Conjugates of Tetrapyrrolic Macrocycles as Potential Anticancer Target-Oriented Photosensitizers

Korolchuk, A.M.; Zolottsev, Vladimir A.; Misharin, A. Yu.

doi:10.1007/s41061-023-00421-0

Cited by 6 publications

(4 citation statements)

References 122 publications

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“…Porphyrins and related compounds are known for their excellent performance as photosensitizers (PS) in PDT [ 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. Currently, applied PS are often based on porphyrins, chlorins, and isobacteriochlorin-type derivatives due to their optical features, namely, their strong absorption in the “therapeutic window” ranging from 650 to 850 nm, and their ability to produce ROS that can be lethal to the undesired tissue when activated by light [ 14 , 15 , 16 , 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

A Comparative Evaluation of the Photosensitizing Efficiency of Porphyrins, Chlorins and Isobacteriochlorins toward Melanoma Cancer Cells

et al. 2023

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Skin cancer is one of the cancers that registers the highest number of new cases annually. Among all forms of skin cancer, melanoma is the most invasive and deadliest. The resistance of this form of cancer to conventional treatments has led to the employment of alternative/complementary therapeutic approaches. Photodynamic therapy (PDT) appears to be a promising alternative to overcome the resistance of melanoma to conventional therapies. PDT is a non-invasive therapeutic procedure in which highly reactive oxygen species (ROS) are generated upon excitation of a photosensitizer (PS) when subjected to visible light of an adequate wavelength, resulting in the death of cancer cells. In this work, inspired by the efficacy of tetrapyrrolic macrocycles to act as PS against tumor cells, we report the photophysical characterization and biological assays of isobacteriochlorins and their corresponding chlorins and porphyrins against melanoma cancer cells through a photodynamic process. The non-tumoral L929 fibroblast murine cell line was used as the control. The results show that the choice of adequate tetrapyrrolic macrocycle-based PS can be modulated to improve the performance of PDT.

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Section: Introductionmentioning

confidence: 99%

A Comparative Evaluation of the Photosensitizing Efficiency of Porphyrins, Chlorins and Isobacteriochlorins toward Melanoma Cancer Cells

et al. 2023

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“…In the type-II mechanism, a tripletexcited photosensitizer reacts with molecular oxygen to give highly reactive singlet oxygen, 1 O 2 , as reactive intermediate, which in turn oxidizes the DNA bases [46]. As a result, various classes of photosensitizers [47][48][49] have been established, for example, porphyrins [50], chlorins [51], phthalocyanines [52], porphycenes [53], metal-organic complexes [54][55][56], dye aggregates [57], as well as nano-drug carriers and metal-based nanoparticles [58,59]. But although these classes of compounds have been intensively studied and already contributed significantly to the field of PDT, there is still a demand for novel DNA-photodamaging ligands that could be applied for specific purposes, e.g., to improve efficacy or to limit side-effects.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

Schlosser,

Fedorova,

Fedorov

et al. 2024

Beilstein J. Org. Chem.

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The photoreactions of selected styrylpyridine derivatives to the corresponding benzo[c]quinolizinium ions are described. It is shown that these reactions are more efficient in aqueous solution (97–44%) than in organic solvents (78–20% in MeCN). The quinolizinium derivatives bind to DNA by intercalation with binding constants of 6–11 × 104 M−1, as shown by photometric and fluorimetric titrations as well as by CD- and LD-spectroscopic analyses. These ligand–DNA complexes can also be established in situ upon irradiation of the styrylpyridines and formation of the intercalator directly in the presence of DNA. In addition to the DNA-binding properties, the tested benzo[c]quinolizinium derivatives also operate as photosensitizers, which induce DNA damage at relative low concentrations and short irradiation times, even under anaerobic conditions. Investigations of the mechanism of the DNA damage revealed the involvement of intermediate hydroxyl radicals and C-centered radicals. Under aerobic conditions, singlet oxygen only contributes to marginal extent to the DNA damage.

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“…Although a variety of chiral moieties have been substituted at the peripheral positions of Chl-a derivatives, [16][17][18][19][20][21][22][23][24][25] the chiral introductions at their cores are limited. Gallium (III), indium (III), and thallium (III) (boron family metals) complexes of Chl-a derivatives were axially coordinated by any anionic ligands, including chloride, hydroxide, methoxide, phenolate, acetate, and thiolate, to produce chiral five-coordinated species in a solution, whose epimers could not be separated by any techniques.…”

Section: Introductionmentioning

confidence: 99%

Determination of N‐centered stereochemistry in N22‐methylated chlorophyll‐a derivatives and their epimer‐dependent optical spectra

Ataka,

Taniguchi,

Monde

et al. 2024

Chirality

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An N‐centered epimeric mixture of chlorophyll‐a derivatives methylated at the inner nitrogen atom was separated by reverse‐phase high‐performance liquid chromatography. Circular dichroism (CD) spectroscopic analyses of the epimerically pure N22‐methyl‐chlorins revealed that the minor first‐eluted and major second‐eluted stereoisomers were (22S)‐ and (22R)‐configurations, respectively. Their visible absorption and CD spectra in solution were dependent on the N22‐stereochemistry. The epimer‐dependent spectral changes were independent of the substituents at the peripheral 3‐position of the core chlorin chromophore.

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Conjugates of Tetrapyrrolic Macrocycles as Potential Anticancer Target-Oriented Photosensitizers

Cited by 6 publications

References 122 publications

A Comparative Evaluation of the Photosensitizing Efficiency of Porphyrins, Chlorins and Isobacteriochlorins toward Melanoma Cancer Cells

A Comparative Evaluation of the Photosensitizing Efficiency of Porphyrins, Chlorins and Isobacteriochlorins toward Melanoma Cancer Cells

Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

Determination of N‐centered stereochemistry in N22‐methylated chlorophyll‐a derivatives and their epimer‐dependent optical spectra

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