A modified coumarinic acid-based cyclic prodrug of an opioid peptide: Its enzymatic and chemical stability and cell permeation characteristics

Pharmaceutical Research

Volumn 19, Issue 6, 2002, Pages 794-801

  Ouyang, Hui ^a,b   Tang, Fuxing ^a   Siahaan, Teruna J ^a   Borchardt, Ronald T ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

Caco 2 cells; Chemical stability; Enzymatic stability; Esterase sensitive prodrugs; MDCK MDR1 cells; MDCK MRP2 cells; MDCK WT cells; Opioid peptides; Peptide delivery

Indexed keywords

ALDEHYDE; COUMARIN; CYCLOSPORIN A; ELACRIDAR; ENKEPHALIN[2 DEXTRO ALANINE 5 DEXTRO LEUCINE]; GLYCOPROTEIN P; MULTIDRUG RESISTANCE PROTEIN 1; MULTIDRUG RESISTANCE PROTEIN 2; OPIATE PEPTIDE; PRODRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BLOOD BRAIN BARRIER; CELL FREE SYSTEM; CELL GROWTH; CELL LINE; CELL STRAIN CACO 2; CONTROLLED STUDY; DRUG DEGRADATION; DRUG PENETRATION; DRUG STABILITY; GENETIC TRANSFECTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; KIDNEY CELL; LIVER HOMOGENATE; MALE; NONHUMAN; PH; PRIORITY JOURNAL; RAT;

ACIDS; ANIMALS; CACO-2 CELLS; CELL LINE; COUMARINS; DOGS; ENKEPHALIN, LEUCINE-2-ALANINE; ENZYME STABILITY; GENES, MDR; HUMANS; LIVER; MALE; MITOCHONDRIAL PROTEINS; PERMEABILITY; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY; RIBOSOMAL PROTEINS; SACCHAROMYCES CEREVISIAE PROTEINS;

EID: 0036288132     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1016148631055     Document Type: Article

References (47)

1. Improvement of oral bioavailability: Peptidomimetics and prodrug strategies
2. Peptide metabolism by gastric, pancreatic, and lysosomal proteinases
3. Human immunodeficiency virus protease inhibitors: From drug design to clinical studies
4. Optimizing oral absorption of peptides using prodrug strategies
5. Orally active peptidommimetics RGD analogue that are glycoprotein IIb/IIIa antagonists
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. Synthesis and evaluation of the physicochemical properties of esterase- sensitive cyclic prodrugs of opioid peptides using coumarinic acid and phenylpropionic acid linkers
10. Synthesis and evaluation of the physicochemical properties of esterase- sensitive cyclic prodrugs of opioid peptides using an (acyloxy)alkoxy linker
11. Phenylpropionic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeation
12. Synthesis and evaluation of novel coumarin-based esterase-sensitive cyclic prodrugs of peptidomimetic RGD analogs with improved membrane permeability
13. Coumarinic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeability
14. Acyloxyalkoxy-based cyclic prodrugs of opioid peptides: Evaluation of the chemical and enzymatic stability as well as their transport properties across Caco-2 cell monolayers
15. Quantitative structure-metabolism relationships: Steric and nonsteric effects in the enzymatic hydrolysis of noncongener carboxylic esters
16. Synthesis and conformation study of a coumarinic acid-based cyclic prodrug of opioid peptide with modified sensitivity to esterase-catalyzed bioconversion
17. Protocols in the application of Caco-2 cells in measuring permeability coefficient of drugs
18. Esterase-sensitive cyclic prodrugs of peptides: Evaluation of an acyloxyalkoxy promoiety in a model hexapeptide
19. Characterization of the efflux transporter(s) responsible for restricting intestinal mucosa permeation of the coumarinic acid-based cyclic prodrug of the opioid peptide DADLE
20. Characterization of the efflux transporter(s) responsible for restricting intestinal mucosa permeation of the acyloxyalkoxy-based cyclic prodrug of the opioid peptide DADLE
21. Effects of a potent and specific P-glycoprotein inhibitor on the blood- brain barrier distribution and antinociceptive effect of morphine in the rat
22. Dose-dependent pharmacokinetics of cyclosporin A in rats: Events in tissues
23. Expression of the apical conjugate export pump, Mrp2, in the polarized hepatoma cell line, WIF-B
24. Prodrugs of peptides and peptidomimetics for improved formulation and delivery
25. An excess acidity analysis of acylal and thioacylal hydrolysis in sulfuric acid. Variation of p with acidity
26. Effect of size and charge on the passive diffusion of peptides across Caco-2 cell monolayers via the paracellular pathway
27. Association of intestinal peptide transport with a protein related to the cadherin superfamily
28. Transcellular transport of oral cephalosporins in human intestinal epithelial cells, Caco-2: Interaction with dipeptide transport systems in apical and basolateral membranes
29. Active secretion and enterocytic drug metabolism barriers to drug absorption
30. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants
31. Classical and novel forms of multidrug resistance and the physiological functions of P-glycoproteins in mammals
32. Expression of the multidrug resistance gene product (P-glycoprotein) in human normal and tumor tissues
33. Characterization of the hepatic canalicular membrane transport of a model oligopeptide: Ditekiren
34. Conjugate export pumps of the multidrug resistance protein (MRP) family: Localization, substrate specificity, and MRP2-mediated drug resistance
35. Drug export activity of the human canalicular multispecific organic anion transporter in polarized kidney MDCK cells expressing cMOAT (MRP2) cDNA
36. Caco-2 monolayers in experimental and theoretical predictions of drug transport
37. Evidence for different ABC-transporters in Caco-2 cells modulating drug uptake
38. Age-dependent expression of P-glycoprotein gp170 in Caco-2 cell monolayers
39. Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2
40. Cell cultures as tools in biopharmacy
41. A retrovirus carrying an MDR1 cDNA confers multidrug resistance and polarized expression of P-glycoprotein in MDCK cells
42. Are MDCK cells transfected with the human MRP2 gene a good model of the human intestinal mucosa?
43. Are MDCK cells transfected with the human MDR1 gene a good model of the human intestinal mucosa?
44. Availability of PSC833, a substrate and inhibitor of P-glycoproteins, in various concentrations of serum