Art. -Nr.: HY-165613

Pam2Cys

(Synonyms: Dipalmitoyl-S-glyceryl-cysteine; S-[2,3-Bis(palmitoyloxy)propyl]cysteine)

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Pam2Cys (Dipalmitoyl-S-glyceryl-cysteine; S-[2,3-Bis(palmitoyloxy)propyl]cysteine) is a TLR2 agonist and immunostimulant. Pam2Cys binds to TLR2 to activate dendritic cells and trigger the TLR2-dependent NF-κB signaling pathway. Pam2Cys also induces dendritic cell maturation by upregulating the expression of cell surface MHC II molecules. Pam2Cys activates innate immune signaling pathways, drives pro-inflammatory and antimicrobial responses, enhances the expression of macrophage activation markers, increases phagocytic activity, induces the release of IL-12 and pro-inflammatory cytokines, and polarizes macrophages into a pro-inflammatory, antimicrobial phenotype without interfering with IL-10-induced macrophage polarization. Pam2Cys also serves as the lipid moiety in synthetic lipopeptide vaccines and possesses self-adjuvant properties. Pam2Cys enhances the immunogenicity of conjugated peptide segments and induces cellular and humoral immune responses. However, it does not activate CD4 T cells in mouse splenocyte cultures when used alone. Pam2Cys activates pulmonary TLR2 signaling pathways, triggers innate immune responses, recruits neutrophils and macrophages, induces the secretion of various cytokines, alleviates symptoms and damages associated with influenza A virus infection in mice without impairing adaptive immunity. Pam2Cys can be used in studies related to tuberculosis and influenza A virus infection.

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Reinheit: 99.82%
CAS. Nr.: 656831-18-4
Formel: C₃₈H₇₃NO₆S
Molecular Weight:672.05

Speicherung:

Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

Pam2Cys Chemical Structure

CAS. Nr.: 656831-18-4

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

TLR2

Alle Toll-like Receptor (TLR) Isoform-spezifische Produkte anzeigen :

Alle NF-κB Isoform-spezifische Produkte anzeigen :

In Vitro

The Pam2Cys-containing lipopeptide construct (0.025-0.25 nmol/mL; 5 h) potently activates NF-κB signaling through TLR2 in HEK293 cells^[1].
Pam2Cys (10-100 ng/mL; 24 h) increases the phagocytic activity of porcine monocyte-derived macrophages, with a stronger effect at the higher dose^[2].
Pam2Cys (10-100 ng/mL; 4 h, 8 h, 24 h) upregulates the gene expression of IL-1β, IL-6, TNF-α, and IL-12p40 at 4, 8, and 24 h, and IL-10 at 4 and 8 h, in porcine monocyte-derived macrophages^[2].
Pam2Cys (10-100 ng/mL; 4 h, 8 h, 24 h) upregulates the gene expression of multiple IFN-α subtypes (IFN-α1, IFN-α2, IFN-α5/6, IFN-α9 at 8 h; IFN-α16 at 24 h), downregulates IFN-α3 at 24 h, and does not alter IFN-β expression, in porcine monocyte-derived macrophages^[2].
Pam2Cys (10-100 ng/mL; 4 h, 8 h, 24 h) downregulates the gene expression of TLR3, TLR4, TLR5, TLR7, TLR8, and TLR9 in porcine monocyte-derived macrophages at multiple time points (4, 8, 24 h) post-treatment^[2].
Pam2Cys (50-100 ng/mL; 72 h) alone does not activate CD4 T cells from L91-immunized mice^[3].
Pam2Cys (10 nmol; 24 h) induced primary mouse lung cells to exhibit significantly elevated levels of IL-6, IL-10, MCP-1, IFN-γ, and TNF-α, with no change in IFN-α levels^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Real Time qPCR^[2]

Cell Line:

porcine monocyte-derived macrophages
Concentration:

10-100 ng/mL
Incubation Time:

4 h, 8 h, 24 h
Result:

Upregulated the gene expression of multiple IFN-α subtypes (IFN-α1, IFN-α2, IFN-α5/6, IFN-α9 at 8 h; IFN-α16 at 24 h), downregulates IFN-α3 at 24 h, and does not alter IFN-β expression.
Upregulated the gene expression of IL-1β, IL-6, TNF-α, and IL-12p40 at 4, 8, and 24 h, and IL-10 at 4 and 8 h.
Downregulated the gene expression of TLR3, TLR4, TLR5, TLR7, TLR8, and TLR9 in porcine monocyte-derived macrophages at multiple time points (4, 8, 24 h) post-treatment

In Vivo

Pam2Cys-containing lipopeptide vaccine (40 nmol; s.c.; 2 doses (days 0 and 28)) induces strong anti-LHRH antibody titres and renders 100% of treated female BALB/c mice infertile^[1].
Immunization with the Pam2Cys-conjugated construct L91 (20-10 nmol per animal; i.p. or s.c., i.p.) induces Th1-skewed dendritic cell activation, robust and enduring CD4 T-cell memory responses, and significantly better protection against Mycobacterium tuberculosis aerosol challenge in mice than BCG, with a 40% reduction in lung bacterial burden relative to BCG^[3].
Pam2Cys (20 nmol; i.n.; single dose) provides dose-dependent viral load reduction of up to 88% in mice challenged with mild IAV, with efficacy persisting for at least 7 days post-administration^[4].
Pam2Cys (20 nmol; i.n.; single dose) prophylaxis preserves the development of functional, memory-phenotype IAV-specific CD8⁺ T cells in mice, with enhanced responses in the spleen and reduced but detectable responses in the lungs^[4].
Pam2Cys (20 nmol; i.n.; single dose) reduces IAV viral load by over 99% in the trachea and lungs of BALB/c mice, with no effect on nasal turbinate infection^[4].
Pam2Cys (20 nmol; i.n.; single dose) provides TLR2-dependent, type 1 interferon-independent protection against virulent IAV in mice, with 92% survival and significant weight loss reduction^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

BALB/c mice with Influenza A virus infection (male and female, 6-12 weeks old)^[4]
Dosage:

20 nmol
Administration:

i.n.; single dose
Result:

Reduced viral titers by 99.4% in the trachea and 99.91% in the lungs relative to saline-treated controls; no reduction was observed in nasal turbinates.
Virus was undetectable in 7 of 11 treated mice’s lungs.\nReduced viral loads by 10-100-fold across nasal turbinates, trachea, and lungs in donor mice relative to saline-treated donors.
Completely prevented transmission to naive recipients when donors were treated 24 or 72 hours prior to challenge; reduced but did not eliminate transmission when donors were treated 5 or 7 days prior to challenge.

Animal Model:

C57BL/6 mice with Innate immune activation (male and female, 6-12 weeks old); TLR2-deficient (TLR2−/−) on C57BL/6 background (male and female, 6-12 weeks old); BALB/c (male and female, 6-12 weeks old)^[4]
Dosage:

20 nmol
Administration:

i.n.; single dose
Result:

Elevated BAL fluid levels of IL-6, IL-10, MCP-1, IFN-γ, and TNF-α significantly, and increased lung populations of neutrophils, interstitial macrophages, alveolar macrophages, lymphocytes, γδ T cells, and activated IFN-γ-producing NK cells significantly in C57BL/6 and BALB/c mice at 72 hours post-administration.
Returned cytokine levels and most innate cell populations to baseline by day 7, but lymphocyte counts remained elevated.
Observed no cytokine or cell population changes in TLR2−/− mice.

Chemical Information

CAS. Nr. 656831-18-4
Appearance Solid
Molecular Weight 672.05
Formel C₃₈H₇₃NO₆S
Color White to off-white
SMILES

O=C([C@@H](N)CSCC(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O)O
Synonyms

Dipalmitoyl-S-glyceryl-cysteine; S-[2,3-Bis(palmitoyloxy)propyl]cysteine
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Lösungsmittel & Löslichkeit

In Vitro:

DMF : 3.33 mg/mL (4.95 mM; ultrasonic and warming and adjust pH to 4 with 1 M HCl and heat to 60°C)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

1.4880 mL

7.4399 mL

14.8798 mL

5 mM

---

10 mM

---

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (275 KB)
SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Zeng W, et al. Structural requirement for the agonist activity of the TLR2 ligand Pam2Cys. Amino Acids. 2010;39(2):471-480. [Content Brief]

[2]. Franzoni G, et al. Targeting Toll-Like Receptor 2: Polarization of Porcine Macrophages by a Mycoplasma-Derived Pam2cys Lipopeptide. Vaccines (Basel). 2021;9(7):692. Published 2021 Jun 23. [Content Brief]

[3]. Gowthaman U, et al. Promiscuous peptide of 16 kDa antigen linked to Pam2Cys protects against Mycobacterium tuberculosis by evoking enduring memory T-cell response. J Infect Dis. 2011;204(9):1328-1338. [Content Brief]

[4]. Tan AC, et al. Intranasal administration of the TLR2 agonist Pam2Cys provides rapid protection against influenza in mice. Mol Pharm. 2012;9(9):2710-2718. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMF	1 mM	1.4880 mL	7.4399 mL	14.8798 mL	37.1996 mL

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Pam2Cys

Anti-Infection Compound Library

Immunology/Inflammation Compound Library

NF-κB Signaling Compound Library

Stem Cell Signaling Compound Library

Antiviral Compound Library

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Pyroptosis Compound Library

Anti-Breast Cancer Compound Library

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Transcription Factor-Targeted Library

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Pattern Recognition Receptors Library

Lactylation Compound Library

Alle Toll-like Receptor (TLR) Isoform-spezifische Produkte anzeigen

Alle NF-κB Isoform-spezifische Produkte anzeigen