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Merck

506350

Pam₃Cys-Ser-(Lys)4, Hydrochloride

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

Synonyme(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

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A propos de cet article

Formule empirique (notation de Hill) :
C81H156N10O13S · 3HCl
Numéro CAS:
112208-00-1
Poids moléculaire :
1619.61
MDL number:
MFCD06801383
UNSPSC Code:
51111800
NACRES:
NA.77

Principaux documents

Voir toute la documentation
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Nom du produit

Pam₃Cys-Ser-(Lys)4, Hydrochloride,

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

assay

≥90% (HPLC)

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

Quality Level

100

Catégories apparentées

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.

Disclaimer

Toxicity: Standard Handling (A)

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.

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.

Preparation Note

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

Legal Information

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Dan-Ning Hu et al.
Experimental eye research, 239, 109749-109749 (2023-12-20)
Pam3CSK4 activates Toll-like receptors 2 and 1 (TLR1/2), which recognize mainly molecules from gram-positive pathogens. The effect of Pam3CSK4 on various cytokine and chemokine expression in cultured human uveal melanocytes (UM) has not been studied systematically. The purpose of this
Shikha Nayar et al.
Nature, 593(7858), 275-281 (2021-04-01)
Crohn's disease is a chronic inflammatory intestinal disease that is frequently accompanied by aberrant healing and stricturing complications. Crosstalk between activated myeloid and stromal cells is critical in the pathogenicity of Crohn's disease1,2, and increases in intravasating monocytes are correlated
Wenjie Zhu et al.
bioRxiv : the preprint server for biology (2024-05-07)
The ocular surface is a mucosal barrier tissue colonized by commensal microbes, which tune local immunity by eliciting IL-17 from conjunctival γδ T cells to prevent pathogenic infection. The commensal Corynebacterium mastitidis (C. mast) elicits protective IL-17 responses from conjunctival
Irina Balan et al.
Translational psychiatry, 11(1), 145-145 (2021-02-28)
We have shown that endogenous neurosteroids, including pregnenolone and 3α,5α-THP inhibit toll-like receptor 4 (TLR4) signal activation in mouse macrophages and the brain of alcohol-preferring (P) rat, which exhibits innate TLR4 signal activation. The current studies were designed to examine
Arpan Acharya et al.
Journal of virology (2020-12-18)
HIV persists in cellular reservoirs despite effective combined antiretroviral therapy (cART) and there is viremia flare up upon therapy interruption. Opioids modulate the immune system and suppress antiviral gene responses, which significantly impact people living with HIV (PLWH). However, the
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