IP Library › Granted Patent US 7,873,398
Granted Patent B2
US 7,873,398 · App. 12/222,579 · Granted Jan 18, 2011

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

Assignee: Terumo Kabushiki Kaisha
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Quick Facts
Patent No.
US 7,873,398
App. No.
12/222,579
Granted
Jan 18, 2011
Kind
B2
Abstract

A saccharide-measuring fluorescence sensor substance including a copolymer of at least the following two compounds (I) and (II) is provided: (I) a fluorescent monomer compound represented by the following formula (1): formula (1) wherein: Q, Q′ and D 3 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 D 1 , D 2 and D 4 each represent a substituent, wherein at least one of D 1 , D 2 and D 4 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, and (II) at least one hydrophilic, polymerizable monomer having a vinyl group.

Claims (27)

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

(I) a fluorescent monomer compound represented by the following formula (1):

wherein:

Q, Q′ and D 3 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;

D 1 , D 2 and D 4 each represent a substituent, wherein at least one of D 1 , D 2 and D 4 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, and

(II) at least one hydrophilic, polymerizable monomer comprising a vinyl group, wherein said polymerizable monomer (II) is a compound represented by the following formula (6):

wherein A is a hydrogen atom or a methyl group, and U and U′ may be the same or different and are each a substituted or unsubstituted alkyl group.

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

(I) a fluorescent monomer compound represented by the following formula (1):

wherein:

Q and Q′ 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 in D 1 , D 2 , D 3 and D 4 ,

(i) D 1 and D 2 may be the same or different and are each a substituted or unsubstituted alkyl group, D 3 is a hydrogen atom, and D 4 is a substituent group represented by the following formula (2), or

(ii) D 1 and D 2 may be the same or different and are each a substituent group represented by the following formula (3), and D 3 and D 4 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:

wherein:

X, in a case of the definition (i), is a substituent group selected from the group consisting of —COO—, —OCO—, —CH 2 NR—, —CH 2 S—, —CH 2 O—, —NR—, —NRCO—, —CONR—, —SO 2 NR—, —NRSO 2 —, —O—, —S—, —SS—, —NRCOO—, —OCONR— and —CO—, and in a case of the definition (ii), represents a C1 to C30 alkylene group comprising at least one substituent group selected from the group consisting of —COO—, —OCO—, —CH 2 NR—, —NR—, —NRCO—, —CONR—, —SO 2 NR—, —NRSO 2 —, —O—, —S—, —SS—, —NRCOO—, —OCONR— and —CO—, in which R represents a hydrogen atom or a substituted or unsubstituted alkyl group,

Y is a substituted or unsubstituted, divalent, organic residual group, and

Z represents —O— or —NR″—, and R″ represents a hydrogen atom or a substituted or unsubstituted alkyl group,

(II) at least one hydrophilic, polymerizable monomer comprising a vinyl group, wherein said polymerizable monomer (II) is a compound represented by the following formula (6):

wherein A is a hydrogen atom or a methyl group, and U and U′ may be the same or different and are each a substituted or unsubstituted alkyl group.

3. The fluorescence sensor substance according to claim 2 ,

wherein D 1 , D 2 , D 3 and D 4 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.

4. The fluorescence sensor substance according to claim 2 ,

wherein D 1 , D 2 , D 3 and D 4 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.

5. The fluorescence sensor substance according to claim 2 , wherein at least a portion of said copolymer comprises intermolecular crosslinks formed therein, and has a three-dimensional crosslinked structure.

6. An implantable, saccharide-measuring sensor comprising the fluorescence sensor substance as defined in claim 1 .

7. An implantable, saccharide-measuring sensor comprising the fluorescence sensor substance as defined in claim 2 .

Priority Claims (2)
JP 2004-216535 · Jul 23, 2004 · national
JP 2004-299991 · Oct 14, 2004 · national
Continuity (3)
Division 1189051800 · Aug 7, 2007
Division 1118782100 · Jul 25, 2005
Related Publication 20080319288A1 · Dec 25, 2008