Sulforhodamine GM1-ganglioside: synthesis and physico-chemical properties

S. Marchesini; L. Demasi; P. Cestone; A. Preti; V. Agmon; A. Dagan; R. Navon; S. Gatt

doi:10.1016/0009-3084(94)90098-1

Sulforhodamine GM₁-ganglioside: synthesis and physico-chemical properties

S. Marchesini
, L. Demasi
, P. Cestone
, A. Preti
, V. Agmon
, A. Dagan
, R. Navon
, S. Gatt

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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 β-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.

Original language	English
Pages (from-to)	143-152
Number of pages	10
Journal	Chemistry and Physics of Lipids
Volume	72
Issue number	2
DOIs	https://doi.org/10.1016/0009-3084(94)90098-1
State	Published - 8 Aug 1994
Externally published	Yes

Keywords

Fluorescent gangliosides
GM-ganglioside
Gangliosides transfer
Sulforhodamine 101

Access to Document

10.1016/0009-3084(94)90098-1

Cite this

@article{5ca3ef6ea680435796f12dda8662a5d4,

title = "Sulforhodamine GM1-ganglioside: synthesis and physico-chemical properties",

abstract = "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 β-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.",

keywords = "Fluorescent gangliosides, GM-ganglioside, Gangliosides transfer, Sulforhodamine 101",

author = "S. Marchesini and L. Demasi and P. Cestone and A. Preti and V. Agmon and A. Dagan and R. Navon and S. Gatt",

note = "Funding Information: We would like to thank Giuliana Benaglia for her skillful technical assistance. This work was supported by a grant from the Consiglio Na-zionale delle Ricerche (C.N.R.), Italy (jointly to SM and SG).",

year = "1994",

month = aug,

day = "8",

doi = "10.1016/0009-3084(94)90098-1",

language = "English",

volume = "72",

pages = "143--152",

journal = "Chemistry and Physics of Lipids",

issn = "0009-3084",

publisher = "Elsevier Ireland Ltd",

number = "2",

}

TY - JOUR

T1 - Sulforhodamine GM1-ganglioside

T2 - synthesis and physico-chemical properties

AU - Marchesini, S.

AU - Demasi, L.

AU - Cestone, P.

AU - Preti, A.

AU - Agmon, V.

AU - Dagan, A.

AU - Navon, R.

AU - Gatt, S.

N1 - Funding Information: We would like to thank Giuliana Benaglia for her skillful technical assistance. This work was supported by a grant from the Consiglio Na-zionale delle Ricerche (C.N.R.), Italy (jointly to SM and SG).

PY - 1994/8/8

Y1 - 1994/8/8

N2 - 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 β-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.

AB - 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 β-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.

KW - Fluorescent gangliosides

KW - GM-ganglioside

KW - Gangliosides transfer

KW - Sulforhodamine 101

UR - https://www.scopus.com/pages/publications/0028170333

U2 - 10.1016/0009-3084(94)90098-1

DO - 10.1016/0009-3084(94)90098-1

M3 - Article

C2 - 7954976

AN - SCOPUS:0028170333

SN - 0009-3084

VL - 72

SP - 143

EP - 152

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

IS - 2