Compound and labeled biological substance using the same
A compound of Formula (1) and a labeled biological substance having the compound. Z 1 and Z 2 represent a specific 6-membered ring, and at least one of Z 1 or Z 2 is a benzene ring having a specific substituent at an ortho position with respect to a nitrogen atom to which L 1 or L 2 is bonded, or a specific nitrogen-containing 6-membered ring in which a ring-constituting atom located at the ortho position is a nitrogen atom. The compound has at least one structure represented by —(CH 2 —CH 2 —O) m —R 21 on a heterocyclic ring, and has at least one substituent capable of being bonded to a carboxy group or a biological substance at a specific position, and in a case where at least one of Z 1 or Z 2 is the specific nitrogen-containing 6-membered ring, the specific substituents may be bonded to each other to form a ring.
1 . A compound represented by General Formula (1),
in the General Formula (1), R 1 to R 4 represent an alkyl group which may have a substituent, an aryl group, a heteroaryl group, or —(CH 2 —CH 2 —O) m —R 21 , where m is 1 to 10 and R 21 represents an alkyl group which may have a substituent,
R 11 to R 13 represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group, or a halogen atom, where at least one of R 11 to R 13 is an aryloxy group or an arylthio group, and adjacent groups may be bonded to each other to form a 5-membered or 6-membered ring,
n is an integer of 1 to 3,
L 1 and L 2 represent an alkyl group which may have a substituent or —(CH 2 —CH 2 —O) m —R 21 , where definitions of R 21 and m are respectively the same as those of R 21 and m in R 1 to R 4 of the General Formula (1),
α1 and α2 are 0 or 1,
a ring Z 1 and a ring Z 2 represent a 6-membered ring formed of a ring-constituting atom selected from a carbon atom and a nitrogen atom, may have a substituent, and may form a fused ring, provided that at least one of the ring Z 1 or the ring Z 2 is a benzene ring represented by General Formula (Zα) or a nitrogen-containing 6-membered ring satisfying the following definition (Zβ),
in the General Formula (Zα), R 22 represents an alkyl group, an alkoxy group, a sulfo group, a sulfonamide group, a nitro group, or a halogen atom,
R 23 to R 25 represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, a sulfo group, a sulfonamide group, a nitro group, or a halogen atom, where adjacent groups may be bonded to each other to form a fused ring,
a structure represented by General Formula (Zα) is bonded, at a position of *, to a heterocyclic ring containing a nitrogen atom in General Formula (1) so that R 22 is at an ortho position with respect to the nitrogen atom to which L 1 or L 2 is bonded,
the definition (Zβ): a nitrogen-containing 6-membered ring in which a ring-constituting atom located at an ortho position with respect to a nitrogen atom to which L 1 or L 2 is bonded is a nitrogen atom, the ring-constituting nitrogen atom located at the ortho position may be substituted with a substituent,
at least one of R 1 to R 4 , L 1 , or L 2 contains a structure represented by —(CH 2 —CH 2 —O) m —R 21 , where definitions of R 21 and m are respectively the same as those of R 21 and m in R 1 to R 4 of the General Formula (1),
at least one of the substituents contained in L 1 and L 2 and possessed by the ring-constituting nitrogen atom located at the ortho position in the definition (Zβ) includes a substituent capable of being bonded to a carboxy group or a biological substance, and
in a case where at least one of Z 1 or Z 2 is the nitrogen-containing 6-membered ring satisfying the definition (Zβ), two of the substituents contained in L 1 , L 2 , and R 1 to R 4 and possessed by the ring-constituting nitrogen atom located at the ortho position may be bonded to each other to form a ring containing a methine chain having a repetition number of 2n+3, provided that the compound represented by the General Formula (1) is a neutral compound.
2 . The compound according to claim 1 ,
wherein the compound is represented by any one of General Formulae (2-1) to (2-3),
in the General Formula (2-3), R 31 represents an alkyl group which may have a substituent or —(CH 2 —CH 2 —O) m —R 21 ,
in the General Formula (2-1) to (2-3), R 32 to R 35 represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, a sulfo group, a sulfonamide group, a nitro group, or a halogen atom, where adjacent groups may be bonded to each other to form a fused ring,
definitions of R 1 to R 4 , R 11 to R 13 , L 1 , L 2 , R 21 to R 25 , and m are respectively the same as those of R 1 to R 4 , R 11 to R 13 , L 1 , L 2 , R 21 and m in the General Formula (1), definitions of R 22 to R 25 are respectively the same as those of R 22 to R 25 in the General Formula (Zα),
1 represents 2 or 3, and
at least one of L 1 , L 2 , or R 31 contains a substituent capable of being bonded to a carboxy group or a biological substance, provided that the compound represented by any one of Formulae (2-1) to (2-3) is a neutral compound.
3 . The compound according to claim 2 ,
wherein at least one of the substituents contained in L 1 and L 2 and possessed by the ring-constituting nitrogen atom located at the ortho position in the definition (Zβ) or R 31 includes a substituent capable of being bonded to a carboxy group or a biological substance, and a structure represented by —(CH 2 —CH 2 —O) m , where m is 1 to 10.
4 . The compound according to claim 1 ,
wherein at least one of R 1 or R 2 and at least one of R 3 or R 4 includes a structure represented by —(CH 2 —CH 2 —O) m —, where m is 1 to 10.
5 . The compound according to claim 1 ,
wherein the compound is represented by any one of General Formulae (5-1) to (5-4),
in the General Formula (5-1) to (5-4), R 1 to R 6 represent an alkyl group which may have a substituent, an aryl group, a heteroaryl group, or —(CH 2 —CH 2 —O) m —R 21 ,
R 31 represents an alkyl group which may have a substituent or —(CH 2 —CH 2 —O) m —R 21 ,
R 32 to R 35 represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, a sulfo group, a sulfonamide group, a nitro group, or a halogen atom, where adjacent groups may be bonded to each other to form a fused ring,
1 represents 2 or 3,
L 3 to L 6 represent an alkylene group or —(CH 2 —CH 2 —O) m -alkylene-*, where * represents a bonding position to U,
a linking group U represents a divalent linking group having a total number of atoms of 1 to 100,
definitions of R 11 to R 13 , R 21 , L 1 , and m are respectively the same as those of R 11 to R 13 , R 21 , L 1 , and m in the General Formula (1),
at least one of R 1 to R 6 , L 1 , R 31 , or L 3 to L 6 includes a structure represented by —(CH 2 —CH 2 —O) m —, where definition of m is the same as the m in the General Formula (1), and
at least one of L 1 , R 31 , L 3 to L 6 , or the linking group U contains a substituent capable of being bonded to a carboxy group or a biological substance, provided that the compound represented by any one of Formulae (5-1) to (5-4) is a neutral compound.
6 . The compound according to claim 5 ,
wherein in the linking group U, a connecting portion to L 3 to L 6 is an —O— group, an —NR 50 — group, a —COO— group, a —CONR 50 — group, or an —SO 2 NR 50 — group, provided that R 50 is a hydrogen atom or an alkyl group.
7 . The compound according to claim 5 ,
wherein at least one of R 1 or R 2 and at least one of R 3 or R 4 includes a structure represented by —(CH 2 —CH 2 —O) m —, where m is 1 to 10.
8 . The compound according to claim 5 ,
wherein all of L 3 to L 6 contains a structure represented by —(CH 2 —CH 2 —O) m —, where m is 1 to 10.
9 . The compound according to claim 5 ,
wherein the linking group U is a divalent linking group having a substituent capable of being bonded to a carboxy group or a biological substance.
10 . A labeled biological substance that is obtained by bonding the compound according to claim 1 to a biological substance.
11 . The labeled biological substance according to claim 10 ,
wherein the biological substance is any one of a protein, an amino acid, a nucleic acid, a sugar chain, or a phospholipid.