91202-74-3Relevant articles and documents
A strategy for the targeting of photosensitizers. Synthesis, characterization, and photobiological property of porphyrins bearing glycodendrimeric moieties
Ballut, Severine,Naud-Martin, Delphine,Loock, Bernard,Maillard, Philippe
scheme or table, p. 2010 - 2028 (2011/06/17)
This paper describes the conception, synthesis, and characterization of new tetrapyrrolic chromophores bearing glycodendrimeric moieties inducing a potential increase of tumor targeting by a cluster effect. Two families of monoglycodendrimeric photosensitizers bearing three glycosyl units were designed, prepared with an acceptable overall efficiency and characterized by NMR, UV-visible, and fluorescence spectroscopies. The polarity and log P were evaluated by HPLC and the stir-flask method, respectively. The in vitro photoefficiency against two human tumor cell lines was assessed. The presence of the glycodendrimeric group does not appear to increase the tumor in vitro targeting.
Selective protection strategies in the synthesis of TRIS-fatty ester derivatives
Adhikari, Raju,Francis, Craig L.,Simpson, Gregory W.,Yang, Qi
, p. 629 - 634 (2007/10/03)
A methodology for the selective synthesis of lipophilic acyl derivatives of the glycinamido triol (1) with either one, two, or three fatty ester groups has been established. Peracylation of (1), with palmitoyl chloride gave the triacylated derivative. Conversion of (1) into the acetonide, followed by acylation with either palmitoyl chloride or lauroyl chloride, and acetal hydrolysis provided the monoacylated derivatives. Treatment of (1) with trimethyl orthoacetate gave the orthoacetate derivative. Mild hydrolysis provided the monoacetate/diol. Acylation of the two hydroxyl groups with palmitoyl chloride gave the dipalmitate/acetate. Selective cleavage of the acetate group afforded the dipalmitate of (1). Analogous chemistry with trimethyl orthoformate provided the same dipalmitate via the orthoformate, monoformate/diol, and dipalmitate/formate. A more robust synthesis of the dipalmitate was achieved by converting the hydroxyl group of the acetonide of (1) into a tert-butyldiphenylsilyl ether, followed by acetal hydrolysis, palmitoylation of the liberated hydroxyl groups, and desilylation.
Vesicles and other supramolecular systems made from double-tailed synthetic glycolipids derived from galactosylated tris(hydroxymethyl)aminomethane
Polidori, Ange,Pucci, Bernard,Zarif, Leila,Lacombe, Jean-Michel,Riess, Jean G.,Pavia, Andre A.
, p. 225 - 251 (2007/10/02)
A series of double-tailed hydrocarbon glycolipids derived from tris(hydroxymethyl)aminomethane (Tris) have been prepared. These amphiphiles consist of three parts: a hydrophilic head derived from mono- or polygalactosylated Tris, a linking arm of peptidic