Detection of CAG repeat DNA sequences by pyrene-functionalized pyrrole-imidazole polyamides

被引:20
作者
Bando, Toshikazu [1 ]
Fujimoto, Jun [1 ]
Minoshima, Masafumi [1 ]
Shinohara, Ken-ichi [1 ]
Sasaki, Shunta [1 ]
Kashiwazaki, Gengo [1 ]
Mizumura, Masatoshi [1 ]
Sugiyama, Hiroshi [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
关键词
pyrene; excimer; Py-Im polyamide; CAG repeat;
D O I
10.1016/j.bmc.2007.07.055
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Five N-methylpyrrole-N-methylimidazole (Py-Im) polyamides possessing a fluorescent pyrene were synthesized by Fmoc solid-phase synthesis using Py/Im monomers and pyrenylbutyl-pyrrole monomer compound 9. The steady state fluorescence of conjugates 1-5 was examined in the presence and absence of (CAG)(12)-containing oligodeoxynucleotides (ODNs) 1 and 2. Of the conjugates, conjugate I showed no background emission around 470 nm in the absence of ODNs, and a clear increase of emission at 475 run was observed upon addition of ODNs I and 2. The emission of conjugate I at 475 nm increased linearly with the concentration of ODN and the number of CAG repeats. The results indicate that conjugate I efficiently forms a pyrene excimer upon binding in the minor groove of DNA. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6937 / 6942
页数:6
相关论文
共 26 条
[1]   Synthesis and biological properties of sequence-specific DNA-alkylating pyrrole-imidazole polyamides [J].
Bando, Toshikazu ;
Sugiyama, Hiroshi .
ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (12) :935-944
[2]   Solid-phase synthesis of DNA binding polyamides on oxime resin [J].
Belitsky, JM ;
Nguyen, DH ;
Wurtz, NR ;
Dervan, PB .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2767-2774
[3]   Recognition of the DNA minor groove by pyrrole-imidazole polyamides:: Comparison of desmethyl- and N-methylpyrrole [J].
Bremer, RE ;
Szewczyk, JW ;
Baird, EE ;
Dervan, PB .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :1947-1955
[4]   Fluorescent sequence-specific dsDNA binding oligomers [J].
Chenoweth, David M. ;
Viger, Anne ;
Dervan, Peter B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (08) :2216-+
[5]   Intercalating nucleic acids with pyrene nucleotide analogues as next-nearest neighbors for excimer fluorescence detection of single-point mutations under nonstringent hybridization conditions [J].
Christensen, UB ;
Pedersen, EB .
HELVETICA CHIMICA ACTA, 2003, 86 (06) :2090-2097
[6]   Recognition of the DNA minor groove by pyrrole-imidazole polyamides [J].
Dervan, PB ;
Edelson, BS .
CURRENT OPINION IN STRUCTURAL BIOLOGY, 2003, 13 (03) :284-299
[7]   Molecular recognition of DNA by small molecules [J].
Dervan, PB .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (09) :2215-2235
[8]   Pyrenemethyl ara-uridine-2′-carbamate:: A strong interstrand excimer in the major groove of a DNA duplex [J].
Dioubankova, NN ;
Malakhov, AD ;
Stetsenko, DA ;
Gait, MJ ;
Volynsky, PE ;
Efremov, RG ;
Korshun, VA .
CHEMBIOCHEM, 2003, 4 (09) :841-847
[9]   Sequence-specific fluorescence detection of DNA by polyamide-thiazole orange conjugates [J].
Fechter, EJ ;
Olenyuk, B ;
Dervan, PB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16685-16691
[10]   Unambiguous detection of target DNAs by excimer-monomer switching molecular beacons [J].
Fujimoto, K ;
Shimizu, H ;
Inouye, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3271-3275