Please use this identifier to cite or link to this item:
|Title: ||Fluorogenic 1,8-naphthalimide derivatives for the detection of pathogenic bacteria|
|Authors: ||Jin, Terry David|
|Issue Date: ||2-Jul-2015|
|Publisher: ||University of Sydney|
Faculty of Pharmacy
|Abstract: ||Novel fluorogenic enzyme substrates were synthesized by the coupling of 6-hydrazinobenz[de]isoquinoline-1,3-diones with β-alanine for the detection of β-alanyl aminopeptidase-producing Pseudomonas aeruginosa. A secondary reaction was also utilized involving the condensation of the 6-hydrazinobenz[de]isoquinoline-1,3-diones with a range of aryl aldehydes to give the corresponding hydrazones as a means for obtaining more favourable fluorescence properties. The photophysical properties of the synthesized hydrazines and their hydrazide and hydrazone derivatives, were examined and they were also incorporated into Columbia agar in order to determine their potential for the detection of pathogenic bacteria.
The synthesized hydrazides and coupled derivatives displayed good fluorescence properties, with an average Stokes’ shift of 67 nm. Incorporation of a secondary reaction with aldehydes enhanced the fluorescence properties, with the exception of hydrazones containing the 4-dimethylamino substituent. Hydrazones prepared from benzaldehyde and 4-chlorobenzaldehyde displayed greatly increased fluorescence intensity, with no bathochromic shift, while the hydrazones from cinnamaldehyde and p-anisealdehyde displayed a favourable bathochromic shift along with a slight increase in fluorescence intensity.
Incorporation of the synthesized compounds into Columbia agar, however, did not have the expected effects, as the majority of observed fluorescence was seen to be due to the substrate, and not the fluorophore. A high degree of localization of fluorescence within bacterial cells was, however, observed, although longer chain N-substituents appeared to have bactericidal effects on the microorganisms tested.|
|Type of Work: ||Masters Thesis|
|Type of Publication: ||Master of Philosophy M.Phil|
|Appears in Collections:||Sydney Digital Theses (Open Access)|
This work is protected by Copyright. All rights reserved. Access to this work is provided for the purposes of personal research and study. Except where permitted under the Copyright Act 1968, this work must not be copied or communicated to others without the express permission of the copyright owner. Use the persistent URI in this record to enable others to access this work.
|JIN Terry - Final Thesis.pdf||Thesis||2.97 MB||Adobe PDF|
Items in Sydney eScholarship Repository are protected by copyright, with all rights reserved, unless otherwise indicated.