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(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoic acid
![(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoic acid - 112208-00-1](/images/structure/BT-278674.png)
(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoic acid
Catalog Number: BT-278674
CAS Number: 112208-00-1
Molecular Formula: C81H159Cl3N10O13S
Molecular Weight: 1510.2 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
TLR1/TLR2 agonist. Synthetic analog of the triacylated N-terminal part of bacterial lipoproteins. Potent adjuvant in vivo. Potent activator of Balb/c splenocytes.
Selective agonist of TLR1/TLR2 complex. Cell permeable, water soluble synthetic cationic lipohexapeptide analog of the immunologically active N-terminal portion of bacterial lipoprotein that potently activates monocytes and macrophages. Potent and effective immune adjuvant. Exerts strong local response, enhances IgG2a and IgG1 titers and upregulates proinflammatory and Th1 cytokine genes. Potent activator of the proinflammatory transcription factor NF-kappaB. Activates/represses at least 140 genes involved in signal transduction and regulation of the immune response.
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.
Selective agonist of TLR1/TLR2 complex. Cell permeable, water soluble synthetic cationic lipohexapeptide analog of the immunologically active N-terminal portion of bacterial lipoprotein that potently activates monocytes and macrophages. Potent and effective immune adjuvant. Exerts strong local response, enhances IgG2a and IgG1 titers and upregulates proinflammatory and Th1 cytokine genes. Potent activator of the proinflammatory transcription factor NF-kappaB. Activates/represses at least 140 genes involved in signal transduction and regulation of the immune response.
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.
Properties
CAS Number
112208-00-1
Product Name
(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoic acid
IUPAC Name
(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoic acid
Molecular Formula
C81H159Cl3N10O13S
Molecular Weight
1510.2 g/mol
InChI
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
LBBMJOSYFJWKTM-PXSLIBMESA-N
SMILES
CCCCCCCCCCCCCCCC(=O)NC(CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)O
Solubility
Soluble in DMSO
Synonyms
N-palmitoyl-5,6-dipalmitoylcysteinyl-seryl-lysine(4)
N-palmitoyl-S-(2,3-bis(palmitoyloxy)propyl)cysteinyl-seryl-lysyl-lysyl-lysyl-lysine
P3C-SK4
P3CSK4
Pam(3)-Cys-Ser-(Lys)(4)
Pam(3)-Cys-Ser-(Lys)4
Pam(3)-Cys-Ser-Lys(4)
Pam3Cys
Pam3Cys-Ser-(Lys)4
tripalmitoyl-cysteinyl-seryl-lysine(4)
N-palmitoyl-S-(2,3-bis(palmitoyloxy)propyl)cysteinyl-seryl-lysyl-lysyl-lysyl-lysine
P3C-SK4
P3CSK4
Pam(3)-Cys-Ser-(Lys)(4)
Pam(3)-Cys-Ser-(Lys)4
Pam(3)-Cys-Ser-Lys(4)
Pam3Cys
Pam3Cys-Ser-(Lys)4
tripalmitoyl-cysteinyl-seryl-lysine(4)
Canonical SMILES
CCCCCCCCCCCCCCCC(=O)NC(CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)O
Isomeric SMILES
CCCCCCCCCCCCCCCC(=O)N[C@@H](CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=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
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