New amphiphilic silicon(IV) phthalocyanines as efficient photosensitizers for photodynamic therapy: synthesis, photophysical properties, and in vitro photodynamic activities

Chemistry : a European Journal
Pui-Chi LoDennis K P Ng

Abstract

A novel series of silicon(IV) phthalocyanines substituted axially with one or two 1,3-bis(dimethylamino)-2-propoxy group(s) have been prepared by ligand substitution and alkoxy exchange reactions. Two dicationic and tetracationic phthalocyanines have also been prepared by methylation of two of these compounds. The nonionic phthalocyanines are essentially nonaggregated in common organic solvents and show a weak fluorescence emission, while the methylated derivatives are also nonaggregated, even in aqueous media, and exhibit a strong fluorescence emission. These new phthalocyanines, in particular the unsymmetrical and amphiphilic analogues, are highly potent against HepG2 human hepatocarcinoma cells and J774 mouse macrophage cells with IC50 values down to 0.02 microM. The photodynamic activities are related to the cellular uptake and the efficiency to generate singlet oxygen. A higher positive charge at the phthalocyanine hinders the uptake, reflected by the lower intracellular fluorescence intensity. Fluorescence microscopic studies have also revealed that the unsymmetrical phthalocyanine SiPc[C3H5(NMe2)2O](OMe) (4) has a high and selective affinity to the mitochondria of HepG2 cells.

Citations

Dec 1, 2005·Photodiagnosis and Photodynamic Therapy·Katie O'RiordanTayyaba Hasan
Jun 1, 2007·Photodiagnosis and Photodynamic Therapy·Pui-Chi LoDennis K P Ng
Mar 21, 2009·Mycoses·Cheung-Wai SoWing-Ping Fong
May 17, 2006·Journal of Controlled Release : Official Journal of the Controlled Release Society·Woo-Dong JangKazunori Kataoka
Sep 22, 2015·Cellular & Molecular Immunology·Hing-Yuen YeungWing-Ping Fong
Apr 22, 2016·ACS Applied Materials & Interfaces·Anzhela GalstyanCristian Alejandro Strassert
Jul 15, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Zekeriya BiyikliogluHakan Alp
Jul 28, 2015·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Leandro M O LourençoJoão P C Tomé
Dec 27, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nawal SekkatNorbert Lange
Nov 18, 2016·Nature Communications·Erin D AndersonMartin J Schnermann
Feb 14, 2009·Chemical Communications : Chem Comm·Jiafei MaoZijian Guo
May 20, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Jian-Yong LiuDennis K P Ng
Mar 5, 2010·Physical Chemistry Chemical Physics : PCCP·Veronika NovakovaTomás Polívka
Apr 29, 2010·Chemical Communications : Chem Comm·Xiong-Jie JiangDennis K P Ng
May 7, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Katherine R JohnsonAna de Bettencourt-Dias
Apr 24, 2020·Chemistry : a European Journal·Katherine R JohnsonAna de Bettencourt-Dias
Mar 24, 2010·Chemistry : a European Journal·Xiong-Jie JiangDennis K P Ng
Jul 12, 2011·Chemistry, an Asian Journal·Jie ZhuChengzhong Yu
Jun 19, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Xiao-Min ShenJian-Dong Huang
Apr 9, 2014·Chemistry : a European Journal·Hiroaki HoriuchiHiroshi Hiratsuka
Oct 19, 2017·Organic & Biomolecular Chemistry·Rubén Ruiz-GonzálezSanti Nonell
Jan 22, 2021·Organic & Biomolecular Chemistry·Koushambi Mitra, Matthew C T Hartman
Jan 15, 2008·Journal of Medicinal Chemistry·Hairong LiM Graça H Vicente
May 22, 2021·Journal of Medicinal Chemistry·Carime V RodriguesAna de Bettencourt-Dias
May 27, 2021·Physical Chemistry Chemical Physics : PCCP·Xue DongQiantao Wang
Jun 5, 2021·Applied Physics Reviews·Jace A WillisVladislav V Yakovlev
Nov 26, 2010·The Journal of Physical Chemistry. a·Yang Yang

❮ Previous
Next ❯

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.

Related Papers

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Kawser KassabOlimpia Coppellotti
Advanced Drug Delivery Reviews
Yoshinori Kakizawa, Kazunori Kataoka
© 2021 Meta ULC. All rights reserved