Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA

被引：14

作者：

Burden, JE

Davis, P

Porreca, F

Spatola, AF ^{[1
]}

机构：

[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA

[2] Univ Arizona, Dept Pharmacol, Tucson, AZ 85721 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 24期

关键词：

D O I：

10.1016/S0960-894X(99)00625-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Tyr-c[D-Lys-Phe-Ala], YKFA, is a potent opioid peptide analog with subnanomolar IC(50)s toward mu and delta receptors. Transposing Phe and Tyr, a modification found to promote mu antagonist activity in opioid/somatostatin hybrids, gave surprisingly high mu agonist activities for several related analogs, considering the lack of a 1-position hydroxyl function. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：3441 / 3446

页数：6

相关论文

共 20 条

[1]

DARLAK K, 1991, PEPTIDES 1990, P401

[2] SYNTHESIS AND PHARMACOLOGICAL CHARACTERIZATION INVITRO OF CYCLIC ENKEPHALIN ANALOGS - EFFECT OF CONFORMATIONAL CONSTRAINTS ON OPIATE RECEPTOR SELECTIVITY [J].

DIMAIO, J ;

NGUYEN, TMD ;

LEMIEUX, C ;

SCHILLER, PW .

JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (12) :1432-1438

[3] A CYCLIC ENKEPHALIN ANALOG WITH HIGH INVITRO OPIATE ACTIVITY [J].

DIMAIO, J ;

SCHILLER, PW .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (12) :7162-7166

[4] TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE AS A USEFUL DEPROTECTING REAGENT IN BOTH SOLUTION AND SOLID-PHASE PEPTIDE SYNTHESES [J].

FUJII, N ;

OTAKA, A ;

IKEMURA, O ;

AKAJI, K ;

FUNAKOSHI, S ;

HAYASHI, Y ;

KURODA, Y ;

YAJIMA, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (04) :274-275

[5] OPIOID PEPTIDE PROCESSING AND RECEPTOR SELECTIVITY [J].

HOLLT, V .

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1986, 26 :59-77

[6] RECENT DEVELOPMENTS IN THE DESIGN OF RECEPTOR SPECIFIC OPIOID-PEPTIDES [J].

HRUBY, VJ ;

GEHRIG, CA .

MEDICINAL RESEARCH REVIEWS, 1989, 9 (03) :343-401

[7] EMERGING APPROACHES IN THE MOLECULAR DESIGN OF RECEPTOR-SELECTIVE PEPTIDE LIGANDS - CONFORMATIONAL, TOPOGRAPHICAL AND DYNAMIC CONSIDERATIONS [J].

HRUBY, VJ ;

ALOBEIDI, F ;

KAZMIERSKI, W .

BIOCHEMICAL JOURNAL, 1990, 268 (02) :249-262

[8] IDENTIFICATION OF 2 RELATED PENTAPEPTIDES FROM BRAIN WITH POTENT OPIATE AGONIST ACTIVITY [J].

HUGHES, J ;

SMITH, TW ;

KOSTERLITZ, HW ;

FOTHERGILL, LA ;

MORGAN, BA ;

MORRIS, HR .

NATURE, 1975, 258 (5536) :577-579

[9] DESIGN AND SYNTHESIS OF SOMATOSTATIN ANALOGS WITH TOPOGRAPHICAL PROPERTIES THAT LEAD TO HIGHLY POTENT AND SPECIFIC MU-OPIOID RECEPTOR ANTAGONISTS WITH GREATLY REDUCED BINDING AT SOMATOSTATIN RECEPTORS [J].

KAZMIERSKI, W ;

WIRE, WS ;

LUI, GK ;

KNAPP, RJ ;

SHOOK, JE ;

BURKS, TF ;

YAMAMURA, HI ;

HRUBY, VJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) :2170-2177

[10]

KAZMIERSKI WM, 1995, INT J PEPT PROT RES, V46, P265