YOYO-1

YOYO-1

Names
IUPAC name {1,1'-(4,4,8,8-tetramethyl-4,8-diazaundecamethylene)bis[4-[(3-methylbenzo-1,3-oxazol-2-yl)methylidene]-l,4-dihydroquinolinium] tetraiodide}
Other names YOYO, YOYO-1, YoYo-1
Identifiers
CAS Number	143413-85-8
3D model (Jmol)	Interactive image
ChEBI	CHEBI:52947
ChemSpider	4942629
PubChem	6438136
InChI InChI=1S/C49H58N6O2.4HI/c1-50-44-22-11-13-24-46(44)56-48(50)36-38-26-30-52(42-20-9-7-18-40(38)42)28-15-32-54(3,4)34-17-35-55(5,6)33-16-29-53-31-27-39(41-19-8-10-21-43(41)53)37-49-51(2)45-23-12-14-25-47(45)57-49;;;;/h7-14,18-27,30-31,36-37H,15-17,28-29,32-35H2,1-6H3;4*1H/q+4;;;;/p-4 Key: GRRMZXFOOGQMFA-UHFFFAOYSA-J
SMILES CN\1c2ccccc2O/C1=C/c3cc[n+](c4c3cccc4)CCC[N+](C)(C)CCC[N+](C)(C)CCC[n+]5ccc(c6c5cccc6)/C=C\7/N(c8ccccc8O7)C.[I-].[I-].[I-].[I-]
Properties
Chemical formula	C49H58I4N6O2
Molar mass	1270.642 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

YOYO-1 is a green fluorescent dye used in DNA staining.^[1] It belongs to the family of monomethine cyanine dyes and is a tetracationic homodimer of Oxazole Yellow (abbreviated YO, hence the name YOYO), typically available as tetraiodide salt. In aqueous buffer, free YOYO-1 dye (absorption: λ_max 458 nm, emission: λ_max 564 nm) has very low fluorescence quantum yield, however the intensity of fluorescence increases 3200 times upon binding through bis-intercalation to double-stranded DNA (absorption: λ_max 489 nm, emission: λ_max 509 nm).^[2]

Synthesis

YOYO-1 is prepared by alkylation of N,N,N’,N’-tetramethyl-1,3-propanediamine with 2 equivalents of N-(3-iodopropyl) analogue of Oxazole Yellow,^[2] which is available in three steps from 2-mercaptobenzoxazole:^[3]

References

1. Bennink, ML; Schärer, OD; Kanaar, R; Sakata-Sogawa, K; et al. (June 1999). "Single-molecule manipulation of double-stranded DNA using optical tweezers: Interaction studies of DNA with RecA and YOYO-1.". Cytometry Part A. 36 (3): 200–208. doi:10.1002/(SICI)1097-0320(19990701)36:3<200::AID-CYTO9>3.0.CO;2-T.
2. Rye, HS; Yue, S; Wemmer, DE; Quesada, MA; et al. (1992). "Stable fluorescent complexes of double-stranded DNA with bis-intercalating asymmetric cyanine dyes: properties and applications". Nucleic Acids Research. 20 (11): 2803–2812. doi:10.1093/nar/20.11.2803.
3. WO 2010141833, Lee Josephson; Elisabeth Garanger & Scott Hilderbrand et al., "Vital fluorochrome conjugates and methods of use", published 2010-12-09, assigned to The General Hospital Corp