Long-wavelength fluorescent probe compounds for calcium ions and their use in ratiometrically measuring calcium ion concentrations
First Claim
1. A fluorescent calcium-binding compound for making wavelength-ratiometric or intensity-ratiometric measurements of calcium ion concentrations having the formula:
- ##STR4## where n represents an integer of 1, 2 or 3 and R represents thiaflavin or ##STR5## wherein R2 is selected from the group consisting of methyl, ethyl, sulfopropyl, sulfobutyl, and carboxymethyl, Y is selected from the group consisting of S, (CH3)2 C, and O;
W is selected from the group consisting of H, Cl, and OCH3 ; and
Z is an optional fused aromatic ring.
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Abstract
Fluorescent, calcium-binding probe compounds having visible-light excitation and emission wavelengths, and a method of usage for these probe compounds in making wavelength-ratiometric or intensity-ratiometric measurements of calcium ion concentration in samples. The probe compounds generally relate to a heterocyclic part as bonded to a Ca2+ binding unit, namely, BAPTA, via an ethylenically unsaturated group; preferred examples of the heterocyclic group include benzothiazole, naphthothiazole, thiaflavin, indolenine, chloroindolenine, methoxybenzothiazole, and methoxyindolenine.
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Citations
18 Claims
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1. A fluorescent calcium-binding compound for making wavelength-ratiometric or intensity-ratiometric measurements of calcium ion concentrations having the formula:
- ##STR4## where n represents an integer of 1, 2 or 3 and R represents thiaflavin or ##STR5## wherein R2 is selected from the group consisting of methyl, ethyl, sulfopropyl, sulfobutyl, and carboxymethyl, Y is selected from the group consisting of S, (CH3)2 C, and O;
W is selected from the group consisting of H, Cl, and OCH3 ; and
Z is an optional fused aromatic ring. - View Dependent Claims (2)
- ##STR4## where n represents an integer of 1, 2 or 3 and R represents thiaflavin or ##STR5## wherein R2 is selected from the group consisting of methyl, ethyl, sulfopropyl, sulfobutyl, and carboxymethyl, Y is selected from the group consisting of S, (CH3)2 C, and O;
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3. A fluorescent calcium-binding compound for making wavelength-ratiometric or intensity-ratiometric measurements of calcium ion concentrations having the formula:
- ##STR6##
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4. A method of making wavelength-ratiometric or intensity-ratiometric measurements of calcium concentration in a sample containing calcium ions using a wavelength of about 400 nm or more, comprising
contacting a sample containing calcium ions with a probe compound of the following formula in sufficient quantity to act as a fluorescent optical indicator independent of concentration of said probe compound: - ##STR7## wherein n represents an integer of 1, 2 or 3 and R represents thiaflavin or ##STR8## wherein R2 is selected from the group consisting of methyl, ethyl, sulfopropyl, sulfobutyl, and carboxymethyl, Y is selected from the group consisting of S, (CH3)2 C, and O;
W is selected from the group consisting of H, Cl, and OCH3 ; and
Z is an optional fused aromatic ring; andmeasuring the calcium concentration in the sample by wavelength-ratiometry or intensity-ratiometry using a wavelength of about 400 nm or more. - View Dependent Claims (5, 6, 7, 8, 9, 10, 11, 12)
- ##STR7## wherein n represents an integer of 1, 2 or 3 and R represents thiaflavin or ##STR8## wherein R2 is selected from the group consisting of methyl, ethyl, sulfopropyl, sulfobutyl, and carboxymethyl, Y is selected from the group consisting of S, (CH3)2 C, and O;
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13. A method of making wavelength-ratiometric or intensity-ratiometric measurements of calcium concentration in a sample containing calcium ions using a wavelength of about 400 nm or more, comprising
contacting a sample containing calcium ions with a probe compound of the following structure in sufficient quantity to act as a fluorescent indicator independent of concentration of said probe compound: - ##STR9## and measuring the calcium concentration in the sample by wavelength-ratiometry or intensity-ratiometry using a wavelength of about 400 nm or more.
- View Dependent Claims (14, 15, 16, 17, 18)
Specification