Cytochrome P450-Like Biomimetic Oxidation Catalysts Based on Mn Porphyrins as Redox Modulators

Pinto, Victor Hugo A.; Falcão, Nathália Kellyne Silva Marinho; Bueno-Janice, Jacqueline C.; Spasojević, Ivan; Batinić‐Haberle, Ines; Rebouças, Júlio S.

doi:10.1007/978-3-319-30705-3_9

Cited by 2 publications

(1 citation statement)

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“…As a characteristic of Mn-porphyrins in general, MnTE-2-PyPCl 5 with Mn in the +3 oxidation state is extremely stable against acid solvolysis: Mn(III) demetallation is difficult even under concentrate H 2 SO 4 conditions [ 2 ]. MnTE-2-PyPCl 5 is relatively stable against oxidative degradation under biological conditions, particularly the presence of many reactive substrates or biological sacrificial reductors [ 35 ]. Not only do Mn-porphyrins withstand major reactive oxygen and nitrogen species (ROS/RNS) but also H 2 O 2 is a key molecule in the therapeutic effects of Mn-porphyrins, as clearly shown by Jaramillo et al [ 36 ] and recently summarized elsewhere [ 1 ].…”

Section: Introductionmentioning

confidence: 99%

Thermal Stability Kinetics and Shelf Life Estimation of the Redox‐Active Therapeutic and Mimic of Superoxide Dismutase Enzyme, Mn(III) meso‐Tetrakis(N‐ethylpyridinium‐2‐yl)porphyrin Chloride (MnTE‐2‐PyPCl₅, BMX‐010)

Maia

Araujo

Freitas-Marques

et al. 2021

Oxidative Medicine and Cellular Longevity

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Mn(III) meso-tetrakis(N-ethylpyridinium-2-yl)porphyrin chloride (MnTE-2-PyPCl5, BMX-010, and AEOL10113) is among the most studied superoxide dismutase (SOD) mimics and redox-active therapeutics, being currently tested as a drug candidate in a phase II clinical trial on atopic dermatitis and itch. The thermal stability of active pharmaceutical ingredients (API) is useful for estimating the expiration date and shelf life of pharmaceutical products under various storage and handling conditions. The thermal decomposition and kinetic parameters of MnTE-2-PyPCl5 were determined by thermogravimetry (TG) under nonisothermal and isothermal conditions. The first thermal degradation pathway affecting Mn-porphyrin structural integrity and, thus, activity and bioavailability was associated with loss of ethyl chloride via N-dealkylation reaction. The thermal stability kinetics of the N-dealkylation process leading to MnTE-2-PyPCl5 decomposition was investigated by using isoconversional models and artificial neural network. The new multilayer perceptron (MLP) artificial neural network approach allowed the simultaneous study of ten solid-state kinetic models and showed that MnTE-2-PyPCl5 degradation is better explained by a combination of various mechanisms, with major contributions from the contraction models R1 and R2. The calculated activation energy values from isothermal and nonisothermal data were about 90 kJ mol–1 on average and agreed with one another. According to the R1 modelling of the isothermal decomposition data, the estimated shelf life value for 10% decomposition ( t 90 % ) of MnTE-2-PyPCl5 at 25°C was approximately 17 years, which is consistent with the high solid-state stability of the compound. These results represent the first study on the solid-state decomposition kinetics of Mn(III) 2-N-alkylpyridylporphyrins, contributing to the development of this class of redox-active therapeutics and SOD mimics and providing supporting data to protocols on purification, handling, storage, formulation, expiration date, and general use of these compounds.

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Section: Introductionmentioning

confidence: 99%

Thermal Stability Kinetics and Shelf Life Estimation of the Redox‐Active Therapeutic and Mimic of Superoxide Dismutase Enzyme, Mn(III) meso‐Tetrakis(N‐ethylpyridinium‐2‐yl)porphyrin Chloride (MnTE‐2‐PyPCl₅, BMX‐010)

Maia

Araujo

Freitas-Marques

et al. 2021

Oxidative Medicine and Cellular Longevity

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Mn(III)-Porphyrin Immobilized on the Graphene Oxide-Magnetite Nanocomposite as an Efficient Heterogeneous Catalyst for the Epoxidation of Alkenes

Hajian

Bahrami

2021

Catal Lett

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Cytochrome P450-Like Biomimetic Oxidation Catalysts Based on Mn Porphyrins as Redox Modulators

Cited by 2 publications

References 152 publications

Thermal Stability Kinetics and Shelf Life Estimation of the Redox‐Active Therapeutic and Mimic of Superoxide Dismutase Enzyme, Mn(III) meso‐Tetrakis(N‐ethylpyridinium‐2‐yl)porphyrin Chloride (MnTE‐2‐PyPCl₅, BMX‐010)

Thermal Stability Kinetics and Shelf Life Estimation of the Redox‐Active Therapeutic and Mimic of Superoxide Dismutase Enzyme, Mn(III) meso‐Tetrakis(N‐ethylpyridinium‐2‐yl)porphyrin Chloride (MnTE‐2‐PyPCl₅, BMX‐010)

Mn(III)-Porphyrin Immobilized on the Graphene Oxide-Magnetite Nanocomposite as an Efficient Heterogeneous Catalyst for the Epoxidation of Alkenes

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Cytochrome P450-Like Biomimetic Oxidation Catalysts Based on Mn Porphyrins as Redox Modulators

Cited by 2 publications

References 152 publications

Thermal Stability Kinetics and Shelf Life Estimation of the Redox‐Active Therapeutic and Mimic of Superoxide Dismutase Enzyme, Mn(III) meso‐Tetrakis(N‐ethylpyridinium‐2‐yl)porphyrin Chloride (MnTE‐2‐PyPCl5, BMX‐010)

Thermal Stability Kinetics and Shelf Life Estimation of the Redox‐Active Therapeutic and Mimic of Superoxide Dismutase Enzyme, Mn(III) meso‐Tetrakis(N‐ethylpyridinium‐2‐yl)porphyrin Chloride (MnTE‐2‐PyPCl5, BMX‐010)

Mn(III)-Porphyrin Immobilized on the Graphene Oxide-Magnetite Nanocomposite as an Efficient Heterogeneous Catalyst for the Epoxidation of Alkenes

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Thermal Stability Kinetics and Shelf Life Estimation of the Redox‐Active Therapeutic and Mimic of Superoxide Dismutase Enzyme, Mn(III) meso‐Tetrakis(N‐ethylpyridinium‐2‐yl)porphyrin Chloride (MnTE‐2‐PyPCl₅, BMX‐010)

Thermal Stability Kinetics and Shelf Life Estimation of the Redox‐Active Therapeutic and Mimic of Superoxide Dismutase Enzyme, Mn(III) meso‐Tetrakis(N‐ethylpyridinium‐2‐yl)porphyrin Chloride (MnTE‐2‐PyPCl₅, BMX‐010)