Studying the intersystem crossing rate and triplet quantum yield of <i>meso</i>-substituted porphyrins by means of pulse train fluorescence technique

Souza, Tiago Gualberto Bezera de; Vivas, Marcelo G.; Mendonça, Cleber Renato; Plunkett, Shane; Filatov, Mikhail A.; Senge, Ma­thias O.; Boni, Leonardo De

doi:10.1142/s1088424616500048

Cited by 52 publications

(16 citation statements)

References 44 publications

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“…Fluorescence spectra of PEG-ZnTCPP and B12-ZnTCPP in DMSO show emission bands around 612 and 666 nm (ESI Figure S6) and the fluorescence quantum yields and lifetimes are similar for the two species. The results are consistent with values reported in literature for comparable porphyrin analogues, and support the hypothesis that the structural change at the periphery of the porphyrin does not drastically affect ϕfl and τf since the fluorescence phenomenon arises from the inner π-electron system on the macrocycle [63][64][65].…”

Section: O2 Generation and Co Release Of Surface Coating Moleculessupporting

confidence: 92%

Photoactivatable Surface-Functionalized Diatom Microalgae for Colorectal Cancer Targeted Delivery and Enhanced Cytotoxicity of Anticancer Complexes

Delasoie¹,

Schiel²,

Vojnović³

et al. 2020

Preprint

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Design, synthesis and characterization of a bio-inspired hybrid multifunctional drug delivery system based on diatom microalgae. The microalgae’s surface was chemically functionalized with hybrid vitamin B<sub>12</sub>-photoactivable molecules and the materials further loaded with highly active rhenium(I) tricarbonyl anticancer complexes. The constructs showed enhanced adherence to colorectal cancer (CRC) cells via transcobalamin (II) receptors and slow release of the chemotherapeutic drugs. The overall toxicity of the hybrid multifunctional drug delivery system was further enhanced by photoactivation of the microalgae surface. Depending on the construct and anticancer drug, a 2-fold increase in the cytotoxic efficacy of the drug was observed upon light irradiation.

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Section: O2 Generation and Co Release Of Surface Coating Moleculessupporting

confidence: 92%

Photoactivatable Surface-Functionalized Diatom Microalgae for Colorectal Cancer Targeted Delivery and Enhanced Cytotoxicity of Anticancer Complexes

Delasoie¹,

Schiel²,

Vojnović³

et al. 2020

Preprint

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“…Fluorescence spectra of PEG-ZnTCPP and B 12 -ZnTCPP in DMSO show emission bands around 612 and 666 nm (ESI Figure S7), and the fluorescence quantum yields and lifetimes are similar for the two species. The results are consistent with values reported in the literature for comparable porphyrin analogs and support the hypothesis that the structural change at the periphery of the porphyrin does not drastically affect Φ f l and τ f since the fluorescence phenomenon arises from the inner π-electron system on the macrocycle [65][66][67]. Nevertheless, it is known that introducing electron-donating or -withdrawing groups onto porphyrin center will slightly influence the fluorescence properties [68].…”

Section: O 2 Generation and Co Release Of Surface Coating Moleculessupporting

confidence: 91%

Photoactivatable Surface-Functionalized Diatom Microalgae for Colorectal Cancer Targeted Delivery and Enhanced Cytotoxicity of Anticancer Complexes

et al. 2020

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Systemic toxicity and severe side effects are commonly associated with anticancer chemotherapies. New strategies based on enhanced drug selectivity and targeted delivery to cancer cells while leaving healthy tissue undamaged can reduce the global patient burden. Herein, we report the design, synthesis and characterization of a bio-inspired hybrid multifunctional drug delivery system based on diatom microalgae. The microalgae’s surface was chemically functionalized with hybrid vitamin B12-photoactivatable molecules and the materials further loaded with highly active rhenium(I) tricarbonyl anticancer complexes. The constructs showed enhanced adherence to colorectal cancer (CRC) cells and slow release of the chemotherapeutic drugs. The overall toxicity of the hybrid multifunctional drug delivery system was further enhanced by photoactivation of the microalgae surface. Depending on the construct and anticancer drug, a 2-fold increase in the cytotoxic efficacy of the drug was observed upon light irradiation. The use of this targeted drug delivery strategy, together with selective spatial–temporal light activation, may lead to lower effective concentration of anticancer drugs, thereby reducing medication doses, possible side effects and overall burden for the patient.

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“…However, it is hard to predict the effect of substituents on ISC and in some cases functionalization (e.g. with strong electron accepting groups) can lead to reduced triplet state yields and lifetimes [23]. Quantitive Structure-Activity Relationship (QSAR) models are commonly used for the prediction of absorption, distribution, metabolism, excretion (ADME), toxicity, and selectivity towards certain cells in pharmacokinetics.…”

Section: Introductionmentioning

confidence: 99%

Singlet oxygen generation by porphyrins and metalloporphyrins revisited: A quantitative structure-property relationship (QSPR) study

Buglak

Filatov

Hussain

et al. 2020

Journal of Photochemistry and Photobiology A: Chemistry

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Porphyrins and metalloporphyrins are used as photosensitizers in photocatalysis, photodynamic therapy (PDT), disinfection, degradation of persistent pollutants and other applications. Their mechanism of action involves intersystem crossing to triplet excited state followed by formation of singlet oxygen (1 O2), which is a highly reactive species and mediates various oxidative processes. The design of advanced sensitizers based on porphyrin compounds have attracted significant attention in recent years. However, it is still difficult to predict the efficiency of singlet oxygen generation for a given structure. Our goal was to develop a quantitative structure-property relationship (QSPR) model for the fast virtual screening and prediction of singlet oxygen quantum yields for pophyrins and metalloporphyrins. We performed QSPR analysis of a dataset containing 32 compounds, including various porphyrins and their analogues (chlorins and bacteriochlorins). Quantum-chemical descriptors were calculated using Density Functional Theory (DFT), namely B3LYP and M062X functionals. Three different machine learning methods were used to develop QSPR models: random forest regression (RFR), support vector regression (SVR), and multiple linear regression (MLR). The optimal QSPR model «structuresinglet oxygen generation quantum yield» obtained using RFR method demonstrated high determination coefficient for the training set (R 2 = 0.949) and the highest predicting ability for the test set (pred_R 2 = 0.875). This proves that the developed QSPR method is realiable and Manuscript File Click here to view linked References 2 can be directly applied in the studies of singlet oxygen generation both for free base porphyrins and their metal complexes. We believe that QSPR approach developed in this study can be useful for the search of new poprhyrin photosensitizers with enhanced singlet oxygen generation ability.

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Studying the intersystem crossing rate and triplet quantum yield of meso-substituted porphyrins by means of pulse train fluorescence technique

Cited by 52 publications

References 44 publications

Photoactivatable Surface-Functionalized Diatom Microalgae for Colorectal Cancer Targeted Delivery and Enhanced Cytotoxicity of Anticancer Complexes

Photoactivatable Surface-Functionalized Diatom Microalgae for Colorectal Cancer Targeted Delivery and Enhanced Cytotoxicity of Anticancer Complexes

Photoactivatable Surface-Functionalized Diatom Microalgae for Colorectal Cancer Targeted Delivery and Enhanced Cytotoxicity of Anticancer Complexes

Singlet oxygen generation by porphyrins and metalloporphyrins revisited: A quantitative structure-property relationship (QSPR) study

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