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 Graça Henriques Vicente
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Abstract
Asymmetrically substituted metal-phthalocyanine compounds are disclosed. These compounds and other phthalocyanine-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.
Claims18
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.
Dependencies are inferred from the claim text.