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GelRed

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GelRed
Names
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) iodide
Other names
Dye No. 35,[1] ET-27[1]
Identifiers
3D model (JSmol)
  • 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
  • NC1=CC2=C(C(C=CC(N)=C3)=C3C(C4=CC=CC=C4)=[N+]2CCCCCC(NCCCOCCOCCOCCCNC(CCCCC[N+]5=C(C6=CC=CC=C6)C7=C(C=CC(N)=C7)C8=C5C=C(N)C=C8)=O)=O)C=C1.[I-].[I-]
Properties
C60H72I2N8O5
Molar mass 1239.07 g/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
0
0
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 biology for agarose gel electrophoresis. GelRed is structurally closely related to ethidium bromide and consists of two ethidium subunits that are bridged by a linear spacer.[1][2]

Its fluorophore, and therefore its optical properties, are essentially identical to those of ethidium bromide. When exposed to ultraviolet light, it will fluoresce 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 DMSO or, more recently, in water.[3]

See also

References

  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" 
  2. ^ GelRed & GelGreen (PDF), Biotium Inc., August 21, 2012, retrieved December 4, 2012
  3. ^ a b c GelRed and GelGreen: Environmentally safe and ultra-sensitive nucleic acid gel stains for replacing EtBr, Biotium Inc., retrieved December 4, 2012
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