Fluorescent 5-alkynyl-2'-deoxyuridines: high emission efficiency of a conjugated perylene nucleoside in a DNA duplex.
Four fluorescent 5-alkynyl-2'-deoxyuridines were studied in DNA oligonucleotides and their duplexes. The fluorescence response to hybridization differs dramatically for nucleosides containing a perylene fluorochrome either conjugated or not conjugated to the nucleobase. The conjugated nucleoside, 5-(perylen-3-ylethynyl)-2'-deoxyuridine, shows enhanced long-wavelength emission in the DNA duplex, in contrast to the blue fluorescence of perylene on a flexible linker (in 5-[(perylen-3-yl)methoxyprop-1-ynyl]-2'-deoxyuridine), which is quenched upon duplex formation.
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow 117997, Russia.
Mikhail V
MV
Skorobogatyi
Andrei D
AD
Malakhov
Anna A
AA
Pchelintseva
Alexander A
AA
Turban
Stanislav L
SL
Bondarev
Vladimir A
VA
Korshun
D004247:DNA / Q000737:chemistry*; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010569:Perylene / Q000737:chemistry*; D012680:Sensitivity and Specificity; D013050:Spectrometry, Fluorescence / Q000379:methods; D013237:Stereoisomerism; D013696:Temperature
C512128:5-((perylen-3-yl)methoxyprop-1-ynyl)-2'-deoxyuridine; C512127:5-(perylen-3-ylethynyl)-2'-deoxyuridine; D009705:Nucleosides; D009943:Organophosphorus Compounds; D010569:Perylene; D004247:DNA; D003857:Deoxyuridine