Molecular Sensors and Therapeutics Research Laboratory, Department of Chemistry, School of Natural Sciences, Shiv Nadar University, NH91, Tehsil Dadri, Gautam Buddha Nagar, Uttar Pradesh 201314, India.
Chemical Sciences and Technology Division, CSIR - National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Industrial Estate, PO Pappanamcode, Trivandrum, Kerala 695019, India.
J Photochem Photobiol B. 2020 Dec;213:112076. doi: 10.1016/j.jphotobiol.2020.112076. Epub 2020 Oct 31.
Reactive carbonyl species (RCSs) including one carbon formaldehyde (FA) and dicarbonyl compounds such as methylglyoxal (MGO) and glyoxal (GO) are produced during demethylase reactions and various glucose metabolic pathways respectively. Elevation of the RCSs concentrations in cells is due to abnormal DNA damage, glycation adducts with macromolecules that lead to various neurotoxic diseases. Hence, regular monitoring of these RCSs with an easy tool is of utmost interest. However, conventional methods such as chromatography and mass spectrometry for the detection of these species are not so economically viable. These issues were well addressed by the non-invasive reactivity-based fluorescence techniques. However, tedious synthesis, only specific to either mono aldehyde is limited to detect multiple RCSs in physiologies by synthesized fluorophores. An alternative, simple small molecules are widely applied as commercial biomarkers such as terephthalate and 2,3-diaminonaphthalene (NAP) for hydroxy radical (OH·) and nitric oxide (NO) respectively. Herein, we report an analogue of NAP, 1,8-diamino naphthalene (DAN) is an efficient chemosensor for highly sensitive detection of FA, MGO and GO with minimum detection limits of 0.95-3.97 μM. Surprisingly, DAN shows a "turn on" response towards RCSs but remaining silent towards NO which are exactly opposite to commercial probe NAP. Exogenous RCSs imaging in vitro cancerous cells shows the efficacy of the probe and its potential application for RCSs monitoring in cancer cells, generation of toxic byproducts.
活性羰基化合物 (RCSs) 包括一碳甲醛 (FA) 和二羰基化合物，如甲基乙二醛 (MGO) 和乙二醛 (GO)，分别在脱甲基酶反应和各种葡萄糖代谢途径中产生。细胞中 RCSs 浓度的升高是由于异常的 DNA 损伤、与大分子的糖化加合物导致各种神经毒性疾病。因此，使用简单的工具定期监测这些 RCSs 非常重要。然而，用于检测这些物质的常规方法，如色谱法和质谱法，在经济上并不可行。这些问题通过基于非侵入性反应的荧光技术得到了很好的解决。然而，繁琐的合成过程，以及仅针对单醛的合成荧光团，限制了它们在生理条件下检测多种 RCSs 的能力。作为替代方案，简单的小分子被广泛应用于商业生物标志物，如对羟基自由基 (OH·) 的对苯二甲酸和 2,3-二氨基萘 (NAP) 以及对一氧化氮 (NO) 的萘。在此，我们报告了 NAP 的类似物 1,8-二氨基萘 (DAN)，它是一种高效的化学传感器，可用于 FA、MGO 和 GO 的高灵敏度检测，最低检测限为 0.95-3.97 μM。令人惊讶的是，DAN 对 RCSs 表现出“开启”响应，但对 NO 保持沉默，这与商业探针 NAP 完全相反。体外癌细胞中 RCSs 的外源成像显示了该探针的功效及其在癌细胞中监测 RCSs、产生毒性副产物的潜在应用。
