Brassinosteroid-BODIPY conjugates: Design, synthesis, and properties

Malachowska-Ugarte, Magdalena; Sperduto, Claudio; Ermolovich, Yurii V.; Sauchuk, A. L.; Jurášek, Michal; Litvinovskaya, R. P.; Straltsova, Darya; Смолич, Игорь Иванович; Жабинский, В. Н.; Drašar, Pavel; Demidchik, Vadim; Хрипач, В. А.

doi:10.1016/j.steroids.2015.07.002

Cited by 16 publications

(4 citation statements)

References 32 publications

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“…Nevertheless, the real overall chemical features of the derived molecules influenced by both the used linker and the fluorescent label have to be borne in mind. The position of the labelling site [ 152 ], and the character and the length of the linker [ 153 , 154 , 155 ] play a crucial role in the bioactivity of the new hormone analogues. Also, the choice of the fluorescent probe has to be considered.…”

Section: Direct Methods For Tracking Auxin Distributionmentioning

confidence: 99%

What Has Been Seen Cannot Be Unseen—Detecting Auxin In Vivo

Pařízková

Pernisová

Novák

2017

IJMS

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Auxins mediate various processes that are involved in plant growth and development in response to specific environmental conditions. Its proper spatio-temporal distribution that is driven by polar auxin transport machinery plays a crucial role in the wide range of auxins physiological effects. Numbers of approaches have been developed to either directly or indirectly monitor auxin distribution in vivo in order to elucidate the basis of its precise regulation. Herein, we provide an updated list of valuable techniques used for monitoring auxins in plants, with their utilities and limitations. Because the spatial and temporal resolutions of the presented approaches are different, their combination may provide a comprehensive outcome of auxin distribution in diverse developmental processes.

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Section: Direct Methods For Tracking Auxin Distributionmentioning

confidence: 99%

What Has Been Seen Cannot Be Unseen—Detecting Auxin In Vivo

Pařízková

Pernisová

Novák

2017

IJMS

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“…Several BR analogues with nitrogen-containing heterocycles (e.g., isoxazoline, oxazole, thiazole and pyridine) were synthesized by Wendeborn's group [25]. Other analogues with nitrogen groups in the side chain were prepared mostly for other chemical modifications, e.g., azide derivatives for photoaffinity labeling [30] or activated esters for conjugation reactions [31,32].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain

Diachkov

Ferrer

Oklešťková

et al. 2020

IJMS

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Brassinosteroids are a class of plant hormones that regulate a broad range of physiological processes such as plant growth, development and immunity, including the suppression of biotic and abiotic stresses. In this paper, we report the synthesis of new brassinosteroid analogues with a nitrogen-containing side chain and their biological activity on Arabidopis thaliana. Based on molecular docking experiments, two groups of brassinosteroid analogues were prepared with short and long side chains in order to study the impact of side chain length on plants. The derivatives with a short side chain were prepared with amide, amine and ammonium functional groups. The derivatives with a long side chain were synthesized using amide and ammonium functional groups. A total of 25 new brassinosteroid analogues were prepared. All 25 compounds were tested in an Arabidopsis root sensitivity bioassay and cytotoxicity screening. The synthesized substances showed no significant inhibitory activity compared to natural 24-epibrassinolide. In contrast, in low concentration, several compounds (8a, 8b, 8e, 16e, 22a and 22e) showed interesting growth-promoting activity. The cytotoxicity assay showed no toxicity of the prepared compounds on cancer and normal cell lines.

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“…It is noteworthy that conjugates based on BODIPY and other classes of small biomolecules are extensively studied. For example, there are bioconjugates of BODIPY derivatives and nucleotides [13,14], lipids [15][16][17], hormones [18,19], vitamins [20], etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Study of Spectral Properties of Amino Acids – Bodipy Conjugates

Ksenofontova

Ksenofontov

Khodov

et al. 2020

IVKKT

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The present work describes direct one-pot synthesis of the two novel amino acids – boron-dipyrromethene (BODIPY) conjugates with histidine and tyrosine residues bound to fluorophore via amino group. The synthesized compounds were fully characterized by means of 1H and 11B nuclear magnetic resonance spectroscopy, infrared spectroscopy, time-of-flight mass spectrometry with matrix-activated laser desorption / ionization. All the data are in accordance with the proposed structures. The amino acids – BODIPY conjugates under study were investigated by means of absorbance and fluorescence spectroscopy. Absorption and emission spectra of the compounds in dimethyl sulfoxide (DMSO) – buffer solution (BS) mixture (1:1) were obtained. Moreover, a number of photophysical characteristics of the conjugates, namely: relative fluorescence quantum yield, molar extinction coefficient, relative fluorescence lifetime, radiative and non-radiative rate constants were calulated. 3D fluorescence spectra of the compounds in DMSO – BS mixture (1:1) were obtained. Absorption and emission titration of the compounds was carried out. The results of the titration allowed us to confirm additionally a stoichiometric composition of the conjugates. Quantum chemical analysis of structural and spectral properties of the compounds in a ground state was carried out. The results of quantum chemical calculations gave an insight to a nature of the BODIPY – amino acid interactions in the conjugates. Besides, the synthesized amino acids – BODIPY conjugates are found to be highly soluble in polar solvents. Thus, a range of unique properties of the objects of the present research enables us to use them for visualization of bioactive macromolecules as well as biochemical processes in living cells.

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Brassinosteroid-BODIPY conjugates: Design, synthesis, and properties

Cited by 16 publications

References 32 publications

What Has Been Seen Cannot Be Unseen—Detecting Auxin In Vivo

What Has Been Seen Cannot Be Unseen—Detecting Auxin In Vivo

Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain

Synthesis and Study of Spectral Properties of Amino Acids – Bodipy Conjugates

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