Sulforhodamine GM1-ganglioside: synthesis and physicochemical properties.
A fluorescent derivative of GM1-ganglioside was synthesized by linking sulforhodamine 101 to the sphingosine moiety through amino dodecanoyl residue. The product (SR-12GM1) was quantitatively converted to SR-12GM2 by treatment with bovine testes beta-galactosidase and in intact cultured human skin fibroblasts was catabolized to sulforhodamine GM2, GM3 and ceramide; the latter product was further converted to sphingomyelin. In aqueous medium SR-12GM1 formed micelles. When transfer from micelles to vesicles and between vesicles was compared with that of pyrene-GM1, the transfer of SR-12GM1 occurred at higher rates, following in both cases a biexponential curve.
Department of Biomedical Sciences and Biotechnology, University of Brescia, Italy.
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Marchesini
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L
Demasi
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P
Cestone
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Preti
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V
Agmon
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A
Dagan
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R
Navon
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Gatt
D000818:Animals; D002417:Cattle; D002478:Cells, Cultured; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D005677:G(M1) Ganglioside / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D008823:Micelles; D010713:Phosphatidylcholines / Q000378:metabolism; D012235:Rhodamines / Q000737:chemistry*; D001616:beta-Galactosidase / Q000378:metabolism
D005456:Fluorescent Dyes; D008823:Micelles; D010713:Phosphatidylcholines; D012235:Rhodamines; D005677:G(M1) Ganglioside; D001616:beta-Galactosidase; C050829:sulforhodamine 101