| 词条 | Nile red | ||
| 释义 |
| Verifiedfields = changed | verifiedrevid = 476992673 | ImageFile = Nilrot.svg | ImageSize = 200px | ImageFile1 = Nile-red-3D-balls.png | ImageSize1 = 200px | IUPACName = 9-diethylamino-5-benzo[a]phenoxazinone | OtherNames = Nile red, Nile blue oxazone | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 58681 | 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 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 144472 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = VOFUROIFQGPCGE-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 7385-67-3 | PubChem = 65182 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 52169 | SMILES = CCN(CC)c1ccc2c(c1)oc-3cc(=O)c4ccccc4c3n2 }} | Section2 = {{Chembox Properties | Formula = C20H18N2O2 | MolarMass = 318.369 g/mol }}Nile red (also known as Nile blue oxazone) is a lipophilic stain. Nile red stains intracellular lipid droplets yellow. In most polar solvents, Nile red will not fluoresce; however, when in a lipid-rich environment can be intensely fluorescent, with varying colours from deep red (for polar membrane lipid) to strong yellow-gold emission (for neutral lipid in intracellular storages). The dye is highly solvatochromic and its emission and excitation wavelength both shift depending on solvent polarity [1] and in polar media will hardly fluoresce at all.[2] Nile red has applications in cell biology, where it can be used as a membrane dye which can be readily visualized using an epifluorescence microscope with excitation and emission wavelengths usually shared with red fluorescent protein. Nile red has also been used as part of a sensitive detection process for microplastics in bottled water.[3][4] SynthesisNile red can be prepared through acid hydrolysis by boiling a solution of Nile blue with sulphuric acid.[5] This process replaces an iminium group with a carbonyl group. Alternatively, Nile red and its analogs (naphthooxazine dyes) can be prepared by acid-catalyzed condensation of corresponding 5-(dialkylamino)-2-nitrosophenols with 2-naphthol. The yields are generally moderate as no co-oxidant is used in this procedure.[6] Since the reaction to generate Nile red does not usually completely exhaust the supply of Nile blue, additional separation steps are required if pure Nile red is needed. References1. ^{{cite journal|author=R Plenderleith|author2=T Swift|author3=S Rimmer|last-author-amp=yes|title=Highly-branched poly(N-isopropyl acrylamide)s with core–shell morphology below the lower critical solution temperature|journal=RSC Advances | date=2014 | volume = 4 | issue = 92 | pages=50932–50937}} {{Use dmy dates|date=March 2019}}2. ^{{cite journal|author=P Greenspan|author2=E. P. Mayer|author3=S. D. Fowler|last-author-amp=yes|title=Nile Red, A Selective Fluorescent Stain for Intracellular Lipid Droplets|journal=Journal of Cell Biology | date=1985 | volume = 100 | issue = 1 | pages=965–973}} 3. ^{{Cite news |title=Plastic: WHO launches health review |date=15 March 2018 |author=David Shukman |url=https://www.bbc.co.uk/news/science-environment-43389031 |newspaper=BBC News Online}} 4. ^{{Cite web |title=Synthetic Polymer Contamination in Bottled Water |date=15 March 2018 |first=Sherri A. |last=Mason |first2=Victoria |last2=Welch |first3=Joseph |last3=Neratko |url=http://news.bbc.co.uk/1/shared/bsp/hi/pdfs/14_03_13_finalbottled.pdf |location=Fredonia |publisher=State University of New York}} 5. ^{{cite journal|author=SD Fowler|author2=P Greenspan|last-author-amp=yes|title=Application of Nile red, a fluorescent hydrophobic probe, for the detection of neutral lipid deposits in tissue sections: comparison with oil red O |journal=Journal of Histochemistry and Cytochemistry | date=1985 | volume = 33 | issue = 8 | pages=833–836}} 6. ^{{cite journal |author=Park, So-Yeon |display-authors=4 |author2=Kubota, Y. |author3=Funabiki, K. |author4=Shiro, M. |author5=Matsui, M. |title=Near-infrared solid-state fluorescent naphthooxazine dyes attached with bulky dibutylamino and perfluoroalkenyloxy groups at 6- and 9-positions |journal=Tetrahedron Letters |volume=50 |pages=1131–1135 |date=2009 |doi=10.1016/j.tetlet.2008.12.081 }} 2 : Oxazine dyes|Vital stains |
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