Meso-monoiodo-substituted tetramacrocyclic compounds and methods for making and using the same

A meso-monoiodo-substituted tetramacrocyclic compound having the formula (I):

• ##STR20## wherein:
• each of A tough D is independently a 5-membered, nitrogen-containg ring having the members necessary to complete a porphyrin, chlorin, bacteriochlorin or isobacteriochlorin nucleus;
• R.sub.1 through are R.sub.8 independently a hydrogen atom, a lower alkyl group, a lower alkyl carboxylic acid or acid ester group, keto, hydroxy, nitro, amino, or R.sub.1 and R.sub.2, R.sub.3 and R.sub.4, R.sub.5 and R.sub.6, or R.sub.7 and R.sub.8, taken together with another ring, ring substituent or meso-substituent, forms a fused 5- or 6-membored ring selected from the group consisting of cyclopentane, furan, thiophene, pyrrole, isopyrrole, 3-isopyrrole pyrazole, 2-isoimidole, 1,2,3-triazole, 1,2,4-triazole, 1,2-dithiole, 1,3-dithiole, 1,2,3-oxathiole, isoxazole, oxazole, thiazole, isothiazole, 1,2,3-oxadiathiazole, 1,2,4-oxdiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-dioxazole, 1,2,4-dioxazole, 1,2,5-oxathiazole, 1,3-oxathiole, benzene, cyclohexane, 1,2-pyran, 1,4-pyran, 1,2-pyrone, 1,4-pyrone, 1,2-dioxin, 1,3-dioxin (dihydro form), pyridine, pyridazine, pyrimidine, pyrazine, piperazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4-oxazine, 1,3,2-oxazine, o-isoxazine, 1,2,5-oxathiazine, 1,4-oxazine, p-isoxazine, 1,2,6-oxathiazine, 1,3,5,2-oxaciazine, morpholine, azepine, oxepin, thiepin and 1,2,4-diazepine;
• and
• each of S.sup.1 through S.sup.3 is H, substituted or unsubstituted alkyl having about 1 to about 18 carbon atoms, and wherein said alkyl group is substituted by a group selected from the group consisting of a halogen atom, a hydroxy group, thiol, a carbonyl group, a primary amino group, a secondary amino group, a tertiary amino group, a quaternary amino group, nitrile, a phosphate group and a sulfonate group, substituted or unsubstituted cycloalkyl having about 3 to about 7 carbon atoms, and wherein said cycloalkyl group is substituted by a group selected from the group consisting of halogen atom, a hydroxy group, thiol, a carbonyl group, a primary amino group, a secondary amino group, a tertiary amino group, a quaternary amino group, nitrile, a phosphate group and a sulfonate group, a substituted or unsubstituted aromatic ring having about 5 to about 12 carbon atoms, or a substituted or unsubstituted heterocyclic ring selected from the group consisting of furan, thiophene, pyrrole, isopyrrole, 3-isopyrrole, pyrazole, 2-isoimidazole, 1,2,3-triazole, 1,2,4-triazole, 1,2-dithiole, 1,3-dithiole, 1,2,3-oxathiazole, isoxazole, oxazole, thiazole, isothiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3,4-oxatriazole, 1,2,3,5-oxatriazole, 1,2,3-dioxazole, 1,2,4-dioxazole, 1,3,2-dioxazole, 1,3,4-dioxazole, 1,2,5-oxathiazole, 1,3-oxathiazole, benzene, 1,2-pyran, 1,4-pyran, 1,2-pyrone, 1,4-pyrone, 1,2-dioxin, 1,3-dioxin, pyridine, N-alkyl pyridinium, pyrdazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, 1,2,4-oxazlne, 1,3,2-oxazine, 1,3,6-oxazine, 1,4-oxazine, o-isoxazine, p-isoxazine, 1,2,5-oxathiazine, 1,4-oxazine, o-isoxazine, p-isoxazine, 1,2,5-oxathiazine, 1,2,6-oxathiazine, 1,4,2-oxadiazine, 1,3,5,2-oxadiazine, azepine, oxepin, thiepin, 1,2,4-diazepine, indene, isoindene, benzofuran, isobenzofuran, thionaphthene, isothionaphthene, indole, indolenine, 2-isobenzazole, 1,4-pyrindine, pyrando›3,4-b!-pyrrole, isoindazole, indoxazine, benzoxazole, anthranil, naphthalene, 1,2-benzopyran, 1,2-benzopyrone, 1,4-benzopyrone, 2,1-benzopyrone, 2,3-benzopyrone, quinoline, isoquinoline, 1,2-benzodiine, 1,3-benzodiazine, naphthyridine, pyrido›3,4-b!-pyridine, pyrido›3,2-b!-pyridine, pyrido›4,3-b!-pyridine, 1,3,2-benzoxazine, 1,4,2-benzoxazine, 2,3,1-benzoxazine, 3,1,4-benzoxazine, 1,2-benzisoxazine, 1,4-benzisoxazine, anthracene, phenanthrene, carbazole, xanthene, acridine and purine.