第一部份：芘駢吡咯及雙芘駢吡咯做為氟離子偵測器之機制研究
第二部分：抗神經退化性藥物之研究：腺苷酸類似物之合成

林佳誼

doi:10.6342/NTU.2007.01462

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第一部份：芘駢吡咯及雙芘駢吡咯做為氟離子偵測器之機制研究第二部分：抗神經退化性藥物之研究：腺苷酸類似物之合成

Part 1. A Mechanistic Study of Pyreno[2,1-b]pyrrole and Bis(pyreno[2,1-b]pyrrole) as Selective Chemosensors of Fluoride Ion Part 2. Synthesis of Adenosine Analogues for Therapy of Huntington’s Disease

林佳誼 , Masters　　Advisor：方俊民　　

英文 DOI： 10.6342/NTU.2007.01462

氟離子；偵測器；神經退化性疾病；腺苷酸類似物； fluoride ； sensor ； nerodegenerative disease ； adenosine analogue

Abstract │ Reference (52) │ Altmetrics

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Part 1. A Mechanistic Study of Pyreno[2,1-b]pyrrole and Bis(pyreno[2,1-b]pyrrole) as Selective Chemosensors of Fluoride Ion
Pyreno[2,1-b]pyrrole and its dimeric derivative display excellent selectivity and sensitivity for detection of fluoride ion, in comparison with other anions. The bonding with fluoride ion, both in formation and in subsequent dissociation, provides remarkable colorimetric and fluorescent changes in the visible region that are advantageous for real-time and on-site application. 
The mechanisms of detection were also investigated by detailed NMR and dynamic fluorescence spectroscopic analyses. The initial interaction modes of pyreno[2,1-b]pyrrole and its dimeric derivative with F− in MeCN can be understood as hydrogen-bonded complexes. Excess F− ions promotes deprotonation of N-protons and results in the bathochromic changes in both absorption and fluorescence spectra. The observation of [FHF]– by 1H NMR in DMSO-d6 also strongly supported the deprotonation mechanism.
Part 2. Synthesis of Adenosine Analogues for Therapy of Huntington’s Disease
We demonstrated the synthesis and biological function of T1-C and T1-11, which are isolated from a Chinese herb, Gastrodia elata (天麻), These compounds have been characterized to exert neuroprotective effect. Previous works has revealed the potency of T1-11 for the therapy of Huntington’s disease. The neuroprotection was mediated by A2A receptor in the apoptotic model of serum-deprived PC12 cells. Because A2A receptor is a GPCR, pharmacophore modeling was used to provide a putative image of the interactions between the target protein, A2A receptor, and its agonists. 
There were two approaches to modify T1-11: the alternation of N6-substituted functional groups and the modification of ribose. A representative library of adenosine analogues was developed on the basis of pharmacophore model and screened for the biological activities assays. We also proposed a dual–function mechanism of T1-11, which acted as both A2A receptor agonist and nucleoside transporter inhibitor. Further development of these compounds may promise a novel therapeutic intervention for HD and other neurodegeneration diseases.

Reference ( 52 ) 〈TOP〉

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5. Yamamura, S. S.; Wade, M. A.; Sikes, J. H. Anal. Chem. 1962, 34, 1308–1312. “Direct spectrophotometric fluoride determination”
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