Pam3CSK4 HCl
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581007

CAS#: 112208-00-1

Description: Pam3CSK4 is a TLR1/2 agonist. Pretreatment of Pam3CSK4 attenuates inflammatory responses caused by systemic infection of methicillin-resistant Staphylococcus aureus in mice. Combination of poly I:C and Pam3CSK4 enhances activation of B cells in vitro and boosts antibody responses to protein vaccines in vivo.


Price and Availability

Size
Price

2mg
USD 480
Size
Price

Size
Price

Pam3CSK4 HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 581007
Name: Pam3CSK4 HCl
CAS#: 112208-00-1
Chemical Formula: C81H159Cl3N10O13S
Exact Mass:
Molecular Weight: 1619.63
Elemental Analysis: C, 60.07; H, 9.90; Cl, 6.57; N, 8.65; O, 12.84; S, 1.98


Synonym: Pam3CSK4; Pam3CSK4 HCl; Palmitoyl-Cys((RS)-2,3-di(palmitoyloxy)-propyl)-Ser-Lys-Lys-Lys-Lys-OH, Pam3CSK4 | Pam3-Cys-Ser-Lys-Lys-Lys-Lys

IUPAC/Chemical Name: Palmitoyl-Cys((RS)-2,3-di(palmitoyloxy)-propyl)-Ser-Lys-Lys-Lys-Lys-OH trihydrochloride

InChi Key: LBBMJOSYFJWKTM-PXSLIBMESA-N

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

SMILES Code: O=C(N[C@@H](CCCCN)C(N[C@@H](CCCCN)C(N[C@@H](CCCCN)C(N[C@@H](CCCCN)C(O)=O)=O)=O)=O)[C@H](CO)N(C([C@@H](NC(CCCCCCCCCCCCCCC)=O)CS)=O)CC(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O.[H]Cl.[H]Cl.[H]Cl


Technical Data

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:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Frans G, van der Werff Ten Bosch J, Moens L, Gijsbers R, Changi-Ashtiani M, Rokni-Zadeh H, Shahrooei M, Wuyts G, Meyts I, Bossuyt X. Functional Evaluation of an IKBKG Variant Suspected to Cause Immunodeficiency Without Ectodermal Dysplasia. J Clin Immunol. 2017 Oct 10. doi: 10.1007/s10875-017-0448-9. [Epub ahead of print] PubMed PMID: 28993958.

2: Andrukhov O, Hong JS, Andrukhova O, Blufstein A, Moritz A, Rausch-Fan X. Response of human periodontal ligament stem cells to IFN-γ and TLR-agonists. Sci Rep. 2017 Oct 9;7(1):12856. doi: 10.1038/s41598-017-12480-7. PubMed PMID: 28993635.

3: Chen S, Ge L, Gombart AF, Shuler FD, Carlson MA, Reilly DA, Xie J. Nanofiber-based sutures induce endogenous antimicrobial peptide. Nanomedicine (Lond). 2017 Sep 29. doi: 10.2217/nnm-2017-0161. [Epub ahead of print] PubMed PMID: 28960168.

4: Meyer V, Saccone DS, Tugizimana F, Asani FF, Jeffery TJ, Bornman L. Methylation of the Vitamin D Receptor (VDR) Gene, Together with Genetic Variation, Race, and Environment Influence the Signaling Efficacy of the Toll-Like Receptor 2/1-VDR Pathway. Front Immunol. 2017 Sep 11;8:1048. doi: 10.3389/fimmu.2017.01048. eCollection 2017. PubMed PMID: 28959253; PubMed Central PMCID: PMC5603903.

5: Huang Z, Yi X, Chen Y, Hou X, Wang X, Zhu P, Zhao K, Wu S, Fu N, Liu B. Pretreatment of Pam3CSK4 attenuates inflammatory responses caused by systemic infection of methicillin-resistant Staphylococcus aureus in mice. Biomed Pharmacother. 2017 Sep 23;95:1684-1692. doi: 10.1016/j.biopha.2017.09.058. [Epub ahead of print] PubMed PMID: 28954388.

6: Phelps D, Brinkman NE, Keely SP, Anneken EM, Catron TR, Betancourt D, Wood CE, Espenschied ST, Rawls JF, Tal T. Microbial colonization is required for normal neurobehavioral development in zebrafish. Sci Rep. 2017 Sep 11;7(1):11244. doi: 10.1038/s41598-017-10517-5. PubMed PMID: 28894128; PubMed Central PMCID: PMC5593827.

7: Pudla M, Kulsantiwong P, Srisaowakarn C, Utaisincharoen P. Regulation of sterile α- and armadillo motif (SARM) containing protein expression in Pam2CSK4- and Pam3CSK4-activated mouse macrophage cell line (RAW264.7) requires TLR9. Inflamm Res. 2017 Sep 9. doi: 10.1007/s00011-017-1090-y. [Epub ahead of print] PubMed PMID: 28889202.

8: Makkawi H, Hoch S, Burns E, Hosur K, Hajishengallis G, Kirschning CJ, Nussbaum G. Porphyromonas gingivalis Stimulates TLR2-PI3K Signaling to Escape Immune Clearance and Induce Bone Resorption Independently of MyD88. Front Cell Infect Microbiol. 2017 Aug 8;7:359. doi: 10.3389/fcimb.2017.00359. eCollection 2017. PubMed PMID: 28848717; PubMed Central PMCID: PMC5550410.

9: Kim YJ, Deok J, Kim S, Yoon DH, Sung GH, Aravinthan A, Lee S, Lee MN, Hong S, Kim JH, Son YJ, Cho JY. Anti-Inflammatory Effect of Piper attenuatum Methanol Extract in LPS-Stimulated Inflammatory Responses. Evid Based Complement Alternat Med. 2017;2017:4606459. doi: 10.1155/2017/4606459. Epub 2017 Jul 25. PubMed PMID: 28811826; PubMed Central PMCID: PMC5547706.

10: Zhou ZQ, Tong DN, Guan J, Li MF, Feng QM, Zhou MJ, Zhang ZY. Circulating follicular helper T cells presented distinctively different responses toward bacterial antigens in primary biliary cholangitis. Int Immunopharmacol. 2017 Oct;51:76-81. doi: 10.1016/j.intimp.2017.08.004. Epub 2017 Aug 12. PubMed PMID: 28806642.

11: Dong X, Zhang Z, Meng S, Pan C, Yang M, Wu X, Yang L, Xu H. Parental exposure to bisphenol A and its analogs influences zebrafish offspring immunity. Sci Total Environ. 2018 Jan 1;610-611:291-297. doi: 10.1016/j.scitotenv.2017.08.057. Epub 2017 Aug 11. PubMed PMID: 28806546.

12: Jongstra-Bilen J, Zhang CX, Wisnicki T, Li MK, White-Alfred S, Ilaalagan R, Ferri DM, Deonarain A, Wan MH, Hyduk SJ, Cummins CL, Cybulsky MI. Oxidized Low-Density Lipoprotein Loading of Macrophages Downregulates TLR-Induced Proinflammatory Responses in a Gene-Specific and Temporal Manner through Transcriptional Control. J Immunol. 2017 Sep 15;199(6):2149-2157. doi: 10.4049/jimmunol.1601363. Epub 2017 Aug 7. PubMed PMID: 28784845.

13: Hally KE, La Flamme AC, Larsen PD, Harding SA. Platelet Toll-like receptor (TLR) expression and TLR-mediated platelet activation in acute myocardial infarction. Thromb Res. 2017 Aug 1;158:8-15. doi: 10.1016/j.thromres.2017.07.031. [Epub ahead of print] PubMed PMID: 28783513.

14: Pierzchalska M, Panek M, Czyrnek M, Gielicz A, Mickowska B, Grabacka M. Probiotic Lactobacillus acidophilus bacteria or synthetic TLR2 agonist boost the growth of chicken embryo intestinal organoids in cultures comprising epithelial cells and myofibroblasts. Comp Immunol Microbiol Infect Dis. 2017 Aug;53:7-18. doi: 10.1016/j.cimid.2017.06.002. Epub 2017 Jun 21. PubMed PMID: 28750869.

15: Murgueitio MS, Ebner S, Hörtnagl P, Rakers C, Bruckner R, Henneke P, Wolber G, Santos-Sierra S. Enhanced immunostimulatory activity of in silico discovered agonists of Toll-like receptor 2 (TLR2). Biochim Biophys Acta. 2017 Nov;1861(11 Pt A):2680-2689. doi: 10.1016/j.bbagen.2017.07.011. Epub 2017 Jul 19. PubMed PMID: 28734965.

16: Prantner D, Shirey KA, Lai W, Lu W, Cole AM, Vogel SN, Garzino-Demo A. The θ-defensin retrocyclin 101 inhibits TLR4- and TLR2-dependent signaling and protects mice against influenza infection. J Leukoc Biol. 2017 Oct;102(4):1103-1113. doi: 10.1189/jlb.2A1215-567RR. Epub 2017 Jul 20. PubMed PMID: 28729359; PubMed Central PMCID: PMC5597516.

17: Hou A, Tin MQ, Tong L. Toll-like receptor 2-mediated NF-kappa B pathway activation in ocular surface epithelial cells. Eye Vis (Lond). 2017 Jul 11;4:17. doi: 10.1186/s40662-017-0082-x. eCollection 2017. PubMed PMID: 28706958; PubMed Central PMCID: PMC5506675.

18: Weir GM, Karkada M, Hoskin D, Stanford MM, MacDonald L, Mansour M, Liwski RS. Combination of poly I:C and Pam3CSK4 enhances activation of B cells in vitro and boosts antibody responses to protein vaccines in vivo. PLoS One. 2017 Jun 29;12(6):e0180073. doi: 10.1371/journal.pone.0180073. eCollection 2017. PubMed PMID: 28662082; PubMed Central PMCID: PMC5491120.

19: Sanui T, Takeshita M, Fukuda T, Tanaka U, Alshargabi R, Aida Y, Nishimura F. Roles of serum in innate immune responses of human leukocytes to synthetic lipopeptide. Int Immunopharmacol. 2017 Sep;50:61-68. doi: 10.1016/j.intimp.2017.06.006. Epub 2017 Jun 19. PubMed PMID: 28633072.

20: Kulsantiwong P, Pudla M, Srisaowakarn C, Boondit J, Utaisincharoen P. Pam2CSK4 and Pam3CSK4 induce iNOS expression via TBK1 and MyD88 molecules in mouse macrophage cell line RAW264.7. Inflamm Res. 2017 Jun 7. doi: 10.1007/s00011-017-1063-1. [Epub ahead of print] PubMed PMID: 28593434.