尼罗红 (染料)

化合物

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
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  checkY
PubChem 65182
ChemSpider 58681
SMILES
 
  • CCN(CC)c1ccc2c(c1)oc-3cc(=O)c4ccccc4c3n2
InChI
 
  • 1/C20H18N2O2/c1-3-22(4-2)13-9-10-16-18(11-13)24-19-12-17(23)14-7-5-6-8-15(14)20(19)21-16/h5-12H,3-4H2,1-2H3
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]

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]

在乙醇中,尼罗红的扩散系数为470 μm2/s.[8]

合成

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

参考文献

  1. ^ 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 . 
  2. ^ 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. 
  3. ^ 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). 
  4. ^ 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 . 
  5. ^ 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. 
  6. ^ Fluorescence SpectraViewer - Nile Red triglycerides. Thermo Fisher Scientific. 2017-05-17 [2020-03-06]. (原始内容存档于2021-03-16). 
  7. ^ Fluorescence SpectraViewer - Nile Red phospholipids. Thermo Fisher Scientific. 2017-05-17 [2020-03-06]. 
  8. ^ 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). 
  9. ^ 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 . 
  10. ^ 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.