{{chembox | verifiedrevid = | ImageFile = GelRed_chemical_structure.png | ImageSize = | ImageFile1 = | ImageFile2 = | PIN = 5,5′-(6,22-Dioxo-11,14,17-trioxa-7,21-diazaheptacosane-1,27-diyl)bis(3,8-diamino-6-phenylphenanthridin-5-ium) diiodide | OtherNames = Dye No. 35,<ref name="US20100323453">{{cite patent | country = US | number = 2010323453 | status = application | title = Methods of Using Dyes in Association with Nucleic Acid Staining or Detection and Associated Technology | invent1 = Mao, Fei | invent2 = Leung, Wai-Yee }}</ref> ET-27<ref name="US20100323453" /> |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 129556851 | UNII_Ref = | UNII = | InChI = InChI=1S/C60H70N8O5.2HI/c61-45-21-25-49-51-27-23-47(63)41-55(51)67(59(53(49)39-45)43-15-5-1-6-16-43)31-11-3-9-19-57(69)65-29-13-33-71-35-37-73-38-36-72-34-14-30-66-58(70)20-10-4-12-32-68-56-42-48(64)24-28-52(56)50-26-22-46(62)40-54(50)60(68)44-17-7-2-8-18-44;;/h1-2,5-8,15-18,21-28,39-42,63-64H,3-4,9-14,19-20,29-38,61-62H2,(H2,65,66,69,70);2*1H | InChIKey = JGBUYEVOKHLFID-UHFFFAOYSA-N | ChEMBL_Ref = | ChEMBL = | StdInChI_Ref = | StdInChI = | StdInChIKey_Ref = | StdInChIKey = | CASNo_Ref = | CASNo = | EINECS = | PubChem =117700725 | ChEBI_Ref = | ChEBI = | SMILES = c1ccccc1-c2c3cc(N)ccc3c4ccc(N)cc4[n+]2CCCCCC(=O)NCCCOCCOCCOCCCNC(=O)CCCCC[n+]5c6cc(N)ccc6c7ccc(N)cc7c5-c8ccccc8.[I-].[I-] | RTECS = | KEGG_Ref = | KEGG = }} |Section2={{Chembox Properties | Formula = C<sub>60</sub>H<sub>72</sub>I<sub>2</sub>N<sub>8</sub>O<sub>5</sub> | MolarMass = 1239.07 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | ExternalSDS = [http://biotium.com/wp-content/uploads/2013/07/MSDS-41003.pdf 10,000X in water, Biotium Inc.] | MainHazards = | FlashPt = > | FlashPtC = 100 | AutoignitionPt = | NFPA-H = 0 | NFPA-F = 0 | NFPA-R = 0 | NFPA-S = }} }}
'''GelRed''' is an intercalating nucleic acid stain used in molecular genetics for agarose gel DNA electrophoresis. GelRed structurally consists of two ethidium subunits that are bridged by a linear oxygenated spacer.<ref name=US20100323453 /><ref name="Biotium_flyer">{{Citation | url = https://biotium.com/wp-content/uploads/2015/12/GelRed-GelGreen-PAGE-Gel-Stains-flyer.pdf | title = GelRed & GelGreen | date = August 21, 2012 | publisher = Biotium Inc. | access-date = December 4, 2012 }}</ref><!-- The compound was identified by comparison of the gel image in Fig. 12 of the patent with the identical gel image in the product information -->
GelRed is a fluorophore, and its optical properties are essentially identical to those of ethidium bromide. When exposed to ultraviolet light, it fluoresces with an orange color that strongly intensifies after binding to DNA.<ref name="Biotium_web">{{Citation|title=GelRed and GelGreen: Environmentally safe and ultra-sensitive nucleic acid gel stains for replacing EtBr|url=https://biotium.com/technology/gelred-gelgreen-nucleic-acid-gel-stains/|publisher=Biotium Inc.|access-date=December 4, 2012}}</ref> The substance is marketed as a less toxic and more sensitive alternative to ethidium bromide.<ref name="Biotium_web" /> GelRed is sold as a solution in anhydrous DMSO or ultrapurified water.<ref name="Biotium_web" /> GelRed is unable to cross cell membranes.<ref>{{Cite book|last1=Carson|first1=Susan|chapter-url=https://www.sciencedirect.com/science/article/pii/B978012385544200003X|title=Molecular Biology Techniques|last2=Miller|first2=Heather B.|last3=Witherow|first3=D. Scott|date=2012-01-01|publisher=Academic Press|isbn=978-0-12-385544-2|edition=3rd|pages=21–29|language=en|chapter=Lab Session 3 - PCR Amplification of egfp and Completion of Vector Preparation|doi=10.1016/B978-0-12-385544-2.00003-X}}</ref>
== See also ==
* Ethidium bromide * GelGreen * SYBR Green I * Gel electrophoresis * Phenanthridine * Molecular genetics {{short description|DNA gel stain for molecular genetics}}
== References ==
<references/>
Category:Aromatic amines Category:Iodides Category:DNA-binding substances Category:Carboxamides Category:Quaternary ammonium compounds Category:Phenanthridine dyes Category:Staining dyes