Macquarie University
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Synthesis of novel fluorescent labels for advanced imaging applications

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posted on 2022-03-28, 19:29 authored by Ketan Madhukar Ahire
A picture is worth a thousand words – they can make large and complex data sets interpretable. In the last six decades, use of fluorescent labelling techniques has extensively increased. Synthesis of fluorescent probes for real-time imaging has become a powerful tool for cell biology, systems biology, microbiology and chemical biology and has largely taken over from radioactive tracers. The accuracy and sensitivity of a fluorescent probe allows the monitoring of complex cellular processes such as enzyme activation, protein-protein interactions, cellular re-organisation and trafficking. This thesis describes the design and synthesis of novel fluorescent labels, studies of their basic photophysical properties, and proof-of-principle applications. Chapter 1 gives a brief introduction of the fluorescence process and fluorescent probes. Chapter 2 consists of the synthesis of novel amino-salicylaldehyde based fluorescent probes. This chapter isdivided into two parts. Firstly, the synthesis of novel pyrylium derivatives as turn-on irreversible protein stain for gel electrophoresis, protein labelling and imaging is described. The second part of the chapter includes the synthesis of novel boranil derivatives and their photophysical properties. Chapter 3 mainly focuses on the resynthesis of a GFP-chromophore analogue, its dual emission, photophysical properties and applications in bioanalytical chemistry. Chapter 4 illustrates the synthesis of a novel turnon, suicide substrates for selected enzymes based on difluoromethyl analogues of wellknown fluorophores. In this chapter, attempts are described towards the synthesis of new fluorogenic fluorescein and BODIPY based derivatives that could be used for the detection of specific enzymes in live cells. Appendices at the end of the thesis provide MS, NMR, U.V and fluorescence measurements.


Table of Contents

Chapter 1. Introduction -- Chapter 2. Synthesis of novel amino-salicylaldehyde based fluorescent probes -- Chapter 3. Synthesis and spectroscopic studies of a dual-emitting GFP-analogue -- Chapter 4. Design and synthesis of novel difluoromethylene based fluorescent probes for specific enzyme studies -- Chapter 5. Appendices.


Empirical thesis.. Includes bibliographical references

Awarding Institution

Macquarie University

Degree Type

Thesis PhD


PhD, Macquarie University, Faculty of Science and Engineering, Department of Molecular Sciences

Department, Centre or School

Department of Molecular Sciences

Year of Award


Principal Supervisor

Peter Karuso


Copyright Ketan Madhukar Ahire 2017. Copyright disclaimer:




1 online resource (xiii, 301 pages) colour illustrations

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