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
[11]  
Li K, 1997, BIOORGAN MED CHEM, V5, P1157
[12]  
Michael K, 1998, CHEM-EUR J, V4, P2091, DOI 10.1002/(SICI)1521-3765(19981102)4:11<2091::AID-CHEM2091>3.0.CO
[13]  
2-3
[14]   SEQUENCE-SELECTIVE DNA RECOGNITION BY SYNTHETIC LIGANDS [J].
NIELSEN, PE .
BIOCONJUGATE CHEMISTRY, 1991, 2 (01) :1-12
[15]   RNA as a drug target [J].
Pearson, ND ;
Prescott, CD .
CHEMISTRY & BIOLOGY, 1997, 4 (06) :409-414
[16]  
REWCASTLE GW, 1985, SYNTHESIS-STUTTGART, P217
[17]   Synthesis and screening of small molecule libraries active in binding to DNA [J].
Shipps, GW ;
Pryor, KE ;
Xian, J ;
Skyler, DA ;
Davidson, EH ;
Rebek, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (22) :11833-11838
[19]   Major groove binding and 'DNA-induced' fit in the intercalation of a derivative of the mixed topoisomerase I/II poison N-(2-(dimethylamino)ethyl)acridine-4-carboxamide (DACA) into DNA:: X-ray structure complexed to d(CG(5-BrU)ACG)2 at 1.3-Å resolution [J].
Todd, AK ;
Adams, A ;
Thorpe, JH ;
Denny, WA ;
Wakelin, LPG ;
Cardin, CJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (04) :536-540
[20]   KINETIC AND EQUILIBRIUM BINDING-STUDIES OF AMSACRINE-4-CARBOXAMIDES - A CLASS OF ASYMMETRICAL DNA-INTERCALATING AGENTS WHICH BIND BY THREADING THROUGH THE DNA HELIX [J].
WAKELIN, LPG ;
CHETCUTI, P ;
DENNY, WA .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (07) :2039-2044