Applications of the ion-pair concept to hydrophilic substances with special emphasis on peptides

Pharmaceutical Research

Volumn 14, Issue 2, 1997, Pages 119-127

  Quintanar Guerrero, David ^a   Allémann, Eric ^b   Fessi, Hatem ^c   Doelker, Eric ^b  

^a Universities of Geneva and Lyon   (France)

^b UNIVERSITY OF GENEVA   (Switzerland)

^c UNIVERSITÉ LYON 1   (France)

Author keywords

Counter ions; Ion pair; Ion pair enhanced absorption; Ion pair extraction; Peptides

Indexed keywords

PEPTIDE;

DIELECTRIC CONSTANT; DRUG ABSORPTION; DRUG INTERACTION; DRUG MANUFACTURE; HYDROPHOBICITY; IN VITRO STUDY; ION EXCHANGE; ION PAIR EXTRACTION; IONIZATION; LIPOPHILICITY; MICROENCAPSULATION; PRIORITY JOURNAL; REVIEW; SOLUBILIZATION; TECHNIQUE; THEORY;

ABSORPTION; DRUG COMPOUNDING; IONS; PEPTIDES; PERMEABILITY; SOLUTIONS;

EID: 0030983071     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1012076022420     Document Type: Review

References (53)

1. V. H. L. Lee. Peptide and Protein Drug Delivery. Marcel Dekker, New York, 1991.
2. X. H. Zhou and A. L. W. Po. Peptide and protein drugs: I. Therapeutic applications, absortion and parenteral administration. Int. J. Pharm. 75:97-115 (1991).
3. H. Sesaki, Y. Takakura, and M. Hashida. Chemical modification and disposition of proteins and peptides: Biopharmaceutical aspects. In D. J. A. Cromelin, and K. K. Midha, (eds.), Topics in Pharmaceutical Sciences 1991, Medipharm Scientific Publishers, Stuttgart, 1992, pp. 47-57.
4. S. J. Lee and S. W. Kim. Hydrophobization of ionic drugs for transport through membranes. J. Contr. Rel. 6:3-13 (1987).
5. R. Neubert. Ion pair transport across membranes. Pharm. Res. 6:743-747 (1989).
6. x: never mix a cation with an anion? Pharm. Int. Aug:156-158 (1980).
7. A. T. Florence and D. Attwood. Physicochemical Principles of Pharmacy, Macmillan, London, 1988.
8. G. Schill. High performance ion-pair chromatography. J. Bioch. Biophys. Methods. 18:249-270 (1989).
9. A. Martin. Physical Pharmacy, Lea and Febiger, Philadelphia, 1993.
10. C. A. Kraus. The ion-pair concept: its evolution and some applications. J. Phys. Chem. 60:129-141 (1956).
11. N. Bjerrum. Kgl. Danske Selskab. Matt.-fys. Medd. 7:No. 9 (1926).
12. H. Freiser. Ion pair partition. Acta Pharm. Suec. 9:609-611 (1972).
13. M. Szwarc. Living polymers: a tool in studies of ions and ion-pairs. Science. 170:23-31 (1970).
14. B. M. Atherton and S. Y. Weissman. Association between sodium and naphthalenide ions. J. Am. Chem. Soc. 83:1330-1334 (1961).
15. A. Bult. Ion-pair and metal complex formation in drug analysis. In D. D. Breimerand and P. Speiser (eds.), Topics in Pharmaceutical Sciences 1983, Elsevier, Amsterdam, 1983, pp. 3-14.
16. G. M. Irwin, H. B. Kostenbauder, L. W. Dittert, R. Staples, A. Misher, and J. V. Swintosky. Enhancement of gastrointestinal absorption of a quaternary ammonium compound by trichloroacetate. J. Pharm. Sci. 58:313-315 (1969).
17. M. Akamatsu, Y. Yoshida, H. Nakamura, M. Asao, H. Iwamura, and T. Fujita. Hydrophobicity of di and tripeptides having unionizable side chains and correlation with substituent and structural parameters. Quant. Struct.-Act. Relat. 8:195-203 (1989).
18. A. Adjei, S. Rao, J. Garren, G. Menon, and M. Vadnere. Effect of ion-pairing on 1-octanol-water partitioning of peptide drugs. I: The nanopeptide leuprolide acetate. Int. J. Pharm. 90:141-149 (1993).
19. H. Sadek and R. M. Fuoss. Electrolyte-solvent interaction. IV. Tetrabutylammonium bromide in methanol-carbon tetrachloride and methanol-heptane mixtures. J. Am. Chem. Soc. 76:5897-5901 (1954).
20. S. Winstein, E. Clippinger, A. H. Fainberg, and G. C. Robinson. Salt effects and ion-pairs in solvolysis. J. Am. Chem. Soc. 76:2597-2598 (1954).
21. R. C. Roberts and M. Szwarc. The chemistry of the radical anion of tetraphenylethylene. J. Am. Chem. Soc. 87:5542-5548 (1965).
22. S. J. Lee, T. Kurihara-Bergstrom, and S. W. Kim Ion-paired drug diffusion through polymer membranes. Int. J. Pharm. 47:59-73 (1987).
23. H. Freiser. Relevance of solubility parameter in ion association extraction systems. Anal. Chem. 41:1354-1355 (1969).
24. T. Higuchi, A. Michaelis, and A. Hurwitz. Ion pair extraction of pharmaceutical amines. Anal. Chem. 39:974-979 (1967).
25. R. M. Diamond. Aqueous solution behavior of large univalent ions. A new type of ion-pairing. J. Phys. Chem. 67:2513-2517 (1963).
26. R. Modin and G. Schill. Quantitative determinations by ion-pair extraction. Part 1. Ions pairs of quaternary ammonium ions with organic anions. Acta Pharm. Suec. 4:301-326 (1967).
27. R. Modin and M. Schröder-Nielsen. Quantitative determinations by ion pair extraction. Part 9. Extraction of penicillins with ion-pairing and adduct-forming agents. Acta Pharm. Suec. 8:573-584 (1971).
28. K. S. Murthy, and G. Zografi. Oil-water partitioning of chlorpromazine and other phenotiazine derivatives using dodecane and n-octanol. J. Pharm. Sci. 59:1281-1285 (1970).
29. J.-Y. Carbon, M. l'Her, and J. Courtot-Coupez. Salt effects on the distribution of metal ions and their complexes between water and propylene carbonate. J. Chem. Research. S:344-345 (1978).
30. B. Y. Zaslavsky, N. M. Mestechkina, L. M. Miheeva, and S. V. Rogozhin. Measurement of relative hydrophobicity of amino acid side-chains by partition in an aqueous two-phase polymeric system: Hydrophobicity scale for non-polar and ionogenic side-chains. J. Chromat. 240:21-28 (1982).
31. E. Ivashkiv. Colorimetric determination of peptide antibiotics: In-process assay of cyclic octapeptidic antibiotics in fermentation broths. J. Pharm. Sci. 64:1401-1403 (1975).
32. M. Narita, M. Doi, H. Sugasawa and K. Ishikawa. Syntheses and properties of oligo-L-leucines containing α-amino-isobutyric acid residues. The novel strategy for solubility improvement in helical oligopeptides based on the restriction of the values of the backbone dihedral angles φ and θ of α-aminoisobutyric acid residues. Bull. Chem. Soc. Jpn. 58:1473-1479 (1985).
33. M. Narita, S. Honda, H. Umeyama and S. Obana. The solubility of peptides intermediates in organic solvents. Solubilizing potential of hexafluoro-2-propanol. Bull. Chem. Soc. Jpn. 61:281-284 (1988).
34. P. G. Green, R. H. Guy and J. Hadgraft. In vitro and in vivo enhancement of skin permeation with oleic and lauric acids. Int. J. Pharm. 48:103-111 (1988).
35. L. S. Schanker. On the mechanism of absorption of drugs from the gastrointestinal tract. J. Med. Pharm. Chem. 2:343-359 (1960).
36. E. Susuki, M. Tsukigi, S. Muranishi, H. Sezaki, and T. L. K. Kakemi. The absorption from gut of quinine and chlorpheniramine given with various anionic agents. J. Pharm. Pharmacol. 24:138-144 (1972).
37. A. Ågren, B. Nilsson, R. Sjökvist, and A. Brodin. Penetration of organic compounds and ion pairs trough nylon membranes. Acta Pharm. Suec. 11:523-532 (1974).
38. T. S. Gaginella, P. Bass, J. H. Perrin, and J. J. Valliner. Effect of bile salts on partitioning behavior and GI absorption of a quaternary ammonium compound isopropamide iodide. J. Pharm. Sci. 62:1121-1125 (1973).
39. W. D. Walking, A. C. Bonfilio, and H. Y. Jacoby. Possible ion-pair-mediated absorption of mixidine I: Partitioning and lethality studies. J. Pharm. Sci. 67:945-948 (1978).
40. P. G. Green, J. Hadgraft and G. Ridout. Enhanced in vitro skin permeation of cationic drugs. Pharm. Res. 6:628-632 (1989).
41. B. J. Poulsen, E. Young, V. Coquilla, and M. Katz. Effect of topical vehicle composition on the in vitro release of fluocinolone acetonide and its acetate ester. J. Pharm. Sci. 57:928-933 (1968).
42. X.-H. Zhou, and A. L. W. Po. Peptide and protein drugs: II. Non-parenteral routes of delivery. Int. J. Pharm. 75:117-130 (1991).
43. T. Nishihata, C.-S. Lee, M. Yamamoto, J. H. Rytting, and T. Higuchi. The effects of salicylate on the rectal absorption of phenylalanine and some peptides, and the effects of these peptides on the rectal absorption of cefoxitin and cefmetazole. J. Pharm. Sci. 73:1326-1328 (1984).
44. H. Okada, Y. Yamazaki, Y. Ogawa, S. Hirai, T. Yashiki, and H. Mima. Vaginal absorption of a potent luteinizing hormone releasing hormone analog (leuprolide) in rats I: Absorption by various routes and absorption enhancement. J. Pharm. Sci. 71:1367-1371 (1982).
45. S. Hirai, T. Yashiki, and H. Mima. Mechanism for the enhancement of the nasal absorption of insulin by surfactants. Int. J. Pharm. 9:173-184 (1981).
46. V. H. L. Lee, A. Yamamoto, and U. B. Kompella. Mucosal penetration enhancers for facilitation of peptide and protein drug absorption. Crit. Rev. Ther. Drug Carriers Syst., 8:91-192 (1991).
47. X. H. Zhou, and A. L. W. Po. Effects of cholic acid and other enhancers on the bioavailability of insulin from a subcutaneous site. Int. J. Pharm. 69:29-41 (1991).
48. R. D., Green, J. Hadgraft, and K. R. Brain. Enhanced penetration of peptides through the skin. J. Pharm. Pharmacol. 43:113P(1991).
49. A. Ganem, F. Falson-Rieg, and P. Buri Permeation enhancement for peptide absorption through palatal mucosa. Proc. Sixth Eur. Congr. Biopharm. Pharmacokinet., 1996, pp. 111.
50. Y. Yamakawa, Y. Tsushima R. Machida, and S. Watanabe Preparation of neurotensin analogue-containing poly(dl-lactic acid) microspheres formed by oil-in-water solvent evaporation. J. Pharm. Sci. 81:899-903 (1992).
51. Y. Yamakawa, Y. Tsushima, R. Machida, and S. Watanabe. In vitro and in vivo release of poly(dl-lactic acid) microspheres containing neurotensin analogue prepared by novel oil-in-water solvent evaporation method. J. Pharm. Sci. 81:808-811 (1992).
52. T. Niwa, H. Takeuchi, T. Hino, N. Kunou, and Y. Kawashima. In vitro drug release behavior of D,L lactide/glycolide copolymer (PLGA) nanospheres with nafarelin acetate prepared by a novel spontaneous emulsification solvent diffusion method. J. Pharm. Sci. 83:727-732 (1994).
53. J.-C. Leroux, E. Allémann, E. Doelker, and R. Gurny. New approach for the preparation of nanoparticles by an emulsification-diffusion method. Eur. J. Pharm. Biopharm. 41:14-18 (1995).