尼罗红 (染料)

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
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（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]。

在乙醇中，尼罗红的扩散系数为470 μm²/s.^[8]。

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。

在紫外光(366 nm)照射下的不同尼罗红溶液。从左至右：1. 水, 2. 甲醇, 3. 乙醇, 4. 乙腈, 5. 二甲基甲酰胺, 6. 丙酮, 7. 乙酸乙酯, 8. 二氯甲烷, 9. 正己烷, 10. 甲基叔丁基醚, 11. 环己烷, 12. 甲苯.
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.
^ 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].
^ 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. ISSN 1463-9084. doi:10.1039/D2CP05578C （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.

[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.

[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.

[Thermo_Fisher_Scientific_2017a-6] Fluorescence SpectraViewer - Nile Red triglycerides. Thermo Fisher Scientific. 2017-05-17 [2020-03-06].

[Thermo_Fisher_Scientific_2017b-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. ISSN 1463-9084. doi:10.1039/D2CP05578C （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 .

[Nile_Red_synthesis_TL_2009-10] 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.

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