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MedKoo Cat#: 464800 | Name: Pam2CSK4 TFA salt
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pam2CSK4 is a synthetic bacterial lipopeptide and an agonist of the toll-like receptor 2 (TLR2). It is selective for the TLR2/TLR6 heterodimer over TLR2/TLR1 (EC50s = 0.015 and 4.12 ng/ml, respectively, in reporter assays using human receptors). Pam2CSK4 increases the levels of inducible nitric oxide synthase (iNOS) and the production of nitric oxide (NO) in RAW 264.7 macrophages when used at a concentration of 100 ng/ml. It stimulates osteoclast formation, induces gingival inflammation, and decreases alveolar bone mass in a mouse model of periodontitis when administered at a dose of 5 µg/animal.3 Pam2CSK4 (10 µg/vaccine), when used as an adjuvant, reduces parasite burden and enhances the response to antigen, as measured by IgG levels, in a mouse model of lymphatic filariasis induced by B. malayi.

Chemical Structure

Pam2CSK4 TFA salt
Pam2CSK4 TFA salt
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 464800

Name: Pam2CSK4 TFA salt

CAS#: unknown

Chemical Formula: C67H127F3N10O14S

Exact Mass: 0.0000

Molecular Weight: 1385.86

Elemental Analysis: C, 58.07; H, 9.24; F, 4.11; N, 10.11; O, 16.16; S, 2.31

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 875.00 2 Weeks
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Related CAS #
No Data
Synonym
Pam2CSK4 TFA salt; Pam2-CSK4 TFA salt; Pam2 CSK4 TFA salt; Pam2Cys-Ser-(Lys)4;
IUPAC/Chemical Name
S-((R)-2,3-bis(palmitoyloxy)propyl)-L-cysteinyl-L-seryl-L-lysyl-L-lysyl-L-lysyl-L-lysine compound with 2,2,2-trifluoroacetic acid (1:1)
InChi Key
WUCKUXUWRPCGSL-WJRQQJDCSA-N
InChi Code
InChI=1S/C65H126N10O12S.C2HF3O2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-41-58(77)86-48-51(87-59(78)42-28-26-24-22-20-18-16-14-12-10-8-6-4-2)49-88-50-52(70)60(79)75-57(47-76)64(83)73-54(38-30-34-44-67)62(81)71-53(37-29-33-43-66)61(80)72-55(39-31-35-45-68)63(82)74-56(65(84)85)40-32-36-46-69;3-2(4,5)1(6)7/h51-57,76H,3-50,66-70H2,1-2H3,(H,71,81)(H,72,80)(H,73,83)(H,74,82)(H,75,79)(H,84,85);(H,6,7)/t51-,52+,53+,54+,55+,56+,57+;/m1./s1
SMILES Code
CCCCCCCCCCCCCCCC(OC[C@H](CSC[C@@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](CCCCN)C(O)=O)=O)CCCCN)=O)CCCCN)=O)CCCCN)=O)CO)=O)N)OC(CCCCCCCCCCCCCCC)=O)=O.OC(C(F)(F)F)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pam2CSK4 is a synthetic bacterial lipopeptide and an agonist of the toll-like receptor 2 (TLR2).
In vitro activity:
Pam2CSK4, but not FSL-1, induced platelet granule secretion and integrin αIIbβ3 activation in a concentration-dependent manner. Moreover, Pam2CSK4 promoted platelet aggregation and increased platelet adhesion to collagen-coated surfaces. Interestingly, Pam2CSK4 showed cooperation with immunoreceptor tyrosine-based activation motif (ITAM)-mediated signaling to enhance platelet activation. Finally, the presence of platelets increased inflammatory responses in HUVECs treated with Pam2CSK4, and platelets challenged with Pam2CSK4 showed increased adhesion to HUVECs under static and physiologically relevant flow conditions. Reference: Front Immunol. 2021 Aug 30;12:729951. https://pubmed.ncbi.nlm.nih.gov/34527000/
In vivo activity:
Treatment with either PAM2 (Pam2CSK4) or LPS induced gingival inflammation, as demonstrated by increased infiltration of inflammatory cells and enhanced angiogenesis, associated with a smaller number of fibroblasts and decreased extracellular matrix. Importantly, treatment not only with LPS but also with PAM2 resulted in a larger number of TRAP+ multinucleated osteoclasts and significant loss of alveolar bone. Collectively, these data demonstrate that PAM2 can induce gingival inflammation and bone loss in mice, broadening the avenues of investigation into the role of lipoproteins in the pathogenesis of periodontal disease. Reference: Braz Oral Res. 2020 Feb 10;34:e012. https://pubmed.ncbi.nlm.nih.gov/32049112/
Solvent mg/mL mM
Solubility
Acetic Acid (0.25%) 1.0 0.72
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,385.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Parra-Izquierdo I, Lakshmanan HHS, Melrose AR, Pang J, Zheng TJ, Jordan KR, Reitsma SE, McCarty OJT, Aslan JE. The Toll-Like Receptor 2 Ligand Pam2CSK4 Activates Platelet Nuclear Factor-κB and Bruton's Tyrosine Kinase Signaling to Promote Platelet-Endothelial Cell Interactions. Front Immunol. 2021 Aug 30;12:729951. doi: 10.3389/fimmu.2021.729951. PMID: 34527000; PMCID: PMC8435771. 2. Noh SY, Kang SS, Yun CH, Han SH. Lipoteichoic acid from Lactobacillus plantarum inhibits Pam2CSK4-induced IL-8 production in human intestinal epithelial cells. Mol Immunol. 2015 Mar;64(1):183-9. doi: 10.1016/j.molimm.2014.11.014. Epub 2014 Dec 4. PMID: 25481370. 3. Souza JAC, Magalhães FAC, Oliveira GJPL, DE Molon RS, Zuanon JA, Souza PPC. Pam2CSK4 (TLR2 agonist) induces periodontal destruction in mice. Braz Oral Res. 2020 Feb 10;34:e012. doi: 10.1590/1807-3107bor-2020.vol34.0012. PMID: 32049112. 4. Halliday A, Turner JD, Guimarães A, Bates PA, Taylor MJ. The TLR2/6 ligand PAM2CSK4 is a Th2 polarizing adjuvant in Leishmania major and Brugia malayi murine vaccine models. Parasit Vectors. 2016 Feb 20;9:96. doi: 10.1186/s13071-016-1381-0. PMID: 26897363; PMCID: PMC4761161.
In vitro protocol:
1. Parra-Izquierdo I, Lakshmanan HHS, Melrose AR, Pang J, Zheng TJ, Jordan KR, Reitsma SE, McCarty OJT, Aslan JE. The Toll-Like Receptor 2 Ligand Pam2CSK4 Activates Platelet Nuclear Factor-κB and Bruton's Tyrosine Kinase Signaling to Promote Platelet-Endothelial Cell Interactions. Front Immunol. 2021 Aug 30;12:729951. doi: 10.3389/fimmu.2021.729951. PMID: 34527000; PMCID: PMC8435771. 2. Noh SY, Kang SS, Yun CH, Han SH. Lipoteichoic acid from Lactobacillus plantarum inhibits Pam2CSK4-induced IL-8 production in human intestinal epithelial cells. Mol Immunol. 2015 Mar;64(1):183-9. doi: 10.1016/j.molimm.2014.11.014. Epub 2014 Dec 4. PMID: 25481370.
In vivo protocol:
1. Souza JAC, Magalhães FAC, Oliveira GJPL, DE Molon RS, Zuanon JA, Souza PPC. Pam2CSK4 (TLR2 agonist) induces periodontal destruction in mice. Braz Oral Res. 2020 Feb 10;34:e012. doi: 10.1590/1807-3107bor-2020.vol34.0012. PMID: 32049112. 2. Halliday A, Turner JD, Guimarães A, Bates PA, Taylor MJ. The TLR2/6 ligand PAM2CSK4 is a Th2 polarizing adjuvant in Leishmania major and Brugia malayi murine vaccine models. Parasit Vectors. 2016 Feb 20;9:96. doi: 10.1186/s13071-016-1381-0. PMID: 26897363; PMCID: PMC4761161.
1: Lagosz-Cwik KB, Wielento A, Lipska W, Kantorowicz M, Darczuk D, Kaczmarzyk T, Gibbs S, Potempa J, Grabiec AM. hTERT-immortalized gingival fibroblasts respond to cytokines but fail to mimic primary cell responses to Porphyromonas gingivalis. Sci Rep. 2021 May 24;11(1):10770. doi: 10.1038/s41598-021-90037-5. PMID: 34031466; PMCID: PMC8144196. 2: Natala SR, Habas A, Stocking EM, Orry A, Price DL, Gill MB, Bonhaus DW, Abagyan R, Wrasidlo W. Structure based design and synthesis of novel Toll-like Receptor 2 (TLR 2) lipid antagonists. Bioorg Med Chem Lett. 2021 May 15;40:127861. doi: 10.1016/j.bmcl.2021.127861. Epub 2021 Feb 23. PMID: 33636302. 3: Mai E, Percopo CM, Limkar AR, Sek AC, Ma M, Rosenberg HF. Respiratory Epithelial Cells Respond to Lactobacillus plantarum but Provide No Cross- Protection against Virus-Induced Inflammation. Viruses. 2020 Dec 22;13(1):2. doi: 10.3390/v13010002. PMID: 33374950; PMCID: PMC7821944. 4: Nakao M, Sugaya M, Fujita H, Miyagaki T, Morimura S, Shibata S, Asano Y, Sato S. TLR2 Deficiency Exacerbates Imiquimod-Induced Psoriasis-Like Skin Inflammation through Decrease in Regulatory T Cells and Impaired IL-10 Production. Int J Mol Sci. 2020 Nov 13;21(22):8560. doi: 10.3390/ijms21228560. PMID: 33202847; PMCID: PMC7696365. 5: Im J, Baik JE, Lee D, Park OJ, Park DH, Yun CH, Han SH. Bacterial Lipoproteins Induce BAFF Production via TLR2/MyD88/JNK Signaling Pathways in Dendritic Cells. Front Immunol. 2020 Oct 2;11:564699. doi: 10.3389/fimmu.2020.564699. PMID: 33123136; PMCID: PMC7566273. 6: Terheyden L, Roider J, Klettner A. Basolateral activation with TLR agonists induces polarized cytokine release and reduces barrier function in RPE in vitro. Graefes Arch Clin Exp Ophthalmol. 2021 Feb;259(2):413-424. doi: 10.1007/s00417-020-04930-2. Epub 2020 Sep 19. PMID: 32949301; PMCID: PMC7843481. 7: Wali S, Flores JR, Jaramillo AM, Goldblatt DL, Pantaleón García J, Tuvim MJ, Dickey BF, Evans SE. Immune Modulation to Improve Survival of Viral Pneumonia in Mice. Am J Respir Cell Mol Biol. 2020 Dec;63(6):758-766. doi: 10.1165/rcmb.2020-0241OC. PMID: 32853024; PMCID: PMC7790135. 8: Nogieć A, Bzowska M, Demczuk A, Varol C, Guzik K. Phenotype and Response to PAMPs of Human Monocyte-Derived Foam Cells Obtained by Long-Term Culture in the Presence of oxLDLs. Front Immunol. 2020 Aug 4;11:1592. doi: 10.3389/fimmu.2020.01592. PMID: 32849539; PMCID: PMC7417357. 9: Karlis GD, Schöningh E, Jansen IDC, Schoenmaker T, Hogervorst JMA, van Veen HA, Moonen CGJ, Łagosz-Ćwik KB, Forouzanfar T, de Vries TJ. Chronic Exposure of Gingival Fibroblasts to TLR2 or TLR4 Agonist Inhibits Osteoclastogenesis but Does Not Affect Osteogenesis. Front Immunol. 2020 Jul 23;11:1693. doi: 10.3389/fimmu.2020.01693. PMID: 32793243; PMCID: PMC7390923. 10: Dietrich L, Lucius R, Roider J, Klettner A. Interaction of inflammatorily activated retinal pigment epithelium with retinal microglia and neuronal cells. Exp Eye Res. 2020 Oct;199:108167. doi: 10.1016/j.exer.2020.108167. Epub 2020 Jul 28. PMID: 32735798. 11: McLeod J , Park C , Cunningham A , O'Donnell L , Brown RS , Kelly F , She Z . Developing a toll-like receptor biosensor for Gram-positive bacterial detection and its storage strategies. Analyst. 2020 Sep 14;145(18):6024-6031. doi: 10.1039/d0an01050b. PMID: 32724992. 12: Evans SE, Tseng CK, Scott BL, Höök AM, Dickey BF. Inducible Epithelial Resistance against Coronavirus Pneumonia in Mice. Am J Respir Cell Mol Biol. 2020 Oct;63(4):540-541. doi: 10.1165/rcmb.2020-0247LE. PMID: 32706609; PMCID: PMC7528913. 13: Deak P, Kimani F, Cassaidy B, Esser-Kahn A. Determining Whether Agonist Density or Agonist Number Is More Important for Immune Activation via Micoparticle Based Assay. Front Immunol. 2020 Apr 9;11:642. doi: 10.3389/fimmu.2020.00642. PMID: 32328073; PMCID: PMC7161694. 14: Grabowski M, Bermudez M, Rudolf T, Šribar D, Varga P, Murgueitio MS, Wolber G, Rademann J, Weindl G. Identification and validation of a novel dual small- molecule TLR2/8 antagonist. Biochem Pharmacol. 2020 Jul;177:113957. doi: 10.1016/j.bcp.2020.113957. Epub 2020 Apr 5. PMID: 32268138. 15: Souza JAC, Magalhães FAC, Oliveira GJPL, DE Molon RS, Zuanon JA, Souza PPC. Pam2CSK4 (TLR2 agonist) induces periodontal destruction in mice. Braz Oral Res. 2020 Feb 10;34:e012. doi: 10.1590/1807-3107bor-2020.vol34.0012. PMID: 32049112. 16: Goldblatt DL, Flores JR, Valverde Ha G, Jaramillo AM, Tkachman S, Kirkpatrick CT, Wali S, Hernandez B, Ost DE, Scott BL, Chen J, Evans SE, Tuvim MJ, Dickey BF. Inducible epithelial resistance against acute Sendai virus infection prevents chronic asthma-like lung disease in mice. Br J Pharmacol. 2020 May;177(10):2256-2273. doi: 10.1111/bph.14977. Epub 2020 Feb 12. PMID: 31968123; PMCID: PMC7174884. 17: Pacentra A, Grasselli F, Bussolati S, Grolli S, Di Lecce R, Cantoni AM, Basini G. The effect of pathogen-associated molecular patterns on the swine granulosa cells. Theriogenology. 2020 Mar 15;145:207-216. doi: 10.1016/j.theriogenology.2019.10.026. Epub 2019 Oct 31. PMID: 31761538. 18: Sharma N, Drobinski P, Kayed A, Chen Z, Kjelgaard-Petersen CF, Gantzel T, Karsdal MA, Michaelis M, Ladel C, Bay-Jensen AC, Lindemann S, Thudium CS. Inflammation and joint destruction may be linked to the generation of cartilage metabolites of ADAMTS-5 through activation of toll-like receptors. Osteoarthritis Cartilage. 2020 May;28(5):658-668. doi: 10.1016/j.joca.2019.11.002. Epub 2019 Nov 14. PMID: 31734268. 19: Ben-David H, Livneh A, Lidar M, Feld O, Haj Yahia S, Grossman C, Ben-Zvi I. Toll-like receptor 2 is overexpressed in Familial Mediterranean fever patients and is inhibited by colchicine treatment. Best Pract Res Clin Rheumatol. 2018 Oct;32(5):651-661. doi: 10.1016/j.berh.2019.01.012. Epub 2019 Feb 19. PMID: 31203923. 20: Souza PPC, Lundberg P, Lundgren I, Magalhães FAC, Costa-Neto CM, Lerner UH. Activation of Toll-like receptor 2 induces B1 and B2 kinin receptors in human gingival fibroblasts and in mouse gingiva. Sci Rep. 2019 Feb 27;9(1):2973. doi: 10.1038/s41598-018-37777-z. PMID: 30814538; PMCID: PMC6393418.

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