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Sigma-Aldrich

Pam₃Cys-Ser-(Lys)₄, Hydrochloride

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Synonym(s):
Pam₃Cys-Ser-(Lys)₄, Hydrochloride, (S)-[2,3-Bis(palmitoyloxy)-(2-RS)-propyl]-N-palmitoyl-(R)-Cys-(S)-Ser-(S)-Lys₄-OH, 3HCl, P₃CSK₄, 3HCl, Pam₃Cys-SK₄, 3HCl, Pam3CSK4, TLR1/TLR2 Agonist I
Empirical Formula (Hill Notation):
C81H156N10O13S · 3HCl
CAS Number:
112208-00-1
Molecular Weight:
1619.61

Assay

≥90% (HPLC)

Quality Level

100

form

lyophilized solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated

solubility

water: 2 mg/mL

shipped in

wet ice

storage temp.

−20°C

InChI

1S/C81H156N10O13S/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-55-73(93)86-72(65-105-64-66(104-75(95)57-42-39-36-33-30-27-24-21-18-15-12-9-6-3)63-103-74(94)56-41-38-35-32-29-26-23-20-17-14-11-8-5-2)80(100)91-71(62-92)79(99)89-68(52-44-48-59-83)77(97)87-67(51-43-47-58-82)76(96)88-69(53-45-49-60-84)78(98)90-70(81(101)102)54-46-50-61-85/h66-72,92H,4-65,82-85H2,1-3H3,(H,86,93)(H,87,97)(H,88,96)(H,89,99)(H,90,98)(H,91,100)(H,101,102)/t66?,67-,68-,69-,70-,71-,72-/m0/s1

InChI key

OEDPHAKKZGDBEV-GFPBKZJXSA-N

General description

A cell-permeable, water-soluble synthetic cationic lipohexapeptide analog of the immunologically active N-terminal portion of bacterial lipoprotein that potently activates monocytes and macrophages. Induces the release of IL-1, IL-6, TNF-α, superoxide, and NO. Promotes the translocation of NF-κB, enhances tyrosine protein phosphorylation and activation of ERK1/2 and MEK1/2. Acts as a selective agonist of TLR2 (Toll-like receptor 2).
A cell-permeable, water-soluble, synthetic, cationic lipohexapeptide analog of the immunologically active N-terminal portion of bacterial lipoprotein that potently activates monocytes and macrophages. Induces the release of IL-1, IL-6, TNF-α, superoxide and NO. Promotes the translocation of NF-κB, enhances tyrosine protein phosphorylation, and activates ERK1/2 and MEK1/2. Acts as a selective TLR-2 (Toll-like receptor 2) agonist.

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Avoid freeze/thaw cycles of solutions.

Other Notes

Barrenschee, M., et al. 2010. PLoS One.5, e13889.
Zahringer, U., et al. 2008. Immunology.213, 205.
Toshchakov, V., et al. 2002. Nat. Immunol.3, 392.
Muller, M.R., et al. 2001. Immunology103, 49.
Vergne, I., and Cezanne, L. 1999. Eur. J. Biochem.264, 369.
Diaz-Guerra, M.J., et al. 1996. J. Biol. Chem.271, 30114.
Offermanns, S., et al. 1992. Biochem. J.282, 551.
Seifert, R., et al. 1990. Biochem. J.267, 795.
Hoffmann, P., et al. 1989. Biol. Chem. Hoppe. Seyler.370, 575.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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