HNQO1-activatable fluorescent probe for imaging cancer cells in-vitro and in-vivo
AssigneeTexas Tech University System
InventorsKalkunte S. Srivenugopal, Surendra R. Punganuru
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Abstract
The present invention includes a probe, an assay, a method of detecting, a human NAD(P)H quinone oxidoreductase-1 (hNQO1) enzyme activity with a fluorescent probe comprising a quinone propionic acid (QPA) conjugated to dicyanoisophorone (DCP), wherein the hNQO1 reduces the probe to releases a fluorescent DCP, and a method of making the same.
Claims25
An assay to detect human NAD(P)H quinone oxidoreductase-1 (hNQO1) enzyme activity comprising:
- contacting an hNQO1 enzyme with a probe comprising a quinone propionic acid (QPA) conjugated to dicyanoisophorone (DCP), wherein the hNQO1 reduces the probe and releases a fluorescent DCP.
A probe comprising a quinone propionic acid (QPA) conjugated to a dicyanoisophorone (DCP).
A method of detecting a cancer cell that expresses a human NAD(P)H quinone oxidoreductase-1 (hNQO1) enzyme comprising:
- contacting the cancer cell with a probe comprising a quinone propionic acid (QPA) conjugated to dicyanoisophorone (DCP), wherein the hNQO1 reduces the probe and releases a fluorescent DCP;
- and detecting fluorescence in the cancer cell.
A method of making a probe comprising a quinone propionic acid (QPA) conjugated to dicyanoisophorone (DCP) comprising:
- carrying out the following reaction:
- wherein the conditions are:
- (a) ammonium acetate, acetic anhydride, acetic acid, toluene, reflux, 12 h;
- (b) piperidine, acetonitrile, 50° C., 6 h;
- (c) SnCl2, HCl, ethyl acetate, 8 h;
- (d) methyl 3,3-dimethylacrylate, methanesulfonic acid, 70° C., 2 h;
- (e)N-Bromosuccinimide, acetonitrile, water, room temperature, 1 h;
- and
- (f) 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide, pyridine, rt, 10 h.
Dependencies are inferred from the claim text.