analog of the immunologically active N-terminal portion of bacterial lipoprotein that potently activates monocytes and macrophages.
  • Potent and effective immune adjuvant. Exerts strong local response, enhances IgG2a and IgG1 titers and upregulates proinflammatory and Th1 cytokine genes.
  • Potent activator of the proinflammatory transcription factor NF-κB.
Product References
  1. Lipopeptide derivatives of bacterial lipoprotein constitute potent immune adjuvants combined with or covalently coupled to antigen or hapten: A. Reitermann, et al.; Biol. Chem. Hoppe Seyler 370, 343 (1989)
  2. Induction of tumor cytotoxicity in murine bone marrow-derived macrophages by two synthetic lipopeptide analogues: P. Hoffmann, et al.; Biol. Chem. Hoppe Seyler 370, 575 (1989)
  3. Activation of superoxide formation and lysozyme release in human neutrophils by the synthetic lipopeptide Pam3Cys-Ser-(Lys)4. Involvement of guanine-nucleotide-binding proteins and synergism with chemotactic peptides: R. Seifert, et al.; Biochem. J. 267, 795 (1990)
  4. Synthesis of novel immunologically active tripalmitoyl-S-glycerylcysteinyl lipopeptides as useful intermediates for immunogen preparations: J. Metzger, et al.; Int. J. Pept. Protein Res. 37, 46 (1991)
  5. The influence of various adjuvants on antibody synthesis following immunization with an hapten: J. Kellner, et al.; Biol. Chem. Hoppe Seyler 373, 51 (1992)
  6. Lipopeptides are effective stimulators of tyrosine phosphorylation in human myeloid cells: S. Offermanns, et al.; Biochem. J. 282, 551 (1992)
  7. Comparison of adjuvant formulations for cytotoxic T cell induction using synthetic peptides: C.E. Hioe, et al.; Vaccine 14, 412 (1996)
  8. Cell Activation and Apoptosis by Bacterial Lipoproteins Through Toll-like Receptor-2: A.O. Aliprantis, et al.; Science 285, 736 (1999)
  9. Adjuvant effects of various lipopeptides and interferon-gamma on the humoral immune response of chickens: M.H. Erhard, et al.; Poult. Sci. 79, 1264 (2000)
  10. Immunostimulation by the synthetic lipopeptide P3CSK4: TLR4-independent activation of the ERK1/2 signal transduction pathway in macrophages: M.R. Muller, et al.; Immunology 103, 49 (2001)
  11. Lipopeptide structure determines TLR2 dependent cell activation level: U. Buwitt-Beckmann, et al.; FEBS J. 272, 6354 (2005)
  12. TLR1- and TLR6-independent recognition of bacterial lipopeptides: U. Buwitt-Beckmann, et al.; J. Biol. Chem. 281, 9049 (2006)
  13. Human Langerhans cells selectively activated via Toll-like receptor 2 agonists acquire migratory and CD4+T cell stimulatory capacity: M. Peiser, et al.; J. Leukoc. Biol. 83, 1118 (2008)
  14. Post-injury immunosuppression and secondary infections are caused by an AIM2 inflammasome-driven signaling cascade: S. Roth, et al.; Immunity 54, 648 (2021)
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