Stereochemical dependence of the self-assembly of the immunoadjuvants Pam(3)Cys and Pam(3)Cys-Ser

Citation
F. Reichel et al., Stereochemical dependence of the self-assembly of the immunoadjuvants Pam(3)Cys and Pam(3)Cys-Ser, J AM CHEM S, 121(35), 1999, pp. 7989-7997
Citations number
38
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
0002-7863 → ACNP
Volume
121
Issue
35
Year of publication
1999
Pages
7989 - 7997
Database
ISI
SICI code
0002-7863(19990908)121:35<7989:SDOTSO>2.0.ZU;2-T
Abstract
The lipopeptide tripalmitoyl-S-glycerylcysteine (Pam(3)Cys) is derived from the N-terminal part of bacterial lipopeptides and is a polyclonal B-lympho cyte and macrophage activator. Derivatives of Pam(3)Cys constitute highly p otent, nontoxic immunoadjuvants, and lipopeptide-antigen conjugates have fo und important applications as novel fully synthetic low-molecular-weight va ccines. To establish a possible correlation between molecular structure, ag gregation properties, and biological activities, we have studied the self-a ssembly and monolayer properties of a range of Pam(3)Cys 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 betwe en these physicochemical properties and biological activities.