Glycoconjugates of porphyrins with carbohydrates: methods of synthesis and biological activity

Titov, Denis V.; Gening, Marina L.; Tsvetkov, Yury E.; Nifantiev, Nikolay E.

doi:10.1070/rc2014v083n06abeh004426

Cited by 19 publications

(8 citation statements)

References 155 publications

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“…96 Following these reports, several meso -substituted glycoporphyrins were studied along with a few more β -pyrrolic-substituted sugar porphyrin conjugates. 113 Among these, the sugars were substituted on porphyrin via sulfur, 116 nitrogen, 114 and carbon groups. 226 One such example was recently reported by Cavaleiro and co-workers shown in Figure 25.…”

Section: Glycosylated Porphyrinsmentioning

confidence: 99%

Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics

et al. 2015

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Section: Glycosylated Porphyrinsmentioning

confidence: 99%

Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics

et al. 2015

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“…In the search for the optimum, a number of porphyrinoid-based glycoconjugates have been reported and evaluated . In some cases, a sugar moiety attached to the porphyrin core provided amphiphilicity of the conjugate, necessary for the desired pharmacokinetic profile of a PDT agent …”

Section: Introductionmentioning

confidence: 99%

“…42 In some cases, a sugar moiety attached to the porphyrin core provided amphiphilicity of the conjugate, necessary for the desired pharmacokinetic profile of a PDT agent. 43 Based on this, we replaced cationic ammonium fragments in conjugate 2 by carbohydrate scaffolds, as shown in structure 1. We also expected that, due to the presence of sugar fragments, conjugate 1 would have affinity to carbohydrate receptors, such as lectine-specific ones, or carbohydrate transporters, widely expressed on the surface of tumor cells.…”

Section: ■ Introductionmentioning

confidence: 99%

Water-Soluble Chlorin/Arylaminoquinazoline Conjugate for Photodynamic and Targeted Therapy

et al. 2019

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A new water-soluble conjugate, consisting of a chlorin-e 6 photosensitizer part, a 4-arylaminoquinazoline moiety with affinity to epidermal growth factor receptors, and a hydrophilic β-D-maltose fragment, was synthesized starting from methylpheophorbide-a in seven steps. The prepared conjugate exhibited low levels of dark cytotoxicity and pronounced photoinduced cytotoxicity at submicromolar concentrations in vitro, with an IC 50 (dark)/IC 50 (light) ratio of ∼368 and a singlet oxygen quantum yield of about 20%. In tumor-bearing Balb/c nude mice, conjugate 1 preferentially accumulates in the tumor tissue. Irradiation of the nude mice bearing A431 xenograft tumors after intravenous administration of the prepared conjugate with a relatively low light dose (50 J/cm 2 ) produced an excellent therapeutic effect with profound tumor regression and low systemic toxicity.

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“…Recently, Che and coauthors disclosed that [Fe(F 20 TPP)Cl (TPP = dianion of tetraphenylporphyrin) is a competent catalyst for the promotion of C–N bond formation by also using organic azides , as aminating agents. While glycoconjugated porphyrins have been used in photodynamic therapy (PDT) for active targeting of membrane receptors, − quite surprisingly there are only a few examples in the literature describing their use in catalysis. − In particular, iron glycoporphyrin complexes have been sparsely used in catalytic reactions and have never been employed to catalyze amination reactions.…”

Section: Introductionmentioning

confidence: 99%

Glycoporphyrin Catalysts for Efficient C–H Bond Aminations by Organic Azides

et al. 2015

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We report herein the synthesis of new glycoporphyrin ligands which bear a glucopyranoside derivative on each meso-aryl moiety of the porphyrin skeleton. The saccharide unit is directly conjugated to the porphyrin or a triazole spacer is placed between the carbohydrate and porphyrin ring. The obtained glycoporphyrin ligands were employed to synthesize cobalt(II), ruthenium(II), and iron-(III) complexes which were tested as catalysts of C−H bond aminations by organic azides. Two of the synthesized complexes were very efficient in promoting catalytic reactions, and the results achieved indicated that ruthenium and iron complexes show an interesting complementary catalytic activity in several amination reactions. The eco-friendly iron catalyst displayed very good chemical stability in catalyzing the amination reaction for three consecutive runs without losing catalytic activity.

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Glycoconjugates of porphyrins with carbohydrates: methods of synthesis and biological activity

Cited by 19 publications

References 155 publications

Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics

Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics

Water-Soluble Chlorin/Arylaminoquinazoline Conjugate for Photodynamic and Targeted Therapy

Glycoporphyrin Catalysts for Efficient C–H Bond Aminations by Organic Azides

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