A novel approach for the development of chemical sensors
Advisor: Chang, Young-TaeSchool: New York University
School Location: United States -- New York
Keyword(s): Fluorescence, Sensors, Chemical sensors, Combinatorial chemistry, Triazine, Artifical tongue, Dapoxyl dyes
Source: DAI-B 68/01, Jul 2007
Source type: Dissertation
Subjects: Biochemistry, Organic chemistry
Publication Number: AAT 3247373
Document URL: [url]http://proquest.umi.com/pqdweb?did=1260822191&sid=2&Fmt=2&clientId=45596&RQT=309&VName=PQD[/url]
ProQuest document ID: 1260822191
Abstract (Document Summary)
Combinatorial chemistry is a powerful approach that can generate number of molecules in the limit of time. One of salient contribution is the generation of active molecules that can envisage the biological process of living system. As the application to material science, combinatorial fluorescent dye library is constructed. Combining with rapid screening through live cells and various analytes, the fluorescent dyes would be identified as probe molecules to provide an insight to understand cellular process with live cell image.
As the effort to discover sensors or biologically active molecules, we developed novel methods based on a combinatorial approach.
Firstly, the triazine library was prepared as the diversity expanded version. Encouraged by our success of previous research, aryl functionalized triazine library was constructed with newly developed various synthetic protocols, named as the sulfone strategy, Suzuki coupling, and Grigard reaction. These protocols were combined to orthogonal solid phase synthesis of triazine library and yielded high purity with diversity.
Secondly, styryl dye library were synthesized via base catalyzed coupling reaction and screened with cancerous cells for the development of fluorescent probes. Among the hit compounds, eight nucleus localized styryl dyes were tested with dsDNA. One of eight styryl dyes showed 13.3 fluorescent intensity increases with addition of dsDNA. As the extension of our application in the intrinsically tagged molecules, the environmentally sensitive dapoxyl fluorescent dye was synthesized with various functionalities. Both solid phase and solution phase synthesis yielded dapoxyl fluorescent library harboring 350 nm of excitation wavelength and 450 nm of emission wavelength.
Lastly, as a broad definition of combinatorial approach, the combinatorial dye array was developed adapting colorful off-the-shelf dyes which were selected though the screening with various analytes. 47 selected dyes which have multi-responses are developed as artificial tongue. 47 cation analytes with six sequentially diluted metal ion solutions (10 mM down to 0.33 [mu]M) were identified as 99.4% accuracy. Furthermore, the success rate at which concentration of each analyte was correctly determined was high 96.8%. The selected pH indicators and boronic acid ensemble can discriminate 23 carbohydrates with 100% accuracy.
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