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Rapidly responsive and highly selective fluorescent probe for bisulfite detection in food jialin Wang, yanfeng Hao, hao Wang, shaoxiang yang, Hong-Yu Tian, Baoguo Sun, and yongguo Liu J. Agric. Food Chem., Just Accepted Manuscript • DOI: 10.1021/acs.jafc.7b00353 • Publication Date (Web): 16 Mar 2017 Downloaded from http://pubs.acs.org on March 17, 2017

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Journal of Agricultural and Food Chemistry is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

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Journal of Agricultural and Food Chemistry

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Rapidly responsive and highly selective fluorescent probe for bisulfite

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detection in food

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Jialin Wang, Yanfeng Hao, Hao Wang, Shaoxiang Yang*, Hongyu Tian, Baoguo

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Sun, and Yongguo Liu

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Beijing Innovation Centre of Food Nutrition and Human Health, Beijing Key

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laboratory of Flavour Chemistry, Beijing Technology and Business University, No.11

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Fucheng Road, Haidian District, Beijing 100048, P.R. China

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*

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86-10-68985382. E-mail: [email protected]

To whom correspondence should be addressed. Telephone: +86-10-68985382. Fax:

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Journal of Agricultural and Food Chemistry

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ABSTRACT: The new fluorescent probe 4-hydroxy-3-((2E, 4E) -5-phenylpenta-2,

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4-dienoyl)-2H-chromen-2-one (probe 1) was designed and synthesized for selective

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detection of sulfite. The fluorescence intensity of the probe was only decreased in the

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presence of HSO3−, all other anions assessed resulted in an increased fluorescence

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response. Hence, probe 1 acts as a highly selective sensor for HSO3−. This sulfite

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sensitivity can also be readily monitored visually, as once treated with sulfite the

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solution shows a marked color change from yellow to colorless. Moreover, probe 1

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can be conveniently used as signal tool to determine the HSO3− levels in various sugar

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samples.

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KEYWORDS: fluorescent probe; bisulfite; Michael-type addition

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Journal of Agricultural and Food Chemistry

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INTRODUCTION

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Bisulfite (HSO3−) is widely used as an antioxidant, antimicrobial agent and an

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enzyme inhibitor for foods, pharmaceutical products and beverages.1, 2 For example,

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the addition of bisulfite to beer and wine has been a worldwide practice for centuries.3

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However, it has been shown that bisulfite may be toxic in high doses, alongside

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potentially triggering asthma attacks and allergic reactions.4 Given the reported

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harmful effects on people’s health, the threshold levels of HSO3− in food and

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medicine are rigorously controlled. In particular, the United States Food and Drug

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Administration require labeling of products that contain more than 10 µg/mL of

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sulfite.5 Furthermore, in China, the total concentration of sulfur (calculated by SO2

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content) in white granulated sugar is strictly regulated to be