New artificial fluoro-cofactor of hydride transfer with novel fluorescence assay for redox biocatalysis

Zhang, Lei; Yuan, Jun; Xu, Yufang; Zhang, Y-H Percival; Qian, Xuhong

doi:10.1039/c6cc02002j

Cited by 17 publications

(10 citation statements)

References 31 publications

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“…Determination of the aqueous solubility was performed according to the published literature. 34 The CYP inhibition assays and measurement of permeability of compound 20g were conducted by WuXi AppTec, and the detailed characterizations are provided in the Supporting Information.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-diones as Potent and Selective Epidermal Growth Factor Receptor (EGFR) Inhibitors against L858R/T790M Resistance Mutation

Hao

Lyu

et al. 2018

J. Med. Chem.

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First-generation epidermal growth factor receptor (EGFR) inhibitors, gefitinib and erlotinib, have achieved initially marked clinical efficacy for nonsmall cell lung cancer (NSCLC) patients with EGFR activating mutations. However, their clinical benefit was limited by the emergence of acquired resistance mutations. In most cases (approximately 60%), the resistance was caused by the secondary EGFR T790M gatekeeper mutation. Thus, it is still desirable to develop novel third-generation EGFR inhibitors to overcome T790M mutation while sparing wild-type (WT) EGFR. Herein, a series of pyrimido[4,5- d]pyrimidine-2,4(1 H,3 H)-dione derivatives were designed and synthesized, among which the most potent compound 20g not only demonstrated significant inhibitory activity and selectivity for EGFR and H1975 cells in vitro but also displayed outstanding antitumor efficiency in H1975 xenograft mouse model. The encouraging mutant-selective results at both in vitro and in vivo levels suggested that 20g might be used as a promising lead compound for further structural optimization as potent and selective EGFR inhibitors.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-diones as Potent and Selective Epidermal Growth Factor Receptor (EGFR) Inhibitors against L858R/T790M Resistance Mutation

Hao

Lyu

et al. 2018

J. Med. Chem.

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“…[8,9] Based on the success of artificial metalloenzyme engineering, there is growing interest in expanding the scope of artificial cofactors to encompass other catalytic modalities. [10,11] For example, photoredox catalysis has shown increased application for chemical synthesis due to its broad utility in bond activation through mechanisms that are often orthogonal or complementary to traditional transition metal chemistry. [12,13] Photoredox transformations operate through photoinduced electron transfer (PET) events, which facilitate the generation of highly reactive intermediates at ambient temperature bypassing thermal barriers and permitting access to unique reactivity patterns.…”

Section: Introductionmentioning

confidence: 99%

“…Based on the success of artificial metalloenzyme engineering, there is growing interest in expanding the scope of artificial cofactors to encompass other catalytic modalities [10,11] . For example, photoredox catalysis has shown increased application for chemical synthesis due to its broad utility in bond activation through mechanisms that are often orthogonal or complementary to traditional transition metal chemistry [12,13] .…”

Section: Introductionmentioning

confidence: 99%

Design and Evaluation of Artificial Hybrid Photoredox Biocatalysts

et al. 2020

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A pair of 9-mesityl-10-phenyl acridinium (MesÀ Acr +) photoredox catalysts were synthesized with an iodoacetamide handle for cysteine bioconjugation. Covalently tethering of the synthetic MesÀ Acr + cofactors with a small panel of thermostable protein scaffolds resulted in 12 new artificial enzymes. The unique chemical and structural environment of the protein hosts had a measurable effect on the photophysical properties and photocatalytic activity of the cofactors. The constructed MesÀ Acr + hybrid enzymes were found to be active photoinduced electron-transfer catalysts, controllably oxidizing a variety of aryl sulfides when irradiated with visible light, and possessed activities that correlated with the photophysical characterization data. Their catalytic performance was found to depend on multiple factors including the MesÀ Acr + cofactor, the protein scaffold, the location of cofactor immobilization, and the substrate. This work provides a framework toward adapting synthetic photoredox catalysts into artificial cofactors and includes important considerations for future bioengineering efforts.

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“…Zhang et al. show an approach to substitute NAD(P)H co‐factors with an artificial fluoro‐containing co‐factor based on a simplified structure . Also, Paul and co‐workers report work on simplified synthetic co‐factors comprising structures of NAD(P)H .…”

Section: Enzymatic Catalysis For Co2 Conversionmentioning

confidence: 99%

Biocatalytic and Bioelectrocatalytic Approaches for the Reduction of Carbon Dioxide using Enzymes

et al. 2017

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In the recent decade, CO2 has increasingly been regarded not only as a greenhouse gas but even more as a chemical feedstock for carbon‐based materials. Different strategies have evolved to realize CO2 utilization and conversion into fuels and chemicals. In particular, biological approaches have drawn attention, as natural CO2 conversion serves as a model for many processes. Microorganisms and enzymes have been studied extensively for redox reactions involving CO2. In this review, we focus on monitoring nonliving biocatalyzed reactions for the reduction of CO2 by using enzymes. We depict the opportunities but also challenges associated with utilizing such biocatalysts. Besides the application of enzymes with co‐factors, resembling natural processes, and co‐factor recovery, we also discuss implementation into photochemical and electrochemical techniques.

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New artificial fluoro-cofactor of hydride transfer with novel fluorescence assay for redox biocatalysis

Cited by 17 publications

References 31 publications

Design, Synthesis, and Biological Evaluation of Pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-diones as Potent and Selective Epidermal Growth Factor Receptor (EGFR) Inhibitors against L858R/T790M Resistance Mutation

Design, Synthesis, and Biological Evaluation of Pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-diones as Potent and Selective Epidermal Growth Factor Receptor (EGFR) Inhibitors against L858R/T790M Resistance Mutation

Design and Evaluation of Artificial Hybrid Photoredox Biocatalysts

Biocatalytic and Bioelectrocatalytic Approaches for the Reduction of Carbon Dioxide using Enzymes

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