4.3 Article

Metal or metal-free phthalocyanines containing morpholine substituents: synthesis, spectroscopic and photophysicochemical properties

Related references

Note: Only part of the references are listed.
Article Chemistry, Applied

Chalcogen bearing tetrasubstituted zinc (II) phthalocyanines for CT26 colon carcinoma cells photodynamic therapy

Sergio D. Ezquerra Riega et al.

Summary: In this study, the synthesis and photochemical properties of six new lipophilic chalcogen tetrasubstituted zinc (II) phthalocyanines and their water-soluble cationic derivatives were investigated. The introduction of sulfur and selenium atoms resulted in red shifts in the absorption spectrum compared to oxygen phthalocyanines. Furthermore, the selenium phthalocyanines had higher absorption coefficients than their sulfur and oxygen analogs, which is important for dosing in photodynamic therapy studies. The fluorescence emission maximum wavelength exhibited a similar trend with the presence of chalcogen atoms, with oxygen < selenium < sulfur. All phthalocyanines were efficient generators of singlet oxygen, with the production efficiency increasing with the atomic number of chalcogen atoms. The replacement of oxygen with sulfur or selenium atoms led to a red shift in the maximum absorption wavelength of triplet-triplet absorption and the introduction of selenium atoms significantly shortened the tau T. The photodynamic effect was evaluated on CT26 colon carcinoma cells, with oxygen phthalocyanines triggering cell death in both the absence and presence of light, while sulfur and selenium phthalocyanines only decreased cell viability in a concentration-dependent manner after light exposure. Among all the novel phthalocyanines, sulfur-bearing phthalocyanines showed the highest photodynamic efficiency.

DYES AND PIGMENTS (2022)

Article Chemistry, Physical

Effects of metal ion in cationic Pd(II) and Ni(II) phthalocyanines on physicochemical and photodynamic inactivation properties

Irem Kulu et al.

Summary: Four novel tetra non-peripheral 2-hydroxypyridine substituted palladium (II) and nickel (II) phthalocyanines and their quaternized derivatives were synthesized and fully characterized. The quaternized phthalocyanines showed good solubility and singlet oxygen generation properties. The palladium (II) phthalocyanine complex demonstrated good uptake and inactivation capabilities towards Gram (+) Methicillin-resistant Staphylococcus aureus (MRSA) while the newly synthesized nickel (II) phthalocyanine lacked inactivation towards both bacterial strains.

JOURNAL OF MOLECULAR STRUCTURE (2022)

Review Chemistry, Inorganic & Nuclear

Recent advances in supramolecular activatable phthalocyanine-based photosensitizers for anti-cancer therapy

Bing-De Zheng et al.

Summary: Phthalocyanines are widely used in photodynamic therapy but lack selectivity. Introducing activatable photosensitizers significantly improves their selectivity and effectiveness. Various phthalocyanine-based activatable photosensitizers have been developed to reduce damage to normal cells and enhance their potential in anti-cancer therapy.

COORDINATION CHEMISTRY REVIEWS (2021)

Article Chemistry, Physical

Synthesis, characterization, photophysical and photochemical properties of peripherally tetra benzodioxane substituted metal-free phthalocyanine and its zinc(II) and magnesium(II) derivatives

Umit Demirbas et al.

Summary: In this study, phthalocyanines with different substituents were synthesized and their photophysical and photochemical properties were investigated in DMSO solutions. Zinc(II) phthalocyanine showed higher singlet oxygen quantum yield compared to metal-free and magnesium(II) phthalocyanine. Additionally, the fluorescence quenching behaviors of phthalocyanines by 1,4-benzoquinone were studied.

JOURNAL OF MOLECULAR STRUCTURE (2021)

Article Chemistry, Inorganic & Nuclear

Dual-purpose both peripheral and non-peripheral triazole substituted ZnII, MgII and PbII phthalocyanines: Synthesis, characterization, photophysicochemical and acetylcholinesterase inhibitory properties

Halit Kantekin et al.

Summary: This study synthesized various metal ion phthalocyanines with different substituents, and investigated their solubility in organic solvents. By comparing the photophysicochemical properties of different phthalocyanines, it was found that zinc(II) phthalocyanine exhibited high singlet oxygen generation in DMSO, and phenethyl phthalocyanine showed superior enzyme inhibitory properties.

POLYHEDRON (2021)

Article Chemistry, Applied

The substituted zinc(II) phthalocyanines using sulfur bridge as the linkages. Synthesis, red-shifted spectroscopic properties and structure-inherent targeted photodynamic activities

Yuan-Yuan Zhao et al.

Summary: A novel zinc(II) phthalocyanine tetra-substituted with sulphonates using "sulfur bridge" as the linkages was developed in this study, which exhibits high water solubility and natural tumor targeting. ZnPc3 possesses red-shifted absorption and fluorescence spectra compared to the unsubstituted zinc(II) phthalocyanine, showing excellent tumor selectivity after intravenous injection without the need for targeting ligands or extra nanomaterials. In vivo phototherapy evaluation suggests that ZnPc3-induced PDT effectively inhibits tumor growth in a mouse model.

DYES AND PIGMENTS (2021)

Article Chemistry, Physical

The new water soluble zinc(II) phthalocyanines substituted with morpholine groups- synthesis and optical properties

Khaoula Khezami et al.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY (2020)

Review Biochemistry & Molecular Biology

Zinc(II) phthalocyanines as photosensitizers for antitumor photodynamic therapy

Leonor P. Roguin et al.

INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY (2019)

Article Chemistry, Inorganic & Nuclear

Non-peripherally tetrasubstituted phthalocyanines: Synthesis, characterization and, photophysical investigation

Sevgican Tuncer et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2017)

Article Chemistry, Medicinal

Synthesis and biological screening for cytotoxic activity of N-substituted indolines and morpholines

Phuong Doan et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2016)

Article Biochemistry & Molecular Biology

Synthesis of novel compounds containing morpholine and 5(4H)-oxazolone rings as potent tyrosinase inhibitors

Hooshang Hamidian et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2015)

Article Biochemistry & Molecular Biology

Antihyperlipidemic morpholine derivatives with antioxidant activity: An investigation of the aromatic substitution

Eleni M. Ladopoulou et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2015)

Article Chemistry, Inorganic & Nuclear

Magnesium Azaphthalocyanines: An Emerging Family of Excellent Red-Emitting Fluorophores

Petr Zimcik et al.

INORGANIC CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Tetra and octa(2,6-di-iso-propylphenoxy)-substituted phthalocyanines: a comparative study among their photophysicochemical properties

Ahmad Tuhl et al.

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES (2012)

Article Optics

The photostability and fluorescence properties of diphenylisobenzofuran

Xian-Fu Zhang et al.

JOURNAL OF LUMINESCENCE (2011)

Article Chemistry, Physical

Electrochromic Switching of Evaporated Thin Films of Bulky, Electronic Deficient Metallo-Phthalocyanines

Stefanie Nagel et al.

JOURNAL OF PHYSICAL CHEMISTRY C (2011)

Article Chemistry, Multidisciplinary

Photocurrent generation in nanostructured organic solar cells

Fan Yang et al.

ACS NANO (2008)

Article Chemistry, Multidisciplinary

Highly efficient drug delivery with gold nanoparticle vectors for in vivo photodynamic therapy of cancer

Yu Cheng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Inorganic & Nuclear

Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines

Tebello Nyokong

COORDINATION CHEMISTRY REVIEWS (2007)

Article Chemistry, Inorganic & Nuclear

Synthesis, photophysical and photochemical properties of substituted zinc phthalocyanines

Ilke Guerol et al.

DALTON TRANSACTIONS (2007)

Review Chemistry, Organic

Photobleaching of sensitisers used in photodynamic therapy

R Bonnett et al.

TETRAHEDRON (2001)

Article Chemistry, Physical

Electronic structure and bonding in metal phthalocyanines, Metal=Fe, Co, Ni, Cu, Zn, Mg

MS Liao et al.

JOURNAL OF CHEMICAL PHYSICS (2001)