Aza-BODIPY dyes with enhanced hydrophilicity

Kamkaew, Anyanee; Burgess, Kevin

doi:10.1039/c5cc03649f

Cited by 84 publications

(54 citation statements)

References 15 publications

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“…Moreover, it can be predicted that after the rational design of the molecular sensor, which means the functionalization of the corresponding fluorophore with an adequate receptor to the target entity or property, BODIPY could be the right choice as the label to visualize the desired molecule or environmental property. Besides, the versatility of this dye makes it feasible to add a further degree of functionalization to enhance its solubility (i.e., in water) or to favor its adsorption or linkage to a specific place of a biomolecule . The use of these kinds of luminescent molecular sensors is very attractive for biochemistry, as will be emphasized in the next section.…”

Section: Discussionmentioning

confidence: 99%

BODIPY Dye, the Most Versatile Fluorophore Ever?

Bañuelos

2016

The Chemical Record

267

175

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BODIPY laser dyes constitute a fascinating topic of research in modern photochemistry due to the large variety of options its chromophore offers, which is ready available for a multitude of synthetic routes. Indeed, in the literature one can find a huge battery of compounds based on the indacene core. The possibility of modulating the spectroscopic properties or inducing new photophysical processes by the substitution pattern of the BODIPY dyes has boosted the number of scientific and technological applications for these fluorophores. Along the following lines, I will overview the main results achieved in our laboratory with BODIPYs oriented to optoelectronic as well to biophotonic applications, stressing the more relevant photophysical issues to be considered in the design of a tailor-made BODIPY for a certain application and pointing out some of the remaining challenges.

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Section: Discussionmentioning

confidence: 99%

BODIPY Dye, the Most Versatile Fluorophore Ever?

Bañuelos

2016

The Chemical Record

267

175

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“…This result supported and confirmed that nucleophilic addition of CN – was taken place at the isothiocyanate moieties of the N1 sensor. Additionally, 1 H‐NMR spectra of the N1 at the position of pyrrole (chemical shift 7.06 ppm), with and without CN − did not exhibit a significant shift, which indicated that the binding of CN − did not occur at the pyrrole (Figure ). This evident strongly indicated that the CN − did not react to pyrrole ring of aza BODIPY N1 , otherwise the significant change of 1 H‐NMR spectra must be observed due to the change of conjugated system of the pyrrole ring after nucleophilic addition of CN − .…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of compounds 1–4 : Using the similar procedure from previous work, the title compounds were prepared. The synthetic steps were demonstrated in Scheme …”

Section: Methodsmentioning

confidence: 99%

“…The synthetic steps were demonstrated in Scheme 1. [19] Synthesis of N1: In a round bottom flask, compound 1 (0.10 g, 0.26 mmol) was dissolved in acetonitrile (15 mL), followed by the addition of carbon disulfide (0.06 mL, 1.01 mmol) and triethylamine (0.07 mL, 0.55 mmol). The mixture was then stirred at 30°C for 5 h. Using a rotary evaporator, the solvent was removed and 20 mL of dichloromethane was then added to the residue.…”

Section: Synthesis Of Compounds 1-4mentioning

confidence: 99%

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A Near‐Infrared Fluorescence Chemosensor Based on Isothiocyanate‐Aza‐BODIPY for Cyanide Detection at the Parts per Billion Level: Applications in Buffer Media and Living Cell Imaging

et al. 2019

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A near‐infrared chemodosimeter based on an aza‐BODIPY dye was designed and synthesized. The sensor contains isothiocyanate groups for cyanide ion sensing. The sensing function was illustrated via the fluorescence changes in near‐infrared frequencies as well as chromogenic changes which could be easily visualized with a detection limit of 19 ppb. The sensor provides high selectivity to CN− and discriminates other anions such as CH3COO−, HPO4−, HSO4−, ClO3−, CO32−, SO42−, NO3−, Cl−, F−, Br−, I−, and phenylalanine (Phe) in 50 % PBS buffer/acetonitrile at physiological pH. The potential of the sensor for CN− detection in both aqueous buffer solutions and living cells imaging was demonstrated.

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“…More recently, interest has been increasing in the 4-bora-3a,4a,8-triazaindacene dyes (commonly referred to as aza-BODIPY dyes) owing to their efficient fluorescence in the far-red and near-IR regions of the spectrum. Aza-BODIPYs are basically BODIPY derivatives with the meso-carbon atom replaced by an imine type nitrogen atom ( Figure 6) (Kamkaew and Burgess, 2015;Ulrich et al, 2008;Wu and O'Shea, 2013).…”

Section: A N U S C R I P Tmentioning

confidence: 99%

Shaping Small Bioactive Molecules to Untangle Their Biological Function: A Focus on Fluorescent Plant Hormones

Lace

Prandi

2016

Molecular Plant

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Modern biology overlaps with chemistry in explaining the structure and function of all cellular processes at the molecular level. Plant hormone research is perfectly located at the interface between these two disciplines, taking advantage of synthetic and computational chemistry as a tool to decipher the complex biological mechanisms regulating the action of plant hormones. These small signaling molecules regulate a wide range of developmental processes, adapting plant growth to ever changing environmental conditions. The synthesis of small bioactive molecules mimicking the activity of endogenous hormones allows us to unveil many molecular features of their functioning, giving rise to a new field, plant chemical biology. In this framework, fluorescence labeling of plant hormones is emerging as a successful strategy to track the fate of these challenging molecules inside living organisms. Thanks to the increasing availability of new fluorescent probes as well as advanced and innovative imaging technologies, we are now in a position to investigate many of the dynamic mechanisms through which plant hormones exert their action. Such a deep and detailed comprehension is mandatory for the development of new green technologies for practical applications. In this review, we summarize the results obtained so far concerning the fluorescent labeling of plant hormones, highlighting the basic steps leading to the design and synthesis of these compelling molecular tools and their applications.

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Aza-BODIPY dyes with enhanced hydrophilicity

Cited by 84 publications

References 15 publications

BODIPY Dye, the Most Versatile Fluorophore Ever?

BODIPY Dye, the Most Versatile Fluorophore Ever?

A Near‐Infrared Fluorescence Chemosensor Based on Isothiocyanate‐Aza‐BODIPY for Cyanide Detection at the Parts per Billion Level: Applications in Buffer Media and Living Cell Imaging

Shaping Small Bioactive Molecules to Untangle Their Biological Function: A Focus on Fluorescent Plant Hormones

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