De novo synthesis of bacteriochlorins
AssigneeNorth Carolina State University
InventorsHan-Je Kim, Jonathan S. Lindsey
Life of this patent
Estimating the term…
Abstract
A method of making a bacteriochlorin is carried out by condensing a pair of compounds of Formula II to produce the bacteriochlorin, wherein R is an acetal or aldehyde group. The condensing may be carried out in an organic solvent, preferably in the presence of an acid. The bacteriochlorins are useful for a variety of purposes such as active agents in photodynamic therapy, luminescent compounds in flow cytometry, solar cells, light harvesting arrays, and molecular memory devices.
Claims29
1-17. (canceled)
A compound of Formula I:
- wherein:
- M is a metal or is absent;
- X is selected from the group consisting of Se, NH, CH2, O and S;
- R1, R2, R3, R4 R5, R6 R7 and R8 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, urea, alkoxylacylamino, aminoacyloxy, linking groups, and surface attachment groups;
- or R1 and R2 together are ═O or spiroalkyl;
- or R3 and R4 together are ═O or spiroalkyl;
- subject to the proviso that (i) neither R1 nor R2 is H, or (ii) neither R3 nor R4 is H;
- and further
- subject to the proviso that, when X is NH:
- R1 is not cycloalkyl;
- or
- R2 is not methyl;
- or
- R5 is not H;
- or
- R6 is not H;
- or
- R7 is not methyl.
43-66. (canceled)
In a method of detecting cells or particles by flow cytometry, wherein said cells or particles are labelled with a detectable luminescent compound, the improvement comprising utilizing a bacteriochlorin as the luminescent compound, wherein said bacteriochlorin is a compound of Formula I:
- wherein:
- M is a metal or is absent;
- X is selected from the group consisting of Se, NH, CH2, 0 and S;
- R1, R2, R3, R4 R5, R6 R7 and R8 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, urea, alkoxylacylamino, aminoacyloxy, linking groups, and surface attachment groups;
- or R1 and R2 together are ═O or spiroalkyl;
- or R3 and R4 together are ═O or spiroalkyl;
- subject to the proviso that (i) neither R1 nor R2 is H, or (ii) neither R3 nor R4 is H.
(canceled)
Dependencies are inferred from the claim text.