Synthesizing and Evaluating the Photodynamic Efficacy of Asymmetric Heteroleptic AB Type Novel Lanthanide Bis-phthalocyanine Complexes

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Apr 15

PMID 35423167

Authors

Emel Onal

Ozge Tuncel

Mohamad Albakour

Gizem Gumusgoz Celik

Ayse Gul Gurek

Serdar Ozcelik

Affiliations

Soon will be listed here.

Abstract

In this study heteroleptic AB type novel Lu(iii) and Eu(iii) lanthanide phthalocyanines (LnPc(Pox)[Pc'(ABSH)]) with high extinction coefficients have been synthesized as candidate photosensitizers with reaction yields higher than 33%. The singlet oxygen quantum yields of LuPc(Pox)[Pc'(ABSH)] and EuPc(Pox)[Pc'(ABSH)], respectively, were measured 17% and 1.4% by the direct method in THF. The singlet oxygen quantum yield of LuPc(Pox)[Pc'(ABSH)] in THF is the highest among lutetium(iii) bis-phthalocyanine complexes to date. The photodynamic efficacy of the heteroleptic lanthanide phthalocyanines was evaluated by measuring cell viabilities of A549 and BEAS-2B lung cells, selected to representing models for testing cancer and normal cells against potential drugs. The cell viabilities demonstrated concentration dependent behavior and were varied by the type of phthalocyanines complexes. Irradiation of the cells for 30 minutes with LED array at 660 nm producing flux of 0.036 J cm s increased cell death for LuPcPox-OAc, LuPc(Pox)[Pc'(ABSH)] and ZnPc. The IC concentrations of LuPc(Pox)[Pc'(ABSH)] and ZnPc were determined to be below 10 nM for both cell lines, agreeing very well with the singlet oxygen quantum yield measurements. These findings suggest that LuPc(Pox)[Pc'(ABSH)] and particularly LuPcPox-OAc are promising drug candidates enabling lowered dose and shorter irradiation time for photodynamic therapy.

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References

Young S, Woodburn K, Wright M, Mody T, Fan Q, Sessler J . Lutetium texaphyrin (PCI-0123): a near-infrared, water-soluble photosensitizer. Photochem Photobiol. 1996; 63(6):892-7. DOI: 10.1111/j.1751-1097.1996.tb09647.x. View

Oluwole D, Yagodin A, Mkhize N, Sekhosana K, Martynov A, Gorbunova Y . First Example of Nonlinear Optical Materials Based on Nanoconjugates of Sandwich Phthalocyanines with Quantum Dots. Chemistry. 2016; 23(12):2820-2830. DOI: 10.1002/chem.201604401. View

Sheng N, Li R, Choi C, Su W, K P Ng D, Cui X . Heteroleptic bis(phthalocyaninato) europium(III) complexes fused with different numbers of 15-crown-5 moieties. Synthesis, spectroscopy, electrochemistry, and supramolecular structure. Inorg Chem. 2006; 45(9):3794-802. DOI: 10.1021/ic0600937. View

Chen L, Hu R, Xu J, Wang S, Li X, Li S . Third-order nonlinear optical properties of a series of porphyrin-appended europium(III) bis(phthalocyaninato) complexes. Spectrochim Acta A Mol Biomol Spectrosc. 2013; 105:577-81. DOI: 10.1016/j.saa.2012.12.063. View

Kyatskaya S, Galan Mascaros J, Bogani L, Hennrich F, Kappes M, Wernsdorfer W . Anchoring of rare-earth-based single-molecule magnets on single-walled carbon nanotubes. J Am Chem Soc. 2009; 131(42):15143-51. DOI: 10.1021/ja906165e. View

Pushkarev V, Kalashnikov V, Tolbin A, Trashin S, Borisova N, Simonov S . meso-Phenyltetrabenzotriazaporphyrin based double-decker lanthanide(III) complexes: synthesis, structure, spectral properties and electrochemistry. Dalton Trans. 2015; 44(37):16553-64. DOI: 10.1039/c5dt01933h. View

Alcon I, Gonidec M, Ajayakumar M, Mas-Torrent M, Veciana J . A surface confined yttrium(iii) bis-phthalocyaninato complex: a colourful switch controlled by electrons. Chem Sci. 2018; 7(8):4940-4944. PMC: 6018459. DOI: 10.1039/c6sc00443a. View

Sessler J, Miller R . Texaphyrins: new drugs with diverse clinical applications in radiation and photodynamic therapy. Biochem Pharmacol. 2000; 59(7):733-9. DOI: 10.1016/s0006-2952(99)00314-7. View

Niedre M, Patterson M, Wilson B . Direct near-infrared luminescence detection of singlet oxygen generated by photodynamic therapy in cells in vitro and tissues in vivo. Photochem Photobiol. 2002; 75(4):382-91. DOI: 10.1562/0031-8655(2002)075<0382:DNILDO>2.0.CO;2. View

10.

Hou C, Zhao L, Geng F, Wang D, Guo L . Donor/acceptor nanoparticle pair-based singlet oxygen channeling homogenous chemiluminescence immunoassay for quantitative determination of bisphenol A. Anal Bioanal Chem. 2016; 408(30):8795-8804. DOI: 10.1007/s00216-016-9584-y. View

11.

Dube E, Oluwole D, Nwaji N, Nyokong T . Glycosylated zinc phthalocyanine-gold nanoparticle conjugates for photodynamic therapy: Effect of nanoparticle shape. Spectrochim Acta A Mol Biomol Spectrosc. 2018; 203:85-95. DOI: 10.1016/j.saa.2018.05.081. View

12.

Ballesteros B, de la Torre G, Shearer A, Hausmann A, Herranz M, Guldi D . Lanthanide(III) bis(phthalocyaninato)-[60]fullerene dyads: synthesis, characterization, and photophysical properties. Chemistry. 2009; 16(1):114-25. DOI: 10.1002/chem.200902200. View

13.

Durmus M, Nyokong T . Synthesis, photophysical and photochemical studies of new water-soluble indium(III) phthalocyanines. Photochem Photobiol Sci. 2007; 6(6):659-68. DOI: 10.1039/b618478b. View

14.

Kaestner L, Cesson M, Kassab K, Christensen T, Edminson P, Cook M . Zinc octa-n-alkyl phthalocyanines in photodynamic therapy: photophysical properties, accumulation and apoptosis in cell cultures, studies in erythrocytes and topical application to Balb/c mice skin. Photochem Photobiol Sci. 2003; 2(6):660-7. DOI: 10.1039/b211348a. View

15.

Ishikawa N, Iino T, Kaizu Y . Interaction between f-electronic systems in dinuclear lanthanide complexes with phthalocyanines. J Am Chem Soc. 2002; 124(38):11440-7. DOI: 10.1021/ja027119n. View

16.

Ayhan M, Singh A, Hirel C, Gurek A, Ahsen V, Jeanneau E . ABAB homoleptic bis(phthalocyaninato)lutetium(III) complex: toward the real octupolar cube and giant quadratic hyperpolarizability. J Am Chem Soc. 2012; 134(8):3655-8. DOI: 10.1021/ja211064a. View

17.

Urdampilleta M, Klyatskaya S, Cleuziou J, Ruben M, Wernsdorfer W . Supramolecular spin valves. Nat Mater. 2011; 10(7):502-6. DOI: 10.1038/nmat3050. View

18.

Nombona N, Antunes E, Litwinski C, Nyokong T . Synthesis and photophysical studies of phthalocyanine-gold nanoparticle conjugates. Dalton Trans. 2011; 40(44):11876-84. DOI: 10.1039/c1dt11151e. View

19.

Al-Sagur H, Komathi S, Khan M, Gurek A, Hassan A . A novel glucose sensor using lutetium phthalocyanine as redox mediator in reduced graphene oxide conducting polymer multifunctional hydrogel. Biosens Bioelectron. 2016; 92:638-645. DOI: 10.1016/j.bios.2016.10.038. View

20.

Gurol I, Durmus M, Ahsen V, Nyokong T . Synthesis, photophysical and photochemical properties of substituted zinc phthalocyanines. Dalton Trans. 2007; (34):3782-91. DOI: 10.1039/b704345g. View