Synthesis, Spectral, Luminescence and Photochemical Properties of the Chlorin е6 Tricationic Derivative with Trimethylammonio Groups

Venediktov, Evgenii A.; Tulikova, E. Yu.; Rozhkova, E. P.; Khudyaeva, I. S.; Белых, Д. В.; Berezin, D. B.

doi:10.6060/mhc170404v

Cited by 6 publications

(4 citation statements)

References 13 publications

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“…Reaction conditions: i: [9] CH 3 NH 2 -H 2 O/THF, room temp., 3 h, yield of 3 -85 %; ii: [9] [(CH 3 ) 2 N=СH 2 ] + I -, CH 2 Cl 2 , r.t., 12 h, yield of 5 -35 %, yield of 4 -30 %; iii: [12] H 2 NCH 2 CH 2 N(CH 3 ) 2 , CH 2 Cl 2 , r.t., yield of 2 -74 %; iv: [13,14] CH 2 (N(CH 3 ) 2 ) 2 , AcOH-THF, boiling for 30 min, yield of 6 -65 %, yield of 7 -45 %; v: [13] CH 3 I, CH 2 Cl 2 , r.t., yields of 8-12 -93-96 %.…”

Section: Resultsmentioning

confidence: 99%

“…Cationic chlorins 8, 10-12 were synthesized according to previously described procedures. [9,[12][13][14] 3( 2)-(N,N-Dimethylaminomethyl)chlorin e 6 13(1)-N-(2-N',N'dimethylaminoethyl)amide-15,17-dimethyl ester (4). A solution of 97.8 mg (0.14 mmol) of compound 2 in 5 mL of СН 2 Cl 2 was mixed with 105 mg (0.58 mmol) of Eschenmoser's salt.…”

Section: Experimental Partmentioning

confidence: 99%

“…The quantum yields (γ) of the photoproduction of singlet oxygen ( 1 О 2 ) were determined based on the intensity of its luminescence in pyridine by the relative method using 5,10,15,20-tetraphenylporphine (Н 2 ТРР) as a standard according to a previously described procedure. [4,14] The value of γ was calculated according to the general formula: [14]…”

Section: Experimental Partmentioning

confidence: 99%

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Dark and Photoinduced Cytotoxicity of Cationic Chlorin e6 Derivatives with Different Numbers of Charged Groups

Pylina¹,

Khudyaeva²,

Startseva³

et al. 2021

MHC

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Dark and photoinduced toxicity of several novel and previously described derivatives of chlorin e 6 with tetraalkylammonium substituents differing from each other in number of cationic groups and their location in the macrocycle were studied in HeLa cells and mammalian erythrocytes. The optimal design of cationic derivatives of chlorin e 6 that provides the most efficient photodynamic effect was shown to require the localization of cationic substituents in the same part of the molecule. In combination with the hydrophobicity of the chlorin macrocycle, it increases the amphiphilic properties of the whole molecule and enhances its interaction with biomembranes.

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Section: Resultsmentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 99%

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Dark and Photoinduced Cytotoxicity of Cationic Chlorin e6 Derivatives with Different Numbers of Charged Groups

Pylina¹,

Khudyaeva²,

Startseva³

et al. 2021

MHC

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“…3(1),3(2)-bis(N,N,N-trimethylaminomethyliodide) chlorin e6 13(1)-N-methylamide-15(2)-methyl,17(3)-phytyl ester (Compound 1, Figure 11) was synthesized from pheophytin a extracted from the air-dry spirulina according to the procedure described earlier [19]. Briefly, two aminomethyl groups were introduced by the aminomethylation of the vinyl group of a 13-methylamide derivative by bis(N,N-dimethylamino)methane, similarly to the previously described procedure for the synthesis of phytol-free cationic Ce6 derivatives [45,46]. As in the latter case, aminomethylation resulted in a mixture of cis-and trans-isomers forming in a 1:1 ratio.…”

Section: Synthesis Of Compoundmentioning

confidence: 99%

Characterization of a Novel Amphiphilic Cationic Chlorin Photosensitizer for Photodynamic Applications

Gradova

Градов

Лобанов

et al. 2022

IJMS

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A novel amphiphilic cationic chlorin e6 derivative was investigated as a promising photosensitizer for photodynamic therapy. Two cationic –N(CH3)3+ groups on the periphery of the macrocycle provide additional hydrophilization of the molecule and ensure its electrostatic binding to the mitochondrial membranes and bacterial cell walls. The presence of a hydrophobic phytol residue in the same molecule results in its increased affinity towards the phospholipid membranes while decreasing its stability towards aggregation in aqueous media. In organic media, this chlorin e6 derivative is characterized by a singlet oxygen quantum yield of 55%. Solubilization studies in different polymer- and surfactant-based supramolecular systems revealed the effective stabilization of this compound in a photoactive monomolecular form in micellar nonionic surfactant solutions, including Tween-80 and Cremophor EL. A novel cationic chlorin e6 derivative also demonstrates effective binding towards serum albumin, which enhances its bioavailability and promotes effective accumulation within the target tissues. Laser confocal scanning microscopy demonstrates the rapid intracellular accumulation and distribution of this compound throughout the cells. Together with low dark toxicity and a rather good photostability, this compound demonstrates significant phototoxicity against HeLa cells causing cellular damage most likely through reactive oxygen species generation. These results demonstrate a high potential of this derivative for application in photodynamic therapy.

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Exo ring opening in methyl pheophorbide a 132-amide derivatives under the action of amines

et al. 2021

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Synthesis, Spectral, Luminescence and Photochemical Properties of the Chlorin е6 Tricationic Derivative with Trimethylammonio Groups

Cited by 6 publications

References 13 publications

Dark and Photoinduced Cytotoxicity of Cationic Chlorin e6 Derivatives with Different Numbers of Charged Groups

Dark and Photoinduced Cytotoxicity of Cationic Chlorin e6 Derivatives with Different Numbers of Charged Groups

Characterization of a Novel Amphiphilic Cationic Chlorin Photosensitizer for Photodynamic Applications

Exo ring opening in methyl pheophorbide a 132-amide derivatives under the action of amines

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