Saccharide-measuring fluorescent monomer, saccharide-measuring fluorescent sensor substance, and implantable, saccharide-measuring sensor

• US 20060020182A1
• Filed: 07/25/2005
• Published: 01/26/2006
• Est. Priority Date: 07/23/2004
• Status: Active Grant

• Current Assignee: Terumo Kabushiki Kaisha
• Original Assignee: Terumo Kabushiki Kaisha
• Inventors: Ochiai, Shouji, Matsumoto, Atsushi, Kawanishi, Tetsuro
• Granted Patent: US 7,388,110 B2
• Time in Patent Office: Days
• US Class Current: 600/315
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B

Abstract

A fluorescent monomer compound represented by the following formula (1) is provided:
wherein Q, Q′ and D³ may be the same or different, may be combined together into a fused ring, and are each a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, and substituted or unsubstituted alkyl, acyl, oxyalkyl, carboxyl, carboxylate ester, carboxamido, cyano, nitro, amino and aminoalkyl groups; and D¹, D² and D⁴ each represent a substituent, wherein at least one of D¹, D² and D⁴ is a substituent group comprising a vinyl group at an end thereof, and wherein the substituent group comprising a vinyl group at an end thereof enables the fluorescent monomer compound to be soluble in water.

Claims

1. A fluorescent monomer compound represented by the following formula (1):

6. A saccharide-measuring fluorescence sensor substance comprising a copolymer of at least the following two compounds (I) and (II):

(I) the fluorescent monomer compound as defined in claim 1, and

(II) at least one hydrophilic, polymerizable monomer having a vinyl group.

7. The fluorescence sensor substance according to claim 6, wherein said polymerizable monomer (II) is a polymerizable monomer comprising a (meth)acrylamide residual group.

18. An implantable, saccharide-measuring sensor comprising the fluorescence sensor substance as defined in claim 6.

2. A fluorescent monomer compound represented by the following formula (1):

3. The fluorescent monomer compound according to claim 2, wherein said substituent group represented by the formula (2) or said substituent group represented by the formula (3) enables the fluorescent monomer compound to be soluble in water.

4. The fluorescent monomer compound according to claim 2, wherein Y contains a structure represented by the following formula (4) or formula (5):

5. The fluorescent monomer compound according to claim 2, wherein D₁, D₂, D₃ and D₄ have the meanings as defined under the definition (i), and Y is a substituted or unsubstituted, linear, divalent, organic residual group having a number of atoms of from 3 to 500.

8. A saccharide-measuring fluorescence sensor substance comprising a copolymer of at least the following two compounds (I) and (II):

(I) the fluorescent monomer compound as defined in claim 2, and

(II) at least one hydrophilic, polymerizable monomer having a vinyl group.

9. The fluorescence sensor substance according to claim 8, wherein said polymerizable monomer (II) is a polymerizable monomer comprising a (meth)acrylamide residual group.

10. The fluorescence sensor substance according to claim 8, wherein D₁, D₂, D₃ and D₄ have the same meanings as defined under said definition (i), and a molar ratio of said fluorescent monomer compound (I) to said polymerizable monomer (II) in said copolymer is from 1:

10 to 1;

4,000.

11. The fluorescence sensor substance according to claim 8, wherein D₁, D₂, D₃ and D₄ have the same meanings as defined under said definition (ii), and a molar ratio of said fluorescent monomer compound (I) to said polymerizable monomer (II) in said copolymer is from 1:

50 to 1;

6,000.

12. The fluorescence sensor substance according to claim 8, wherein said polymerizable monomer (II) is a compound represented by the following formula (6):

13. The fluorescence sensor substance according to claim 8, wherein at least a portion of said copolymer comprises intermolecular crosslinks formed therein, and has a three-dimensional crosslinked structure.

19. An implantable, saccharide-measuring sensor comprising the fluorescence sensor substance as defined in claim 8.

14. A fluorescence sensor substance represented by the following formula (7):

15. The fluorescent monomer compound according to claim 14, wherein Y comprises a structure represented by the following formula (4) or formula (5):

16. The fluorescent monomer compound according to claim 14, wherein D¹⁰, D²⁰, D³⁰ and D⁴⁰ have the meanings as defined under said definition (x), and Y is a substituted or unsubstituted, linear, divalent, organic residual group having a number of atoms of from 3 to 500.

17. The fluorescence sensor substance according to claim 14, wherein at least a portion of said copolymer comprises intermolecular crosslinks formed therein, and has a three-dimensional crosslinked structure.

20. An implantable, saccharide-measuring sensor comprising the fluorescence sensor substance as defined in claim 14.