TY - JOUR
T1 - Stereochemical dependence of the self-assembly of the immunoadjuvants Pam3Cys and Pam3Cys-Ser
AU - Reichel, Frank
AU - Roelofsen, Annie M.
AU - Geurts, Hubertus P.M.
AU - Hämäläinen, Taina I.
AU - Feiters, Martinus C.
AU - Boons, Geert Jan
PY - 1999/9/8
Y1 - 1999/9/8
N2 - The lipopeptide tripalmitoyl-S-glycerylcysteine (Pam3Cys) is derived from the N-terminal part of bacterial lipopeptides and is a polyclonal B- lymphocyte and macrophage activator. Derivatives of Pam3Cys constitute highly potent, nontoxic immunoadjuvants, and lipopeptide-antigen conjugates have found important applications as novel fully synthetic low-molecular- weight vaccines. To establish a possible correlation between molecular structure, aggregation properties, and biological activities, we have studied the self-assembly and monolayer properties of a range of Pam3Cys derivatives using transmission electron microscopy (TEM) and a Langmuir-film balance combined with a Brewster angle microscopy (BAM). It was found that the chirality of the glyceryl moiety and the additional serine unit impacted on the mode of aggregation and the monolayer properties. Correlations are discussed between these physicochemical properties and biological activities.
AB - The lipopeptide tripalmitoyl-S-glycerylcysteine (Pam3Cys) is derived from the N-terminal part of bacterial lipopeptides and is a polyclonal B- lymphocyte and macrophage activator. Derivatives of Pam3Cys constitute highly potent, nontoxic immunoadjuvants, and lipopeptide-antigen conjugates have found important applications as novel fully synthetic low-molecular- weight vaccines. To establish a possible correlation between molecular structure, aggregation properties, and biological activities, we have studied the self-assembly and monolayer properties of a range of Pam3Cys derivatives using transmission electron microscopy (TEM) and a Langmuir-film balance combined with a Brewster angle microscopy (BAM). It was found that the chirality of the glyceryl moiety and the additional serine unit impacted on the mode of aggregation and the monolayer properties. Correlations are discussed between these physicochemical properties and biological activities.
UR - http://www.scopus.com/inward/record.url?scp=0033536492&partnerID=8YFLogxK
U2 - 10.1021/ja991319q
DO - 10.1021/ja991319q
M3 - Article
AN - SCOPUS:0033536492
SN - 0002-7863
VL - 121
SP - 7989
EP - 7997
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 35
ER -