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Enkephalins analogs

It appears from the spectral map that the K-receptor is a highly specific receptor which produces strong contrasts in binding affinities of opioid analgesics. The contrast is most evident in ketazocine, ethylketazocine and buprenorphine which possess much more affinity for the K-receptor than for the two others. The contrast is also strong with dihydromorphine, beta-endorphin, an enkephalin analog and two experimental compounds (LY and FK) which have little or no affinity for the K-receptor. [Pg.405]

DiMaio J, Schiller PW. A cyclic enkephalin analog with high in vitro opiate activity. Proc Natl Acad Sci USA 1980 77 7162-7166. [Pg.175]

DiMaio J, Nguyen TM-D, Lemieux C, Schiller PW. Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogs effect of conformational constraints on opiate receptor selectivity. J Med Chem 1982 25 1432-1438. [Pg.176]

Hussain MA, Seetharam R, Wilk RR, Aungst BJ, Kettner CA (1995) Nasal mucosal metabolism and absorption of pentapeptide enkephalin analogs having varying N-terminal amino acids. J Pharm Sci 84 62-64. [Pg.131]

Development of Cyclic Enkephalin Analogs with High Receptor SpecTn city--------------- ---------------------------------... [Pg.15]

On examination of the structures of the enkephalin and the structure-activity relationships published by late 1980, we were struck two observations. First, highly potent enkephalin analogs could be prepared by substituting Gly-2 by a large variety of D-amlno acids, and Met-5 (or Leu-5) could be replaced by a large variety of L- or D-amlno acid and lead to a potent enkephalin analog. Second, the Gly-2, Met-5 combination Is highly reminiscent of the Met-4, Gly-10 situation In o-MSH. [Pg.17]

Table II. Receptor Blading Affinities of Enkephalin Analogs for [ H]-Labelled Naloxone ([ HJNAL) and [ H)-Labelled CD Ala, D-Leu lEnkephalln (I HlDAPLE) In Rat Brain Homogenates ... Table II. Receptor Blading Affinities of Enkephalin Analogs for [ H]-Labelled Naloxone ([ HJNAL) and [ H)-Labelled CD Ala, D-Leu lEnkephalln (I HlDAPLE) In Rat Brain Homogenates ...
M.M. Hann, P.G. Sammes, P.D. Kennewell, J.B. Taylor, On double bond isosteres of the peptide bond an enkephalin analog, J. Chem. Soc. Chem. Commun. (1980) 234-235. [Pg.730]

The first significant advances towards parenterally-active opioid peptides were made by a Sandoz group (Roemer et al., 1977 Pless et al., 1979). Within the pentapeptide [D-Ala2,MePhe4,Met(0)-ol5]enkephalin (FK 33-824, DAMME) several approaches towards a stable enkephalin analog have been combined. FK 33-824 has been reported to be several orders of magnitude more potent than morphine when applied i.c.v. and to be orally active. [Pg.154]

Mosberg, H.I., Hurst, R., Hruby, V.J., Gee, K., Akiyama. K., Yamamura, H.I., Galligan, J.J., Burks, T.F. Cyclic penicillamine containing enkephalin analogs display profound delta receptor selectivities, Life Sci 1983, 33 Suppl. 1, 447-50. [Pg.158]

Fig. 3. Structure of a cyclic enkephalin analog designed by Schiller and co-workers (DiMaio el al., 1982). Fig. 3. Structure of a cyclic enkephalin analog designed by Schiller and co-workers (DiMaio el al., 1982).
This hypothesis of delta receptors in the mouse vas deferens was later further substantiated by the observation of the lack of cross-tolerance between a stable enkephalin analog [D-Ala2, D-leu5]enkephalin (DADLE, see below) and sulphentanyl (a mu agonist) in this tissue after chronic administration in vivo [8]. [Pg.2]

One of the simplest methods of improving the uptake of a dmg to the brain involves the conversion of the drag to a more lipophilic prodrug (see Section 1.3.4.1). Using this approach, moderate increases in transport across the BBB have been achieved for enkephalin analogs and TRH. [Pg.329]

The 2-nitrile derivative 191 was exploited subsequently 118) to give a methionine enkephalin analog with either (-)- or (+)-metazocine in place of the enkephalin tyrosine unit, by standard chemistry (Scheme 4.19). Each compound was, at best, weakly antinociceptive. [Pg.193]

Finally, reference is made to nmr work on enkephalin analogs with terminal Pro residues that are highly active at /x-receptors (p. 352). Both H... [Pg.368]

Photoaffinity labels have also been investigated. These are enkephalin analogs containing a photosensitive group [e.g., 4-azidophenyl or 2-nitro-4-azidophenyl (NAP)] that form a covalent bond upon irradiation with UV light. Thus, both the peptide 11<37) and the Leu-enkephalins 12(38) bind strongly to brain membranes on photolysis, and the latter pair have been shown to cause a 20-30% inactivation of opioid receptors. Further work on affinity labels and related topics is described in the 1982 and 1983 reports of the International Narcotics Research Conference/39 ... [Pg.455]

Similar stereochemical arguments can be extended to larger peptides. For example, the elution order of diastereoisomeric nonpolar peptides of the type l-X-l-Y-l-Z, l-X-l-Y-d-Z, l-X-d-Y-l-Z can be predicted on conformational grounds to be lll < lld < ldl and this has been observed experimentally, e.g., enkephalin analogs 112). Furthermore, the introduction of the glycinyl residue into an endo position between two chiral amino acids decreases both the k and a values for the dias-tereoisomers 46). [Pg.127]

The work of Veber et al. established that valuable information about the bioactive conformation of a flexible peptide could be obtained by applying the principles of conformational restriction, and several additional examples soon were reported that followed this strategy. Conformationally restricted enkephalin analogs, e.g., 02-13), were formed by cyclizing between positions 2 and 5 of enkephalins (4a-b) (39). Cyclization of a-mela-notropin (14) gave the unusually active analog... [Pg.637]


See other pages where Enkephalins analogs is mentioned: [Pg.402]    [Pg.12]    [Pg.17]    [Pg.18]    [Pg.244]    [Pg.701]    [Pg.352]    [Pg.155]    [Pg.157]    [Pg.458]    [Pg.464]    [Pg.465]    [Pg.4]    [Pg.7]    [Pg.58]    [Pg.65]    [Pg.66]    [Pg.67]    [Pg.67]    [Pg.36]    [Pg.338]    [Pg.345]    [Pg.357]    [Pg.365]    [Pg.372]    [Pg.200]    [Pg.122]   


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Affinity labeling, analogs enkephalins

Enkephalin analogs conformationally restricted

Enkephalin analogs delta receptors

Enkephalin analogs dimeric

Enkephalin analogs receptor binding affinities

Enkephalin analogs with antagonist activity

Enkephalins

Enkephalins cyclic analogs

Leu-enkephalin analogs

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