Fluorescent labeling agent and fluorescent dye
A fluorescent labeling agent contains a fluorescent dye represented by general formula (1). General formula (1): Q-Z—R 1 —R 2 —R 3 (In the formula, Q represents the residue of a fluorescent dye. Z represents a direct bond, alkylene group, or arylene group. R 1 represents a direct bond, —O—, —OP(═O)R 4 —, —OC(═O)—, —OS(═O) 2 —, —OSiR 5 R 6 —, —C(═O)—, or —C(═O)NH—. R 2 represents a group selected from the group consisting of alkylene groups, arylene groups, and heterocyclic groups, or represents a group provided by combining these groups. R 3 represents —COOM 1 , —NR 7 R 8 , or —N + R 9 R 10 R 11 . Here, R 4 represents a hydrogen atom, hydroxyl group, alkyl group, aryl group, alkoxy group, aryloxy group, or heterocyclic group. R 5 and R 6 each independently represent an alkyl group, aryl group, or heterocyclic group. R 7 -R 11 each independently represent a hydrogen atom, alkyl group, or aryl group. M 1 represents a monovalent cation).
1 . A fluorescent labeling agent comprising:
a fluorescent dye containing a phthalocyanine dye represented by the following general formula (2),
here, X 1 -X 16 each independently represent —Z—R 1 —R 2 —R 3 , a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted heterocyclic group, -AB, —SO 3 M 5 , or —COOM 6 ,
in the -AB, A represents a Group 16 element, B represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted heterocyclic group,
the M 5 and M 6 each independently represent a monovalent cation, or
in the X 1 -X 16 , adjacent substituents may be linked to each other to form a ring,
X 17 represents —Z—R 1 —R 2 —R 3 , a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, —OP(═O)X 18 X 19 , —OC(═O)X 20 , —OS(═O) 2 X 21 , or —OSiX 22 X 23 X 24 ,
the X 18 and X 19 each independently represent a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group,
the X 20 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
the X 21 represents a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
the X 22 -X 24 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
Y represents a trivalent to pentavalent metal atom, and k is an integer, in a case where Y is a trivalent metal atom, k is 1, and, in a case where Y is a tetravalent or pentavalent metal atom, k is 2,
here, at least one of X 1 -X 17 is —Z—R 1 —R 2 —R 3 ,
Z represents a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group,
R 1 represents —OP(═O)R 4 —, —OC(═O)—, —OS(═O) 2 —, —C(═O)—, or —C(═O)NH—,
R 2 represents a group selected from the group consisting of unsubstituted alkylene groups, substituted or unsubstituted arylene groups, and substituted or unsubstituted heterocyclic groups, or represents a group provided by combining these groups,
R 3 represents —COOM 1 , —NR 7 R 8 , —OM 2 , or —P(═O)(OM 3 )OM 4 ,
the R 4 represents a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group,
the R 7 -R 8 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and
the M 1 , M 2 , M 3 , and M 4 each independently represent a hydrogen atom or a monovalent cation.
2 . The fluorescent labeling agent according to claim 1 that is a phospholipid accumulation-type fluorescent labeling agent.
3 . The fluorescent labeling agent according to claim 1 ,
wherein X 17 in the general formula (2) is —Z—R 1 —R 2 —R 3 .
4 . A compound represented by the following general formula (3),
here, X 1 -X 16 each independently represent —Z—R 1 —R 2 —R 3 , a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted heterocyclic group, -AB, —SO 3 M 5 , or —COOM 6 ,
in the -AB, A represents a Group 16 element, B represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted heterocyclic group,
the M 5 and M 6 each independently represent a monovalent cation, or
in the X 1 -X 16 , adjacent substituents may be linked to each other to form a ring,
X 17 represents —Z—R 1 —R 2 —R 3 , a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, —OP(═O)X 18 X 19 , —OC(═O)X 2 O, —OS(═O) 2 X 21 , or —OSiX 22 X 23 X 24 ,
the X 18 and X 19 each independently represent a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group,
the X 20 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
the X 21 represents a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
the X 22 -X 24 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
Y represents a trivalent to pentavalent metal atom, and k is an integer, in a case where Y is a trivalent metal atom, k is 1, and, in a case where Y is a tetravalent or pentavalent metal atom, k is 2,
here, at least one of X 1 -X 17 is —Z—R 1 —R 2 —R 3 ,
here, Z represents a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group,
R 1 represents —OP(═O)R 4 —, —OC(═O)—, —OS(═O) 2 —, —C(═O)—, or —C(═O)NH—,
R 2 represents a group selected from the group consisting of unsubstituted alkylene groups, substituted or unsubstituted arylene groups, and substituted or unsubstituted heterocyclic groups, or represents a group provided by combining these groups,
R 3 represents —COOM 1 , —NR 7 R 8 , —OM 2 , or P(═O)(OM 3 )OM 4 ,
the R 4 represents a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group,
the R 7 -R 8 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and
the M 1 , M 2 , M 3 , and M 4 each independently represent a hydrogen atom or a monovalent cation.
5 . The fluorescent labeling agent of claim 1 , wherein
in General Formula (2),
X 17 represents —Z—R 1 —R 2 —R 3 ,
Z represents a direct bond,
R 1 represents —OP(═O)R 4 —,
R 3 represents —COOM 1 , and
the M 1 represents a hydrogen atom or a monovalent cation.