A novel photosensitizer based on a ruthenium(ii) phenanthroline bis(perylenediimide) dyad: synthesis, generation of singlet oxygen and in vitro photodynamic therapy

Aksakal, Nuray Esra
Kazan, Hasan Huseyin
Ecik, Esra Tanriverdi
In this study, a novel photosensitizer having two perylenediimide units and a phenanthroline ruthenium(ii) coordination moiety (Ru-BP) has been developed for photodynamic therapy (PDT) of cancer cells. This new compound was prepared via reactions of two newly designed molecules, namely, 5,6,12,13-tetrakis(4-(tert-butyl)phenoxy)-2-(2,6-diisopropylphenyl)-9-(4-hydroxyphenyl)anthra[2,1,9-def:6,5,10-def]diisoquinoline-1,3,8,10(2H,9H)-tetraone (P6) and a bis(2,2-bipyridyl)-(4,7-dichlorophenanthroline)ruthenium(ii) complex (7). The singlet oxygen production of P6 and Ru-BP was investigated by a chemical method using 1,3-diphenylisobenzofurane as a trap molecule. Additionally, photodynamic therapy efficacy of the novel Ru-BP complex and P6 was evaluated in vitro. Ru-BP significantly decreased the viability of human chronic myeloid leukemia cells under red light but not in the dark, pointing out that the complex, itself, was not cytotoxic and singlet oxygen formation was required for the initiation of cell death mechanisms. Thus, Ru-BP can be effectively used as a photosensitizer in photodynamic therapy, which makes the novel Ru-BP a promising singlet oxygen generator for further biological applications.


Novel BODIPY-subphthalocyanine dyads with reasonable photodynamic therapy behaviours
Kazan, Hasan Huseyin; Ozcan, Emrah; ÇOŞUT, BÜNYEMİN; YENİLMEZ ÇİFTÇİ, GÖNÜL; TANRIVERDİ EÇİK, Esra (Royal Society of Chemistry (RSC), 2020-08-01)
In this study, a set of bio-compatible and NIR emissive BODIPY-subphthalocyanine dyads (SP-DBD1-3) that contain amphiphilic triethyleneglycol units supporting partial water solubility and red absorbing BODIPY monomers (DBD1-3) were prepared. The photophysical and photochemical activities of these monomers, including fluorescence behaviors, singlet oxygen production, absorption, and emission profiles were investigated. The effect of the presence of halogen atoms and the BODIPY unit in dyads on the ability of...
2,1,3-Benzooxadiazole, thiophene and benzodithiophene based random copolymers for organic photovoltaics: thiophene versus thieno[3,2-b]thiophene as pi-conjugated linkers
Goker, SEZA; HIZALAN, Gonul; AKTAS, Ece; KUTKAN, Seda; Çırpan, Ali; Toppare, Levent Kamil (Royal Society of Chemistry (RSC), 2016-12-01)
Three conjugated random copolymers comprising benzodithiophene and thiophene as the donor units and benzooxadiazole as the acceptor unit, spaced with thiophene and thieno[3,2-b]thiophene pi-bridges, were designed and synthesized. The effects of different linkers on the optical and electrochemical properties were investigated. The polymer containing a thieno[3,2-b]thiophene pi-bridge revealed a red shifted absorption compared to its thiophene analogue. Morphological and photovoltaic properties of a polymer:f...
A newly designed anthracene and isoindigo based polymer: synthesis, electrochemical characterization and biosensor applications
Soylemez, Saniye; Goker, Seza; Toppare, Levent Kamil (Royal Society of Chemistry (RSC), 2019-09-21)
A glucose biosensor based on a newly designed and synthesized polymer, poly[(E)-6-methyl-6 '-(10-methylanthracen-9-yl)-1,1 '-diundecyl-[3,3 '-biindolinylidene]-2,2 '-dione] (namely PIIDAnth), and single walled carbon nanotubes (SWCNTs) was fabricated via an easy one pot electrode preparation and explored as a glucose electrochemical sensor. The key aim of this paper is to emphasize creation of the new surface design of sensing platforms based on a novel polymer and nanomaterial for glucose detection. With t...
A novel asymmetric synthesis of highly enantiomerically enriched norbornane-type diamine derivatives
BOLM, CARSTEN; SCHİFFERS, INGO; ATODİRESEİ, IULİANA; Özçubukçu, Salih; RAABE, GERHARD (Royal Society of Chemistry (RSC), 2003-01-01)
The simple and highly enantioselective methanolysis of norbornene dicarboxylic acid anhydride mediated by quinidine leads to the corresponding cis-monomethyl ester with 98% ee. By means of selective ester epimerization, followed by Curtius degradation of the intermediate trans-diacyl azide, two optically active norbornane-type diamines are obtained as their hydrochloric salts. Liberating the amine with an excess of triethylamine in situ and subsequent derivatization affords potential C-1-symmetric ligands f...
A novel electrospun hydroxypropyl methylcellulose/polyethylene oxide blend nanofibers: Morphology and physicochemical properties
AYDOGDU, AYÇA; Şümnü, Servet Gülüm; Şahin, Serpil (Elsevier BV, 2018-02-01)
The objective of this study was to fabricate and characterize Hydroxypropyl methylcellulose (HPMC) - based homogenous nanofibers by using electrospinning method. As the concentrations of the solutions increased, viscosity and electrical conductivity of the solutions increased. The morphology of the fibers changed from the beaded structure to the uniform fiber structure by increasing the concentrations of the solutions. Water vapor permeability (WVP) of electrospun HPMC nanofibers decreased with increasing p...
Citation Formats
N. E. Aksakal, H. H. Kazan, E. T. Ecik, and F. YÜKSEL, “A novel photosensitizer based on a ruthenium(ii) phenanthroline bis(perylenediimide) dyad: synthesis, generation of singlet oxygen and in vitro photodynamic therapy,” NEW JOURNAL OF CHEMISTRY, pp. 17538–17545, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/67358.