Tetraazaporphyrin-Based Compounds and Their Uses
AssigneeBoard of Supervisors of Louisiana State University and Agricultural and Mechanical College
InventorsRobert P. Hammer, Steven a. Soper, Serhii Pakhomov, Timothy J. Jensen, Michael W. Allen, Irina v. Nesterova, Maria da Graca Henriques Vicente
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Abstract
Asymmetrically substituted metal-phthalocyanine compounds are disclosed. These compounds and other phthalo-cyanine-derivatives are used in bioimaging, bioanalysis, FRET and quenching techniques, photodynamic therapy, DNA analysis for cells, proteins, tissues and other biological entities, and other applications. Near-infrared fluorescence minimizes matrix effects typically seen in other methods of analyzing biochemical entities in cells, proteins, tissues and other biological entities.
Claims28
A compound having the structure:
- wherein
- M is selected from the group consisting of 2H, Zn, Ni, Cu, SnY2, Pd, AlY, Pt, SiY2, GaY, and CoY;
- Y is selected from the group consisting of F, Cl, Br, I, OR, OH, SR, —CCR, C═CR, OPh, CH3, C2H5, Pr, i-Pr, Bu, i=Bu, Ph and mixtures thereof;
- n is 3, 4, 5, or 6;
- wherein each n is the same;
- m is 1 or 2;
- wherein the m's may be the same or different;
- k is 1 or 2;
- R is selected from the group consisting of CH3, H, CH2CH3, iPr, iBu, and SO3H, wherein the R's may be the same or different;
- W is selected from the group consisting of O, S, and NH, wherein each W is the same;
- X is selected from the group consisting of —O-Ph-CO2H, NH2, NO2, SO3H, O(CH2CH2)nOR′, —N═C═S, —NH(CO)CH2Cl, —NH(CO)CH2Br, —NH(CO)CH2I, —NH(CO)NHNH2, —OPh-(CO)H, —O-Ph-(CO)NHNH2;
- —NHCO(CH2)jCOOH;
- j is from 2 to 12;
- R′ is selected from the group consisting of CH3, H, CH2CH3, iPr, iBu, and SO3H;
- and
- X and R(OCH2CH2)nW are different.
A compound having the structure:
- wherein:
- M is selected from the group consisting of 2H, Zn, Ni, Cu, SnY2, Pd, AlY, Pt, SiY2, GaY, and CoY;
- Y is selected from the group consisting of F, Cl, Br, I, OR, OH, SR, —CCR, C═CR, OPh, CH3, C2H5, Pr, i-Pr, Bu, i=Bu, Ph and mixtures thereof;
- n is 3, 4, 5, or 6;
- wherein each n is the same;
- R is selected from the group consisting of CH3, H, CH2CH3, iPr, iBu, and SO3H;
- wherein the R's may be the same or different;
- W is selected from the group consisting of O, S, and NH;
- wherein each W is the same;
- Z is selected from the group consisting of NR″R′″, SR″ and OR″, where R″ and R′″ are selected from the group H, Ph-CO2H, O, ((CH2)n)mOR, C═S, (CO)CH2Br, (CO)CH2I, (CO)NHNH2, Ph(CO)H, Ph(CO)NHNH2, and CO(CH2)COOH, wherein R″ and R′″ may be different or the same.
A compound having the structure:
- wherein
- M is selected from the group consisting of 2H, Zn, Ni, Cu, SnY2, Pd, AlY, Pt, SiY2, GaY, and CoY;
- Y is selected from the group consisting of F, Cl, Br, I, OR, OH, SR, —CCR, C═CR, OPh, CH3, C2H5, Pr, i-Pr, Bu, i=Bu, Ph and mixtures thereof;
- n is 3, 4, 5, or 6;
- wherein each n is the same;
- R is selected from the group consisting of CH3, H, CH2CH3, iPr, iBu, and SO3H;
- where the R's may be the same or different;
- and
- W is selected from the group consisting of O, S, and NH;
- wherein each W is the same.
A method for administering and using a fluorophore in a living cell;
- said method comprising the steps of:
- (a) contacting the cells with a compound comprising the fluorophore, wherein the compound is taken up by the cells;
- (b) exposing the cells to near-infrared irradiation within the absorption band of the fluorophore;
- and
- (c) allowing the fluorophore to conduct one or more of the following steps within the cell:
- preferentially staining endosomes, inducing apoptosis, labeling a biomolecule, repressing fluorescence by proximity to a quencher, or enhancing fluorescence by proximity to a chromophore;
- wherein the fluorophore has the structure:
- wherein
- M is selected from the group consisting of 2H, Zn, Ni, Cu, SnY2, Pd, AlY, Pt, SiY2, GaY, and CoY;
- Y is selected from the group consisting of F, Cl, Br, I, OR, OH, SR, —CCR, C═CR, OPh, CH3, C2H5, Pr, i-Pr, Bu, i=Bu, Ph and mixtures thereof;
- R is selected from the group consisting of CH3, H, CH2CH3, iPr, iBu, and SO3H;
- where the R's may be the same or different;
- A is selected from the group consisting of —O-Ph-CO2H, NH2, NO2, SO3H, O(CH2CH2)nOR′, —N═C═S, —NH(CO)CH2Cl, —NH(CO)CH2Br, —NH(CO)CH2I, —NH(CO)NHNH2, —OPh-(CO)H, —O-Ph-(CO)NHNH2;
- —NHCO(CH2)jCOOH;
- and
- R′ is selected from the group consisting of CH3, H, CH2CH3, iPr, iBu, and SO3H.
A method comprising conducting polymerase chain reaction amplification of an oligonucleotide, wherein oligonucleotide products produced by the polymerase chain reaction amplification are differentially labeled, wherein the labels used for the different bases may be distinguished from one another by different fluorescence absorption, different fluorescence emission, or different fluorescence lifetimes, but without having substantially different electrophoretic mobilities among the different labels used;
- and wherein each of the labels comprises a fluorophore having the structure:
- wherein
- M is selected from the group consisting of 2H, Zn, Ni, Cu, SnY2, Pd, AlY, Pt, SiY2, GaY, and CoY;
- Y is selected from the group consisting of F, Cl, Br, I, OR, OH, SR, —CCR, C═CR, OPh, CH3, C2H5, Pr, i-Pr, Bu, i=Bu, Ph and mixtures thereof;
- R is selected from the group consisting of CH3, H, CH2CH3, iPr, iBu, and SO3H;
- where the R's may be the same or different;
- A is selected from the group consisting of —O-Ph-CO2H, NH2, NO2, SO3H, O(CH2CH2)nOR′, —N═C═S, —NH(CO)CH2Cl, —NH(CO)CH2Br, —NH(CO)CH2I, —NH(CO)NHNH2, —OPh-(CO)H, —O-Ph-(CO)NHNH2;
- —NHCO(CH2)jCOOH;
- and
- R′ is selected from the group consisting of CH3, H, CH2CH3, iPr, iBu, and SO3H.
Dependencies are inferred from the claim text.