YOYO-1

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YOYO-1
YOYO-1 fluorescent dye.png
Identifiers
CAS number 143413-85-8
PubChem 6438136
ChemSpider 4942629
ChEBI CHEBI:52947
Jmol-3D images Image 1
Properties
Molecular formula C49H58I4N6O2
Molar mass 1270.642 g/mol
Except where noted otherwise, 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: λmax 458 nm, emission: λmax 564 nm) has very low fluorescence quantum yield, however the intensity of fluorescence increases 3200 times upon binding to double-stranded DNA (absorption: λmax 489 nm, emission: λmax 509 nm).[2]

Synthesis[edit]

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]

YOYO-1 synthesis

References[edit]

  1. ^ Bennink, ML; Schärer, OD, Kanaar, R, Sakata-Sogawa, K, Schins, JM, Kanger, JS, de Grooth, BG, Greve, J (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. ^ a b Rye, HS; Yue, S; Wemmer, DE; Quesada, MA; Haugland, RP; Mathies, RA; Glazer, AN (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