Cited by 27Click Chemistry and ApplicationsMass Spectrometry Techniques and ApplicationsAdvanced Proteomics Techniques and Applications

Detection of Alkynes via Click Chemistry with a Brominated Coumarin Azide by Simultaneous Fluorescence and Isotopic Signatures in Mass Spectrometry

Yang, Lihua, Chumsae, Chris, Kaplan, Jenifer B., Moulton, Kevin Ryan, Wang, Dongdong, Lee, David H., Zhou, Zhaohui Sunny·2017·Bioconjugate Chemistry

Abstract

Alkynes are a key component of click chemistry and used for a wide variety of applications including bioconjugation, selective tagging of protein modifications, and labeling of metabolites and drug targets. However, challenges still exist for detecting alkynes because most 1,2,3-triazole products from alkynes and azides do not possess distinct intrinsic properties that can be used for their facile detection by either fluorescence or mass spectrometry. To address this critical need, a novel brominated coumarin azide was used to tag alkynes and detect alkyne-conjugated biomolecules. This tag has several useful properties: first, it is fluorogenic and the click-chemistry products are highly fluorescent and quantifiable; second, its distinct isotopic pattern facilitates identification by mass spectrometry; and third, its click-chemistry products form a unique pair of reporter ions upon fragmentation that can be used for the quick screening of data. Using a monoclonal antibody conjugated with alkynes, a general workflow has been developed and examined comprehensively.

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Registry

Crossref · 10.1021/acs.bioconjchem.7b00354

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48 of 48 references verified0 citation errors · 0 not checkable

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  • The practice of labeling functional groups in uncharacterized NP mixtures using a non-targeted metabolomics approach is uncommon in NP discovery, and there are currently only a few existing examples.

    “Although these approaches have been in certain cases efficiently applied for NP discovery, the practice of labeling functional groups in uncharacterized NP mixtures using a non-targeted metabolomics approach is uncommon in NP discovery, and there are currently only a few existing examples.124–128”

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Authors
Yang, L., Chumsae, C., Kaplan, J. B., Moulton, K. R., Wang, D., Lee, D. H., & Zhou, Z. S.
Affiliations
  • AbbVie Bioresearch Center, 100 Research Drive, Worcester, Massachusetts 01605, United States
  • Northeastern University (US)
Corresponding author
Chumsae, Chris
Venue
Bioconjugate Chemistry
Published
2017-09-11
Volume
28
Issue
9
Pages
2302-2309
ISSN
  • 1043-1802 (ISSN-L)
  • 1520-4812
OpenAlex
W2746101075
Cited by
27
References
48
Citations by year
2026: 2 · 2025: 1 · 2024: 7 · 2023: 2 · 2022: 1 · 2021: 2 · 2020: 4 · 2019: 6 · 2018: 1 · 2017: 1
FWCI
1.37
Type
journal article
Language
en
Open access
closed
Locations
  • Bioconjugate Chemistry (publishedVersion)
  • PubMed (publishedVersion)
Funders
National Institute of General Medical Sciences (1 R01 GM101396)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
  • Physical Sciences › Chemistry › Spectroscopy › Mass Spectrometry Techniques and Applications
  • Physical Sciences › Chemistry › Spectroscopy › Advanced Proteomics Techniques and Applications
Keywords
click chemistry, 1,2,3-triazoles, fluorogenic labeling, isotopic signatures, monoclonal antibody conjugation, bioconjugation, fluorescence detection, mass spectrometry identification
MeSH terms
Alkynes, Amino Acid Sequence, Animals, Antibodies, Monoclonal, Azides, Coumarins, Cricetulus, Fluorescence, Fluorescent Dyes, Humans, Models, Molecular, Recombinant Proteins, Spectrometry, Fluorescence, Mass Spectrometry, Triazoles, CHO Cells, Halogenation, Click Chemistry

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