GelRed

GelRed
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, ET-27
Identifiers
3D model (JSmol)	Interactive image;
PubChem CID	117700725;
CompTox Dashboard (EPA)	DTXSID701030499 ;
	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 c1ccccc1-c2c3cc(N)ccc3c4ccc(N)cc4[n+]2CCCCCC(=O)NCCCOCCOCCOCCCNC(=O)CCCCC[n+]5c6cc(N)ccc6c7ccc(N)cc7c5-c8ccccc8.[I-].[I-];
Properties
Chemical formula	C60H72I2N8O5
Molar mass	1239.07 g/mol
Hazards
NFPA 704 (fire diamond)	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). Infobox references

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]

References

^ ^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"
^ GelRed & GelGreen (PDF), Biotium Inc., August 21, 2012, retrieved December 4, 2012
^ ^a ^b ^c GelRed and GelGreen: Environmentally safe and ultra-sensitive nucleic acid gel stains for replacing EtBr, Biotium Inc., retrieved December 4, 2012
^ Carson, Susan; Miller, Heather B.; Witherow, D. Scott (2012-01-01). "Lab Session 3 - PCR Amplification of egfp and Completion of Vector Preparation". Molecular Biology Techniques (3rd ed.). Academic Press. pp. 21–29. doi:10.1016/B978-0-12-385544-2.00003-X. ISBN 978-0-12-385544-2.{{cite book}}: CS1 maint: date and year (link)