Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1996-11-20
1998-06-30
Fonda, Kathleen K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 172, 536 179, 536 185, 536124, C07H 1500
Patent
active
057735964
DESCRIPTION:
BRIEF SUMMARY
This is the U.S. national stage entry under 35 U.S.C. 371 of PCT/JP95/00951, filed May 18, 1995.
FIELD OF THE INVENTION
The present invention relates to a ganglioside having a fluorescently labeled ceramide moiety, intermediates for the synthesis thereof, and a process for the preparation thereof.
PRIOR ART
Glycolipids in mammalian cells belong to the group of sphingoglycolipids comprising a lipid portion called as a ceramide which consists of a sphingosine as a long chain aminoalcohol and a long chain fatty acid bonded to the sphingosine through an amide linkage, various oligosaccharide chains and a sialic acid. In particular, ganglioside is the collective name for sphingoglycolipids having a sialic acid group.
In general, most of the above ganglioside molecules are localized in the cell surfaces of animals, and the recent studies have revealed that their sialic saccharide chains are oriented outside the cells and that they play important roles in fundamental life phenomena such as discrimination in cells, reception of or response to information in cells, functions as receptors for hormones, viruses, bacteria, cell toxins, etc., intercellular distinction, proliferation and metastasis of cells, malignant alteration, immunity, and the like.
The gangliosides attract attentions as the molecules which exhibit a wide variety of physiological activities which relate to the information transfer, proliferation and metastasis of the cells.
A derivative of the ganglioside into which a fluorescent dye is introduced while maintaining its inherent physiological activities will provide a novel method for the study of cells, if such a derivative can be synthesized, since the ganglioside receptor can be identified and its behavior can be monitored visually.
A ganglioside into which fluorescein is introduced has been prepared based on the above idea. However, it has not achieved satisfactory results.
A method for detecting a bond between a ganglioside and bacteria or viruses using the ganglioside labeled with a radioisotope has been developed. However, a new method alternative to this method has been sought since this method has various problems in handling, and labeling with a fluorescence is thought to be effective.
A ganglioside labeled with a fluorescent dye will be useful as a detection and diagnostic agent for the above pathogens.
SUMMARY OF THE INVENTION
The first object of the present invention is to provide a ganglioside derivative into which a labeling dye has been introduced without deterioration of the physiological activities of the ganglioside.
The second object of the present invention is to provide an intermediate for the synthesis of such a ganglioside derivative.
The third object of the present invention is to provide processes for the preparation of such ganglioside derivative and the intermediate for the same.
According to the first aspect of the present invention, a ganglioside derivative labeled with a fluorescent dye is provided, represented by the formula (I): ##STR2## wherein --O--R--O-- is a saccharide chain constituting the ganglioside, R' is an ether, sulfide, amide, urethane, thiourea or amino group having a fluorescent dye, one of R.sup.5 or R.sup.6 is a single bond and the other is a hydrogen atom, I is an integer of 1 to 8, m is an integer of at least 2, and n is an integer of 0 to 12.
According to the second aspect of the present invention, a ganglioside derivative labeled with a fluorescent dye is provided, represented by the formula (II): ##STR3## wherein R.sup.2' is a protecting group for a carboxylic acid, R.sup.3', R.sup.7', R.sup.8' and R.sup.9' are protecting groups for hydroxyl groups, one of R.sup.5' or R.sup.6' is a single bond and the other is a hydrogen atom, and --O--R--O--, R', I, m and n are the same as defined above.
DETAILED DESCRIPTION OF THE INVENTION
The ganglioside of the present invention is characterized in that the fluorescent dye as a label is introduced in the ceramide moiety of the ganglioside.
The kind of fluorescent dye is not limited. Preferable exa
REFERENCES:
Spiegel, Biochemistry, vol. 24, pp. 5947-5952 (1985).
Hakomori, J. Biol. Chem., vol. 265, pp. 18713-18716 (Nov. 1990).
Brewer et al. Biochemistry, vol. 31, pp. 1816-1820 (1992).
Song et al. Biochemistry, vol. 28, pp. 4194-4200 (1989).
Kozteb et al. Biologicheskie Membrany, vol. 6, No. 1, pp. 34-41 (1989) No Translation Provided.
Iida Takao
Ohira Yutaka
Daikin Industries Ltd.
Fonda Kathleen K.
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