Fluorescent probe for the quantitation of zinc
View Patent ↗A compound represented by general formula (IA) or a salt thereof useful as a fluorescent probe for zinc: wherein R 1 and R 2 represent a hydrogen atom or a group represented by formula (A), wherein X 1 , X 2 , X 3 , and X 4 represent a hydrogen atom, an alkyl group, a 2-pyridylmethyl group, or a protective group for an amino group, and m and n represent 0 or 1 provided that R 1 and R 2 do not simultaneously represent hydrogen atoms; R 3 and R 4 represent a hydrogen atom or a halogen atom; and R 5 and R 6 represent a hydrogen atom, an alkylcarbonyl group, or an alkylcarbonyloxymethyl group, and R 7 represents a hydrogen atom or an alkyl group.
1. A compound represented by general formula (IB) or a salt thereof:
wherein R 1 and R 2 independently represent a hydrogen atom or a group represented by formula (A):
wherein X 1 , X 2 , X 3 , and X 4 independently represent a hydrogen atom, an alkyl group, a 2-pyridylmethyl group, or a protective group for an amino group, and m and n independently represent 0 or 1, and at least one of m and n is 1, provided that R 1 and R 2 do not simultaneously represent hydrogen atoms; R 3 and R 4 independently represent a hydrogen atom or a halogen atom;
R 6 represents a hydrogen atom, an alkylcarbonyl group, or an alkylcarbonyloxymethyl group, and R 7 represents a hydrogen atom or an alkyl group.
2. A compound represented by general formula (II) or a salt thereof:
wherein R 13 and R 14 independently represent a hydrogen atom or a halogen atom; R 17 represents a hydrogen atom or an alkyl group; and R 18 represents a hydrogen atom or a protective group for an amino group.
3. The compound or a salt thereof according to claim 2 , wherein R 17 and R 18 independently represent hydrogen atoms.
4. The compound or a salt thereof according to claim 2 , wherein both of R 13 and R 14 are hydrogen atoms, or both of R 13 and R 14 are chlorine atoms.
5. A compound represented by general formula (IIIB) or a salt thereof:
wherein R 21 and R 22 independently represent a hydrogen atom or a group represented by formula (B):
wherein X 11 , X 12 , X 13 , and X 14 independently represent a hydrogen atom, an alkyl group, a 2-pyridylmethyl group, or a protective group for an amino group, and p and q are independently 0 or 1, provided that R 21 and R 22 do not simultaneously represent hydrogen atoms; Y represents —CO—NH— or —NH—CO—; R 23 and R 24 independently represent a hydrogen atom or a halogen atom; R 26 represents a hydrogen atom, an alkylcarbonyl group, or an alkylcarbonyloxymethyl group; and R 27 represents a hydrogen atom or an alkyl group.
6. A fluorescent probe for zinc which comprises a compound according to claim 1 , provided that a compound is excluded wherein a protective group for an amino group is introduced, or a salt thereof.
7. A zinc complex which is formed by a compound according to claim 1 , provided that a compound is excluded wherein a protective group for an amino group is introduced, or a salt thereof together with a zinc ion.
8. A method for measuring a zinc ion which comprises
(a) reacting a compound according to claim 1 , provided that a compound is excluded wherein a protective group for an amino group is introduced, or a salt thereof with a zinc ion to form a zinc complex; and
measuring fluorescence intensity of the zinc complex.
9. The compound or a salt thereof according to claim 3 , wherein both of R 13 and R 14 are hydrogen atoms, or both of R 13 and R 14 are chlorine atoms.