Okoh Okoh, Adeyi (2013) The Synthesis and Evaluation of Non-Targeted Near-Infrared Heptamethine Molecular Probes. Doctoral thesis, University of Central Lancashire.
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Detecting and quantifying biomolecules is an important tool in biological research. Ideal dyes have to have a number of characteristics i.e. low toxicity and limited autofluorescence. The properties of near infrared dyes make these ideal for cell and tissue imaging.
The work within this thesis focuses on the development of three families of NIR dyes (linear, rigid and substituted polymethine) and these are actively compared against the clinical standard Indocyanine Green (ICG) and its structural derivative New Indocyanine Green (IR-820). The ultimate aim being to identify dyes which can be used alongside the clinical standards.
The compounds developed within this thesis are structurally based on the NIR heptamethine cyanine (Cy7) dyes. To expand, variations fall into three categories, linear, rigid and polymethine substituted, each being synthesised using either existing methodology or through the development of a novel cascade reaction. The photophysical properties of each dye have been evaluated experimentally, focusing on absorption and emission wavelengths, fluorescence quantum yields and Stokes shifts. It is noted that most dyes synthesised within this thesis, show comparable Stokes shift but increased fluorescence quantum yields when compared against ICG and IR-820. All dyes absorb and emit within the NIR region based on excitation at 785 nm.
The growth inhibition characteristic is an important criterion which determines the practical use of the dyes in living cells. Most of the dyes which showed no growth inhibition were the dyes bearing the sulfonic acid group, suggesting the sulfonic acid limited cellular uptake as a result of decreased membrane permeability. Dyes possessing growth inhibitory characteristics all contain linear N-alkyl moieties. It is thus postulated that the increased lipophilicity of these molecules result in increased lipid distortion and subsequent toxicity.
|Item Type:||Thesis (Doctoral)|
|Additional Information:||Publications 1. Promising Near-Infrared Non-Targeted Probes-Benzothiazole Heptamethine Cyanine Dyes. Journal of Sulfur Chemistry, 2013 DOl: 10.1080/17415993.2013.778258 Okoh Adeyi Okoh, Roger H. Bisby,Clare L. Lawrence,Carole E. Rolph and Robert B. Smith 2. "N-Aikylated 2,3,3-Trimethylindolenines and 2- Methylbenzothiazoles. Potential Lead Compounds in the Fight against Saccharomyces cerevisiae Infections". European Journal of Medicinal Chemistry, 2013 Andrew Tyler, Adeyi Okoh Okoh, Clare L. Lawrence, Vicky C. Jones,Colin Moffatt and Robert B. Smith doi.org/10.1016/j.ejmech.2013.03.031|
|Uncontrolled Keywords (separate with ;):||Near-Infrared cyanine dyes; heptamethine cyanine dyes; molecular probes; lndocyanine green; organic chemistry|
|Subjects:||Physical sciences > Chemistry|
|Schools:||Faculty of Science and Technology > School of Forensic and Applied Sciences|
|Deposited By:||Hayley Gayle Moran|
|Deposited On:||19 Dec 2013 17:44|
|Last Modified:||10 Feb 2017 12:41|
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