Synthesis, properties and in vitro photodynamic activity of water-soluble azaphthalocyanines and azanaphthalocyanines

Photochemistry and Photobiology
Petr ZimcikEmil Rudolf

Abstract

In this work zinc azaphthalocyanines (AzaPcs) from the group of tetrapyrazinoporphyrazines and zinc azanaphthalocyanines from the group of tetra[6,7]quinoxalinoporphyrazines (TQP) with eight diethylaminoethylsulfanyl substituents were synthesized. Tertiary amines were later quaternized with ethyl iodide to obtain water-soluble photosensitizers (PSs). Quaternized compounds showed high singlet oxygen quantum yields as determined in DMF by monitoring decomposition of 1,3-diphenylisobenzofuran. In water medium, quaternized AzaPc derivatives appeared in monomeric form in a wide range of concentrations while quaternized TQP derivatives showed aggregation at higher concentrations (over 1 microM). Photodynamic activity was tested on Hep2 cells using light of lambda > 640 nm. Both quaternized dyes showed high photodynamic activity (IC(50) = 104 and 220 nm for AzaPc and TQP, respectively). Dark toxicity was not detected even at the highest concentration used in in vitro tests (200 microM) which indicates a promising therapeutic index of these new substances. Tested compounds localized inside the cells mainly within the lysosomes thus suggesting an endocytic mechanism of cellular uptake. No localization within mitochondria was detected. A...Continue Reading

References

Feb 1, 1997·Journal of Photochemistry and Photobiology. B, Biology·H DumminH W Zimmermann
Jun 24, 1998·Journal of the National Cancer Institute·T J DoughertyQ Peng
May 23, 2002·Photochemistry and Photobiology·Alexei FeofanovPaul Vigny
Feb 22, 2003·Chemistry : a European Journal·Frieder MitzelRüdiger Faust
Jul 1, 2005·Angewandte Chemie·Kazuya KameyamaYoshiaki Kobuke
Jan 24, 2006·Journal of Photochemistry and Photobiology. B, Biology·Clara FabrisGiulio Jori
Jan 31, 2006·Journal of Photochemistry and Photobiology. B, Biology·Itumeleng Seotsanyana-MokhosiTebello Nyokong
Oct 13, 2006·The Oncologist·Martijn TriesscheijnFiona A Stewart
Nov 2, 2006·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Zibo ZhangAiping Wang
May 23, 2007·Bioorganic & Medicinal Chemistry·Vanya MantarevaDieter Wöhrle
Jan 15, 2008·Journal of Medicinal Chemistry·Hairong LiM Graça H Vicente
Apr 9, 2008·Anti-cancer Agents in Medicinal Chemistry·Mark Wainwright
Mar 1, 2007·Photodiagnosis and Photodynamic Therapy·Paolo AmerioAntonio Tulli
Dec 1, 2004·Photodiagnosis and Photodynamic Therapy·Ana P CastanoMichael R Hamblin

❮ Previous
Next ❯

Citations

Sep 3, 2011·Photochemistry and Photobiology·Bonnie I Kruft, Alexander Greer
Mar 18, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Antonin CidlinaPetr Zimcik
May 31, 2018·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Miroslav MiletinVeronika Novakova
Jul 23, 2019·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Fernanda Savacini SagrilloJosé A S Cavaleiro
Aug 27, 2015·Chemistry : a European Journal·Veronika NovakovaPetr Zimcik
Jul 27, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Veronika NovakovaPetr Zimcik
Jul 27, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Lenka VachovaPetr Zimcik
Feb 5, 2019·Journal of Materials Chemistry. C, Materials for Optical and Electronic Devices·Sergey M BorisovIngo Klimant
Jan 16, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Jan SuchánekPavel Kubát
Jan 23, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bruno M F LadeiraM Amparo F Faustino

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.