Prevalent Bioimaging Scaffolds: Synthesis, Photophysical Properties and Applications

Colas, Kilian; Doloczki, Susanne; Urrutia, Mauricio Posada; Dyrager, Christine

doi:10.1002/ejoc.202001658

Cited by 28 publications

(29 citation statements)

References 127 publications

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“…3 pK values were obtained photometrically (for details see Figure S10). 4 As a widely used reference, fluorophore with a well-known pH dependence of fluorescence and a starting material.…”

Section: Photophysical Properties Of 8-fumb and 6-fumbmentioning

confidence: 99%

“…Coumarins are a large family of natural and synthetic compounds with a variety of biological activities and bioanalytical applications [1][2][3][4][5]. Thus, novel approaches in coumarin scaffold functionalization are in steady demand, and the known strategies are permanently needed in more efficient and preferably more convenient and greener synthetic solutions, therefore assigning a large and still growing number of research publications in this field [6,7].…”

Section: Introductionmentioning

confidence: 99%

“…The Duff reaction is an example of regioselective derivatization routinely used for ortho-formylation of aromatic phenols [8]. In turn, umbelliferones (7-hydroxycoumarins) are among the most abundant, widely available, and applicable coumarins [1][2][3][4][5]. The Duff ortho-formylation of umbelliferones was numerously reported earlier [9][10][11][12][13][14][15][16][17][18][19], while the vast majority of reports were notably focused on the preparation of 8-formylumbelliferones, which are well-described and routinely used dyes.…”

Section: Introductionmentioning

confidence: 99%

“…Considering the rising trend in the studies of 6-formylumbelliferone (6-FUmb) biological activities [21][22][23][24], its prospective beneficial spectral properties based on the relevance of 6-formyl vs. 8-formyl positioning [4,25], and the routine usage of 8-formylumbelliferone (8-FUmb) as a reference compound for the above-mentioned studies, we found it important to revise the Duff ortho-formylation of unsubstituted umbelliferone (Umb) and re-evaluate the 8-FUmb and 6-FUmb yields in this convenient and cost-effective reaction.…”

Section: Introductionmentioning

confidence: 99%

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Twice as Nice: The Duff Formylation of Umbelliferone Revised

et al. 2021

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More efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff ortho-formylation of unsubstituted umbelliferone was revised in this study. The reaction conditions were optimized based upon data from the literature analysis and resulted in unexpectedly rapid ortho-formylation of umbelliferone, yielding a mixture of ortho-formyl position isomers. Thorough studies on the separation of ortho-formylated umbelliferones using chromatographic and recrystallization methods as well as the evaluation of their solubility in common organic solvents led to complete resolution of 8-formyl- and 6-formylumbelliferones. The precise protocol for simultaneous preparation, extraction, and purification of 8-formyl- and 6-formylumbelliferones is provided, and the prospective studies of biological and pharmacological activities of these compounds are synopsized.

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“…3 pK values were obtained photometrically (for details see Figure S10). 4 As a widely used reference, fluorophore with a well-known pH dependence of fluorescence and a starting material.…”

Section: Photophysical Properties Of 8-fumb and 6-fumbmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Twice as Nice: The Duff Formylation of Umbelliferone Revised

et al. 2021

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“…Among all the existing types of optical responses, fluorescence and luminescence are the most commonly exploited ones, both in vitro and in vivo [1]. Conventional fluorescent imaging probes usually consist of organic dyes, engineered fluorescent proteins, semiconductor quantum dots, or carbon dots [2][3][4][5][6][7]. Despite their good performance in terms of sensitivity, accuracy, and response time, the previously mentioned classes of tracers show severe limitations, concerning, for instance, their reduced photostability, difficult preparation, high cost, or potential toxicity [8].…”

Section: Introductionmentioning

confidence: 99%

Photoluminescent nanocluster-based probes for bioimaging applications

Bergamaschi

Metrangolo

Dichiarante

2022

Photochem Photobiol Sci

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In the continuous search for versatile and better performing probes for optical bioimaging and biosensing applications, many research efforts have focused on the design and optimization of photoluminescent metal nanoclusters. They consist of a metal core composed by a small number of atoms (diameter < 2-3 nm), usually coated by a shell of stabilizing ligands of different nature, and are characterized by molecule-like quantization of electronic states, resulting in discrete and tunable optical transitions in the UV-Vis and NIR spectral regions. Recent advances in their size-selective synthesis and tailored surface functionalization have allowed the effective combination of nanoclusters and biologically relevant molecules into hybrid platforms, that hold a large potential for bioimaging purposes, as well as for the detection and tracking of specific markers of biological processes or diseases. Here, we will present an overview of the latest combined imaging or sensing nanocluster-based systems reported in the literature, classified according to the different families of coating ligands (namely, peptides, proteins, nucleic acids, and biocompatible polymers), highlighting for each of them the possible applications in the biomedical field.

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Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

Crawford

Dimitriadi

Bassin

et al. 2022

Chemistry A European J

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The last decade has seen an increasingly large number of studies reporting on the development of novel small organic conjugated systems for mitochondrial imaging exploiting optical signal transduction pathways. Mitochondria are known to play a critical role in a number of key biological processes, including cellular metabolism. Importantly, irregularities on their working function are nowadays understood to be intimately linked to a range of clinical conditions, highlighting the importance of targeting mitochondria for therapeutic benefits. In this work we carry out an in‐depth evaluation on the progress to date in the field to pave the way for the realization of superior alternatives to those currently existing. The manuscript is structured by commonly used chemical scaffolds and comprehensively covers key aspects factored in design strategies such as synthetic approaches as well as photophysical and biological characterization, to foster collaborative work among organic and physical chemists as well as cell biologists.

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Prevalent Bioimaging Scaffolds: Synthesis, Photophysical Properties and Applications

Cited by 28 publications

References 127 publications

Twice as Nice: The Duff Formylation of Umbelliferone Revised

Twice as Nice: The Duff Formylation of Umbelliferone Revised

Photoluminescent nanocluster-based probes for bioimaging applications

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

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