Novel metal complexes of boronated chlorin e6 for photodynamic therapy

Ol’shevskaya, V. A.; Savchenko, Arina N.; Зайцев, А. В.; Kononova, Elena G.; Petrovskii, P. V.; Рамонова, А. Г.; Tatarskiy, Victor V.; Уваров, О. В.; Moisenovich, M. M.; Калинин, В. Н.; Shtil, Alexander A.

doi:10.1016/j.jorganchem.2008.11.013

Cited by 39 publications

(21 citation statements)

References 35 publications

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“…Pheophytin a ( 1 ) was extracted from Spirulina pacifica alga as previously published and its spectroscopic characterization agreed with the published data. 34 All compounds synthesized were purified and isolated in ≥ 95% purity, as evidenced by analytical TLC in at least two solvent systems, and confirmed by the absence of extraneous tetrapyrrole resonances in 1 H- and 13 C-NMR spectra.…”

Section: Methodsmentioning

confidence: 94%

Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e₆ conjugates

et al. 2016

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Chlorin e6 is a tricarboxylic acid degradation product of chlorophyll a. Four chlorin e6 bis(amino acid) conjugates were regioselectively synthesized bearing two aspartate conjugates in the 131,173- and 152,173-positions, or at the 131,152 via an ethylene diamine linker. One additional conjugate bearing two different amino acids, lysine at 131 via an ethylene diamine linker and an aspartate at 152 via a β-alanine linker was also synthesized. The cytotoxicity and uptake of four di(amino acid) chlorin e6 conjugates were investigated in human HEp2 cells, and compared with chlorin e6. The most cytotoxic and most taken up conjugates were the zwitterionic 131,152-disubstituted conjugates 28 and 33; these also localized in multiple organelles. In contrast, the tetra-anionic 131,173- and 152,173-di-aspartyl chlorin e6 conjugates 12 and 13 showed low dark cytoxicity and lower phototoxicity compared with chlorin e6.

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Section: Methodsmentioning

confidence: 94%

Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e₆ conjugates

et al. 2016

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“…An attempt was made to synthesize the proposed chlorin e 6 derivative using the one-step nucleophilic attack of either of the lysine differentially mono-protected nitrogens upon the 13 1 -carbonyl of methyl pheophorbide a [14]. This procedure failed to yield a useful product under a variety of solvent conditions.…”

Section: Resultsmentioning

confidence: 99%

Syntheses and PDT activity of new mono- and di-conjugated derivatives of chlorin e₆

Chen

Humble

Jinadasa

et al. 2017

J. Porphyrins Phthalocyanines

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Syntheses of three new chlorin e6 conjugates for PDT of tumors are reported. One of the new compounds 17 is conjugated with lysine at the 131-position, but the others are mono-conjugated 14 or diconjugated 15 with the non-amino acid species ethanolamine. Cellular experiments with the three new compounds and previously synthesized non-amino acid 152-conjugates (7–10), 131-monoconjugates 14, 16, and a 131,152-diconjugate 12 are reported. In vitro cytotoxicity experiments show that the 131-conjugates are more toxic than the 152-conjugates, and the most toxic derivative (dark- and photo-toxicity) is the 131-ethylenediamine conjugate 11. The most useful PDT photosentitizers appear to be the ethanolamine derivatives, conjugated at the 152- and the 131,152-positions; these show high phototoxicity but relatively low dark toxicity compared with 11, and also the highest dark/photo cytotoxicity ratios.

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“…25,40 We took advantage of this high yielding isocyclic ring-opening reaction to develop a potentially high yielding synthetic route to novel chlorin e 6 photosensitizers, directly from pheophytin a ( 1 ) in four steps. Nucleophilic ring-opening of the isocyclic ring with ethylenediamine produced molecule ( 12 ) in 91% yield.…”

Section: Resultsmentioning

confidence: 99%

Syntheses and Cellular Investigations of 17³-, 15²-, and 13¹-Amino Acid Derivatives of Chlorin e₆

Jinadasa

Vicente

et al. 2011

J. Med. Chem.

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A series of amino acid conjugates of chlorin e6, containing lysine or aspartic acid residues in positions 173, 152 or 131 of the macrocycle were synthesized and investigated as photosensitizers for photodynamic therapy of tumors. All three regioisomers were synthesized in good yields and in 5 steps or less from pheophytin a (1). In vitro investigations using human carcinoma HEp2 cells show that the 152-lysyl regioisomers accumulate the most within cells, and the most phototoxic are the 131 regioisomers. The main determinant of biological efficacy appears to be the conjugation site, probably because of molecular conformation. Molecular modeling investigations reveal that the 173-substituted chlorin e6 conjugates are L-shaped, the 152 and 131 regioisomers assume extended conformations, and the 131 derivatives are nearly linear. It is hypothesized that the 131-aspartylchlorin e6 conjugate may be a more efficient photosensitizer for PDT than the commercial currently used 152 derivative.

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Novel metal complexes of boronated chlorin e6 for photodynamic therapy

Cited by 39 publications

References 35 publications

Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e₆ conjugates

Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e₆ conjugates

Syntheses and PDT activity of new mono- and di-conjugated derivatives of chlorin e₆

Syntheses and Cellular Investigations of 17³-, 15²-, and 13¹-Amino Acid Derivatives of Chlorin e₆

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Novel metal complexes of boronated chlorin e6 for photodynamic therapy

Cited by 39 publications

References 35 publications

Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e6 conjugates

Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e6 conjugates

Syntheses and PDT activity of new mono- and di-conjugated derivatives of chlorin e6

Syntheses and Cellular Investigations of 173-, 152-, and 131-Amino Acid Derivatives of Chlorin e6

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Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e₆ conjugates

Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e₆ conjugates

Syntheses and PDT activity of new mono- and di-conjugated derivatives of chlorin e₆

Syntheses and Cellular Investigations of 17³-, 15²-, and 13¹-Amino Acid Derivatives of Chlorin e₆