Synthesis and Opioid Activity of Side-Chain-to-Side-Chain Cyclic Dynorphin A-(1-11) Amide Analogues Cyclized between Positions 2 and 5. 1. Substitutions in Position 3

Journal of Medicinal Chemistry

Volumn 47, Issue 2, 2004, Pages 446-455

  Vig, Balvinder S ^a,d   Murray, Thomas F ^b   Aldrich, Jane V ^c  

^a UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^b UNIVERSITY OF GEORGIA   (United States)

^c UNIVERSITY OF KANSAS   (United States)

^d BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENYLATE CYCLASE; DIPRENORPHINE; DYNORPHIN A DERIVATIVE; DYNORPHIN[1-13]; DYNORPHIN[1-13] AMIDE [CYCLO (DEXTRO ASPARTYL 2,3 DIAMINOPROPIONIC ACID)]; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; ENKEPHALIN[2,5 DEXTRO PENICILLAMINE]; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; TRYPTOPHAN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; GUINEA PIG; ILEUM; LINEAR SYSTEM; MOLECULAR CLONING; NONHUMAN; PEPTIDE SYNTHESIS; RECEPTOR AFFINITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ADENYLATE CYCLASE; ANIMALS; CHO CELLS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRICETINAE; DYNORPHINS; PEPTIDES, CYCLIC; RADIOLIGAND ASSAY; RECEPTORS, OPIOID; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0346962964     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030298e     Document Type: Article

References (40)

1. 5]enkephalin; Dyn A, dynorphin A; ESI-MS, electrospray ionization mass spectrometry; Fmoc, 9-fluorenylmethoxycarbonyl; HOBt, 1-hydroxybenzotriazole; HPLC, high performance liquid chromatography; MALDI-TOF, matrix-assisted laser desorption ionization-time of flight; MBHA, 4-methylbenzhydrylamine; NMM, N-methylmorpholine; PAL, peptide amide linker; Pbf, 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl; PEG, poly(ethylene glycol); Pip, 2-phenylisopropyl; PS, polystyrene; PyBOP, benzotriazol-1-yloxytrispyrrolidinophosphonium hexafluorophosphate; SEM, standard error of the mean; TFA, trifluoroacetic acid; Tos, tosyl.
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