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Electrochemical labelling of hydroxyindoles with chemoselectivity for site-specific protein bioconjugation.
Nat Chem
March 2024
Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, MA, USA.
Electrochemistry has recently emerged as a powerful approach in small-molecule synthesis owing to its numerous attractive features, including precise control over the fundamental reaction parameters, mild reaction conditions and innate scalability. Even though these advantages also make it an attractive strategy for chemoselective modification of complex biomolecules such as proteins, such applications remain poorly developed. Here we report an electrochemically promoted coupling reaction between 5-hydroxytryptophan (5HTP) and simple aromatic amines-electrochemical labelling of hydroxyindoles with chemoselectivity (eCLIC)-that enables site-specific labelling of full-length proteins under mild conditions.
View Article and Find Full Text PDFRadiopharmaceuticals used for diagnosis and therapy of NETs.
Hell J Nucl Med
November 2023
Department of Nuclear Medicine - PET/CT, Greece.
The first description of the in vivo visualization of somatostatin receptor-positive tumors in patients was based on the use of a radioiodine (I) labelled somatostatin analogue (Krenning et al. 1989). In the years that followed an Indium-111 (In) labelled somatostatin analogue, chelated with diethylenetriaminepentaacetic acid (DTPA), was successfully developed.
View Article and Find Full Text PDFAssisted Reductive Amination for Quantitation of Tryptophan, 5-Hydroxytryptophan, and Serotonin by Ultraperformance Liquid Chromatography Coupled with Tandem Mass Spectrometry.
Molecules
June 2023
Department of Biotechnology, School of Environment and Life Sciences, Fooyin University, Kaohsiung 83102, Taiwan.
Herein, we used isotopic formaldehyde and sodium cyanoborohydride via reductive amination to label two methyl groups on primary amine to arrange the standards (-formaldehyde-modified) and internal standards (ISs, -formaldehyde-modified) of tryptophan and its metabolites, such as serotonin (5-hydroxytryptamine) and 5-hydroxytryptophan. These derivatized reactions with a high yield are very satisfactory for manufacturing standards and ISs. This strategy will generate one or two methyl groups on amine to create different mass unit shifts with 14 vs.
View Article and Find Full Text PDFPhotoredox-Catalyzed Labeling of Hydroxyindoles with Chemoselectivity (PhotoCLIC) for Site-Specific Protein Bioconjugation.
Angew Chem Int Ed Engl
July 2023
Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, MA, 02467, USA.
We have developed a novel visible-light-catalyzed bioconjugation reaction, PhotoCLIC, that enables chemoselective attachment of diverse aromatic amine reagents onto a site-specifically installed 5-hydroxytryptophan residue (5HTP) on full-length proteins of varied complexity. The reaction uses catalytic amounts of methylene blue and blue/red light-emitting diodes (455/650 nm) for rapid site-specific protein bioconjugation. Characterization of the PhotoCLIC product reveals a unique structure formed likely through a singlet oxygen-dependent modification of 5HTP.
View Article and Find Full Text PDFProtocol for modulation of the serotonergic DR-PBC neural circuit to prevent SUDEP in the acoustic and PTZ-induced DBA/1 mouse models of SUDEP.
STAR Protoc
March 2023
Department of Anesthesiology, the Fourth Clinical School of Medicine, Zhejiang Chinese Medical University, Hangzhou 310006, China; Department of Anesthesiology, Affiliated Hangzhou First People's Hospital, Zhejiang University School of Medicine, Hangzhou 310006, China; Westlake Laboratory of Life Sciences and Biomedicine, Hangzhou 310006, China. Electronic address:
The dorsal raphe nucleus (DR) and the pre-Bötzinger complex (PBC) may play an important role in regulating seizure-induced respiratory arrest (S-IRA), the main contributor to sudden unexpected death in epilepsy. Here, we describe pharmacological, optogenetic, and retrograde labeling approaches to specifically modulate the DR to PBC serotonergic pathway. We detail steps for implanting optical fibers and viral infusion into DR and PBC regions and optogenetic techniques for exploring the role of 5-hydroxytryptophan (5-HT) neural circuit of DR-PBC in S-IRA.
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