Specifically glyco-substituted porphyrins and chlorins for photodynamic therapy

A tetrapyrrolic compound having a structure of Formula 1, 2, or 3:

• wherein B is
• O—R1 is a substituent in the meta or para position of the phenyl ring,
• R1 is a glyco-substituent derived from a mono-, di-, or trisaccharide group, and
• each R2 is independently selected from the group consisting of a linear or branched (fluoro-)alkyl group with 3 to 8 carbon atoms, phenyl, pentafluorophenyl, 3,5-bis(trifluoromethyl)phenyl, 4-(1′-thio-β-D-glucosyl)-2,3,5,6-tetrafluorophenyl, 4-(1′-thio-β-D-galactosyl)-2,3,5,6-tetrafluorophenyl, meta- or para-hydroxyphenyl, meta- or para-carboxyphenyl, and meta- or para-YO-phenyl with Y being a polyethyleneglycol-residue with (CH2CH2O)nCH3 with n=1-30,
• wherein
• (a) in Formula 1 or 2, if B is
• O—R1 is a substituent in the para position of the phenyl ring and R1 is glucosyl, then each R2 is independently selected from the group consisting of a linear or branched alkyl group with 5 to 8 carbon atoms, a linear or branched fluoroalkyl group with 3 to 8 carbon atoms, 3,5-bis(trifluoromethyl)phenyl, 4-(1′-thio-β-D-glucosyl)-2,3,5,6-tetrafluorophenyl, 4-(1′-thio-β-D-galactosyl)-2,3,5,6-tetrafluorophenyl, meta- or para-hydroxyphenyl, meta- or para-carboxyphenyl, and meta- or para-YO-phenyl with Y being a polyethyleneglycol-residue with (CH2CH2O)nCH3 with n=1-30,
• (b) in Formula 1 or 2, if B is
• O—R1 is a substituent in the para position of the phenyl ring and R1 is galactosyl, then each R2 is independently selected from the group consisting of a linear or branched (fluoro-)alkyl group with 3 to 8 carbon atoms, pentafluorophenyl, 3,5-bis(trifluoromethyl)phenyl, 4-(1′-thio-β-D-glucosyl)-2,3,5,6-tetrafluorophenyl, 4-(1′-thio-β-D-galactosyl)-2,3,5,6-tetrafluorophenyl, meta- or para-hydroxyphenyl, meta- or para-carboxyphenyl, and meta- or para-YO-phenyl with Y being a polyethyleneglycol-residue with (CH2CH2O)nCH3 with n=1-30,
• (c) in Formula 1 or 2, if O—R1 is a substituent in the meta position of the phenyl ring and R1 is glucosyl and R2 is n-hexyl, phenyl or 3,5-bis(trifluoromethyl)phenyl, then B is
• (d) in Formula 1 or 2, if O—R1 is a substituent in the meta position of the phenyl ring and R1 is galactosyl and R2 is phenyl, then B is
• (e) in Formula 3, if B is
• O—R1 is a substituent in the para position of the phenyl ring and R1 is glucosyl, then each R2 is independently selected from the group consisting of a linear or branched (fluoro-)alkyl group with 5 to 8 carbon atoms, pentafluorophenyl, 3,5-bis(trifluoromethyl)phenyl, 4-(1′-thio-β-D-glucosyl)-2,3,5,6-tetrafluorophenyl, 4-(1′-thio-β-D-galactosyl)-2,3,5,6-tetrafluorophenyl, meta- or para-hydroxyphenyl, meta- or para-carboxyphenyl, and meta- or para-YO-phenyl with Y being a polyethyleneglycol-residue with (CH2CH2O)nCH3 with n=1-30,
• (f) in Formula 3, if B is
• O—R1 is a substituent in the meta position of the phenyl ring and R1 is glucosyl, then each R2 is independently selected from the group consisting of a linear or branched (fluoro-)alkyl group with 3 to 8 carbon atoms, pentafluorophenyl, 3,5-bis(trifluoromethyl)phenyl, 4-(1′-thio-β-D-glucosyl)-2,3,5,6-tetrafluorophenyl, 4-(1′-thio-β-D-galactosyl)-2,3,5,6-tetrafluorophenyl, meta- or para-hydroxyphenyl, meta- or para-carboxyphenyl, and meta- or para-YO-phenyl with Y being a polyethyleneglycol-residue with (CH2CH2O)nCH3 with n=1-30, and
• (g) in Formula 3, if B is
• O—R1 is a substituent in the para position of the phenyl ring and R1 is galactosyl, then each R2 is independently selected from the group consisting of a linear or branched (fluoro-)alkyl group with 3 to 8 carbon atoms, pentafluorophenyl, 3,5-bis(trifluoromethyl)phenyl, 4-(1′-thio-β-D-glucosyl)-2,3,5,6-tetrafluorophenyl, 4-(1′-thio-β-D-galactosyl)-2,3,5,6-tetrafluorophenyl, meta- or para-hydroxyphenyl, meta- or para-carboxyphenyl, and meta- or para-YO-phenyl with Y being a polyethyleneglycol-residue with (CH2CH2O)nCH3 with n=1-30.