Phthalocyanines Structure Versus Photodynamic Effectiveness towards Pathogenic Microorganisms: Our Recent Experience
Ivan Angelov
(Login required)
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
Institute of Electronics, Bulgarian Academy of Sciences, Sofia, Bulgaria
Paper #3445 received 28 Jul 2021; revised manuscript received 10 Sep 2021; accepted for publication 12 Sep 2021; published online 25 Sep 2021.
DOI: 10.18287/JBPE21.07.040202
Abstract
The present review paper aims to summarize our recent experience in research and development of new phthalocyanine complexes and investigations of the main photophysical, photochemical and photobiological properties which are related to antimicrobial photodynamic therapy (aPDT) as alternative method for inactivation of the resistant pathogens. The effect of functionalization of Zn(II) phthalocyanine (ZnPc) with biologically-active natural substances such as amino acids, sugars and steroids was studied in comparison to the basic ZnPc ring molecule. The structural features of the substitution groups were chosen to facilitate the main properties responsible for PDT outcome. For example, the linkage groups of amino acids tyrosine, phenylalanine, lysine and arginine have positive charge in physiological media to the better attachment to bacterial wall and some of them have a good fluorescence for a contribution to the visualization of the infected area. Also, ZnPcs linked to sugars and steroids was expecting to possess receptor specific selectivity. The physicochemical properties of the novel functionalized ZnPcs are presented in respect to their efficiency for a number of pathogenic bacterial and fungal species. Additionally, the complexes of two heavy metal ions such as lutetium(III) (Lu(III)) and tin(IV) (Sn(IV)) were synthesized and evaluated for antimicrobial PDT. These complexes were designed with the same structural skeleton as our previous water-soluble methylpiridyloxy-substituted phthalocyanine complexes with zinc (II), silicon (IV), germanium (IV), indium (III) and gallium (III), all with relatively promising antibacterial efficiency.
Keywords
Full Text:
PDFReferences
1. N. Moldonado-Carmona, T.-S. Ouk, M. J. F. Calvete, M. M. Pereira, N. Villandier, and S. Leroy-Lhez, “Conjugating biomaterials with photosensitizers: advances and perspectives for photodynamic antimicrobial chemotherapy,” Photochemical & Photobiological Sciences 19(4), 445–461 (2020).
2. P.-C. Lo, M. S. Rodriges-Morgade, R. K. Pandey, D. K. P. Ng, T. Torres, and F. Dumoulin, “The unique features and promises of phthalocyanines as advanced photosensitisers for photodynamic therapy of cancer,” Chemical Society Reviews 49(4), 1041–1056 (2020).
3. X. Li, B.-D. Zheng, X.-H. Peng, S.-Z. Li, J.-W. Ying, Y. Zhao, J.-D. Huang, and J. Yoon, “Phthalocyanines as medicinal photosensitizers: Developments in the last five years,” Coordination Chemistry Review 379, 147–160 (2019).
4. N. Sekkat, H. van der Bergh, T. Nyokong, and N. Lange, “Like a Bolt from the Blue: Phthalocyanines in Biomedical Optics,” Molecules 17(1), 98–144 (2012).
5. A. Segalla, C. D. Borsarelli, S. E. Braslavsky, J. D. Spikes, G. Roncucci, D. Dei, G. Chiti, G. Jori, and E. Reddi, “Photophysical, photochemical and antibacterial photosensitizing properties of a novel octacationic Zn(ii)-phthalocyanine,” Photochemical & Photobiological Sciences 1(9), 641–648 (2002).
6. T. C. White, K. A. Marr, and R. A. Bowden, “Clinical, cellular, and molecular factors that contribute to antifungal drug resistance,” Clinical Microbiology Reviews 11(2), 382–402 (1998).
7. J. M. Dabrowski, B. Pucelik, A. Regiel-Futyra, M. Brindell, O. Mazuryk, A. Kyzioł, G. Stochel, W. Macyk, and L. G. Arnaut, “Engineering of relevant photodynamic processes through structural modifications of metallotetrapyrrolic photosensitizers,” Coordination Chemistry Reviews 325, 67–101 (2016).
8. L. Sobotta, P. Skupin-Mrugalska, J. Piskorz, and J. Mielcarek, “Porphyrinoid photosensitizers mediated photodynamic inactivation against bacteria,” European Journal of Medicinal Chemistry 175, 72–106 (2019).
9. V. Almeida-Marrero, J. A. Gonzales-Delgado, and T. Torres, “Emerging Perspectives on Applications of Porphyrinoids for Photodynamic Therapy and Photoinactivation of Microorganisms,” Macroheterocycles 12(1), 8–16 (2019).
10. V. Mantareva, I. Angelov, D. Wöhrle, E. Borisova, and V. Kussovski, “Metallophthalocyanines for antimicrobial photodynamic therapy: an overview of our experience,” Journal of Porphyrins and Phthalocyanines 17(6–7), 399–416 (2013).
11. F. M. Lauro, P. Pretto, L. Covolo, G. Jori, and G. Bertoloni, “Photoinactivation of bacterial strains involved in periodontal diseases sensitized by porphycene-polylysine conjugates,” Photochemical & Photobiological Sciences 1(7), 468–470 (2002).
12. T. N. Demidova, M. R. Hamblin, “Effect of cell-photosensitizer binding and cell density on microbial photoinactivation,” Antimicrobial Agents and Chemotherapy 49(6), 2329–2335 (2005).
13. C. A. Pereira, R. L. Romeiro, A. C. B. P. Costa, A. K. S. MacHado, J. C. Junqueira, and A. O. C. Jorge, “Susceptibility of Candida albicans, Staphylococcus aureus, and Streptococcus mutans biofilms to photodynamic inactivation: an in vitro study,” Lasers in Medical Science 26(3), 341–348 (2011).
14. M. A. DiPalma, M. G. Alvarez, A. L. Ochoa, M. E. Milanesio, and E. N. Durantini, “Optimization of cellular uptake of zinc(II) 2,9,16,23-tetrakis[4-(N-methylpyridyloxy)] phthalocyanine for maximal photoinactivation of Candida albicans,” Fungal Biology 117(11–12), 744–751 (2013).
15. B. S. Vig, K. M. Huttunen, K. Laine, and J. Rautio, “Amino acids as promoieties in prodrug design and development,” Advanced Drug Delivery Reviews 65(10), 1370-1385 (2013).
16. L. S. Li, Z. P. Luo, Z. Chen, J. C. Chen, S. Y. Zhou, P. Xu, P. Hu, J. D. Wang, N. S. Chen, J. L. Huang, and M. D. Huang, “Enhanced Photodynamic Efficacy of Zinc Phthalocyanine by Conjugating to Heptalysine,” Bioconjugate Chemistry 23(11), 2168–2172 (2012).
17. T. Dougherty, “An update on photodynamic therapy applications,” Journal of Clinical Laser Medicine & Surgery 20(1), 3–7 (2002).
18. R. Malik, A. Manocha, and D. K. Suresh, “Photodynamic therapy – A strategic review,” Indian Journal of Dental Research 21(2), 285–291 (2010).
19. V. Mantareva, V. Kussovski, and I. Angelov, “Cationic Metal Phthalocyanines as Effective Photosensitizers Towards Pathogenic Microorganisms,” Chapter 5 in Photosensitizers: Types, Uses and selected Research, C. Withmire (Ed.), Nova Science Publishers, New York (2016).
20. M. Garcia-Iglesias, E. Huerta, “Towards new multivalent supramolecular helical structures based on phthalocyanines for PDT applications,” Journal of Porphyrins and Phthalocyanines 21(11), 745–750 (2017).
21. M. Wainwright, Photosensitizers in Biomedicine, John Wiley and Sons, Chichester, UK (2009). ISBN: 978-0-470-74494-9.
22. M.-R. Ke, J. M. Eastel, K. L. K. Ngai, Y.-Y. Cheung, P. K. S. Chan, M. Hui, D. K. P. Ng, and P.-C. Lo, “Photodynamic inactivation of bacteria and viruses using two monosubstituted zinc(II) phthalocyanines,” European Journal of Medicinal Chemistry 84, 278–283 (2014).
23. J. D. Miller, E. D. Baron, H. Scull, A. Hsia, J. C. Berlin, T. Mc Cormick, V. Colussi, M. E. Kenney, K. D. Cooper, and N. L. Oleinick, “Photodynamic therapy with the phthalocyanine photosensitizer Pc 4: the case experience with preclinical mechanistic and early clinical-translational studies,” Toxicology and Applied Pharmacology 224(3), 290–299 (2007).
24. F. Dumoulin, M. Durmus, V. Ahsen, and T. Nyokong, “Synthetic pathways to water-soluble phthalocyanines and close analogs,” Coordination Chemistry Reviews 254(23–24), 2792–2847 (2010).
25. N. Kuznetsova, N. Gretsova, E. Kalmykova, E. Makarova, S. Dashkevich, V. Negrimovskii, O. Kaliya, and E. Lukyanets, “Relationship between the photochemical properties and structure of pophyrins and related compounds,” Russian Journal of General Chemistry 70(1), 133–140 (2000) [in Russian].
26. A. V. Ziminov, Y. A. Sidunets, V. S. Fundamensky, V. V. Gurzhiy, and S. M. Rams, “Synthesis, characterization, and investigation of photochemical properties of tetra-substituted zinc phthalocyanines bearing 4-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl moiety with different linker heteroatoms,” Inorganica Chimica Acta 501, 119306 (2020).
27. E. Guzel, A. Gunsel, B. Tuzun, G. Y. Atmaca, A. T. Bilgicli, A. Erdogmus, and M. N. Yarasir, “Synthesis of tetra-substituted metallophthalocyanines: Spectral, structural, computational studies and investigation of their photophysical and photochemical properties,” Polyhedron 158, 316–324 (2019).
28. S. A. Mikhalenko, L. I. Soloveela, and E. A. Lukyanetz, “Phthalocyanines and Related Compounds: XXXVII. Synthesis of Covalent Conjugates of Carboxy-substituted Phthalocyanines with α-Amino Acids,” Russian Journal of General Chemistry 74(3), 451–459 (2004).
29. E. A. Lukyanetz, V. N. Nemykin, “The key role of peripheral substituents in the chemistry of phthalocyanines and their analogs,” Journal of Porphyrins and Phthalocyanines 14(01), 1–40 (2010).
30. Ao Wang, R. Zhou, L. Zhou, K. Sun, J. Jiang, and S. Wei, Positively charged phthalocyanine-arginine conjugates as efficient photosensitizer for photodynamic therapy, Bioorganic & Medicinal Chemistry 25(1), 1643–1651 (2017).
31. N. Nombona, E. Antunes, W. Chidawanyika, P. Kleyi, Z. Tshentu, and T. Nyokong, “Synthesis, photophysics and photochemistry of phthalocyanine-ɛ-polylysine conjugates in the presence of metal nanoparticles against Staphylococcus aureus,” Journal of Photochemistry and Photobiology A: Chemistry 233, 24–33 (2012).
32. Q. Sun, B.-Y. Zheng, Y.-H. Zhang, J.-J. Zhuang, M.-R. Ke, and J. D. Huang, “Highly photocytotoxic silicon(IV) phthalocyanines axially modified with l-tyrosine derivatives: Effects of mode of axial substituent connection and of formulation on photodynamic activity,” Dyes and Pigments 141, 521–529 (2017).
33. M. R. Ke, J. M. Eastel, K. L. K. Ngai, Y. Y. Cheung, P. K. S. Chan, M. Hui, D. K. P. Ng and P. C. Lo, “Oligolysine-conjugated zinc(II) phthalocyanines as efficient photosensitizers for antimicrobial photodynamic therapy,” Chemistry–An Asian Journal 9(7), 1868–1875 (2014).
34. D. Wöhrle, M. Eskes, K. Shigehara, and A. Yamada, “A Simple Synthesis of 4, 5-Disubstituted 1, 2-Dicyanobenzenes and 2, 3, 9, 10, 16, 17, 23, 24-Octasubstituted Phthalocyanines,” Synthesis 1993(02), 194–196 (1993).
35. S. E. Maree, T. Nyokong, “Syntheses and photochemical properties of octasubstituted phthalocyaninato zinc complexes,” Journal of Porphyrins and Phthalocyanines 5(11), 782–792 (2001).
36. M. B. Aliosman, I. Z. Eneva, I. B. Stoineva, M. Durmus, and V. N. Mantareva, “Aminophenoxy-substituted zinc (II) phthalocyanines as basic photosensitizers for conjugation with biologically active moieties via amide bond,” Bulgarian Chemical Communications 49, (2017), 79-85.
37. X.-F. Zhang, X. Li, L. Niu, L. Sun, and L. Liu, “Charge Transfer Photophysics of Tetra(α-amino) Zinc Phthalocyanine,” Journal of Fluorescence 19(6), 947–954 (2009).
38. L. Sobotta, S. Lijewski, J. Dlugaszewska, J. Nowicka, J. Mielcarek, and T. Goslinski, “Photodynamic inactivation of Enterococcus faecalis by conjugates of zinc (II) phthalocyanines with thymol and carvacrol loaded into lipid vesicles,” Inorganica Chimica Acta 489, 180–190 (2019).
39. D. Lin, Y. Wang, Q. Zhan, J. Zhou, L. Zhou, and S. Wei, “The substituted amino group type dependent sensitivity enhancing of cationic phthalocyanine derivatives for photodynamic activity,” Journal of Photochemistry and Photobiology A: Chemistry 315, 107–120 (2016).
40. A. Shrestha, A. Kishen, “Polycationic Chitosan-Conjugated Photosensitizer for Antibacterial Photodynamic Therapy,” Photochemistry and Photobiology 88(3), 577–583 (2012).
41. V. Mantareva, I. Angelov, V. Kussovski, R. Dimitrov, L. Lapok, and D. Wörhle, “Photodynamic efficacy of water-soluble Si(IV) and Ge(IV) phthalocyanines towards Candida albicans planktonic and biofilm cultures,” European Journal of Medicinal Chemistry 46(9), 4430–4440 (2011).
42. I. Angelov, A. Kril, R. Dimitrov, E. Borisova, L. Avramov, and V. Mantareva, “Light enhancement of in vitro antitumor activity of galactosylated phthalocyanines,” Photonics & Lasers in Medicine 5(2), 123–140 (2016).
43. V. Mantareva, M. Syuleyman, A. Slavova-Kazakova, I. Angelov, and M. Durmus, “Mestranol moieties clicked to Zn(II)phthalocyanine for controllable photosensitized oxidation of cholesterol,” Archives of Biotechnology and Biomedicine, 041–048 (2021).
44. M. Aliosman, I. Angelov, Y. Mitrev, I. Iliev, M. Durmuş, and V. Mamtareva, “Novel Zn(II) phthalocyanine with tyrosine moieties for photodynamic therapy: Synthesis and comparative study of light-associated properties,” Polyhedron 162, 121–128 (2019).
45. V. Mantareva, M. Aliosman, M. Durmuş, and I. Angelov, “Amino acids substituted phthalocyanine complexes: an overview on the synthetic approaches and UV-vis properties related to photodynamic applications,” Bulgarian Chemical Communications 50, 185–192 (2018).
46. S. Hermann, A. H. Wagenknecht, “Synthesis of N,N-dimethylaminopyrene-modified short peptides for chemical photocatalysis,” Journal of Peptide Science 23(7–8), 563-566 (2017).
47. B. Kiyak, A. A. Esenpinar, and M. Balut, “Synthesis, characterization, photophysical and photochemical properties of zinc and indium phthalocyanines bearing a vanillylacetone moiety known as an anticarcinogenic agent,” Polyhedron 90, 183–196 (2015).
48. A. Ogunsipe, D. Maree, and T. Nyokong, “Solvent effects on the photochemical and fluorescence properties of zinc phthalocyanine derivatives,” Journal of Molecular Structure 650(1–3), 131–140 (2003).
49. S. K. Sharma, T. Dai, G. B. Kharkwal, Y.-Y. Huang, L. Huang, V. J. B. de Arce, G. P. Tegos, and M. R. Hamblin, “Drug discovery of antimicrobial photosensitizers using animal models,” Current Pharmaceutical Design 17(13), 1303–1319 (2011).
50. W. C. M. A. Melo, L. F. Castro, and R. M. M. T. S. Dal’Mas, “Effectiveness of photodynamic therapy on gram-negative bacteria,” in Science Against Microbial Pathogens: Communicating Current Researchand Technological Advances 3, Badajos, Spain, 662–667 (2011).
51. V. Kussovski, V. Mantareva, I. Angelov, P. Orozova, D. Wohrle, G. Schnurpfeil, E. Borisova, and L. Avramov, “Photodynamic inactivation of Aeromonas hydrophila by cationic phthalocyanines with different hydrophobicity,” FEMS Microbiology Letters 294(2), 133–140 (2009).
52. V. Mantareva, I. Angelov, V. Kussovski, D. Woehrle, and S. Dimitrov, “Metallophthalocyanines as photodynamic sensitizers for treatment of pathogenic bacteria. Uptake and photoinactivation properties,” Comptes Rendus de l’Acade’mie Bulgare des Sciences 63(1), 77–84 (2010).
53. V. Mantareva, I. Angelov, D. Wohrle, V. Dogandhiyska, S. Dimitrov, and V. Kussovski, “Water-soluble phthalocyanine complexes of Ga(III) and In(III) in the photodynamic inactivation of pathogenic fungus,” Proceedings of SPIE 7747, 774712 (2011).
54. V. Mantareva, I. Angelov, V. Kussovski, and S. Dimitrov, “Advanced photodynamic inactivation of dental pathogenic microorganisms with water-soluble and cationic phthalocyanines,” in Science Against Microbial Pathogens: Communicating Current Research and Technological Advances 1(11), FORMATEX Research Centre, Badajos, Spain, 650-661 (2011).
55. I. Angelov, V. Mantareva, V. Kussovski, D. Woehrle, H. Kisov, M. Belcheva, T. Georgieva, and S. Dimitrov, “Susceptibility of representative Dental Pathogens to inactivation by the PDT with water-soluble photosensitizers,” Proceedings of SPIE 7994, 79941A (2011).
56. R. Gergova, T. Georgieva, I. Angelov, V. Mantareva, S. Valkanov, I. Mitov, and S. Dimitrov, “Photodynamic therapy with water-soluble phtalocyanines against bacterial biofilms in teeth root canals,” Proceedings of SPIE 8427, 842744 (2012).
57. V. Kussovski, V. Mantareva, I. Angelov, L. Avramov, E. Popova, and S. Dimitrov, “Al(III), Pd(II) and Zn(II) phthalocyanines for inactivation of dental pathogen Aggregatibacter actinomycetemcomitans as planktonic and biofilm-cultures,” Proceedings of SPIE 8427, 84273X (2012).
58. C. Gol, M. Durmus, “Investigation of photophysical, photochemical and bovine serum albumin binding properties of novel water-soluble zwitterionic zinc phthalocyanine complexes,” Synthetic Metals 162(7–8), 605-613 (2012).
59. G. Dilber, M. Durmus, and H. Kantekin, “Non-aggregated zwitterionic Zinc (II) phthalocyanine complexes in water with high singlet oxygen quantum yield,” Dyes and Pigments 160, 267–284 (2019).
60. S. Colak, M. Durmus, and S. Z. Yildiz, “Investigation of the photophysical and photochemical properties of peripherally tetra-substituted water-soluble zwitterionic and cationic zinc (II) phthalocyanines,” Dalton Transactions 45(25), 10402–10410 (2016).
61. V. N. Nemykin, E. A. Luk’yanets, “11 The Key Role of Peripheral Substituents in Chemistry of Phthalocyanines,” in Handbook of Porphyrin Science vol. 3, K. Kadish, K. M. Smith, and R. Guilard (Eds.), Word Scientific Publishing, Singapore, 1–323 (2010).
62. F. Foschi, C. R. Fontana, K. Ruggiero, R. Riahi, A. Vera, A. G. Doukas, T.C. Pagonis, R. Kent, P. P. Stashenko, and N. S. Soukos, “Photodynamic inactivation of Enterococcus faecalis in dental root canals in vitro,” Lasers in Surgery and Medicine: The Official Journal of the American Society for Laser Medicine and Surgery 39(10), 782–787 (2007).
63. E. P. Prochnow, M. R. Martins, C. B. Campagnolo, R. C. Vianna, M. A. Villetti, and K. Z. Kantorski, “Antimicrobial photodynamic effect of phenothiazinic photosensitizers in formulations with ethanol on Pseudomonas aeruginosa biofilms,” Photodiagnosis and Photodynamic Therapy 13, 291–296 (2016).
64. V. Mantareva, C. Gol, V. Kussovski, M. Durmus, and I. Angelov, “Impact of water-soluble zwitterionic Zn(II) phthalocyanines against pathogenic bacteria,” Zeitschrift für Naturforschung C 74(7–8), 183–191 (2019).
65. V. Mantareva, V. Kussovski, I. Angelov, D. Wöhrle, R. Dimitrov, E. Popova, and S. Dimitrov, “Non-aggregated Ga (III)-phthalocyanines in the photodynamic inactivatio planktonic and biofilm cultures of pathogenic microorganisms,” Photochemical & Photobiological Sciences 10(1), 92–102 (2011).
66. V. Mantareva, V. Kussovski, I. Angelov, E. Borisova, L. Avramov, G. Schnurpfeil, and D. Wöhrle, “Photodynamic activity of water-soluble phthalocyanine zinc (II) complexes against pathogenic microorganisms,” Bioorganic & Medicinal Chemistry 15(14), 4829–4835 (2007).
67. M. Wainwrigh, T. Maisch, S. Nonell, K. Plaetzer, A. Almeida, G. P. Tegos, and M. R. Hamblin, “Photoantimicrobials–are we afraid of the light?” The Lancet Infectious Diseases 17(2), e49–e55 (2017).
68. V. Kussovski, V. Mantareva, M. Durmus, and I. Angelov, “Quaternized Zn (II) phthalocyanines for photodynamic strategy against resistant periodontal bacteria,” Zeitschrift für Naturforschung C 73(5–6), 221–228 (2018).
69. T. Nyokong, “Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines,” Coordination Chemistry Reviews 251(13–14), 1707–1722 (2007).
70. M. Durmus, S. Yeslot, B. Cosut, A. Gul Gurek, A. Kilic, and V. Ahsen, “Comparison of photophysicochemical properties of hexaphenoxycyclotriphosphazenyl-substituted metal-free, mono-and bis-lutetium phthalocyanines,” Synthetic metals 160(5–6), 436–444 (2010).
71. R. Zugle, C. Litwinski, and T. Nyokong, “Photophysical characterization of dysprosium, erbium and lutetium phthalocyanines tetrasubstituted with phenoxy groups at non-peripheral positions,” Polyhedron 30(9), 1612–1619 (2011).
72. F. L. Lu, “The effects of substituents, molecular symmetry, ionic radius of the rare earth metal, and macrocycle on the electronic absorption spectra characteristics of sandwich-type bis(phthalocyaninato) and mixed (phthalocyaninato)(porphyrinato) rare earth complexes,” Polyhedron 26(14), 3939–3946 (2007).
73. J. L. Sessler, G. Hemmi, T. D. Mody, T. Murai, A. K. Burrell, and S. W. Young, “Texaphyrins: synthesis and applications,” Accounts of Chemical Research 27(2), 43–50 (1994).
74. V. Mantareva, M. Durmus, M. Aliosman, I. Stoineva, and I. Angelov, “Lutetium(III) acetate phthalocyanines for photodynamic therapy applications: Synthesis and photophysicochemical properties,” Photodiagnosis and Photodynamic Therapy 14, 98–103 (2016).
75. V. Mantareva, V. Kussovski, M. Durmus, E. Borisova, and I. Angelov, “Photodynamic inactivation of pathogenic species Pseudomonas aeruginosa and Candida albicans with lutetium (III) acetate phthalocyanines and specific light irradiation,” Lasers in Medical Science 31(8), 1591–1598 (2016).
76. N. Masilela, T. Nyokong, “The synthesis and photophysical properties of novel cationic tetra pyridyloxy substituted aluminium, silicon and titanium phthalocyanines in water,” Journal of Luminescence 130(10), 1787–1793 (2010).
77. D. Wöhrle, N. Iskander, G. Graschew, H. Sinn, E. Friedrich, W. Maier-Borst, J. Stern, and P. Schlag, “Synthesis of positively charged phthalocyanines and their activity in the photodynamic therapy of cancer cells,” Photochemistry and Photobiology 51(3), 351–356 (1990).
78. I. Eneva, M. Aliosman, I. Angelov, K. Popov, and V. Mantareva, “Mono-ring phthalocyanine complexes of large ions Lu3+ and Sn4+: synthesis and comparison of photophysical properties,” Bulgarian Chemical Communications 49(D), 246–252 (2017).
Сontact
34 Moskovskoe shosse, Samara, 443086, Russian Federation
Email: j-bpe@ssau.ru
Phone: +7-846-267-4550
© 2014-2025 J-BPE