Liu Guoqiang, Shegiwal Ataulla, Zeng Yuan, Wei Yen, Boyer Cyrille, Haddleton David, Tao Lei
The Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.
Centre for Advanced Macromolecular Design (CAMD) and Australian Centre for NanoMedicine (ACN), School of Chemical Engineering, UNSW Australia, Sydney, NSW 2052, Australia.
ACS Macro Lett. 2018 Nov 20;7(11):1346-1352. doi: 10.1021/acsmacrolett.8b00697. Epub 2018 Oct 22.
Formaldehyde (FA) has been detected via the Hantzsch reaction for many decades. However, the Hantzsch reaction has been rarely used to detect FA in biological systems due to the disadvantages of small-molecule probes (including toxicity and poor water solubility). In this study, polymeric fluorescent probes were developed to resolve these issues associated with small molecules, and FA in living systems was successfully detected via the Hantzsch reaction. These water-soluble polymers were easily scaled-up (∼25 g) by radical polymerization using commercial monomers. These polymers exhibited similar, albeit better, sensitivity to FA compared to water-soluble small molecules, primarily indicative of the advantages of polymers for the detection of FA via the Hantzsch reaction. The polymer structures were highly biocompatible with the probes; thus, these polymers can effectively detect endogenous FA in cells or zebrafish in a safe manner. This result confirmed the superiority of polymers in safety as biocompatible materials. This study highlights a straightforward method for exploring probes for the detection of FA in living systems. It offers functional polymers for bioimaging and extends the application scope of the Hantzsch reaction, reflecting the utility of a broad study of organic reactions in interdisciplinary fields as well as possible key implications in organic chemistry, analytical chemistry, and polymer chemistry.
几十年来，一直通过汉茨希反应检测甲醛（FA）。然而，由于小分子探针存在缺点（包括毒性和水溶性差），汉茨希反应很少用于检测生物系统中的FA。在本研究中，开发了聚合物荧光探针来解决与小分子相关的这些问题，并通过汉茨希反应成功检测了活系统中的FA。这些水溶性聚合物通过使用市售单体的自由基聚合很容易扩大规模（约25克）。与水溶性小分子相比，这些聚合物对FA表现出相似但更好的灵敏度，这主要表明聚合物通过汉茨希反应检测FA的优势。聚合物结构与探针具有高度生物相容性；因此，这些聚合物可以安全地有效检测细胞或斑马鱼中的内源性FA。这一结果证实了聚合物作为生物相容性材料在安全性方面的优越性。本研究突出了一种探索活系统中FA检测探针的直接方法。它为生物成像提供了功能聚合物，并扩展了汉茨希反应的应用范围，反映了有机反应在跨学科领域广泛研究的实用性以及在有机化学、分析化学和高分子化学中可能的关键意义。
