Analysis of noncovalent complexes between human telomeric DNA and polyamides containing N-methylpyrrole and N-methylimidazole by using electrospray ionization mass spectrometry

被引:12
作者
Zhou, J [1 ]
Yuan, G [1 ]
机构
[1] Peking Univ, Dept Biol Chem, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China
关键词
DNA recognition; human telomeric DNA; mass spectrometry; noncovalent interactions; polyamides;
D O I
10.1002/chem.200400803
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Electrospray ionization mass spectrometry (ESI-MS) was used to investigate noncovalent complexes formed between four novel polyamides containing N-methylpyrrole (Py) and N-methylimidazole (1m), and human telomeric DNA. Of the four polyamides investigated, PyPyPygammaImImImbetaDp (3) had the highest binding affinity towards the duplex d(TTAGGGTTAGGG/CCCTAACCCTAA) (D1). Results of competition analysis showed that the polyamides had binding affinities with D1 in the order PyPyPygammaImImImbetaDp (3) > PyPyPyPygammaPyImImPybetaDp (4) > PyPyPybetaImImImbetaDp (2)>ImImImbetaDp (1). MS/MS spectra confirmed that binding between D1 and the hairpin polyamides is more stable than that with the three-ring polyamides. By contrast, in the case of single-stranded d(TTAGGGTTAGGG)(D2), the binding order changes to ImImImbetaDp (1)>PyPyPygammaImImImbetaDp (3) > PyPyPybetaImImImbetaDp (2).
引用
收藏
页码:1157 / 1162
页数:6
相关论文
共 28 条
[1]   Mammalian telomeres and telomerase [J].
Collins, K .
CURRENT OPINION IN CELL BIOLOGY, 2000, 12 (03) :378-383
[2]   Investigation of quadruplex oligonucleotide-drug interactions by electrospray ionization mass spectrometry [J].
David, WM ;
Brodbelt, J ;
Kerwin, SM ;
Thomas, PW .
ANALYTICAL CHEMISTRY, 2002, 74 (09) :2029-2033
[3]   NMR characterization of hairpin polyamide complexes with the minor groove of DNA [J].
deClairac, RPL ;
Geierstanger, BH ;
Mrksich, M ;
Dervan, PB ;
Wemmer, DE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :7909-7916
[4]   Sequence-specific DNA recognition by polyamides [J].
Dervan, PB ;
Bürli, RW .
CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (06) :688-693
[5]   Recognition of the minor groove of DNA by hairpin polyamides containing α-substituted-β-amino acids [J].
Floreancig, PE ;
Swalley, SE ;
Trauger, JW ;
Dervan, PB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) :6342-6350
[6]  
Gabelica V, 1999, J MASS SPECTROM, V34, P1328, DOI 10.1002/(SICI)1096-9888(199912)34:12<1328::AID-JMS889>3.0.CO
[7]  
2-F
[8]   OBSERVATION OF DUPLEX DNA-DRUG NONCOVALENT COMPLEXES BY ELECTROSPRAY-IONIZATION MASS-SPECTROMETRY [J].
GALE, DC ;
GOODLETT, DR ;
LIGHTWAHL, KJ ;
SMITH, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6027-6028
[9]   Regulation of gene expression by small molecules [J].
Gottesfeld, JM ;
Neely, L ;
Trauger, JW ;
Baird, EE ;
Dervan, PB .
NATURE, 1997, 387 (6629) :202-205
[10]   Characterization of low-affinity complexes between RNA and small molecules using electrospray ionization mass spectrometry [J].
Griffey, RH ;
Sannes-Lowery, KA ;
Drader, JJ ;
Mohan, V ;
Swayze, EE ;
Hofstadler, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :9933-9938