Comparison of the effect of N-methyl and N-aryl groups on the hydrolytic stability and electronic properties of betalain dyes

Pioli, Renan Moraes; Mattioli, Renan Rodini; Esteves, Larissa Cerrato; Dochev, Stefan; Bastos, E. L.

doi:10.1016/j.dyepig.2020.108609

Cited by 17 publications

(17 citation statements)

References 51 publications

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“… [75] Other applications include the preparation of pseudo‐NP dyes from betelamic acid. [76] These examples indicate that the concept might have been intuitively employed previously, without the intellectual framework and guidance of the design principles delineated here.…”

Section: Discussionmentioning

confidence: 95%

Pseudo Natural Products—Chemical Evolution of Natural Product Structure

et al. 2021

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Pseudo‐natural products (PNPs) combine natural product (NP) fragments in novel arrangements not accessible by current biosynthesis pathways. As such they can be regarded as non‐biogenic fusions of NP‐derived fragments. They inherit key biological characteristics of the guiding natural product, such as chemical and physiological properties, yet define small molecule chemotypes with unprecedented or unexpected bioactivity. We iterate the design principles underpinning PNP scaffolds and highlight their syntheses and biological investigations. We provide a cheminformatic analysis of PNP collections assessing their molecular properties and shape diversity. We propose and discuss how the iterative analysis of NP structure, design, synthesis, and biological evaluation of PNPs can be regarded as a human‐driven branch of the evolution of natural products, that is, a chemical evolution of natural product structure.

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Section: Discussionmentioning

confidence: 95%

Pseudo Natural Products—Chemical Evolution of Natural Product Structure

et al. 2021

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“…Compounds 3, 6 and 9 (Scheme 1) were synthesized according to the previously reported literature. [26][27][28] The spectra and data of 1 H NMR and 13 C NMR of compounds 3 and 6 are displayed in Fig. S1-S4.…”

Section: Methodsmentioning

confidence: 99%

Indolocarbazole-core linked triphenylamine as an interfacial passivation layer for perovskite solar cells

et al. 2022

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“…Betalamic acid was extracted from base-hydrolyzed red beetroot juice and processed as described previously. 21,22 Aqueous solutions were prepared using deionized water UV-Vis: λ abs max = 460 nm, ε 460 nm = 35,000 ± 2400 L mol -1 cm -1 (pH 6) (Figs. S1 and S2).…”

Section: General Informationmentioning

confidence: 99%

Design of an Antioxidant Nitrone Scaffold Based on Plant Pigments

Pinheiro¹,

Fazzi²,

Esteves³

et al. 2021

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<div> <div> <div> <p>Nitrones derived from natural antioxidants are emerging as highly specific therapeutics against various human diseases, including stroke, neurodegenerative pathologies, and cancer. However, the development of useful pseudo-natural nitrones requires the judicious choice of a secondary metabolite as the precursor. Betalains are nitrogen-containing natural pigments that exhibit marked antioxidant capacity and pharmacological properties and, hence, are ideal candidates for designing multifunctional nitrones. In this work, we describe the semisynthesis and properties of a biocompatible, antioxidant betalain-nitrone called OxiBeet. This bio-based compound is a better radical scavenger than ascorbic acid, gallic acid, and most non-phenolic antioxidants and undergoes concerted proton-coupled electron transfer. The autoxidation of OxiBeet produces a persistent nitroxide radical, which, herein, is studied via electron paramagnetic resonance spectroscopy. In addition, femtosecond transient absorption spectroscopy reveals that excited state formation is not required for the oxidation of OxiBeet. The results are compared with those obtained using betanin, a natural betalain, and pBeet, the imine analog of OxiBeet. The findings of this study will enable the development of antioxidant nitrones based on the novel N-oxide 1,7-diazaheptamethinium scaffold and betalain dyes with enhanced hydrolytic stability in aqueous alkaline media. </p> </div> </div> </div>

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Comparison of the effect of N-methyl and N-aryl groups on the hydrolytic stability and electronic properties of betalain dyes

Cited by 17 publications

References 51 publications

Pseudo Natural Products—Chemical Evolution of Natural Product Structure

Pseudo Natural Products—Chemical Evolution of Natural Product Structure

Indolocarbazole-core linked triphenylamine as an interfacial passivation layer for perovskite solar cells

Design of an Antioxidant Nitrone Scaffold Based on Plant Pigments

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