The synthetic fluorinated tetracarboranylchlorin as a versatile antitumor photoradiosensitizer

Ol’shevskaya, V. A.; Av, Zaĭtsev; Petrova, Albina S.; Arkhipova, A. Yu.; Moisenovich, Mikhail M.; Kostyukov, Alexey A.; Egorov, Anton E.; Koroleva, Olga; Golovina, G. V.; Volodina, Yulia L.; Кузьмин, В. А.; Sakurai, Yoshinori; Tanaka, Hiroki; Miyoshi, Norio; Shtil, Alexander А.

doi:10.1016/j.dyepig.2020.108993

Cited by 14 publications

(17 citation statements)

References 61 publications

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“…To evaluate the plasma membrane integrity in HCT116 cells treated with CuO + NAC, we used laser confocal microscopy. Pht served as a reference compound since photoactivation of tetrapyrrolic compounds is known to trigger primary loss of plasma membrane integrity [ 26 , 27 ]. Accordingly, microscopic laser illumination of Pht loaded cells during imaging resulted in PI influx within the initial 3–5 min ( Figure S1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Then, the cells were incubated with CuO NPs (1 µg/mL) and NAC (1 mM) for 1–24 h followed by washing with PBS. Photolon (10 µM, 3 h, illumination at 660 nm, 33 J/cm 2 ) was a reference compound for light-activated oxidative stress and rapid organelle damage, a property of chlorin e6 derivatives [ 26 , 37 ]. For labeling mitochondria and nuclei, dihydrorhodamine 123 (DHR 123; (488 nm/510–570 nm)) and Hoechst 33342 (405 nm/415–470 nm), respectively, were used as recommended by the manufacturer (Thermo Fisher Sci.).…”

Section: Methodsmentioning

confidence: 99%

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Copper-Containing Nanoparticles and Organic Complexes: Metal Reduction Triggers Rapid Cell Death via Oxidative Burst

Tsymbal

Moiseeva

Agadzhanian

et al. 2021

IJMS

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Copper-containing agents are promising antitumor pharmaceuticals due to the ability of the metal ion to react with biomolecules. In the current study, we demonstrate that inorganic Cu2+ in the form of oxide nanoparticles (NPs) or salts, as well as Cu ions in the context of organic complexes (oxidation states +1, +1.5 and +2), acquire significant cytotoxic potency (2–3 orders of magnitude determined by IC50 values) in combinations with N-acetylcysteine (NAC), cysteine, or ascorbate. In contrast, other divalent cations (Zn, Fe, Mo, and Co) evoked no cytotoxicity with these combinations. CuO NPs (0.1–1 µg/mL) together with 1 mM NAC triggered the formation of reactive oxygen species (ROS) within 2–6 h concomitantly with perturbation of the plasma membrane and caspase-independent cell death. Furthermore, NAC potently sensitized HCT116 colon carcinoma cells to Cu–organic complexes in which the metal ion coordinated with 5-(2-pyridylmethylene)-2-methylthio-imidazol-4-one or was present in the coordination sphere of the porphyrin macrocycle. The sensitization effect was detectable in a panel of mammalian tumor cell lines including the sublines with the determinants of chemotherapeutic drug resistance. The components of the combination were non-toxic if added separately. Electrochemical studies revealed that Cu cations underwent a stepwise reduction in the presence of NAC or ascorbate. This mechanism explains differential efficacy of individual Cu–organic compounds in cell sensitization depending on the availability of Cu ions for reduction. In the presence of oxygen, Cu+1 complexes can generate a superoxide anion in a Fenton-like reaction Cu+1L + O2 → O2−.+ Cu+2L, where L is the organic ligand. Studies on artificial lipid membranes showed that NAC interacted with negatively charged phospholipids, an effect that can facilitate the penetration of CuO NPs across the membranes. Thus, electrochemical modification of Cu ions and subsequent ROS generation, as well as direct interaction with membranes, represent the mechanisms of irreversible membrane damage and cell death in response to metal reduction in inorganic and organic Cu-containing compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Copper-Containing Nanoparticles and Organic Complexes: Metal Reduction Triggers Rapid Cell Death via Oxidative Burst

Tsymbal

Moiseeva

Agadzhanian

et al. 2021

IJMS

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“…IC 50 values were 20 ± 1.8 and 16 ± 0.9 μM, respectively (see Supplementary Materials Figure S15 ). As positive controls, the disodium salt of chlorin e6 (Photolon) and the fluorinated carboranylchlorin FBCh with the reported PS characteristics were used [ 68 ].…”

Section: Resultsmentioning

confidence: 99%

Multicomponent Molecular Systems Based on Porphyrins, 1,3,5-Triazine and Carboranes: Synthesis and Characterization

et al. 2022

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2,4,6-Trichloro-1,3,5-triazine (cyanuric chloride) is an excellent coupling reagent for the preparation of highly structured multifunctional molecules. Three component systems based on porphyrin, cyanuric chloride and carborane clusters were prepared by a one-pot stepwise amination of cyanuric chloride with 5-(4-aminophenyl)-10,15,20-triphenylporphyrin, followed by replacement of the remaining chlorine atoms with carborane S- or N-nucleophiles. Some variants of 1,3,5-triazine derivatives containing porphyrin, carborane and residues of biologically active compounds such as maleimide, glycine methyl ester as well as thioglycolic acid, mercaptoethanol and hexafluoroisopropanol were also prepared. A careful control of the reaction temperature during the substitution reactions will allow the synthesis of desired compounds in a good to high yields. The structures of synthesized compounds were determined with UV-vis, IR, 1H NMR, 11B NMR, MALDI-TOF or LC-MS spectroscopic data. The dark and photocytotoxicity as well as intracellular localization and photoinduced cell death for compounds 8, 9, 17, 18 and 24 were evaluated.

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“…Boronated tetrapyrrole derivatives based on porphyrins, chlorins and phthalocyanines are promising dual sensitizers for BNCT and PDT due to their low dark cytotoxicity, high boron content, and good tumor affinity. [14][15][16] Exploring the antitumor potential of transition metal complexes in photosensitizers, Ru(II) and Ir(III) phenanthroline-based carborane complexes were synthesized and also characterized as efficient dual anti-cancer agents for PDT and BNCT. 17 BNCT and PDT are promising anticancer modalities 18 which are based on the selective accumulation and retention of non-toxic photosensitizers in tumor cells, and these cells are next treated with thermal neutrons (BNCT) or with light of a specific wavelength that activates the photosensitizer (PDT) to generate highly reactive oxygen species (ROS).…”

Section: Introductionmentioning

confidence: 99%

BODIPY derivatives modified with carborane clusters: synthesis, characterization and DFT studies

et al. 2023

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The synthetic fluorinated tetracarboranylchlorin as a versatile antitumor photoradiosensitizer

Cited by 14 publications

References 61 publications

Copper-Containing Nanoparticles and Organic Complexes: Metal Reduction Triggers Rapid Cell Death via Oxidative Burst

Copper-Containing Nanoparticles and Organic Complexes: Metal Reduction Triggers Rapid Cell Death via Oxidative Burst

Multicomponent Molecular Systems Based on Porphyrins, 1,3,5-Triazine and Carboranes: Synthesis and Characterization

BODIPY derivatives modified with carborane clusters: synthesis, characterization and DFT studies

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