Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

Cabanes, Juana; Escribano, Josefa; García-Carmona, Francisco; Jiménez-Atiénzar, Mercedes

doi:10.1016/j.dyepig.2016.06.037

Cited by 16 publications

(23 citation statements)

References 40 publications

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“…Thus, the analysis in water and methanol gives lower values than in ethylene glycol [37,[39][40][41]. This response has also been shown for betaxanthin molecules present in gelificating media, where fluorescence intensity increases with the time course of the process [42]. These results…”

Section: Photophysicssupporting

confidence: 63%

“…Increased fluorescence due to betaxanthins can be linked to enhanced activities of enzymes of biotechnological interest, allowing high-throughput screening techniques in organisms such as Saccharomyces cerevisiae (D) [81]. Macromolecules condensed with one molecule of betalamic acid become fluorescent in a tagging procedure suitable for proteins in solution and in electrophoresis gels (E) [42]. Increased production of betalains in plant cell bioreactors can be specifically and easily followed through fluorescence (F) [77].…”

Section: Visualization Of Natural Betalains In Vivo and In Vitromentioning

confidence: 99%

“…One notable advance in this process has been to use free amine groups present in proteins to add a molecule of betalamic acid. This results in the synthesis of the so-called yellow protein-betaxanthins [42]. Spectral properties of the molecules are analogous to betaxanthins of low molecular weight and are fluorescent.…”

Section: Protein Labelingmentioning

confidence: 99%

“…Spectral shapes are equivalent and present maximum excitation wavelength of 476 nm and a maximum emission centered at 551 nm. The proteins studied were albumin, ovalbumin, and trypsin [42], but the phenomenon might well be generalizable to any protein, as demonstrated by the use of standard molecular weight markers, where all proteins turned into protein-betaxanthins. This reaction results in a labeling procedure where proteins incorporating one molecule of betalamic acid turned fluorescent.…”

Section: Protein Labelingmentioning

confidence: 99%

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Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

Guerrero-Rubio

Escribano

García-Carmona

2020

Trends in Plant Science

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The discovery of visible fluorescence in the plant pigments betalains revealed the existence of fluorescent patterns in flowers of plants of the order Caryophyllales, where betalains substitute anthocyanins. The serendipitous initial discovery led to a systemized characterization of the role of different substructures on the photophysical phenomenon. Strong fluorescence is general to all members of the family of betaxanthins linked to the structural property that the betalamic acid moiety is connected to an amine group. This property has led to bioinspired tailor-made probes and to the development of novel biotechnological applications in screening techniques or microscopy labeling. Here, we comprehensively review the photophysics, photochemistry, and photobiology of betalain fluorescence and describe all current applications. BetalainsBetalains are nitrogenous plant pigments that are characteristic for plants belonging to the order Caryophyllales. These pigments are divided into the yellow betaxanthins and the violet betacyanins [1]. The presence of both types of pigments is required for the orange and red colors that coexist in nature with the pure yellow and violet colors. Betalains substitute anthocyanins and play their roles in the colored tissues of most plant families of the Caryophyllales. Both families of pigments are watersoluble and mutually exclusive [2,3]. Numerous studies were performed on the color properties of betalains since they were described as a novel family of pigments, different to 'nitrogenous anthocyanins' [4,5]. However, it was not until 2005 that their natural fluorescence was discovered [6]. In addition, it was demonstrated that under physiological conditions, light emission was exhibited in the plant tissues that contain them, including flowers [7,8].Among the Caryophyllales plants, red beet roots (Beta vulgaris) and the fruits of cacti belonging to the genus Opuntia are the best known sources of betalains, with betanin and indicaxanthin being, respectively, their main pigments [9,10]. Current research has described the betalain content of novel sources, such as the tubers from Ullucus tuberosus [11] or the betalain-containing berries of Rivina humilis [12]. Also, the multiple shades of quinoa grains (Chenopodium quinoa) have recently been reported to be based on betacyanins and betaxanthins [13]. In addition, betalains have in recent years been shown to have promising bioactive properties. Early investigations revealed a strong free radical scavenging capacity of betalains purified from beet root [14]. Subsequent research revealed the existence of an intrinsic activity, present in all betalains, that is modulated by structural factors [15,16]. Furthermore, studies with different human cancer cell lines have demonstrated the potential of betalains in the chemoprevention of cancer [17,18]. In vivo experiments have shown that very low concentrations of dietary pigments inhibit the formation of tumors in mice [19,20] and extend the lifespan of the model animal Caenorhabditis elegans [21...

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Section: Photophysicssupporting

confidence: 63%

Section: Visualization Of Natural Betalains In Vivo and In Vitromentioning

confidence: 99%

Section: Protein Labelingmentioning

confidence: 99%

Section: Protein Labelingmentioning

confidence: 99%

See 2 more Smart Citations

Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

Guerrero-Rubio

Escribano

García-Carmona

2020

Trends in Plant Science

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“…120,123 Em 2012 foi preparada a betalaína fluorescente cBeet120, derivada da 7-amino-4-metilcumarina (c120) e com rendimento de fluorescência próximo ao da indicaxantina (0,04%) (Figura 7). 54,124 A conversão de c120 em cBeet120 provocou o deslocamento batocrômico das bandas de absorção e emissão de fluorescência (λ max 520 nm, λ em 570…”

Section: 122unclassified

Mecanismos moleculares da interação entre betalaínas cumarínicas fluorescentes e células de glioma humano

Pettigiani¹

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Versão corrigida da Tese defendidaData do depósito na SPG: 22/02/2017Ficha Catalográfica Elaborada pela Divisão de Biblioteca e Documentação do Conjunto das Químicas da USP. Lopes, Nathana Barbosa L864mMecanismos moleculares da interação entre betalaínas cumarínicas fluorescentes e células de glioma humano / Nathana Barbosa Lopes. --São Paulo, 2 017 . Charles Bukowski (1920Bukowski ( -1994 em "As pessoas parecem flores finalmente"x xi

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Betalain

Kumar

2022

Nutraceuticals and Health Care

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Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

Cited by 16 publications

References 40 publications

Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

Mecanismos moleculares da interação entre betalaínas cumarínicas fluorescentes e células de glioma humano

Betalain

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