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Exploring the flexible chemistry of 4-fluoro-3-nitrophenyl azide for biomolecule immobilization and bioconjugation

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Abstract

Bioconjugation and functionalization of polymer surfaces are two major tasks in materials chemistry which are accomplished using a variety of coupling agents. Immobilization of biomolecules onto polymer surfaces and the construction of bioconjugates are essential requirements of many biochemical assays and chemical syntheses. Different linkers with a variety of functional groups are used for these purposes. Among them, the benzophenones, aryldiazirines, and arylazides represent the most commonly used photolinker to produce the desired chemical linkage upon their photo-irradiation. In this review, we describe the versatile applications of 4-fluoro-3-nitrophenyl azide, one of the oldest photolinkers used for photoaffinity labeling in the late 1960s. Surprisingly, this photolinker, historically known as 1-fluoro-2-nitro-4-azidobenzene (FNAB), has remained unexplored for a long time because of apprehension that FNAB forms ring-expanded dehydroazepine as a major product and hence cannot activate an inert polymer. The first evidence of photochemical activation of an inert surface by FNAB through nitrene insertion reaction was reported in 2001, and the FNAB-activated surface was found to conjugate a biomolecule without any catalyst, reagent, or modification. FNAB has distinct advantages over perfluorophenyl azide derivatives, which are contemporary nitrene-generating photolinkers, because of its simple, single-step preparation and ease of thermochemical and photochemical reactions with versatile polymers and biomolecules. Covering these aspects, the present review highlights the flexible chemistry of FNAB and its applications in the field of surface engineering, immobilization of biomolecules such as antibodies, enzymes, cells, carbohydrates, oligonucleotides, and DNA aptamers, and rapid diagnostics.

An overview of the FNAB-engineered activated polymer surfaces for covalent ligation of versatile biomolecules

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Acknowledgments

This work was supported by the CARDIOMED (BSC0122) project of the Council of Scientific and Industrial Research, New Delhi, India. S.K. thanks the SERB-Department of Science and Technology, Government of India, for the award of Fast Track Young Scientist Fellowship. R. A. thanks the Council of Scientific and Industrial Research, New Delhi, India for the Senior Research Fellowship.

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Author notes

  1. Pradip Nahar

    Present address: Dr. Nahar’s New Idea lab, C-202, Ramkrishan Cooperative Group Housing Society, Plot 12, Sector 23, Dwarka, New Delhi, India

Authors and Affiliations

  1. CSIR - Institute of Genomics and Integrative Biology, Mall Road, 110007, Delhi, India

    Saroj Kumar, Rajesh Ahirwar & Pradip Nahar

  2. Department of Biotechnology, Delhi Technological University, Main Bawana Road, 110042, Delhi, India

    Saroj Kumar

  3. Department of Pharmaceutical Sciences, University of Colorado, Denver, Colorado, 80045, USA

    Dileep Kumar

  4. Academy of Scientific and Innovative Research, Mathura Road, Jasola, 110020, New Delhi, India

    Rajesh Ahirwar & Pradip Nahar

Authors
  1. Saroj Kumar
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  2. Dileep Kumar
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  3. Rajesh Ahirwar
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  4. Pradip Nahar
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Corresponding author

Correspondence to Pradip Nahar.

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Additional information

Saroj Kumar, Dileep Kumar and Rajesh Ahirwar contributed equally to this work.

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Kumar, S., Kumar, D., Ahirwar, R. et al. Exploring the flexible chemistry of 4-fluoro-3-nitrophenyl azide for biomolecule immobilization and bioconjugation. Anal Bioanal Chem 408, 6945–6956 (2016). https://doi.org/10.1007/s00216-016-9803-6

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  • DOI: https://doi.org/10.1007/s00216-016-9803-6

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