Mitochondria-targeting fluorescent potassium+ sensor and method of making the same
AssigneeArizona Board of Regents on behalf of Arizona State University
InventorsXiangxing Kong, Yanqing Tian, Fengyu Su, Liqiang Zhang, Deirdre Meldrum
Life of this patent
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Abstract
Mitochondria-targeting potassium sensors and method(s) for making such sensors. The sensor shows a response to potassium and displays a 130-fold dynamic range of fluorescence intensity and high brightness. The sensors response to potassium concentrations was demonstrated to be unaffected by cellular pH value and/or concentrations of other ions. The sensors can be used for monitoring the mitochondrial potassium efflux/influx.
Claims9
A potassium-sensing compound, comprising a sensing range of potassium ion concentration from about 30 mM to about 500 mM potassium, of formula (I):
- or a salt form thereof, wherein:
- R1, R3, R4 in formula (I) are independently selected from the group consisting of H, CH3, and CH2CH3;
- R2, R5 in formula (I) are independently selected from the group consisting of H, CH3, CH2CH3, CO2H, CO2CH3, CO2Et, CH2CH2COOCH3, CH2CH2COOCH2CH3, CH2CH2COOH, and 2-thiophene;
- and
- Rx in formula (I) is selected from the group consisting of
A method of synthesizing the compound formula (II):
- the method comprising:
- mixing 4-(6-Bromohexyloxy)-benzaldehyde and triphenylphosphine to obtain a first solid;
- mixing the first solid and 2,4-dimethylpyrrole under nitrogen to obtain a first mixture;
- adding dichloromethane and trifluoroacetic acid to the first mixture to obtain a second mixture;
- stirring the second mixture at room temperature;
- adding p-chloranil, trimethylamine, and boron trifluoride diethyl etherate (BF3OEt2) to the second mixture to obtain a third mixture;
- separating an organic phase from the third mixture to obtain a second solid;
- refluxing the second solid with TAC-CHO in a fourth mixture of benzene, acetic acid, and piperidine to obtain a fifth mixture;
- and
- separating an organic layer of the fifth mixture to obtain said compound.
Dependencies are inferred from the claim text.