Mechanochemical <i>in situ</i> generated gas reactant for the solvent-free hydrogenation of porphyrins

Piñeiro, Marta; Gomes, Carla; Peixoto, Mariana

doi:10.1080/17518253.2021.1921283

Cited by 4 publications

(5 citation statements)

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“…In recent years, some examples of mechanochemical synthesis of porphyrin derivatives were reported by Pineiro and colleagues [ 95 , 96 ] ( Figure 12 b). Meso -tetrasubstituted porphyrins were synthesized by one-step and two-step approaches, i.e., by separating or not separating the cyclization of pyrrole and aldehyde to form porphyrinogen from its oxidation to porphyrin, using mechanochemistry in a vibration ball mill [ 96 ].…”

Section: Developments Of Mechanochemistry In Portugalmentioning

confidence: 98%

“…Sustainability was also assessed by the E-factor and EcoScale, two sustainability metrics, which allowed for a comparison between the two used methods. In the search for more sustainable processes for the reduction of meso -tetraarylporphyrins, the authors decided to test the mechanochemical reduction of porphyrins with hydrazines to selectively synthesize chlorins [ 95 ]. The procedure consisted of the hydrogenation of porphyrins using diimide generated and consumed under mechanical activation, under neat grinding conditions.…”

Section: Developments Of Mechanochemistry In Portugalmentioning

confidence: 99%

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Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis

et al. 2021

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In Portugal, publications with mechanochemical methods date back to 2009, with the report on mechanochemical strategies for the synthesis of metallopharmaceuticals. Since then, mechanochemical applications have grown in Portugal, spanning several fields, mainly crystal engineering and supramolecular chemistry, catalysis, and organic and inorganic chemistry. The area with the most increased development is the synthesis of multicomponent crystal forms, with several groups synthesizing solvates, salts, and cocrystals in which the main objective was to improve physical properties of the active pharmaceutical ingredients. Recently, non-crystalline materials, such as ionic liquids and amorphous solid dispersions, have also been studied using mechanochemical methods. An area that is in expansion is the use of mechanochemical synthesis of bioinspired metal-organic frameworks with an emphasis in antibiotic coordination frameworks. The use of mechanochemistry for catalysis and organic and inorganic synthesis has also grown due to the synthetic advantages, ease of synthesis, scalability, sustainability, and, in the majority of cases, the superior properties of the synthesized materials. It can be easily concluded that mechanochemistry is expanding in Portugal in diverse research areas.

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Section: Developments Of Mechanochemistry In Portugalmentioning

confidence: 98%

Section: Developments Of Mechanochemistry In Portugalmentioning

confidence: 99%

Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis

et al. 2021

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“…This approach uses less solvents and is more facile; however, both the reduction and oxidation steps yielded the respective chlorin and porphyrin as by‐products (10%). Mechanochemistry has also been applied to the diimide reduction of porphyrins giving m THPC in 55% of m THPP (46).…”

Section: Chemistrymentioning

confidence: 99%

The Photosensitizer Temoporfin (mTHPC) – Chemical, Pre‐clinical and Clinical Developments in the Last Decade^†^‡

Wiehe

Senge

2022

Photochem & Photobiology

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This review follows the research, development and clinical applications of the photosensitizer 5,10,15,20-tetra(mhydroxyphenyl)chlorin (mTHPC, temoporfin) in photodynamic (cancer) therapy (PDT) and other medical applications. Temoporfin is the active substance in the medicinal product Foscanâ authorized in the EU for the palliative treatment of head and neck cancer. Chemistry, biochemistry and pharmacology, as well as clinical and other applications of temoporfin are addressed, including the extensive work that has been done on formulation development including liposomal formulations. The literature has been covered from 2009 to early 2022, thereby connecting it to the previous extensive review on this photosensitizer published in this journal [Senge, M. O. and J. C. Brandt (2011) Photochem. Photobiol. 87, 1240-1296] which followed its way from initial development to approval and clinical application.

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“…Due to its structural features, chlorin derivatives show unique spectral properties including: (1) an intense absorption band at ca. 650 nm; (2) high emission quantum yield and (3) upon coordination with metal ions, several metallochlorins can be obtained with more valuable physicochemical properties that enable a broader range of applications, such as in theranostics of cancer [ 3 , 4 , 5 , 6 ], nonlinear optics [ 7 , 8 , 9 ], photoacoustic imaging [ 10 , 11 , 12 ] and for dye sensitised solar cells [ 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

“…Chlorins can be obtained from porphyrins by a variety of synthetic approches, including through hydrogenation [ 14 ], annulation [ 20 ] and cycloaddition [ 21 ] with diverse entities. Using 1,3-dipolar cycloaddition (1,3-DC) reaction of porphyrins with azomethine ylides [ 22 ], we recently reported the synthesis of carboxylated pyrrolidine-fused chlorin (TCPC) and its application in the successful detection of the explosive triacetone triperoxide (TATP) in the gas phase [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin

et al. 2023

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We report the use of a carboxylated pyrrolidine-fused chlorin (TCPC) as a fluorescent probe for the determination of glutathione (GSH) in 7.4 pH phosphate buffer. TCPC is a very stable, highly emissive molecule that has been easily obtained from meso-tetrakis(4-methoxycarbonylphenyl) porphyrin (TCPP) through a 1,3-dipolar cycloaddition approach. First, we describe the coordination of TCPC with Hg(II) ions and the corresponding spectral changes, mainly characterized by a strong quenching of the chlorin emission band. Then, the TCPC-Hg2+ complex exhibits a significant fluorescence turn-on in the presence of low concentrations of the target analyte GSH. The efficacy of the sensing molecule was tested by using different TCPC:Hg2+ concentration ratios (1:2, 1:5 and 1:10) that gave rise to sigmoidal response curves in all cases with modulating detection limits, being the lowest 40 nM. The experiments were carried out under physiological conditions and the selectivity of the system was demonstrated against a number of potential interferents, including cysteine. Furthermore, the TCPC macrocycle did not showed a significant fluorescent quenching in the presence of other metal ions.

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Mechanochemical in situ generated gas reactant for the solvent-free hydrogenation of porphyrins

Cited by 4 publications

References 35 publications

Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis

Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis

The Photosensitizer Temoporfin (mTHPC) – Chemical, Pre‐clinical and Clinical Developments in the Last Decade^†^‡

Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin

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Mechanochemical in situ generated gas reactant for the solvent-free hydrogenation of porphyrins

Cited by 4 publications

References 35 publications

Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis

Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis

The Photosensitizer Temoporfin (mTHPC) – Chemical, Pre‐clinical and Clinical Developments in the Last Decade†‡

Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin

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The Photosensitizer Temoporfin (mTHPC) – Chemical, Pre‐clinical and Clinical Developments in the Last Decade^†^‡