Catatonic Bacteriochlorophyll Derivatives

A bacteriochlorophyll derivative of the formula I, II or III:

• wherein
• M represents 2H, a divalent metal atom selected from the group consisting of Pd, Pt, Co, Sn, Ni, Cu, Zn and Mn, or a trivalent metal atom selected from the group consisting of Fe, Mn, Co, Au, Al, Gd, Er, Yb and Cr;
• R1, R′2 and R6 each independently is Y—R8, —NRR′ or —N+R9R′9R″9A−;
• Y is O or S;
• R2 is H, OH or COOR9;
• R3 is H, OH, C1-C12 alkyl or C1-C12 alkoxy;
• R4 is —CH═CR9R′9, —CH═CR9Hal, —CH═CH—CH2—NR9R′9—CH═CH—CH2—N+R9R′9R″9A−, —CHO, —CH═NR9, —CH═N+R9R′9R″9A−, —CH2—OR9, —CH2—SR, —CH2—Hal, —CH2—R, —CH2—NR9R′9, —CH2—N+R9R′9R″9A−, —CH2—CH2R, —CH2—CH2Hal, —CH2—CH2OR, —CH2—CH2SR9, —CH2—CH2—NR9R′9, —CH2—CH2—N+R9R′9R″9A−, —COCH3, C(CH3)═CR9R′9, —C(CH3)═CR9Hal, —C(CH3)═NR, —CH(CH3)═N+R9R′9A−, —CH(CH3)—Hal, —CH(CH3)—OR, —CH(CH3)—SR, —CH(CH3)—NR9R′, —CH(CH3)—N+R9R′9R″9A−, or —C≡CR9;
• R5 is ═O, ═S, ═N—R, ═N+R9R′9A−, ═CR9R′9, or
• ═CR—Hal;
• R7, R8, R, R′9 and R′9 each independently is:
• (a) H;
• (b) C1-C25 hydrocarbyl;
• (c) C1-C25 hydrocarbyl, preferably C1-C25 alkyl, more preferably C1-C10 or C1-C6 alkyl, substituted by one or more functional groups selected from the group consisting of halogen, nitro, oxo, OR, SR, epoxy, epithio, —CONRR′, —COR, COOR, —OSO3R, —SO3R, —SO2R, —NHSO2R, —SO2NRR′, ═N—OR, —(CH2)—CO—NRR′, —O—(CH2)—OR, —O—(CH2)—O—(CH2)—R, —OPO3RR′, —PO2HR, and —PP3RR′, wherein R and R′ each independently is H, hydrocarbyl or heterocyclyl and R″ is hydrocarbyl or heterocyclyl;
• (d) C1-C25 hydrocarbyl, preferably C1-C25 alkyl, more preferably C1-C10 or C1-C6 alkyl, substituted by one or more functional groups selected from the group consisting of positively charged groups, negatively charged groups, basic groups that are converted to positively charged groups under physiological conditions, and acidic groups that are converted to negatively charged groups under physiological conditions;
• (e) C1-C25 hydrocarbyl, preferably C1-C25 alkyl, more preferably C1-C10 or C1-C6 alkyl, containing one or more heteroatoms and/or one or more carbocyclic or heterocyclic moieties;
• (f) C1-C25 hydrocarbyl, preferably C1-C25 alkyl, more preferably C1-C10 or C1-C6 alkyl, containing one or more heteroatoms and/or one or more carbocyclic or heterocyclic moieties and substituted by one or more functional groups as defined in (c) and (d) above;
• (g) C1-C25 hydrocarbyl, preferably C1-C25 alkyl, more preferably C1-C10 or C1-C6 alkyl, substituted by a residue of an amino acid, a peptide, a protein, a monosaccharide, an oligosaccharide, or a polysaccharide;
• or
• (h) a residue of an amino acid, a peptide, a protein, a monosaccharide, an oligosaccharide, or a polysaccharide;
• R8 may further be H+ or a cation R+10 when R1, R′2 and R6 each independently is Y—R;
• R+10 is a metal, an ammonium group or an organic cation;
• A− is a physiologically acceptable anion;
• m is 0 or 1;
• and
• pharmaceutically acceptable salts and optical isomers thereof;
• provided that, when in formula I R2 and R3 are both H, R5 is not ═N—R9 and/or R4 is not —C(CH3)═NR;
• and further provided that the bacteriochlorophyll derivative of formula I, II or III has at least one positively charged group and/or at least one basic group that is converted to a positively charged group under physiological conditions.