Naphthalene dicarboxaldehyde as an electrophilic fluorogenic moiety for affinity labeling: Application to opioid receptor affinity labels with greatly improved fluorogenic properties

被引：16
作者：
McCurdy, CR
Le Bourdonnec, B
Metzger, TG
El Kouhen, R
Zhang, Y
Law, PY
Portoghese, PS [1 ]
机构：
[1] Univ Minnesota, Coll Pharm, Dept Med Chem, Minneapolis, MN 55455 USA
[2] Univ Minnesota, Sch Med, Dept Pharmacol, Minneapolis, MN 55455 USA
来源：
JOURNAL OF MEDICINAL CHEMISTRY | 2002年 / 45卷 / 14期
关键词：
D O I：
10.1021/jm015586u
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
To develop ligands with fluorogenic properties amenable for following the kinetics of cross-linking to receptors, a naphthalene dicarboxaldehyde moiety has been attached to an opiate pharmacophore 2 and evaluated in mu opioid receptors. The fluorescence of the benzo[f]isoindole formed upon cross-linking of mu opioid receptors by 2 permitted the time-course of covalent bonding to be followed. This demonstrated proof-of-concept suggests the usefulness of naphthalene dicarboxaldehyde-containing affinity labels as kinetic probes.
引用
收藏
页码：2887 / 2890
页数：4
相关论文
共 13 条
[1]   Probing single secretory vesicles with capillary electrophoresis [J].
Chiu, DT ;
Lillard, SJ ;
Scheller, RH ;
Zare, RN ;
Rodriguez-Cruz, SE ;
Williams, ER ;
Orwar, O ;
Sandberg, M ;
Lundqvist, JA .
SCIENCE, 1998, 279 (5354) :1190-1193
[2]  
COLEMAN RF, 1997, PROTEIN FUNCTION, P155
[3]   NAPHTHALENE-2,3-DICARBOXALDEHYDE CYANIDE ION - A RATIONALLY DESIGNED FLUOROGENIC REAGENT FOR PRIMARY AMINES [J].
DEMONTIGNY, P ;
STOBAUGH, JF ;
GIVENS, RS ;
CARLSON, RG ;
SRINIVASACHAR, K ;
STERNSON, LA ;
HIGUCHI, T .
ANALYTICAL CHEMISTRY, 1987, 59 (08) :1096-1101
[4]  
GILMAN SD, 1995, ANAL METHOD INSTRUM, V2, P133
[5]  
LAI F, 1993, BIOTECHNIQUES, V14, P642
[6]   Reporter affinity labels:: An o-phthalaldehyde derivative of β-naltrexamine as a fluorogenic ligand for opioid receptors [J].
Le Bourdonnec, B ;
El Kouhen, R ;
Lunzer, MM ;
Law, PY ;
Loh, HH ;
Portoghese, PS .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (13) :2489-2492
[7]  
MALLOULI A, 1980, SYNTHESIS-STUTTGART, P689
[8]  
MIURA T, 1986, ANAL SCI, V2, P473
[9]   USE OF 2,3-NAPHTHALENEDICARBOXALDEHYDE DERIVATIZATION FOR SINGLE-CELL ANALYSIS OF GLUTATHIONE BY CAPILLARY ELECTROPHORESIS AND HISTOCHEMICAL-LOCALIZATION ION BY FLUORESCENCE MICROSCOPY [J].
ORWAR, O ;
FISHMAN, HA ;
ZIV, NE ;
SCHELLER, RH ;
ZARE, RN .
ANALYTICAL CHEMISTRY, 1995, 67 (23) :4261-4268
[10]   Affinity labels as tools for the identification of opioid receptor recognition sites [J].
Portoghese, PS ;
El Kouhen, R ;
Law, PY ;
Loh, HH ;
Le Bourdonnec, B .
FARMACO, 2001, 56 (03) :191-196
12