Interactions of porphyrins with DNA: A review focusing recent advances in chemical modifications on porphyrins as artificial nucleases

Mathew, Diana; Sujatha, S.

doi:10.1016/j.jinorgbio.2021.111434

Cited by 31 publications

(13 citation statements)

References 159 publications

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“…In general, many other factors such as differences in overall charge and octanol–water partition coefficients, self-aggregation, and different degrees of freedom for accumulation in bacteria or at bacterial membranes as well as interaction with target structures like bacterial DNA may be considered [ 77 ]. Based on our analysis, substantial differences in the proportion of tetracationic molecules and therefore overall charge in the investigated synthesis products for meta -TMPyP and para -TMPyP are very unlikely.…”

Section: Discussionmentioning

confidence: 99%

The Meta-Substituted Isomer of TMPyP Enables More Effective Photodynamic Bacterial Inactivation than Para-TMPyP In Vitro

et al. 2022

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Porphyrinoid-based photodynamic inactivation (PDI) provides a promising approach to treating multidrug-resistant infections. However, available agents for PDI still have optimization potential with regard to effectiveness, toxicology, chemical stability, and solubility. The currently available photosensitizer TMPyP is provided with a para substitution pattern (para-TMPyP) of the pyridinium groups and has been demonstrated to be effective for PDI of multidrug-resistant bacteria. To further improve its properties, we synthetized a structural variant of TMPyP with an isomeric substitution pattern in a meta configuration (meta-TMPyP), confirmed the correct structure by crystallographic analysis and performed a characterization with NMR-, UV/Vis-, and IR spectroscopy, photostability, and singlet oxygen generation assay. Meta-TMPyP had a hypochromic shift in absorbance (4 nm) with a 55% higher extinction coefficient and slightly improved photostability (+6.9%) compared to para-TMPyP. Despite these superior molecular properties, singlet oxygen generation was increased by only 5.4%. In contrast, PDI, based on meta-TMPyP, reduced the density of extended spectrum β-lactamase-producing and fluoroquinolone-resistant Escherichia coli by several orders of magnitude, whereby a sterilizing effect was observed after 48 min of illumination, while para-TMPyP was less effective (p < 0.01). These findings demonstrate that structural modification with meta substitution increases antibacterial properties of TMPyP in PDI.

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Section: Discussionmentioning

confidence: 99%

The Meta-Substituted Isomer of TMPyP Enables More Effective Photodynamic Bacterial Inactivation than Para-TMPyP In Vitro

et al. 2022

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“…Several naturally occurring acids and the synthesis of a number of medicinally active hydroxylamine derivatives has been reported in recent years while some of the hydroxamic acids have already found applications in drug-delivery system 24,25 in iron-solubilisation and transport 26 and in DNA cleavage. [27][28][29] Studies regarding antitumour applications of the organotin are still not enough to have complete understanding of the mechanism. It is established that the drug molecules goes through a series of procedures such as crossing of cell-membrane,chemical hydrolysis, transfer in the physiological intermediate, and subsequently arrive at the close of goal DNA molecule and figure active intermediates R2Sn2+ which may have direct interaction with the phosphate group of DNA structures, invoking cancer cells via damaging the DNA, which leads to cell-death.…”

Section: Organotin As Anti-tumor Agentmentioning

confidence: 99%

Toxicity and anti-tumour activity of organotin (IV) compounds

Graisa¹,

Zainulabdeen

Salman

et al. 2022

Baghdad J. Biochem. Appl. Biol. Sci.

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This review focuses on organotin toxicity and its effect on human health. Organotins are utilized widely as anti-tumor, anti-inflammatory, anti-fungal, or antimicrobial agents in both agricultural and industrial applications. These materials are more toxic than inorganic cans which are poorly absorbed and are excreted on the surface of the can, which consequently results in increasing the level of toxicity to a variety of organisms and damaging the environment. An investigation of chemical compounds in organotin led to different methods for quantifying and qualifying individual molecules. Tributyltins, a highly toxic component of organotin, have recently been given great attention.

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“…Inspired by nature that is using metalloporphyrins as antennae molecules, redox shuttles and redox and photo catalysts [ 1 ], researchers have tried to use artificial porphyrin complexes for various purposes in the last decades [ 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. Cobalt porphyrins provide a rich electrochemistry consisting of both metal- (Co(I)/Co(II)/Co(III) and porphyrin-centred redox processes.…”

Section: Introductionmentioning

confidence: 99%

CO2 to CO Electroreduction, Electrocatalytic H2 Evolution, and Catalytic Degradation of Organic Dyes Using a Co(II) meso-Tetraarylporphyrin

et al. 2022

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The meso-tetrakis(4-(trifluoromethyl)phenyl)porphyrinato cobalt(II) complex [Co(TMFPP)] was synthesised in 93% yield. The compound was studied by 1H NMR, UV-visible absorption, and photoluminescence spectroscopy. The optical band gap Eg was calculated to 2.15 eV using the Tauc plot method and a semiconducting character is suggested. Cyclic voltammetry showed two fully reversible reduction waves at E1/2 = −0.91 V and E1/2 = −2.05 V vs. SCE and reversible oxidations at 0.30 V and 0.98 V representing both metal-centred (Co(0)/Co(I)/Co(II)/Co(III)) and porphyrin-centred (Por2−/Por−) processes. [Co(TMFPP)] is a very active catalyst for the electrochemical formation of H2 from DMF/acetic acid, with a Faradaic Efficiency (FE) of 85%, and also catalysed the reduction of CO2 to CO with a FE of 90%. Moreover, the two triarylmethane dyes crystal violet and malachite green were decomposed using H2O2 and [Co(TMFPP)] as catalyst with an efficiency of more than 85% in one batch.

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Interactions of porphyrins with DNA: A review focusing recent advances in chemical modifications on porphyrins as artificial nucleases

Cited by 31 publications

References 159 publications

The Meta-Substituted Isomer of TMPyP Enables More Effective Photodynamic Bacterial Inactivation than Para-TMPyP In Vitro

The Meta-Substituted Isomer of TMPyP Enables More Effective Photodynamic Bacterial Inactivation than Para-TMPyP In Vitro

Toxicity and anti-tumour activity of organotin (IV) compounds

CO2 to CO Electroreduction, Electrocatalytic H2 Evolution, and Catalytic Degradation of Organic Dyes Using a Co(II) meso-Tetraarylporphyrin

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