合成三聯吡啶衍生物作為篩選轉醣酶抑制劑之感測器

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doi:10.6342/NTU201701211

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合成三联吡啶衍生物作为筛选转醣酶抑制剂之感测器

Synthesis of Terpyridine Derivatives as Sensors for Screening of Transglycosylase Inhibitors

徐欣传 , 硕士　　导师：方俊民　　

英文 DOI： 10.6342/NTU201701211

转醣酶；抑制剂；感测器； Transglycosylase ； Inhibitors ； Sensors

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摘要 │ 参考文献 (29) │ 国际计量

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Transglycosylase (TGase) is an attractive target for development of new antibiotics due to its location outside the membrane of bacteria and essential role in peptidoglycan synthesis. Some TGase inhibitors have been identified, but none of them have been developed into antibiotics for human. The existing TGase assays are not fast enough to develop new antibiotics. Therefore a continuous, quantitative, and high-throughput assay for TGase will facilitate the discovery of new and effective inhibitors.
We chose 4′-(4-N,N-dimethylaminophenyl)-2,2′:6′,2″-terpyridine as the ligand (L) of Zn(II) ion to form a complex ZnCl2L (9) as the TGase probe, which has been reported as a fluorescent sensor of inorganic pyrophosphate. To establish a model system, we first synthesized GlcNAc–GPP (23) instead of lipid II, and the commercially available farnesyl pyrophosphate (FPP) was used as the truncated analogue of undecaprenyl pyrophosphate (C55-PP) to compare the binding behavior with sensor 9. 
The experiment showed that FPP was selectively bound with 9 to emit fluorescence at 650 nm. In contrast, GlcNAc–GPP 23–9 did not emit fluorescence. Next, the sensor 9 was applied in TGase assay which was in a more complex solution system. NBD–lipid II was utilized as the substrate for the TGase assay, and sensor 9 was added to monitor the change of fluorescence between the reacted group and unreacted group. The result showed an unexpected fluorescence quenching effect of NBD-lipid II at 550 nm, but enhancement at a longer wavelength of 650 nm that was presumably caused by complexation of NBD-lipid II with 9. Although the result was opposite to our prediction, the TGase catalyzed reaction could still be monitored by fluorescence at 550 nm.
In summary, we successfully developed a TGase assay in which sensor 9 was utilized to track the enzymatic reaction. This system could be operated as a high-throughput assay for screening TGase inhibitors in the future.

参考文献 ( 29 ) 〈TOP〉

1. Broussard, J. A.; Rappaz, B.; Webb, D. J.; Brown, C. M. Nature Protocols. 2013, 8, 265−281. Fluorescence resonance energy transfer microscopy as demonstrated by measuring the activation of the serine/threonine kinase Akt.
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3. Cho, H. K.; Lee, D. H.; Hong, J.-I. Chem Commun. 2005, 1690–1692. A fluorescent pyrophosphate sensor via excimer formation in water.
连结：
4. Kim, M. J.; K. M. K. Swamy, Lee, K. M.; Jagdale, A. R.; Kim, Y.; Kim, S. J.; Yoo, K. H.; Yoon, J. Chem. Commun. 2009, 7215–7217. Pyrophosphate selective ﬂuorescent chemosensors based on coumarin–DPA–Cu( II ) complexes.
连结：
5. Chen, K. H.; Liao, J. H.; Chan, H. Y.; Fang, J. M. J. Org. Chem. 2009, 74, 895–898. A fluorescence sensor for detection of geranyl pyrophosphate by the chemo-ensemble method.
连结：
6. Wongkongkatep, J.; Miyahara, Y.; Ojida, A.; Hamachi, I. Angew. Chem. Int. Ed. 2006, 45, 665–668. Label-free, real-time glycosyltransferase assay based on a fluorescent artificial chemosensor.
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引用含有DOI的文献

DOI可强化引用精确性、增强学术圈连结，并给予使用者跨平台的良好使用经验，目前在全世界已有超过五千万个对象申请DOI。 如想对DOI的使用与概念有进一步了解，请参考 （ ） 。

DOI可强化引用精确性、增强学术圈连结，并给予使用者跨平台的良好使用经验，目前在全世界已有超过五千万个对象申请DOI。如想对DOI的使用与概念有进一步了解，请参考（）。