Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
1999-04-29
2001-06-05
Peselev, Elli (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C536S103000
Reexamination Certificate
active
06242430
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a novel dye having a rotaxane type structure with cyclodextrin, a labeling agent using the dye, and a labeling method using the agent.
2. Related Background Art
In the field of bioscience, including genetic engineering, one of the most commonly employed analytical methods among those for detecting various substances or those for labeling specified substances is the method relying on dyes: particularly, fluorometric analysis relying on fluorescent dyes. To such end, there have been developed and used labeling agents that rely on dyes having a variety of properties, particularly fluorescent dyes.
However, problems existed: (1) A problem that dyes known in the art or labeling agents using the same were not adequate in their water-solubility; (2) A further problem that there was no availability for labeling agents which rely on dyes of the multi-wavelength type capable of conforming to multiple coloration—a strong demand in recent years—as well as for labeling methods using the aforementioned agents.
SUMMARY OF THE INVENTION
It is an objective of this invention to provide a dye displaying excellent water-solubility and capable of multiple coloration. Further, it is another objective of the invention to provide a labeling agent containing such dye, as well as a labeling method relaying on said labeling agent.
The present inventors made thorough investigations in an effort to solve the drawbacks encountered in the prior art as described above, and have discovered that by making a dye, which is water-insoluble or sparingly water-soluble, into a rotaxane structure combined with cyclodextrin (water-soluble), one can obtain a dye of the multi-wavelength type that is excellent in water-solubility and, in addition, that is capable of conforming to multiple coloration. It has also been discovered that one can obtain a labeling agent containing such dye that has a rotaxane structure. Furthermore, a labeling method using said labeling agent has been developed.
Particularly, it has been discovered that when said dye is a fluorescent dye, it leads to a fluorescent dye of the mutli-wavelength type which possesses excellent water-solubility and, in addition, which is capable of conforming to multiple coloration, to a labeling agent containing this fluorescent dye, and further to a labeling method using this labeling agent; thus, this invention has been accomplished.
Specifically, the structure of a rotaxane type dye according to this invention is based on that which (1) combines a dye molecule with cyclodextrin and which (2) links the dye molecule to at least one terminus of a chain group penetrating said cyclodextrin ring. Therefore, the dye having such cyclodextrin-rotaxane structure possesses excellent water-solubility, because it is provided with cyclodextrin. Further, it is possible that the dye has a structure which links dye molecules to both termini of the chain group penetrating the cyclodextrin ring. In this case, it becomes also possible to bind not only the same kind of dye but also different kinds of dye.
In addition, the dye according to the invention can be made into a labeling agent for labeling various substances in aqueous solution by the introduction of various functional groups the dye molecule itself has or by the introduction of various reactive groups. The dyes according to the invention encompass both those having fluorescent nature and those having no fluorescent nature.
More specifically, the dye according to the invention is one that is characterized by a rotaxane type wherein a dye is bound to at least one terminus of a chain group and the chain group penetrates a cyclodextrin ring.
Further, the dye according to the invention is a rotaxane type dye represented by the following formula 1:
wherein each of FL1 and FL2 represents a dye; n represents an integer of 8-12; m represents an integer of 6-8; and X represents any one of OH, Cl, Br, I, NH
2
, NCO, NHCO, and (CH
2
)
3
CO
2
H.
Also, the dye according to the invention is a rotaxane type dye represented by the following formula 2:
wherein FL3 represents a dye; k represents an integer of 6-8; and 1 represents an integer of 8-12.
Further, the dye according to the invention is a rotaxane type dye wherein the dye is a fluorescent dye.
In addition, the labeling agent according to the invention is one that is characterized by the use of the dye as described above.
Furthermore, the labeling method according to the invention is one that is characterized by the use of the labeling agent as described above.
Since the rotaxane type dye according to the invention has a rotaxane structure which binds dye molecules to both of the termini of a chain group penetrating a cyclodextrin ring, it is the one that can possess excellent water-solubility and can be provided with plural different dyes.
Still further, with the use of various bonding groups for labeling reaction that are contained in the dye molecules, CD, or chain group of the rotaxane type dye according to the invention, it becomes possible to label various substances under aqueous solution conditions.
This invention will be explained in more detail based on embodiment hereinbelow.
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Nohta Hitoshi
Okazaki Shigetoshi
Suzuki Tomomi
Laboratory of Molecular Biophotonics
Leydig , Voit & Mayer, Ltd.
Peselev Elli
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