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506350

Pam₃Cys-Ser-(Lys)4, Hydrochloride

≥90% (HPLC), lyophilized solid, TLR1/TLR2 agonist, Calbiochem®

別名:

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

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この商品について

実験式（ヒル表記法）:
C81H156N10O13S · 3HCl
CAS番号:
112208-00-1
分子量:
1619.61
MDL number:
MFCD06801383
UNSPSC Code:
51111800
NACRES:
NA.77
Assay:
≥90% (HPLC)
Form:
lyophilized solid
Storage condition:
OK to freeze, desiccated
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製品名

Pam₃Cys-Ser-(Lys)4, Hydrochloride,

assay

≥90% (HPLC)

Quality Segment

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

SMILES string

S(C[C@H](NC(=O)CCCCCCCCCCCCCCC)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)O)CC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC

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

Pam3CSK4 is a selective toll-like receptor 1/2 (TLR1/2) agonist used in the investigation of TLR1/2 function. It is a synthetic lipopeptide for TLR1/2 and mimics the acylated amino terminus of bacterial lipopeptides. Pam3CSK4, with its three lipid chains, facilitates receptor heterodimerization. The two ester-bound lipid chains are inserted into a pocket in TLR2, while the amide-bound lipid chain is inserted into a hydrophobic channel in TLR1. In the context of human uveitis, endophthalmitis, and experimental uveitis models, Pam3CSK4 triggers the expression and secretion of various cytokines and chemokines in intraocular fluids and/or tissues. 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.

Application

Pam₃Cys-Ser-(Lys)₄, Hydrochloride has been used to stimulate MODE-K cells to access its effects on epithelial neuropilin-1 (NRP1) protein expression. It has been used as a toll-like receptor 2 (TLR2) ligand to study TLR2 functionalities.

Preparation Note

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

Disclaimer

Toxicity: Standard Handling (A)

保管分類

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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