GelRed

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GelRed
File:GelRed chemical structure.png
Names
Preferred IUPAC name
5,5′-(6,22-Dioxo-11,14,17-trioxa-7,21-diazaheptacosane-1,27-diyl)bis(3,8-diamino-6-phenylphenanthridin-5-ium) diiodide
Other names
Dye No. 35,[1] ET-27[1]
Identifiers
3D model (JSmol)
ChemSpider
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  • 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
    Key: JGBUYEVOKHLFID-UHFFFAOYSA-N
  • c1ccccc1-c2c3cc(N)ccc3c4ccc(N)cc4[n+]2CCCCCC(=O)NCCCOCCOCCOCCCNC(=O)CCCCC[n+]5c6cc(N)ccc6c7ccc(N)cc7c5-c8ccccc8.[I-].[I-]
Properties
C60H72I2N8O5
Molar mass 1239.07 g/mol
Hazards
NFPA 704 (fire diamond)

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0
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Flash point > 100 °C (212 °F; 373 K)
Safety data sheet (SDS) 10,000X in water, Biotium Inc.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1][2]

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.[3] The substance is marketed as a less toxic and more sensitive alternative to ethidium bromide.[3] GelRed is sold as a solution in anhydrous DMSO or ultrapurified water.[3] GelRed is unable to cross cell membranes.[4]

See also

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References

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  1. ^ a b c US application 2010323453, Mao, Fei & Leung, Wai-Yee, "Methods of Using Dyes in Association with Nucleic Acid Staining or Detection and Associated Technology" 
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