GelRed

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
Jmol interactive 3D	Image
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 Key: JGBUYEVOKHLFID-UHFFFAOYSA-N
SMILES 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
Chemical formula	C60H72I2N8O5
Molar mass	1239.07 g/mol
Hazards
Safety data sheet	10,000X in water, Biotium Inc.
R-phrases	R25 R36/37/38
S-phrases	S22 S24/25 S26 S36/37/39 S45 S53
NFPA 704	0 0 0
Flash point	> 100 °C (212 °F; 373 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

• Ethidium bromide
• GelGreen
• SYBR Green I
• Agarose gel electrophoresis and gel electrophoresis of nucleic acids
• Phenanthridine

References

1. 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. GelRed and GelGreen: Environmentally safe and ultra-sensitive nucleic acid gel stains for replacing EtBr, Biotium Inc., retrieved December 4, 2012