Synthesis and conformational analysis of a coumarinic acid-based cyclic prodrug of an opioid peptide with modified sensitivity to esterase-catalyzed bioconversion

Journal of Peptide Research

Volumn 59, Issue 4, 2002, Pages 183-195

  Ouyang, H ^a   Borchardt, R T ^c   Siahaan, T J ^b   Vander Velde, D G ^c  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b UNIVERSITY OF KANSAS   (United States)

^c NONE

Author keywords

Esterase sensitive prodrug; Molecular dynamics simulation; Opioid peptide; Peptide delivery

Indexed keywords

3 (2 HYDROXYPHENYL)ALANINE; ALDEHYDE; BENZOFURAN DERIVATIVE; CARBOXYLIC ACID; ENKEPHALIN[2 DEXTRO ALANINE 5 DEXTRO LEUCINE]; PHENOL DERIVATIVE; PRODRUG; TETRAPEPTIDE;

ARTICLE; CALCULATION; CATALYSIS; CATALYST; CIRCULAR DICHROISM; DILUTION; DRUG CLEARANCE; DRUG CONFORMATION; DRUG DIFFUSION; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; INTESTINE MUCOSA; MOLECULAR DYNAMICS; MOLECULAR SIZE; NUCLEAR MAGNETIC RESONANCE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ANIMALS; BIOTRANSFORMATION; CHEMISTRY, PHYSICAL; CIRCULAR DICHROISM; DRUG RESISTANCE; ENKEPHALIN, LEUCINE-2-ALANINE; ESTERASES; INTESTINAL MUCOSA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES, CYCLIC; PERMEABILITY; PRODRUGS; PROTEIN CONFORMATION; RATS;

EID: 0036209529     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2002.1o983.x     Document Type: Article

References (57)

1. Development of opioid peptide analogs as pharmacologic tools and as potential drugs: Current status and future directions
2. New opioid peptides, peptidomimetics, and heterocyclic compounds from combinatorial libraries
3. From peptides to peptidomimetics: Design of nonpeptide ligands for major histocompatibility proteins
4. Improvement of oral bioavailability: Peptidomimetics and prodrug strategies
5. Peptide metabolism by Gastric, Pancreatic, and Lysosomal proteinases
6. Synthesis of a novel esterase-sensitive cyclic prodrug of a hexapeptide using an (acyloxy)alkoxy promoiety
7. Synthesis of a novel esterase-sensitive cyclic prodrug system for peptides that utilizes a 'trimethyl lock'-facilitated lactonization reaction
8. A coumarin-based prodrug strategy to improve the oral absorption of RGD peptidomimetics
9. Chemical feasibility studies of a coumarin-based prodrug system
10. Coumarin-based prodrugs 2. Synthesis and bioreversibility studies of an esterase-sensitive cyclic prodrug DADLE, an opoid peptide
11. Synthesis and evaluation of the physicochemical properties of esterase-sensitive cyclic prodrugs of opioid peptides using coumarinic acid and phenylpropionic acid linkers
12. Coumarinic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeability
13. Quantitative structure-metabolism relationships: Steric and nonsteric effects in the enzymatic hydrolysis of noncongener carboxylic esters
14. Lipid-induced conformation and lipid-binding properties of cytolytic and antimicrobial peptides: Determination and biological specificity
15. The effect of conformation on the membrane permeation of coumarinic acid- and phenylpropionic acid-based cyclic prodrugs of opioid peptides
16. The effect of conformation of the acyloxyalkoxy-based cyclic prodrugs of opioid peptides on their membrane permeability
17. How do peptides interact with lipid membranes and how does this affect their biological activity?
18. Synthesis and evaluation of novel coumarin-based esterase-sensitive cyclic prodrugs of peptidomimetic RGD analogs with improved membrane permeability
19. Two new improved approaches to the synthesis of coumarin-based prodrugs
20. Improved spectral resolution in cosy 1H NMR spectra of proteins via double quantum filtering
21. The effect of conformation on membrane permeability of an acyloxyalkoxy-linked cyclic prodrug of a model hexapeptide
22. An explanation for the rare occurrence of cis peptide units in proteins and polypeptides
23. An excess acidity analysis of acylal and thioacylal hydrolysis in sulfuric acid. Variation of p with acidity
24. Synthesis and hydrolysis of some pivaloyloxymethyl and pivaloyl derivatives of phenolic compounds
25. Palladium-catalyzed reaction of tributyltin hydride. Selective and very mild deprotection of allyl and allyloxycarbonyl derivatives of amino-acids
26. Amino acid derivatives. I. Carboallyloxy derivatives of alpha-amino acids
27. Selective palladium-catalyzed deprotection of the allyl and allyloxycarbonyl groups in phosphate chemistry and in the presence of propargyl and propargyloxycarbonyl groups
28. The basis for the physiological activity of certain -onium compounds. III. Choline derivatives
29. The preparation of alpha-halogeno-sec.-alkyl esters of aliphatic acids
30. Comments on the preparation of alpha-halogeno-sec.-alkyl esters
31. The preparation of alpha-haloalkyl esters
32. Homogeneous nucleophile exchange. 2. Silver-free, direct synthesis of primary alkyl sulfonates from alkyl halides
33. Metathetical reactions of silver salts in solution. II. The synthesis of alkyl sulfonates
34. Chlorosulfates as reagents in the synthesis of carboxylic acid esters under phase-transfer conditions
35. A simple preparation of chloromethyl esters of blocked amino acids
36. Chemical delivery system for some penicillinase-resistant semisynthetic penicillins
37. Steric hindrance is a key factor in coupling α-haloalkyl ester with phenol
38. Value of the vinyloxycarbonyl unit in hydroxyl protection: Application to the synthesis of nalorphine
39. Synthesis and properties of some hydroxycinnamonyl esters of quinic acid
40. Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives
41. Trichloroethoxycarbonyl: A general applicable protecting group
42. New methods in peptide synthesis. Part III. Protection of carboxyl group
43. The beta-phenacyl ester as a temporary protecting group to minimize cyclic imide formation during subsequent treatment of aspartyl peptides with HF
44. The phenacyl protecting group for acids and phenols
45. Prodrug strategies to enhance the intestinal absorption of peptides
46. Drug-like properties and the causes of poor solubility and poor permeability
47. Effects of a potent and specific P-glycoprotein inhibitor on the blood-brain barrier distribution and antinociceptive effect of morphine in the rat
48. Expression of the apical conjugate export pump, Mrp2, in the polarized hepatoma cell line, WIF-B
49. 33, a substrate and inhibitor of P-glycoproteins, in various concentrations of serum
50. Biochemical, cellular, and pharmacological aspects of the multidrug transporter
51. Characterization of the hepatic canalicular membrane transport of a model oligopeptide: Ditekiren
52. A general pattern for substrate recognition by P-glycoprotein
53. How does P-glycoprotein recognize its substrates?