Syntheses of reactive fluorescent stains derived from 5(2)‐aryl‐2(5)‐(4‐pyridyl)oxazoles and bifunctionally reactive linkers

Litak, Peter T.; Kauffman, Joel M.

doi:10.1002/jhet.5570310236

Cited by 6 publications

(4 citation statements)

References 38 publications

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“…Instead, the use of 7, which was prepared following a literature procedure, afforded the expected product (Scheme 3). [31] Compound 10 was obtained by reaction of 1 with 9, which was prepared following a literature procedure (Scheme 4). [32] Functionalisation of l-cysteine methyl ester hydrochloride with the cross-linking reagents was carried out by mixing the compounds in a solution of acetonitrile or tetrahydrofuran and water (Scheme 5).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Photochemistry of a New Class of Photocleavable Protein Cross‐linking Reagents

Milanesi

Reid

Beddard

et al. 2004

Chemistry A European J

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A new series of photocleavable protein cross-linking reagents based on bis(maleimide) derivatives of diaryl disulfides have been synthesised. They have been functionalised with cysteine and transient absorption spectra for the photolysis reaction have been recorded by using the pump-probe technique with a time resolution of 100 femtoseconds. Photolysis of the disulfide bond yields the corresponding thiyl radicals in less than a picosecond. There is a significant amount of geminate recombination, but some of the radicals escape the solvent cage and the quantum yield for photocleavage is 30 % in water.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Photochemistry of a New Class of Photocleavable Protein Cross‐linking Reagents

Milanesi

Reid

Beddard

et al. 2004

Chemistry A European J

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“…As expected, based on the well-known high efficiency of this reaction, Luc-labeled peptides (Luc-GKY20, Luc-ApoB L , Luc-p53pAnt and Luc-RGD) and aLuc-labeled peptides (aLuc-GKY20, aLuc-ApoB L , aLuc-p53pAnt and aLuc-RGD) were obtained with yields close to 100% after very short incubation times (30-60 min). (C)GKY20 was also treated with 6-methoxy-2-cyanobenzothiazole to obtain an mLuclabeled peptide (mLuc-GKY20) and with PyMPO maleimide, the thiol-reactive version of PyMPO, a widely used photostable solvatochromic fluorophore [33][34][35], to obtain the peptide PyMPO-(C)GKY20. After purification (Section 4 and Supplementary Materials), the mass of all labeled peptides was confirmed by MALDI-MS (Table S1).…”

Section: Preparation and Labeling Of The Peptidesmentioning

confidence: 99%

“…Although Luc is a fairly stable molecule, in order to evaluate the photostability of Luc-labeled peptides, we monitored the fluorescence of Luc-GKY20, aLuc-GKY20 and mLuc-GKY20 for 60 min, constantly exciting the three labeled peptides at their respective maximum absorption. As comparative control, we used the very photostable fluorophore PyMPO [33] by treating PyMPO-(C)GKY20 in the same conditions. Luc-GKY20 lost only 30% of its initial fluorescence (Figure S3), thus proving to be even more photostable than PyMPO-(C)GKY20, which lost 43% of its initial fluorescence.…”

Section: Stability and Biological Activity Of Luc-labeled Peptidesmentioning

confidence: 99%

Environment-Sensitive Fluorescent Labelling of Peptides by Luciferin Analogues

Siepi

Oliva

Masino

et al. 2021

IJMS

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Environment-sensitive fluorophores are very valuable tools in the study of molecular and cellular processes. When used to label proteins and peptides, they allow for the monitoring of even small variations in the local microenvironment, thus acting as reporters of conformational variations and binding events. Luciferin and aminoluciferin, well known substrates of firefly luciferase, are environment-sensitive fluorophores with unusual and still-unexploited properties. Both fluorophores show strong solvatochromism. Moreover, luciferin fluorescence is influenced by pH and water abundance. These features allow to detect local variations of pH, solvent polarity and local water concentration, even when they occur simultaneously, by analyzing excitation and emission spectra. Here, we describe the characterization of (amino)luciferin-labeled derivatives of four bioactive peptides: the antimicrobial peptides GKY20 and ApoBL, the antitumor peptide p53pAnt and the integrin-binding peptide RGD. The two probes allowed for the study of the interaction of the peptides with model membranes, SDS micelles, lipopolysaccharide micelles and Escherichia coli cells. Kd values and binding stoichiometries for lipopolysaccharide were also determined. Aminoluciferin also proved to be very well-suited to confocal laser scanning microscopy. Overall, the characterization of the labeled peptides demonstrates that luciferin and aminoluciferin are previously neglected environment-sensitive labels with widespread potential applications in the study of proteins and peptides.

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“…They developed a one-step synthesis of a labeled compound containing the isothiocyanate functionality ([ 18 F]fluoromethyl)phenyl isothiocyanate) and investigated the reaction of 18 F-labeled oligonucleotide at 5′-position with a hexylamine linker [57]. The mentioned precursors (1–8) in Figure 8 have been prepared by following the procedure described in the literature [55,57,58,59]. Isothiocyanates containing leaving groups, such as bromide, iodide, and tosyl, were used as substrates in nucleophilic substitution reactions with [ 18 F]fluoride to produce compound 8 (Figure 8) [57].…”

Section: Radiolabeling Of Ligands For Pet Imagingmentioning

confidence: 99%

Radiolabeling of Nucleic Acid Aptamers for Highly Sensitive Disease-Specific Molecular Imaging

2018

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Aptamers are short single-stranded DNA or RNA oligonucleotide ligand molecules with a unique three-dimensional shape, capable of binding to a defined molecular target with high affinity and specificity. Since their discovery, aptamers have been developed for various applications, including molecular imaging, particularly nuclear imaging that holds the highest potential for the clinical translation of aptamer-based molecular imaging probes. Their easy laboratory production without any batch-to-batch variations, their high stability, their small size with no immunogenicity and toxicity, and their flexibility to incorporate various functionalities without compromising the target binding affinity and specificity make aptamers an attractive class of targeted-imaging agents. Aptamer technology has been utilized in nuclear medicine imaging techniques, such as single photon emission computed tomography (SPECT) and positron emission tomography (PET), as highly sensitive and accurate biomedical imaging modalities towards clinical diagnostic applications. However, for aptamer-targeted PET and SPECT imaging, conjugation of appropriate radionuclides to aptamers is crucial. This review summarizes various strategies to link the radionuclides to chemically modified aptamers to accomplish aptamer-targeted PET and SPECT imaging.

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Syntheses of reactive fluorescent stains derived from 5(2)‐aryl‐2(5)‐(4‐pyridyl)oxazoles and bifunctionally reactive linkers

Cited by 6 publications

References 38 publications

Synthesis and Photochemistry of a New Class of Photocleavable Protein Cross‐linking Reagents

Synthesis and Photochemistry of a New Class of Photocleavable Protein Cross‐linking Reagents

Environment-Sensitive Fluorescent Labelling of Peptides by Luciferin Analogues

Radiolabeling of Nucleic Acid Aptamers for Highly Sensitive Disease-Specific Molecular Imaging

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