Synthesis, photodynamic activities, and cytotoxicity of new water-soluble cationic gallium(III) and zinc(II) phthalocyanines

Fujishiro, Rei; Sonoyama, Hayato; Ide, Yuki; Fujimura, Takuya; Sasai, Ryo; Nagai, Atsushi; Mori, Shigeki; Kaufman, Nichole E. M.; Zhou, Zehua; Vicente, M. Graça H.; Ikeue, Takahisa

doi:10.1016/j.jinorgbio.2018.11.013

Cited by 41 publications

(15 citation statements)

References 57 publications

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“…An article recently described ZnPcs bearing several amphiphilic pyridinium groups and bulky axial ligands to minimize aggregation ( Zn-8 ). 173 The Q-band of Zn-8 was observed around 675 nm. Upon exposure to low irradiation (1.5 J cm −2 ), Zn-8 was highly toxic (IC 50 = 5.3 μM vs. >100 μM in the dark).…”

Section: Phototoxic First-row Transition Metal Complexesmentioning

confidence: 98%

Phototherapeutic anticancer strategies with first-row transition metal complexes: a critical review

2022

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Section: Phototoxic First-row Transition Metal Complexesmentioning

confidence: 98%

Phototherapeutic anticancer strategies with first-row transition metal complexes: a critical review

2022

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“…Table 3 shows that compounds (3a) and (4a) have very high singlet oxygen yields when compared with unsubstituted ZnPc and ClGaPc. [47] The observed trend for the singlet oxygen quantum yield values corresponds well to the increase in the atomic number of the center atom. When compared with the central metal atom, gallium Pc complexes have higher Φ Δ values than zinc Pc complexes because the gallium is a very heavy metal.…”

Section: Singlet Oxygen Quantum Yields (φ δ )mentioning

confidence: 65%

“…In aqua medium, GaCl derivative (4a) also has the highest singlet oxygen yields compared with (2a) and (3a) due to lower aggregation behavior owing to the effect of steric hindrance between the peripheral groups and the Cl atom, being its axial ligand. [47] These results showed that especially the zinc and chlorogallium phthalocyanines bearing methyl-1H-imidazole-2-thiol moieties have high level of F I G U R E 4 Absorption (711, 728), excitation (730), and emission (742) spectra of (2a) in DMSO F I G U R E 5 Absorption (727), excitation (727), and emission (749) spectra of (4a) in DMSO F I G U R E 6 A typical spectrum for the determination of singlet oxygen quantum yield of (2a) in DMSO F I G U R E 7 A typical spectrum for the determination of singlet oxygen quantum yield of (3a) in DMSO F I G U R E 8 A typical spectrum for the determination of singlet oxygen quantum yield of (3a) in water photosensitization with the good singlet oxygen generation capacity in DMSO.…”

Section: Singlet Oxygen Quantum Yields (φ δ )mentioning

confidence: 99%

Synthesis of water‐soluble phthalocyanines containing 1‐methyl‐1H‐imidazole‐2‐thiol: Investigation of DNA nuclease, α‐glucosidase inhibitory, and photo‐physicochemical properties

Günsel

Kalkan

Atmaca

et al. 2021

Applied Organom Chemis

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In this work, we have presented on the synthesis and characterization of novel 3-(1-methyl-1H-imidazole-2-thiol)phthalonitrile (1) as a ligand and its nonperipherally (M = 2H (2), Zn(II) (3), and GaCl(III) ( 4)) phthalocyanines and their highly water-soluble hydrochloride derivatives (2a-4a), containing 1-methyl-1H-imidazole-2-thiol substituents. All compounds were supported by FT-IR, UV-Vis, 1 H-NMR, 13 C-NMR, and MALDI-TOF mass spectra. The molecular structure of the novel compound (1) and its intermolecular interactions have been elucidated by analyzing the results of X-ray diffraction measurements. In order to determine the supercoiled pBR322 plasmid DNA nuclease properties of compounds (2a-4a), agarose gel electrophoresis was used. The plasmid DNA nuclease did not observe without light irradiation on increasing concentrations (2a-4a). When irradiated at 10 and 20 J/cm 2 , the band intensities changed on agarose gel, displaying photonuclease activity on supercoiled pBR322 plasmid DNA of compounds (2a-4a); 4a had the highest photonuclease activities in a concentration-dependent manner at 10 and 20 J/cm 2 . The in vitro α-glucosidase inhibitory effects of compounds (2a-4a) were investigated to determine whether they can be used in potential agents for diabetes mellitus. Compounds (2a-4a) showed higher inhibitory effects than acarbose (63.03 ± 2.14 μM) against α-glucosidase enzyme. Lineweaver-Burk analysis showed that K m increased and V max remained the same on increasing concentrations of compounds (2a-4a). The finding results claimed that the compounds inhibited α-glucosidase enzyme via competitive manner. Dixon plots showed that K i values of compounds (2a-4a) were 14.70 ± 0.70, 11.20 ± 0.50, and 12.60 ± 0.20 μM, respectively. Besides, the effect of including metal ion on photochemical and photophysical features of the compounds was studied in DMSO and water, comparatively. The compounds gave high singlet oxygen quantum yields (Φ Δ = 0.86 for (4a), 0.77 for (3a), and 0.59 for (2a)) in DMSO. The results showed that the compounds are also very suitable for photodynamic therapy applications.

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“…Metal-phthalocyanine synthesis is key to improving the use of these complexes in PDT (Allison et al, 2004;Boyar and Çamur, 2019;Fujishiro et al, 2019). Among such complexes, rutheniumphthalocyanine has emerged as a promising molecule because ruthenium complexes generally have octahedral geometry, and ruthenium-phthalocyanine is a hexacoordinated species that can still bind two new axial ligands (Heinrich et al, 2014;Teles Ferreira et al, 2017).…”

Section: Discussionmentioning

confidence: 99%

The Influence of Some Axial Ligands on Ruthenium–Phthalocyanine Complexes: Chemical, Photochemical, and Photobiological Properties

Martins

Negri

Pernomian

et al. 2021

Front. Mol. Biosci.

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This work presents a new procedure to synthesize ruthenium–phthalocyanine complexes and uses diverse spectroscopic techniques to characterize trans-[RuCl(Pc)DMSO] (I) (Pc = phthalocyanine) and trans-[Ru(Pc)(4-ampy)2] (II) (4-ampy = 4-aminopyridine). The triplet excited-state lifetimes of (I) measured by nanosecond transient absorption showed that two processes occurred, one around 15 ns and the other around 3.8 μs. Axial ligands seemed to affect the singlet oxygen quantum yield. Yields of 0.62 and 0.14 were achieved for (I) and (II), respectively. The lower value obtained for (II) probably resulted from secondary reactions of singlet oxygen in the presence of the ruthenium complex. We also investigate how axial ligands in the ruthenium–phthalocyanine complexes affect their photo-bioactivity in B16F10 murine melanoma cells. In the case of (I) at 1 μmol/L, photosensitization with 5.95 J/cm2 provided B16F10 cell viability of 6%, showing that (I) was more active than (II) at the same concentration. Furthermore, (II) was detected intracellularly in B16F10 cell extracts. The behavior of the evaluated ruthenium–phthalocyanine complexes point to the potential use of (I) as a metal-based drug in clinical therapy. Changes in axial ligands can modulate the photosensitizer activity of the ruthenium phthalocyanine complexes.

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Synthesis, photodynamic activities, and cytotoxicity of new water-soluble cationic gallium(III) and zinc(II) phthalocyanines

Cited by 41 publications

References 57 publications

Phototherapeutic anticancer strategies with first-row transition metal complexes: a critical review

Phototherapeutic anticancer strategies with first-row transition metal complexes: a critical review

Synthesis of water‐soluble phthalocyanines containing 1‐methyl‐1H‐imidazole‐2‐thiol: Investigation of DNA nuclease, α‐glucosidase inhibitory, and photo‐physicochemical properties

The Influence of Some Axial Ligands on Ruthenium–Phthalocyanine Complexes: Chemical, Photochemical, and Photobiological Properties

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