Solid-phase synthesis of acridine-peptide conjugates and their analysis by tandem mass spectrometry

被引:30
作者
Carlson, CB [1 ]
Beal, PA [1 ]
机构
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
关键词
D O I
10.1021/ol005809v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel and high-yielding synthesis of 9-anilinoacridine-4-carboxylic acid is reported. This acid has been used in the solid-phase synthesis of a small combinatorial library of acridine-peptide conjugates, Tandem mass spectrometry IES (ES-MS/MS) can be used for structure determination of these compounds at a sensitivity of similar to 10 pmol. This work makes possible the generation of acridine-peptide libraries for the discovery of structure-specific nucleic acid ligands via affinity chromatography selection with mass spectrometric detection.
引用
收藏
页码:1465 / 1468
页数:4
相关论文
共 22 条
[1]   Crystal structure of the topoisomerase II poison 9-amino-[N-(2-dimethylamino)ethyl]acridine-4-carboxamide bound to the DNA hexanucleotide d(CGTACG)2 [J].
Adams, A ;
Guss, JM ;
Collyer, CA ;
Denny, WA ;
Wakelin, LPG .
BIOCHEMISTRY, 1999, 38 (29) :9221-9233
[2]   The binding mode of drugs to the TAR RNA of HIV-1 studied by electric linear dichroism [J].
Bailly, C ;
Colson, P ;
Houssier, C ;
Hamy, F .
NUCLEIC ACIDS RESEARCH, 1996, 24 (08) :1460-1464
[3]   SEQUENCE SPECIFICITY OF THE BINDING OF 9-AMINOACRIDINE-CARBOXAMIDE AND AMSACRINE-4-CARBOXAMIDE TO DNA STUDIED BY DNASE-I FOOTPRINTING [J].
BAILLY, C ;
DENNY, WA ;
MELLOR, LE ;
WAKELIN, LPG ;
WARING, MJ .
BIOCHEMISTRY, 1992, 31 (13) :3514-3524
[4]   Interaction of a DNA-threading netropsin-amsacrine combilexin with DNA and chromatin [J].
BourdouxheHousiaux, C ;
Colson, P ;
Houssier, C ;
Waring, MJ ;
Bailly, C .
BIOCHEMISTRY, 1996, 35 (14) :4251-4264
[5]  
BourdouxheHousiaux C, 1996, ANTI-CANCER DRUG DES, V11, P509
[6]   INTERACTIONS OF ACRIDINE ANTITUMOR AGENTS WITH DNA - BINDING-ENERGIES AND GROOVE PREFERENCES [J].
CRENSHAW, JM ;
GRAVES, DE ;
DENNY, WA .
BIOCHEMISTRY, 1995, 34 (41) :13682-13687
[7]   POTENTIAL ANTI-TUMOR AGENTS .36. QUANTITATIVE RELATIONSHIPS BETWEEN EXPERIMENTAL ANTI-TUMOR ACTIVITY, TOXICITY, AND STRUCTURE FOR THE GENERAL-CLASS OF 9-ANILINOACRIDINE ANTI-TUMOR AGENTS [J].
DENNY, WA ;
CAIN, BF ;
ATWELL, GJ ;
HANSCH, C ;
PANTHANANICKAL, A ;
LEO, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (03) :276-315
[8]   GENERAL-METHOD FOR RAPID SYNTHESIS OF MULTICOMPONENT PEPTIDE MIXTURES [J].
FURKA, A ;
SEBESTYEN, F ;
ASGEDOM, M ;
DIBO, G .
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1991, 37 (06) :487-493
[9]  
GUCLEV VM, 2000, CHEM BIOL, V7, P1
[10]   Characterization of SH2 - Ligand interactions via library affinity selection with mass spectrometric detection [J].
Kelly, MA ;
Liang, HB ;
Sytwu, II ;
Vlattas, I ;
Lyons, NL ;
Bowen, BR ;
Wennogle, LP .
BIOCHEMISTRY, 1996, 35 (36) :11747-11755