# US 7,465,814 B2 · Sulfonate compound and fluorescent probe using the same

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- Number: US 7,465,814 B2
- Document ID: US7465814B2
- Status: Granted
- Kind: B2
- Application number: 11/328,744
- Filed: 2006-01-10
- Published: 2006-05-18
- Granted: 2008-12-16
- Earliest claimed: 2003-07-11
- Assignees: Osaka Industrial Promotion Organization
- Inventors: Hatsuo Maeda; Norio Itoh
- Web page: https://patentgrep.com/patent/US7465814B2

## CPC

- C12Q 1/485: {involving kinase}
- C07D 265/38: [b, e]-condensed with two six-membered rings
- C07D 311/12: substituted in position 3 and unsubstituted in position 7
- C07D 311/82: Xanthenes
- C07D 493/10: Spiro-condensed systems
- C12Q 1/26: involving oxidoreductase
- C12Q 1/44: involving esterase
- C12Q: MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS (immunoassay G01N33/53); COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides a sulfonate compound, including a structure represented by a general formula (I) below, where, in the formula (I), an atomic group A-O is an atomic group that forms a fluorescent compound upon cleavage of a covalent bond between the atomic group A-O and a sulfonyl group, one or a plurality of atomic groups B—SO3— are bonded to an atomic group A, B is a ring that is substituted by one or a plurality of electron-withdrawing groups, the electron-withdrawing group is at least one selected from the group consisting of an alkyl halide group, a nitro group and a cyano group, and B may be the same or different in kind in the case where the plurality of B exist.

## Claims

### Claim 1

A sulfonate compound represented by a formula (I) below,
where, in the formula (I), an atomic group A-O is an atomic group that forms a fluorescent compound upon cleavage of a covalent bond between the atomic group A-O and a sulfonyl group,
one or a plurality of atomic groups B—SO3— are bonded to an atomic group A,
B is benzene ring that is substituted by one or a plurality of electron-withdrawing groups,
the electron-withdrawing group is at least one selected from the group consisting of an alkyl halide group (except a monochloroalkyl group, a monobromoalkyl group and a monoiodoalkyl group), a nitro group and a cyano group, and
B may be the same or different in kind in the case where the plurality of B exist,
the atomic group B is at least one selected from the group consisting of: a 2,4-dinitrophenyl group; a 2-nitro-(4-trifluoromethyl)phenyl group; a 2-nitro-4-methoxyphenyl group; a 4-nitro-2-methoxyphenyl group; a 2-nitro-4-methylphenyl group; a 4-nitro-2-methylphenyl group; a 2-nitro-4,6-dimethylphenyl group; a 4-nitro-2,6-dimethylphenyl group; a 2-nitro-4-chlorophenyl group; a 4-nitro-2-chlorophenyl group; and a 2-nitro-4-isopropylphenyl group,
A is a formula represented by a formula (X-1) or (X-2) below,
where, in the above formulae, each of X1, X2, Y1 and Y2 is hydrogen atom, a straight or branched alkyl group having 1 to 6 carbon atoms or a halogen, X1, X2, Y1 and Y2 may be the same or different,
R3 is a hydrogen atom, a nitro group, a methyl group, a chloro group or a methoxy group, and
R4 is a hydrogen atom, a nitro group, a trifluoromethyl group, a methyl group, an isopropyl group, a chloro group or a methoxy group,
wherein a fluorescent compound formed upon cleavage of the covalent bond between the atomic group A-O and the sulfonyl group is at least one selected from the group consisting of: fluorescein and its derivatives.

### Claim 2 (depends on 1)

The sulfonate compound according to claim 1, wherein the alkyl halide group is a perfuoroalkyl group.

### Claim 3 (depends on 1)

The sulfonate compound according to claim 1, represented by any of formulae (i) and (ii) below,
where, in the formulae (i) and (ii),
each of X1, X2, Y1 and Y2 is a hydrogen atom, a straight or branched alkyl group having 1 to 6 carbon atoms or a halogen, X1, X2, Y1 and Y2 may be the same or different,
X3 is a straight or branched alkyl group having 1 to 6 carbon atoms or a trifluoromethyl group,
each of R1 and R3 is a hydrogen atom, a nitro group, a methyl group, a chloro group or a methoxy group, R1 and R3 may be the same or different,
each of R2 and R4 is a hydrogen atom, a nitro group, a trifluoromethyl group, a methyl group, an isopropyl group, a chloro group or a methoxy group, R2 and R4 may be the same or different,
at least one of R1 and R2 is a nitro group, at least one of R3 and R4 is a nitro group, and in the case where, in the formula (iv), X3 is a straight or branched alkyl group having 1 to 6 carbon atoms, both of R1 and R2are groups except a hydrogen atom.

### Claim 4 (depends on 1)

The sulfonate compound according to claim 1, represented by any of formulae into 1d, 1d, 3,4a to 4e, 8a, 8b and 8c below:

### Claim 5 (depends on 1)

The sulfonate compound according to claim 1 represented by any of formulae 8a, 8b and 8c below:

### Claim 6

A fluorescent probe, consisting of the sulfonate compound represented by a formula (I) below, and forming a fluorescent compound upon cleavage of a covalent bond between an atomic group A-O and a sulfonyl group,
where, in the formula (I), an atomic group A-O is an atomic group that forms a fluorescent compound upon cleavage of a covalent bond between the atomic group A-O and a sulfonyl group,
one or a plurality of atomic groups B—SO3— are bonded to an atomic group A,
B is a ring that is substituted by one or a plurality of electron-withdrawing groups,
the electron-withdrawing group is at least one selected from the group consisting of an alkyl halide group, a nitro group and a cyano group,
A is a formula represented by a formula (X-1) or (X-2) below,
where, in the above formulae, each of X1, X2, Y1 and Y2 is hydrogen atom, a straight or branched alkyl group having 1 to 6 carbon atoms or a halogen, X1, X2, Y1 and Y2 may be the same or different,
R3 is a hydrogen atom, a nitro group, a methyl group, a chloro group or a methoxy group, and
R4 is a hydrogen atom, a nitro group, a trifluoromethyl group, a methyl group, an isopropyl group, a chloro group or a methoxy group, and
B may be the same or different in kind in the case where the plurality of B exist.