Synthesis and characterization of hydrazine-appended BODIPY dyes and the related aminomethyl complexes

Hanson, Tanner B.; Chudomelka, Drayko D.; Heiden, Zachariah M.

doi:10.1039/c9nj02859e

New J. Chem.

2019

DOI: 10.1039/c9nj02859e

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Synthesis and characterization of hydrazine-appended BODIPY dyes and the related aminomethyl complexes

Tanner B. Hanson

Drayko D. Chudomelka

Zachariah M. Heiden

Abstract: The synthesis and characterization of three new organic hydrazines containing BODIPY dyes and the respective aminomethyl complexes is described.

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Cited by 6 publications

References 50 publications

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Synthesis of New Bodipy Hydrazide Fluorescent Probes for the Detection of Carbonylated Proteins Generated by Oxidative Stress

Nina‐Diogo,

Hyzewicz,

Hamon

et al. 2024

ChemBioChem

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Oxidative stress is a cellular disorder implicated in various severe diseases and redox biology and represents an important field of research for the last decades. One of the major consequences of oxidative stress is the carbonylation of proteins, which is also a reliable marker to assess protein oxidative modifications. Accumulation of carbonylated proteins has been associated with aging and age‐related diseases and can ultimately causes cell death. Detection of these oxidative modifications is essential to understand and discover new treatments against oxidative stress. We describe the design and the synthetic pathway of new BODIPY fluorescent probes functionalized with hydrazide function for protein carbonyl labeling to improve existing methodologies such as 2D‐Oxi electrophoresis. Hydrazide BODIPY analogues show very good fluorescent properties such as NIR emission up to 633 nm and quantum yield up to 0.88. These new probes were validated for the detection and quantification of carbonylated proteins with 2D‐Oxi electrophoresis using mouse muscle protein extracts, as well as both flow cytometry and microscopy using oxidant stressed C2C12 cells.

show abstract

Synthesis of New Bodipy Hydrazide Fluorescent Probes for the Detection of Carbonylated Proteins Generated by Oxidative Stress

Nina‐Diogo,

Hyzewicz,

Hamon

et al. 2024

ChemBioChem

View full text Add to dashboard Cite

show abstract

A static and dynamic NMR study of 10‐hydrazino‐BODIPY

Reviriego

Peña‐Cabrera

Kokate

et al. 2021

Magnetic Reson in Chemistry

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10‐Hydrazino‐BODIPY, BoNHNH2, presents slow rotation about the C10–NH bond that results in anisochronous 1H and 13C NMR signals. The assignment of the different signals has been made using traditional two‐dimensional methods as well as spin–spin coupling constants and confirmed by DFT calculations (B3LYP) using the 6‐311++G(d,p) basis set. The rotational barrier has been determined in three pairs of proton signals and compared with the calculated barrier.

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Development of a portable colorimetric sensor using Prussian blue nanoparticles for the detection of hydrazine

Nghia,

Hieu,

Khanh

et al. 2025

Microchemical Journal

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Synthesis and characterization of hydrazine-appended BODIPY dyes and the related aminomethyl complexes

Abstract: The synthesis and characterization of three new organic hydrazines containing BODIPY dyes and the respective aminomethyl complexes is described.

Cited by 6 publications

References 50 publications

Synthesis of New Bodipy Hydrazide Fluorescent Probes for the Detection of Carbonylated Proteins Generated by Oxidative Stress

Synthesis of New Bodipy Hydrazide Fluorescent Probes for the Detection of Carbonylated Proteins Generated by Oxidative Stress

A static and dynamic NMR study of 10‐hydrazino‐BODIPY

Development of a portable colorimetric sensor using Prussian blue nanoparticles for the detection of hydrazine

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