Amphiphilic Cationic Phthalocyanines for Photodynamic Therapy of Cancer

Halaskova, Marie; Kostelansky, Filip; Demuth, Jiří; Hlbocanova, Ingrid; Miletín, Miroslav; Zimčík, Petr; Macháček, Miloslav; Novakova, Veronika

doi:10.1002/cplu.202200133

Cited by 3 publications

(2 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The addition of ionic or non‐ionic substituents to Pcs makes them biocompatible by providing water solubility. Substitution of ionic groups on Pcs provides advantages such as increased water solubility and reduced aggregation, as well as high singlet oxygen formation [31–33] . On the other hand, these ionic structures also have disadvantages such as interacting with components of biological fluids and interfaces and causing serious side effects [34] .…”

Section: Introductionmentioning

confidence: 99%

“…Substitution of ionic groups on Pcs provides advantages such as increased water solubility and reduced aggregation, as well as high singlet oxygen formation. [31][32][33] On the other hand, these ionic structures also have disadvantages such as interacting with components of biological fluids and interfaces and causing serious side effects. [34] Therefore, the addition of nonionic water-soluble substituents to Pcs is advantageous.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

et al. 2023

View full text Add to dashboard Cite

This study describes the synthesis and characterization of peripherally and non‐peripherally substituted copper(II) and cobalt(II) phthalocyanines bearing tetraethyleneglycol monomethyl ether chains. In addition, the metal‐free and zinc(II) phthalocyanine derivatives were prepared according to the referred procedure. All newly synthesized phthalocyanines were characterized using some spectroscopic techniques such as elemental analysis and fourier transform infrared, ultraviolet‐visible, and mass spectroscopies. The effects of solvent type and concentration on aggregation properties of phthalocyanines were studied, as well. The biological activities of a series of these peripherally and non‐peripherally tetra‐substituted phthalocyanines were investigated. The effects of the central metal ion and the position of the substituent on biological activities of phthalocyanines were also compared. When the antioxidant activities of the synthesized molecules were evaluated by the 2,2‐diphenyl‐1‐picrylhydrazyl method, 1,8/11,15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatocobalt(II) (63.17±0.012 %) showed the highest activity. The highest reducing power activity was obtained with the 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatozinc(II) molecule. In the antibacterial activity studies using the disc diffusion method, 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy) ethoxy)ethoxy)ethoxy]phthalocyaninatocopper(II) exhibited the highest inhibition activity on both gram negative (18±0.23 mm) and gram positive (23±0.07 mm) strains. On the other hand, 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy) ethoxy)ethoxy]phthalocyaninatozinc(II) and 1,8/11,15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalo‐cyaninatozinc(II) compounds presented hemolytic activity against sheep blood in the hemolytic activity studies. The results confirmed that the synthesized molecules demonstrated average antioxidant activity compared to standard antioxidants. 2,9/10,16/17,23/24‐Tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalo‐cyaninatocopper(II), 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxy ethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatozinc(II) and 1,8/11, 15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy) ethoxy]phthalocyaninatozinc(II) complexes could remarkably inhibit S. aureus and CuPc‐1 complex E. coli growth.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

et al. 2023

View full text Add to dashboard Cite

show abstract

Elucidating the Supramolecular Interaction of Positively Supercharged Fluorescent Protein with Anionic Phthalocyanines

Saarinen,

Khan,

Patrian

et al. 2024

Advanced Biology

View full text Add to dashboard Cite

Developing bioinspired materials to convert sunlight into electricity efficiently is paramount for sustainable energy production. Fluorescent proteins are promising candidates as photoactive materials due to their high fluorescence quantum yield and absorption extinction coefficients in aqueous media. However, developing artificial bioinspired photosynthetic systems requires a detailed understanding of molecular interactions and energy transfer mechanisms in the required operating conditions. Here, the supramolecular self‐assembly and photophysical properties of fluorescent proteins complexed with organic dyes are investigated in aqueous media. Supercharged mGreenLantern protein, mutated to have a charge of +22, is complexed together with anionic zinc phthalocyanines having 4 or 16 carboxylate groups. The structural characterization reveals a strong electrostatic interaction between the moieties, accompanied by partial conformational distortion of the protein structure, yet without compromising the mGreenLantern chromophore integrity as suggested by the lack of emission features related to the neutral form of the chromophore. The self‐assembled biohybrid shows a total quenching of protein fluorescence, in favor of an energy transfer process from the protein to the phthalocyanine, as demonstrated by fluorescence lifetime and ultrafast transient absorption measurements. These results provide insight into the rich photophysics of fluorescent protein–dye complexes, anticipating their applicability as water‐based photoactive materials.

show abstract

Design rules for oxoporphyrinogen (‘OxP’) as a versatile chromophore for efficient singlet oxygen generation

Hynek

Chahal

Payne

et al. 2023

J. Porphyrins Phthalocyanines

View full text Add to dashboard Cite

Meso-5,10,15,20-tetrakis-3,5-di-tert-butyl-4-oxocyclohexadienylideneporphyrinogen, OxP, is a versatile, highly colored chromophore with strong broad absorption in the visible range. It is derived from meso-5,10,15,20-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin by two-electron oxidation, and the OxP tetrapyrrole moiety exists in a saddle conformation. N-Alkylation of the OxP core nitrogen atoms can be used to functionalize the chromophore leading to a class of stable molecules with highly substituted peripheries. Substituted OxPs can act as singlet oxygen generators under light irradiation and the efficacy of this process is influenced by the multiplicity of N-substitution, and by the chemical identity of those substituents. Bromination of the macrocyclic [Formula: see text]-positions can also be used to control singlet oxygen generation by the relevant derivatives. We report the quantum yields of singlet oxygen generation for a series of differently substituted OxP derivatives whose metrics indicate that these compounds possess significant potential in the corresponding applications including photodynamic therapy, bacterial inactivation therapy, and organic transformations.

show abstract

Amphiphilic Cationic Phthalocyanines for Photodynamic Therapy of Cancer

Cited by 3 publications

References 39 publications

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

Elucidating the Supramolecular Interaction of Positively Supercharged Fluorescent Protein with Anionic Phthalocyanines

Design rules for oxoporphyrinogen (‘OxP’) as a versatile chromophore for efficient singlet oxygen generation

Contact Info

Product

Resources

About