Design, synthesis, and validation of a branched flexible linker for bioactive peptides

被引:16
作者
Bowen, Martina E.
Monguchi, Yasunari
Sankaranarayanan, Rajesh
Vagner, Josef
Begay, Lucinda J.
Xu, Liping
Jagadish, Bhumasamudram
Hruby, Victor J.
Gillies, Robert J.
Mash, Eugene A. [1 ]
机构
[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
[2] Arizona Canc Ctr, Dept Biochem & Mol Biophys, Tucson, AZ 85724 USA
关键词
D O I
10.1021/jo062276g
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
A branched flexible linker that incorporates a fluorescent dansyl moiety was synthesized and used to connect two high affinity NDP-alpha-MSH ligands or two low affinity MSH(4) ligands. The linker was incorporated into the conjugate by solid-phase synthesis. In vitro biological evaluations showed that potency of binding to the human melanocortin 4 receptor was not diminished for linker-ligand combinations relative to the corresponding ligand alone.
引用
收藏
页码:1675 / 1680
页数:6
相关论文
共 37 条
[1]
Synthesis and fluorescence of N,N,N-trimethyl-2-[methyl (7-nitrobenzo[c][1,2,5]oxadiazol-4-yl) amino]ethanaminium iodide, a pH-insensitive reporter of organic cation transport [J].
Aavula, BR ;
Ali, MA ;
Mash, EA ;
Bednarczyk, D ;
Wright, SH .
SYNTHETIC COMMUNICATIONS, 2006, 36 (06) :701-705
[2]
MASKING THE CARBOXY GROUP AS A 2,6,7-TRIOXABICYCLO[2.2.2]OCTANE - APPLICATION TO THE SYNTHESIS OF ALKYLCOBALOXIMES CONTAINING ESTER AND CARBOXY GROUPS [J].
ATKINS, MP ;
GOLDING, BT ;
HOWES, DA ;
SELLARS, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (05) :207-208
[3]
CARBOCYCLIC RING EXPANSION REACTIONS VIA RADICAL CHAIN PROCESSES .2. [J].
BALDWIN, JE ;
ADLINGTON, RM ;
ROBERTSON, J .
TETRAHEDRON, 1991, 47 (33) :6795-6812
[4]
Solution- and solid-phase synthesis of components for tethered bilayer membranes [J].
Bendavid, A ;
Burns, CJ ;
Field, LD ;
Hashimoto, K ;
Ridley, DD ;
Sandanayake, KRAS ;
Wieczorek, L .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :3709-3716
[5]
ALPHA-MELANOTROPIN - THE MINIMAL ACTIVE SEQUENCE IN THE LIZARD SKIN BIOASSAY [J].
CASTRUCCI, AML ;
HADLEY, ME ;
SAWYER, TK ;
WILKES, BC ;
ALOBEIDI, F ;
STAPLES, DJ ;
DEVAUX, AE ;
DYM, O ;
HINTZ, MF ;
RIEHM, JP ;
RAO, KR ;
HRUBY, VJ .
GENERAL AND COMPARATIVE ENDOCRINOLOGY, 1989, 73 (01) :157-163
[6]
A SHORT 3-COMPONENT TOTAL SYNTHESIS OF 12-HYDROXYEICOSA-5,8,14(Z),10(E)-TETRAENOIC ACID (12-HETE) VIA THE CORRESPONDING KETONE [J].
COREY, EJ ;
KYLER, K ;
RAJU, N .
TETRAHEDRON LETTERS, 1984, 25 (45) :5115-5118
[7]
GANTZ I, 1993, J BIOL CHEM, V268, P15174
[8]
Expression-driven reverse engineering of targeted imaging and therapeutic agents [J].
Gillies, RJ ;
Hruby, VJ .
EXPERT OPINION ON THERAPEUTIC TARGETS, 2003, 7 (02) :137-139
[9]
Gillies Robert J, 2005, Mol Imaging, V4, P98
[10]
CALCIUM-DEPENDENT PROLONGED EFFECTS ON MELANOPHORES OF [4-NORLEUCINE, 7-D-PHENYLALANINE]-ALPHA-MELANOTROPIN [J].
HADLEY, ME ;
ANDERSON, B ;
HEWARD, CB ;
SAWYER, TK ;
HRUBY, VJ .
SCIENCE, 1981, 213 (4511) :1025-1027