“Click”-reaction: An alternative tool for new architectures of porphyrin based derivatives

Ladomenou, Kalliopi; Nikolaou, Vasilis; Charalambidis, Georgios; Coutsolelos, Athanassios G.

doi:10.1016/j.ccr.2015.06.002

Cited by 77 publications

(44 citation statements)

References 153 publications

(171 reference statements)

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“…Actually, derivatives with triazolyl substituents demonstrated marked anticancer effect on several malignant tumor cell lines [36][37][38][39][40]. Triazoles have been also used to functionalize porphyrin derivatives, mainly by the "click chemistry" approach [41,42]. This copper(I) catalyzed azide-alkyne cycloaddition has been applied in the derivatization of several tetrapyrrolic molecules such as porphyrins, phthalocyanines, and corroles [41] and many studies have been conducted on the use of these "click-made" porphyrins as polymers [43], in biochemistry [18,24], in materials chemistry [44], and for the preparation of PSs for PDT [45][46][47][48].…”

Section: Introductionmentioning

confidence: 99%

“…Triazoles have been also used to functionalize porphyrin derivatives, mainly by the "click chemistry" approach [41,42]. This copper(I) catalyzed azide-alkyne cycloaddition has been applied in the derivatization of several tetrapyrrolic molecules such as porphyrins, phthalocyanines, and corroles [41] and many studies have been conducted on the use of these "click-made" porphyrins as polymers [43], in biochemistry [18,24], in materials chemistry [44], and for the preparation of PSs for PDT [45][46][47][48]. However, in such studies a systematic evaluation of the role of the triazole moiety on the PDT efficacy of porphyrins bearing this type of units has not yet been performed.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

et al. 2020

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Novel triazole-porphyrin derivatives (TZ-PORs) were synthesized through the Heck reaction and then incorporated into polyvinylpyrrolidone (PVP) micelles. After verifying that this incorporation did not compromise the photophysical and chemical features of TZ-PORs as photosensitizers, the phototoxicity of the formulations towards cancer cells was screened. Biological studies show high photodynamic activity of all PVP-TZ-POR formulations against a bladder cancer cell line with a particular highlight to PVP-TZ-POR 7e and 7f that are able to significantly reduce HT-1376 cell viability, while they had no effect on control ARPE-19 cells.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

et al. 2020

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“…The CuAAC reaction is considered as the most robust and straightforward synthetic procedure for various organic syntheses [188], especially in building novel structures, including natural products modifications [189], the synthesis of porphyrin based derivatives [190], the iterative click construction of dendrimers that are terminated with various functional groups [191], and polymers [192]. In the case of the dendrimer the "click" synthesis of a water soluble dendrimer that contained 9 intradendritic triazole rings and terminated by 27 triethylene glycol (TEG) termini was reported and used as nanoparticle stabilizer and catalyst template.…”

Section: Applications Of the Cuaac "Click" Reactionsmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

293

162

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Highlights-The review is focused on the mechanistic aspects and recent trends (since 2012) of the metal-catalyzed azide-alkyne cycloaddition (MAAC) so-called "click" reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.-These MAAC reactions are by far the most common click reactions relevant to the "green chemistry" concept.-Mechanistic investigations are essential to reaction improvements and subsequent applications, and indeed as shown in this review the proposed mechanisms have been multiple during the last decade based on theoretical computations and experimental search of intermediates.-New trends are also presented here often representing both exciting approaches for various applications and new challenges for further mechanistic investigations.

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“…The covalent linkage prevents metal‐cofactor dissociation phenomena and reduces the possibility of axial ligand dissociation and/or scrambling. Numerous strategies have been developed to afford elaborate peptide‐porphyrin architectures . The systems herein described point out that an increase in the catalytic activity is strictly related to the complexity of the cofactor environment.…”

Section: Heme‐protein Model Based On Covalent Peptide‐porphyrin Systemsmentioning

confidence: 99%

Oxidation catalysis by iron and manganese porphyrins within enzyme‐like cages

et al. 2018

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Inspired by natural heme-proteins, scientists have attempted for decades to design efficient and selective metalloporphyrin-based oxidation catalysts. Starting from the pioneering work on small molecule mimics in the late 1970s, we have assisted to a tremendous progress in designing cages of different nature and complexity, able to accommodate metalloporphyrins. With the intent of tuning and controlling their reactivity, more and more sophisticated and diverse environments are continuously exploited. In this review, we will survey the current state of art in oxidation catalysis using iron- and manganese-porphyrins housed within designed or engineered protein cages. We will also examine the innovative metal-organic framework (MOF) systems, exploited to achieving an enzyme-like environment around the metalloporphyrin cofactor.

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“Click”-reaction: An alternative tool for new architectures of porphyrin based derivatives

Cited by 77 publications

References 153 publications

Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Oxidation catalysis by iron and manganese porphyrins within enzyme‐like cages

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