Photosensitizing effects and physicochemical properties of chlorophyll a derivatives with hydrophilic oligoethylene glycol fragments at the macrocycle periphery

Malatesti, N., Munitic, I., & Jurak, I. (2017). Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents. Biophysical Reviews, 9, 149–168.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Abrahamse, H., & Hamblin, M. R. (2016). New photosensitizers for photodynamic therapy. Biochemical Journal, 473, 347–364.

Article  CAS  PubMed  Google Scholar 

Imran, M., Ramzan, M., Qureshi, A., Khan, M., & Tariq, M. (2018). Emerging applications of porphyrins and metalloporphyrins in biomedicine and diagnostic magnetic resonance imaging. Biosensors, 8, 95.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Koifman, O. I., Ageeva, T. A., Kuzmina, N. S., Otvagin, V. F., Nyuchev, A. V., Fedorov, AYu., Belykh, D. V., Lebedeva, NSh., Yurina, E. S., Syrbu, S. A., Koifman, M. O., & Gubarev, Y. A. (2022). Synthesis strategy of tetrapyrrolic photosensitizers for their practical application in photodynamic therapy. MHC, 15, 207–304.

Article  Google Scholar 

Hamblin, M. R. (2016). Antimicrobial photodynamic inactivation: A bright new technique to kill resistant microbes. Current Opinion in Microbiology, 33, 67–73.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Kustov, A. V., Kustova, T. V., Belykh, D. V., Khudyaeva, I. S., & Berezin, D. B. (2020). Synthesis and investigation of novel chlorin sensitizers containing the myristic acid residue for antimicrobial photodynamic therapy. Dyes and Pigments, 173, 107948.

Article  CAS  Google Scholar 

Pylina, Y., Shadrin, D., Shevchenko, O., Startseva, O., Velegzhaninov, I., Belykh, D., & Velegzhaninov, I. (2017). Dark and photoinduced cytotoxic activity of the new chlorophyll-a derivatives with oligoethylene glycol substituents on the periphery of their macrocycles. IJMS, 18, 103.

Article  PubMed  PubMed Central  Google Scholar 

Aggarwal, A., Samaroo, D., Jovanovic, I. R., Singh, S., Tuz, M. P., & Mackiewicz, M. R. (2019). Porphyrinoid-based photosensitizers for diagnostic and therapeutic applications: An update. Journal of Porphyrins and Phthalocyanines, 23, 729–765.

Article  CAS  Google Scholar 

Grin, M., Suvorov, N., Ostroverkhov, P., Pogorilyy, V., Kirin, N., Popov, A., Sazonova, A., & Filonenko, E. (2022). Advantages of combined photodynamic therapy in the treatment of oncological diseases. Biophysical Reviews, 14, 941–963.

Article  PubMed  PubMed Central  Google Scholar 

Singh, S., Aggarwal, A., Bhupathiraju, N. V. S. D. K., Arianna, G., Tiwari, K., & Drain, C. M. (2015). Glycosylated porphyrins, phthalocyanines, and other porphyrinoids for diagnostics and therapeutics. Chemical Reviews, 115, 10261–10306.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Koifman, O. I., Ageeva, T. A., Beletskaya, I. P., Averin, A. D., Yakushev, A. A., Tomilova, L. G., Dubinina, T. V., Tsivadze, AYu., Gorbunova, Y. G., Martynov, A. G., Konarev, D. V., Khasanov, S. S., Lyubovskaya, R. N., Lomova, T. N., Korolev, V. V., Zenkevich, E. I., Blaudeck, T., Von Borczyskowski, C., Zahn, D. R. T., … Yurina, E. S. (2020). Macroheterocyclic compounds—A key building block in new functional materials and molecular devices. Macroheterocycles, 13, 311–467.

Article  CAS  Google Scholar 

Lebedeva, NSh., Gubarev, Y. A., Koifman, M. O., & Koifman, O. I. (2020). The application of porphyrins and their analogues for inactivation of viruses. Molecules, 25, 4368.

Article  CAS  PubMed Central  Google Scholar 

Kustov, A. V., Smirnova, N. L., Privalov, O. A., Moryganova, T. M., Strelnikov, A. I., Morshnev, P. K., Koifman, O. I., Lyubimtsev, A. V., Kustova, T. V., & Berezin, D. B. (2021). Transurethral resection of non-muscle invasive bladder tumors combined with fluorescence diagnosis and photodynamic therapy with chlorin e6-type photosensitizers. JCM, 11, 233.

Article  PubMed  PubMed Central  Google Scholar 

Otvagin, V. F., Kuzmina, N. S., Kudriashova, E. S., Nyuchev, A. V., Gavryushin, A. E., & Fedorov, AYu. (2022). Conjugates of porphyrinoid-based photosensitizers with cytotoxic drugs: Current progress and future directions toward selective photodynamic therapy. Journal of Medicinal Chemistry, 65, 1695–1734.

Article  CAS  PubMed  Google Scholar 

Suvorov, N., Pogorilyy, V., Diachkova, E., Vasil’ev, Y., Mironov, A., & Grin, M. (2021). Derivatives of natural chlorophylls as agents for antimicrobial photodynamic therapy. International Journal of Molecular Sciences, 22, 6392.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Pylina, Y. I., Khudyaeva, I. S., & Belykh, D. V. (2022). Dark and photoinduced cytotoxicity of chlorophyll a derivatives and their analogues towards HeLa Cells: Some structure—Activity relationships. MHC, 15, 25–33.

Article  CAS  Google Scholar 

Pylina, Y. I., Khudyaeva, I. S., Startseva, O. M., Shadrin, D. M., Shevchenko, O. G., Velegzhaninov, I. O., Kukushkina, N. V., Berezin, D. B., & Belykh, D. V. (2021). Dark and photoinduced cytotoxicity of cationic chlorin e6 derivatives with different numbers of charged groups. MHC, 14, 317–322.

Article  CAS  Google Scholar 

Berezin, D. B., Solodukhin, T. N., Shukhto, O. V., Belykh, D. V., Startseva, O. M., Khudyaeva, I. S., & Kustov, A. V. (2018). Association of hydrophilic derivatives of chlorophyll a in ethanol–water and ethanol–water–solubilizer systems. Russian Chemical Bulletin, 67, 1273–1279.

Article  CAS  Google Scholar 

Belykh, D. V., Startseva, O. M., & Patov, S. A. (2014). Novel pH-independent amphiphilic chlorophyll a derivatives with oligoethyleneglycol substituents as a hydrophilic part: Synthesis and hydrophilicity estimation. MHC, 7, 401–413.

Article  Google Scholar 

Tarabukina, I. S., Startseva, O. M., Patov, S. A., & Belykh, D. V. (2015). Novel Dicationic chlorin e6 derivatives. MHC, 8, 168–176.

Article  Google Scholar 

Shukhto, O. V., Berezin, D. B., Khudyaeva, I. S., & Belykh, D. V. (2021). Aggregation of hydrophobic chlorins with fragments of antimicrobial drugs in aqueous solutions of ethanol and tween 80. ChemChemTech, 64, 86–96.

Article  CAS  Google Scholar 

Berezin, D. B., Kustov, A. V., Krest’yaninov, M. A., Shukhto, O. V., Batov, D. V., & Kukushkina, N. V. (2019). The behavior of monocationic chlorin in water and aqueous solutions of non-ionic surfactant Tween 80 and potassium iodide. Journal of Molecular Liquids, 283, 532–536.

Article  CAS  Google Scholar 

Gerola, A. P., Tsubone, T. M., Santana, A., De Oliveira, H. P. M., Hioka, N., & Caetano, W. (2011). Properties of chlorophyll and derivatives in homogeneous and microheterogeneous systems. The Journal of Physical Chemistry B, 115, 7364–7373.

Article  CAS  PubMed  Google Scholar 

Lindhagen, E., Nygren, P., & Larsson, R. (2008). The fluorometric microculture cytotoxicity assay. Nature Protocols, 3, 1364–1369.

Article  CAS  PubMed  Google Scholar 

Lyublinskaya, O. G., Antonov, S. A., Gorokhovtsev, S. G., Pugovkina, N. A., Kornienko, J. S., Ivanova, J. S., Shatrova, A. N., Aksenov, N. D., Zenin, V. V., & Nikolsky, N. N. (2018). Flow cytometric HyPer-based assay for hydrogen peroxide. Free Radical Biology and Medicine, 128, 40–49.

Article  CAS  PubMed  Google Scholar 

Lyublinskaya, O. G., Ivanova, J. S., Pugovkina, N. A., Kozhukharova, I. V., Kovaleva, Z. V., Shatrova, A. N., Aksenov, N. D., Zenin, V. V., Kaulin, Y. A., Gamaley, I. A., & Nikolsky, N. N. (2017). Redox environment in stem and differentiated cells: A quantitative approach. Redox Biology, 12, 758–769.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Shcherbo, D., Souslova, E. A., Goedhart, J., Chepurnykh, T. V., Gaintzeva, A., Shemiakina, I. I., Gadella, T. W., Lukyanov, S., & Chudakov, D. M. (2009). Practical and reliable FRET/FLIM pair of fluorescent proteins. BMC Biotechnology, 9, 24.

Article  PubMed  PubMed Central  Google Scholar 

R Core Team (2021). R: A language and environment for statistical computing. R Foundation for Statistical Computing, Vienna, Austria. URL https://www.R-project.org/.

Ritz, C., Baty, F., Streibig, J. C., & Gerhard, D. (2015). Dose-response analysis using R. PLoS ONE, 10, e0146021.

Article  PubMed  PubMed Central  Google Scholar 

Agostinis, P., Berg, K., Cengel, K. A., Foster, T. H., Girotti, A. W., Gollnick, S. O., Hahn, S. M., Hamblin, M. R., Juzeniene, A., Kessel, D., Korbelik, M., Moan, J., Mroz, P., Nowis, D., Piette, J., Wilson, B. C., & Golab, J. (2011). Photodynamic therapy of cancer: An update. CA: A Cancer Journal for Clinicians, 61, 250–281.

PubMed  Google Scholar 

Van Straten, D., Mashayekhi, V., De Bruijn, H., Oliveira, S., & Robinson, D. (2017). Oncologic photodynamic therapy: Basic principles, current clinical status and future directions. Cancers, 9, 19.

Article  PubMed  PubMed Central  Google Scholar 

D. A. Smith, H. van de Waterbeemd, D. K. Walker, R. Mannhold, H. Kubinyi and H. Timmerman. (2001). In Methods and Principles in Medicinal Chemistry, Mannhold R., Kubinyi H, Timmerman H, editors. Weinheim, Wiley–VCH Verlag. p. 141.

Kustov, A. V., Berezin, D. B., Zorin, V. P., Morshnev, P. K., Kukushkina, N. V., Krestyaninov, M. A., Kustova, T. V., Strelnikov, A. I., Lyalyakina, E. V., Zorina, T. E., Abramova, O. B., & Kozlovtseva, E. A. (2022). Monocationic chlorin as a promising photosensitizer for antitumor and antimicrobial photodynamic therapy. Pharmaceutics, 15, 61.

Article  PubMed  PubMed Central  Google Scholar 

Kustov, A. V., Belykh, D. V., Smirnova, N. L., Venediktov, E. A., Kudayarova, T. V., Kruchin, S. O., Khudyaeva, I. S., & Berezin, D. B. (2018). Synthesis and investigation of water-soluble chlorophyll pigments for antimicrobial photodynamic therapy. Dyes and Pigments, 149, 553–559.

Article  CAS  Google Scholar 

Kustov, A. V., & Belykh, D. V. (2016). New sensitizers developed on a methylpheophorbide a platform for photodynamic therapy: Synthesis, singlet oxygen generation and modeling of passive membrane transport. Pharmaceutica Analytica Acta. https://doi.org/10.4172/2153-2435.1000480

Article  Google Scholar 

Dąbrowski, J. M. (2017). Advances in inorganic chemistry (Vol. 70, pp. 343–394). Amsterdam: Elsevier.

Google Scholar 

Castano, A. P., Demidova, T. N., & Hamblin, M. R. (2004). Mechanisms in photodynamic therapy: Part one—photosensitizers, photochemistry and cellular localization. Photodiagnosis and Photodynamic Therapy, 1, 279–293.

Article  CAS  PubMed 

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