尼羅紅 (染料)

尼羅紅
	IUPAC名; 9-(Diethylamino)-5H-benzo[a]phenoxazin-5-one
別名	尼羅藍噁嗪酮
識別
CAS號	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
性質
化學式	C20H18N2O2
摩爾質量	318.376 g/mol g·mol⁻¹
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

尼羅紅（英語：Nile red），又稱尼羅藍噁嗪酮（英語：Nile blue oxazone）是一種親脂性染料。可將細胞內的脂滴染成黃色。在大多數極性溶劑中，尼羅紅不會發出熒光；然而在富含脂質的環境中，它會發出強烈的熒光，顏色從深紅色（極性膜脂質）到強烈的黃金色（細胞內儲存的非極性脂質）不等。尼羅紅具有溶劑化顯色特性，其激發波長和發射波長隨溶劑極性變化而變化^[1]，在極性介質中幾乎不會發出熒光^[2]。

尼羅紅在細胞生物學中常作為膜的染色劑，其激發與發射波長與紅色熒光蛋白相同，利用熒光顯微鏡可觀察到其熒光效應。尼羅紅還被用作瓶裝水中微塑料的靈敏檢測所需試劑^[3]^[4]。此外，尼羅紅是製造用於檢測環境變化（如氣味、氣體、pH值等）的不同傳感器膜的候選材料^[5] 。

在三酸甘油酯（非極性脂質）中，尼羅紅的最大激發波長約為515 nm（綠色），最大發射波長約為585 nm（黃橙色）^[6]。相反，在磷脂（極性脂質）中最大激發波長為554 nm（綠色），最大發射波長為638 nm（紅色）^[7]。

在乙醇中，尼羅紅的擴散係數為470 μm²/s.^[8]。

合成

尼羅紅可以通過尼羅藍與硫酸沸煮水解，尼羅藍中亞胺離子基團被羰基取代轉變成尼羅紅^[9]。尼羅紅與其同系物（萘並噁嗪染料）也可以通過5-二烷基氨基-2-亞硝基苯酚與2-萘酚經酸催化縮合得到。此反應不使用共氧化劑，因此產量通常適中^[10]。由於生成尼羅紅的反應通常不會完全耗盡尼羅藍，因此則需要額外的分離步驟來獲得純尼羅紅。

在紫外光(366 nm)照射下的不同尼羅紅溶液。從左至右：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. 環己烷, 12. 甲苯.
用尼羅紅染色的枯草桿菌。該菌株部分以細胞鏈的形式生長，因此膜染料可能有助於區分內部細胞邊界

參考文獻

^ 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]. （原始內容存檔於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]. （原始內容存檔於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. （原始內容存檔於2024-07-28）（英語）.
^ 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 [2024-07-12]. （原始內容存檔於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.

[Thermo_Fisher_Scientific_2017a-6] Fluorescence SpectraViewer - Nile Red triglycerides. Thermo Fisher Scientific. 2017-05-17 [2020-03-06]. （原始內容存檔於2021-03-16）.

[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 [2024-07-12]. ISSN 1463-9084. doi:10.1039/D2CP05578C. （原始內容存檔於2024-07-28）（英語）.

[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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]