Macrophage-activating lipopeptide 2

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Macrophage-activating lipopeptide 2
Names
IUPAC name
S-[(2R)-2,3-bis[(1-oxohexadecyl)oxy]propyl]-L-cysteinylglycyl-L-asparaginyl-L-asparaginyl-L-α-aspartyl-L-α-glutamyl-L-seryl-L-asparaginyl-L-isoleucyl-L-seryl-L-phenylalanyl-L-lysyl-L-α-glutamyl-L-Lysine
Other names
MALP-2, S-[2,3-bis(Palmityloxy)-(2R)-propyl-cysteinyl-GNNDESNISFKEK
Identifiers
3D model (JSmol)
Abbreviations XGNNDESNISFKEK
ChemSpider
UNII
  • InChI=1S/C99H167N19O30S/c1-5-8-10-12-14-16-18-20-22-24-26-28-33-43-84(131)147-59-64(148-85(132)44-34-29-27-25-23-21-19-17-15-13-11-9-6-2)60-149-61-65(102)87(133)106-56-80(124)107-71(52-77(103)121)92(138)113-72(53-78(104)122)93(139)115-74(55-83(129)130)94(140)110-68(46-48-82(127)128)90(136)116-75(57-119)96(142)114-73(54-79(105)123)95(141)118-86(62(4)7-3)98(144)117-76(58-120)97(143)112-70(51-63-39-31-30-32-40-63)91(137)108-66(41-35-37-49-100)88(134)109-67(45-47-81(125)126)89(135)111-69(99(145)146)42-36-38-50-101/h30-32,39-40,62,64-76,86,119-120H,5-29,33-38,41-61,100-102H2,1-4H3,(H2,103,121)(H2,104,122)(H2,105,123)(H,106,133)(H,107,124)(H,108,137)(H,109,134)(H,110,140)(H,111,135)(H,112,143)(H,113,138)(H,114,142)(H,115,139)(H,116,136)(H,117,144)(H,118,141)(H,125,126)(H,127,128)(H,129,130)(H,145,146)/t62-,64+,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,86-/m0/s1
    Key: DMWMUMWKGKGSNW-OPMCLZTFSA-N
  • [C@H](CC1=CC=CC=C1)(C(N[C@H](C(N[C@H](C(N[C@@H](CCCCN)C(O)=O)=O)CCC(O)=O)=O)CCCCN)=O)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@H](CSC[C@@H](COC(CCCCCCCCCCCCCCC)=O)OC(CCCCCCCCCCCCCCC)=O)N)=O)=O)CC(N)=O)=O)CC(N)=O)=O)CC(O)=O)=O)CCC(O)=O)=O)CO)=O)CC(N)=O)=O)[C@H](CC)C)=O)CO)=O
Properties
C99H167N19O30S
Molar mass 2135.59 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Macrophage-activating lipopeptide 2 (MALP-2) is a lipopeptide Toll-like receptor (TLR)-2 and 6 agonist. It is used in immunological research to simulate Mycoplasma bacterial infections and activate immune cells. MALP-2 holds promise as a novel vaccine adjuvant due to its activation of TLRs.[1][2] It also promotes vascular, bone, and wound healing.[3][4]

Structure[edit]

MALP-2 has the structure S-2,3-bis(palmityloxy)-(2R)-propyl-cysteinyl-GNNDESNISFKEK and is a post-translationally modified CGNNDESNISFKEK peptide in which in the N-terminus cysteine residue sidechain is linked to a diacylglycerol moiety where the two acyl groups are both derived from palmitic acid.[5]

Discovery[edit]

MALP-2 was initially named mycoplasma-derived high-molecular-weight material (MDHM) and, as the name suggests, had originally been isolated from Mycoplasma fermentans as an amphiphilic molecule with macropage-activating properties. This discovery helped explain how Mycoplasma bacteria can provoke immune responses despite lacking a cell wall.[6][7]

References[edit]

  1. ^ Hamley IW (August 2021). "Lipopeptides for Vaccine Development". Bioconjugate Chemistry. 32 (8): 1472–1490. doi:10.1021/acs.bioconjchem.1c00258. PMC 8382226. PMID 34228433.
  2. ^ Moyle PM, Toth I (2008). "Self-adjuvanting lipopeptide vaccines". Current Medicinal Chemistry. 15 (5): 506–516. doi:10.2174/092986708783503249. PMID 18289006.
  3. ^ Liao D, Su X, Wang J, Yu J, Luo H, Tian W, et al. (January 2023). "Pushing the envelope: Immune mechanism and application landscape of macrophage-activating lipopeptide-2". Frontiers in Immunology. 14: 1113715. doi:10.3389/fimmu.2023.1113715. PMC 9902699. PMID 36761746.
  4. ^ Knorr C, Hübschle T, Murgott J, Mühlradt P, Gerstberger R, Roth J (April 2008). "Macrophage-activating lipopeptide-2 (MALP-2) induces a localized inflammatory response in rats resulting in activation of brain sites implicated in fever". Brain Research. 1205: 36–46. doi:10.1016/j.brainres.2008.02.021. PMID 18353287. S2CID 206317405.
  5. ^ "MALP-2". Enzo Life Sciences, Inc.
  6. ^ Mühlradt PF, Frisch M (September 1994). "Purification and partial biochemical characterization of a Mycoplasma fermentans-derived substance that activates macrophages to release nitric oxide, tumor necrosis factor, and interleukin-6". Infection and Immunity. 62 (9): 3801–3807. doi:10.1128/iai.62.9.3801-3807.1994. PMC 303034. PMID 8063396.
  7. ^ Mühlradt PF, Kiess M, Meyer H, Süssmuth R, Jung G (June 1997). "Isolation, structure elucidation, and synthesis of a macrophage stimulatory lipopeptide from Mycoplasma fermentans acting at picomolar concentration". The Journal of Experimental Medicine. 185 (11): 1951–8. doi:10.1084/jem.185.11.1951. PMC 2196331. PMID 9166424.
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