New heavy-atom-free bis(BODIPY)-based photosensitizer and its Pluronic® F127 water-soluble forms

被引:6
作者
Antina, Lubov A. [1 ]
Kalinkina, Valeria A. [1 ,2 ]
Sherudillo, Artem S. [1 ]
Kalyagin, Alexander A. [1 ]
Lukanov, Michail M. [1 ]
Ksenofontov, Alexander A. [1 ]
Berezin, Mikhail B. [1 ]
Antina, Elena V. [1 ]
机构
[1] Russian Acad Sci, GA Krestov Inst Solut Chem, 1 Akad Skaya Str, Ivanovo 153045, Russia
[2] Ivanovo State Univ Chem & Technol, 7 Sheremetievskiy Ave, Ivanovo 153000, Russia
基金
俄罗斯科学基金会;
关键词
CH(R)-bis(BODIPY) dimers; Photoinduced spin-orbital charge transfer enhanced ISC (SOCT-ISC); Pluronic (R) F127; Polymer micelles; Aggregation; EXCITED TRIPLET-STATE; PHOTODYNAMIC THERAPY; BODIPY-DIMERS; NUCLEOPHILIC-SUBSTITUTION; CANCER; NANOPARTICLES; DERIVATIVES; GENERATION;
D O I
10.1016/j.jlumin.2023.120411
中图分类号
O43 [光学];
学科分类号
070207 ; 0803 ;
摘要
Photosensitizers (PS) with optimal photophysical characteristics are necessary for an integrated approach to the diagnosis and treatment of diseases various types using photodynamic therapy (PDT). This study explores the potential of CH(R)-bis(BODIPY) dyes 1-4, 3a, and 3b as heavy-atom-free photosensitizers. A detailed computer study of CH(R)-bis(BODIPY) dyes demonstrates the role of SOCT-ISC (photoinduced spin-orbital charge transfer enhanced ISC) in the 4,4-CH2-bis(BODIPY) 4 photosensitizing properties implementation. The design strategies of a novel water-soluble polymer nanophotosensitizes 4-NPs, based on a dimeric dye 4 and a biocompatible amphiphilic block copolymer Pluronic (R) F127 are presented. A comparative analysis of dye 4 solubilization efficiency and its spectral properties in the composition of supramolecular 4-NP systems obtained by different techniques, as well as the sizes of the resulting nanostructures, was carried out.
引用
收藏
页数:12
相关论文
共 89 条
[1]   Photodynamic Therapy of Cancer: An Update [J].
Agostinis, Patrizia ;
Berg, Kristian ;
Cengel, Keith A. ;
Foster, Thomas H. ;
Girotti, Albert W. ;
Gollnick, Sandra O. ;
Hahn, Stephen M. ;
Hamblin, Michael R. ;
Juzeniene, Asta ;
Kessel, David ;
Korbelik, Mladen ;
Moan, Johan ;
Mroz, Pawel ;
Nowis, Dominika ;
Piette, Jacques ;
Wilson, Brian C. ;
Golab, Jakub .
CA-A CANCER JOURNAL FOR CLINICIANS, 2011, 61 (04) :250-281
[2]   Acidic Condensation of BODIPYs with Aldehydes: A Quick and Versatile Route to Alkenyl-BODIPYs and C(sp3)-Connected DYEmers [J].
Ahrens, Johannes ;
Cordes, Birte ;
Wicht, Richard ;
Wolfram, Benedikt ;
Broering, Martin .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (30) :10320-+
[3]   Potential applications of porphyrins in photodynamic inactivation beyond the medical scope [J].
Alves, Eliana ;
Faustino, Maria A. F. ;
Neves, Maria G. P. M. S. ;
Cunha, Angela ;
Nadais, Helena ;
Almeida, Adelaide .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS, 2015, 22 :34-57
[4]   Application of Porphyrins in Antibacterial Photodynamic Therapy [J].
Amos-Tautua, Bamidele M. ;
Songca, Sandile P. ;
Oluwafemi, Oluwatobi S. .
MOLECULES, 2019, 24 (13)
[5]   Amphiphilic Near-IR-Emitting 3,5-Bis(2-Pyrrolylethenyl)BODIPY Derivatives: Synthesis, Characterization, and Comparison with Other (Hetero)Arylethenyl-Substituted BODIPYs [J].
Ansteatt, Sara ;
Meares, Adam ;
Ptaszek, Marcin .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (13) :8755-8765
[6]   Aggregation behavior and spectroscopic properties of red-emitting distyryl-BODIPY in aqueous solution, Langmuir-Schaefer films and Pluoronic® F127 micelles [J].
Antina, Lubov A. ;
Bumagina, Natalia A. ;
Kalinkina, Valeria A. ;
Lukanov, Michail M. ;
Ksenofontov, Alexander A. ;
Kazak, Alexander V. ;
Berezin, Mikhail B. ;
Antina, Elena V. .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2022, 278
[7]   Effects of ms-aryl substitution on the structure and spectral properties of new CH(Ar)-bis(BODIPY) luminophores [J].
Antina, Lubov A. ;
Kalyagin, Alexander A. ;
Ksenofontov, Alexander A. ;
Pavelyev, Roman S. ;
Lodochnikova, Olga A. ;
Islamov, Daut R. ;
Berezin, Mikhail B. ;
Antina, Elena, V .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2022, 265
[8]   Effect of polar protic solvents on the photophysical properties of bis (BODIPY) dyes [J].
Antina, Lubov A. ;
Kalyagin, Alexander A. ;
Ksenofontov, Alexander A. ;
Pavelyev, Roman S. ;
Lodochnikova, Olga A. ;
Islamov, Daut R. ;
Antina, Elena, V ;
Berezin, Mikhail B. .
JOURNAL OF MOLECULAR LIQUIDS, 2021, 337
[9]   The influence of alkylation on the photophysical properties of BODIPYs and their labeling in blood plasma proteins [J].
Antina, Lyubov A. ;
Ksenofontov, Alexander A. ;
Kalyagin, Alexander A. ;
Bocharov, Pavel S. ;
Kharitonova, Nadezhda, V ;
Kazak, Alexander, V ;
Antina, Elena, V ;
Berezin, Mikhail B. .
JOURNAL OF MOLECULAR LIQUIDS, 2020, 304
[10]   Luminescent properties of new 2,2-, 2,3-and 3,3-CH2-bis(BODIPY)s dyes: Structural and solvation effects [J].
Antina, Lyubov A. ;
Ksenofontov, Alexander A. ;
Kalyagin, Alexander A. ;
Antina, Elena V. ;
Berezin, Mikhail B. ;
Khodov, Ilya A. .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2019, 218 :308-319