Photophysical properties of betaxanthins: miraxanthin V – insight into the excited-state deactivation mechanism from experiment and computations

Niziński, Stanisław; Wendel, Monika; Rode, Michał F.; Prukała, Dorota; Sikorski, Marek; Wybraniec, Sławomir; Burdziński, Gotard

doi:10.1039/c6ra28110a

Cited by 27 publications

(36 citation statements)

References 62 publications

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“…In betalains it has been demonstrated that this value is proportional to the viscosity of the solvent used (Table 1). 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].…”

Section: Photophysicsmentioning

confidence: 61%

“…Betanin 0.0007 0.0013 0.0047 [37] Indicaxanthin 0.0053 0.0081 0.033 [39] Miraxanthin V 0.003 0.0047 0.015 [41] Vulgaxanthin I 0.0073 0.011 0.039 [40] Miraxanthin I 0.0084 -- [34] show that an increase in the viscosity of the medium makes the convection of the acquired energy difficult, favoring the path of the fluorescence. The presence of aromatic rings linked to the electron resonance system characteristic of betalamic acid implies a marked decrease in the fluorescence intensity.…”

Section: Photophysicsmentioning

confidence: 99%

“…Only the fully planar aniline-derived betalain presents fluorescence intensity comparable with betaxanthins. The effect of the medium was also studied by taking indicaxanthin, vulgaxanthin I, and miraxanthin V as model betaxanthins, describing how higher viscosity in the solutions increased the fluorescence quantum yields and the lifetimes of the excited states [39][40][41].…”

Section: Photophysicsmentioning

confidence: 99%

“…Transient absorption spectroscopy UV-vis-near infrared has been used for the characterization of the properties of the S 1 state, since this excited state has a very short life [37,[39][40][41]. The excitation wavelength is adjusted to the electronic transition S 0 / S 1 and is close to the maximum of the stationary absorption.…”

Section: Photophysicsmentioning

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: Photophysicsmentioning

confidence: 61%

Section: Photophysicsmentioning

confidence: 99%

Section: Photophysicsmentioning

confidence: 99%

Section: Photophysicsmentioning

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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“…Embora a largura do pulso a meia altura seja de ca.6 ps, observa-se no intervalo < 1 ps a mudança do máximo desta transição, bem como da emissão estimulada (SE, banda negativa próxima a 620 nm), para comprimentos de onda mais longos, fato que pode estar relacionado a solvatação da espécie localmente excitada.As duas bandas negativas, uma com máximo em 578 nm e outra em 634 nm, referem-se à recomposição do estado fundamental (branqueamento, bleaching) e à emissão estimulada (SE), respectivamente. Este perfil observado é similar aos dados da literatura para as betalaínas Bn, BtP, vulgaxantina-I e miraxantina-V 36,37,39,40. Todos os processos observados tem tempo de vida próximo a 14 ps, valor calculado através do ajuste não linear da variação da absorção em função do tempo com função monoexponencial (anexo 7.7).…”

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BeetBlue: semissíntese e propriedades espectroscópicas de um corante polimetínico quiral bioinspirado

Freitas-Dörr¹

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AgradecimentosAo meu orientador, Prof. Dr. Erick L. Bastos, pela confiança, pelas oportunidades, pelas conversas e discussões e pela paciência durante essa jornada.À Deus e aos meus guias espirituais por estarem presentes em todos os momentos da minha vida me protegendo, por serem a luz dos meus caminhos e o refúgio nos bons e maus momentos.Ao meu marido Felipe pelo apoio incondicional, por ser a calmaria no meu temporal e a razão no meu turbilhão de emoções. Por ser meu companheiro, meu melhor amigo, por me completar e fazer a minha vida muito mais feliz. Você foi essencial para esta conquista.Aos meus pais, Marcos e Mara, pelo amor incondicional, pela torcida e por sempre me acompanharem de perto e me apoiarem em todas as minhas loucuras. Obrigada por serem minha base e por me ensinarem a valorizar o que realmente importa nessa vida. Amo vocês! Ao meu irmão Vinicius por tornar minha vida mais doce, pelas maluquices e por ser super companheiro. Tenho muito orgulho de ser sua irmã. Te amo! À Jaque, irmã que a vida me deu, por todo incentivo, apoio, carinho e, principalmente, pela paciência e compreensão nas minhas ausências. À toda minha família pelo apoio e pela torcida. À família Contente Silva. Thá e Di pelos conselhos, por acreditarem e confiarem em mim e por todos os puxões de orelha necessários. E Be e Theo por encherem a minha vida de alegria e amor. Ao time BastosLab e aos colegas do 461 pela ajuda e pelas discussões que contribuíram muito para a execução deste trabalho. ii Aos amigos que o Doutorado me deu: Amanda, Arthur, Ana Clara, Karina e Renan. Muito obrigada por toda ajuda, pelo apoio, pela companhia diária, pelas comilanças e por tornarem tudo mais leve. Aos técnicos do IQ, principalmente ao Joca e à Helena pela sempre disponibilidade em ajudar e pelas conversas. À Clélia e ao Walter por me apresentarem o mundo acadêmico, pelos conselhos, pelo carinho e pelo cuidado. Aos técnicos da Central Analítica, Janaína, Cristiane, Vânia, Giovana, Adriana e Wilton pela ajuda essencial para o desenvolvimento deste trabalho. Ao Prof. Ernani por ter me iniciado na academia e por ter deixado a porta do seu laboratório sempre aberta para mim, seja para experimentos ou para conversas. Obrigada Felipe pelas análises de espectrometria de massas. Ao Prof. Jacinto por me receber tão bem em seu laboratório e por todos os ensinamentos. Aos colegas de Uppsala pela acolhida e ao Mohamed e Daniel pela ajuda nos experimentos. Aos Profs. Willi, Maurício, Frank, Omar, Cassius, Thiago Correra e Thiago Paixão e seus alunos, pelas explicações, ensinamentos e pelo uso dos equipamentos em seus laboratórios. À FAPESP pela bolsa concedida (2014/10563-5) e CNPq e Capes pelo financiamento dos projetos iii "Experimentei algo que depois, ao longo de minha vida, se repetiu frequentemente: a alegria do novo" Elena Ferrante em "A amiga genial" iv v Resumo FREITAS-DÖRR, B. C. BeetBlue: semissíntese e propriedades espectroscópicas de um corante polimetínico quiral bioinspirado 2018. 158f Tese (Doutorado) -Instituto de Química, Universidade d...

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The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

Han

2017

WIREs Comput Mol Sci

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Recent research has indicated that fluorescent probes have tremendous potential for the selective detection of chemical and biological species. Over the past decade, researchers have proposed a series of fluorescence‐based sensing mechanisms of such probes by the calculation of their electronic excited states. Investigations of sensing mechanisms have been based on deep insights into the interactions between probe molecules and their target species, as well as their fluorescence properties. Advances in calculation methods, modeling software, and computational power have enabled researchers to use excited‐state theoretical calculations to reproduce experimental fluorescence phenomena and then provide molecular‐level explanations thereof. In this advanced review, we describe the evolution of theoretical studies on excited‐state sensing mechanisms for fluorescent probes that respond to target species. Focusing on calculation methods that facilitate investigation of the photophysical properties and excited‐state dynamics of probes, we emphasize sensing mechanisms mainly reported by our group. Most of these studies have been supported by theoretical predictions based on time‐dependent density functional theory. For this most popular excited‐state calculation method, vertical excitation energy, excited‐state geometrical optimization and a scan of the excited‐state potential energy surface should be noted in the calculation of electronic and molecular differences between the excited‐state probe and its reaction product with the target analyte. These state‐of‐the‐art calculations are of great importance for unraveling details of fluorescence‐based sensing mechanisms, including photochemical reactions (such as twist intramolecular charge transfer and excited‐state proton transfer) and excited‐state electronic processes (such as intramolecular charge transfer and photoinduced electron transfer). These studies have generated new and inspirational mechanistic proposals and have provided a systematic approach for the development of efficient fluorescent sensors. WIREs Comput Mol Sci 2018, 8:e1351. doi: 10.1002/wcms.1351 This article is categorized under: Structure and Mechanism > Computational Biochemistry and Biophysics Theoretical and Physical Chemistry > Spectroscopy

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Photophysical properties of betaxanthins: miraxanthin V – insight into the excited-state deactivation mechanism from experiment and computations

Abstract: Fast radiationless S1 → S0 transition in photo-excited betaxanthins is due to conical intersection seam between S1 and S0 surfaces.

Cited by 27 publications

References 62 publications

Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

BeetBlue: semissíntese e propriedades espectroscópicas de um corante polimetínico quiral bioinspirado

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

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Photophysical properties of betaxanthins: miraxanthin V – insight into the excited-state deactivation mechanism from experiment and computations

Abstract: Fast radiationless S1 → S0 transition in photo-excited betaxanthins is due to conical intersection seam between S1 and S0 surfaces.

Cited by 27 publications

References 62 publications

Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

BeetBlue: semissí­ntese e propriedades espectroscópicas de um corante polimetí­nico quiral bioinspirado

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

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BeetBlue: semissíntese e propriedades espectroscópicas de um corante polimetínico quiral bioinspirado