In vitro evaluation of quercetin-3-O-acyl esters as topical prodrugs

International Journal of Pharmaceutics

Volumn 336, Issue 2, 2007, Pages 257-262

  Montenegro, Lucia ^a   Carbone, Claudia ^a   Maniscalco, Claudio ^a   Lambusta, Daniela ^b   Nicolosi, Giovanni ^b   Ventura, Cinzia A ^c   Puglisi, Giovanni ^a  

^a UNIVERSITY OF CATANIA   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF MESSINA   (Italy)

Author keywords

Human skin; In vitro skin permeation; Quercetin esters; Topical prodrugs

Indexed keywords

PRODRUG; QUERCETIN 3 O ACYL ESTER 1; QUERCETIN 3 O ACYL ESTER 2; QUERCETIN 3 O ACYL ESTER 3; QUERCETIN 3 O ACYL ESTER 4; QUERCETIN 3 O ACYL ESTER 5; QUERCETIN 3 O ACYL ESTER 6; QUERCETIN 3 O ACYL ESTER DERIVATIVE; QUERCETIN BUTYL 3; QUERCETIN DERIVATIVE; QUERCETIN ETHYL 1ESTER; QUERCETIN HEXYL 4 ESTER; QUERCETIN PROPYL 2; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; HUMAN; HUMAN TISSUE; HYDROLYSIS; IN VITRO STUDY; LIPOPHILICITY; PRIORITY JOURNAL; SKIN PERMEABILITY;

ADMINISTRATION, CUTANEOUS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG STABILITY; ESTERS; FLAVONOIDS; HALF-LIFE; HUMANS; HYDROLYSIS; HYDROPHOBICITY; PERMEABILITY; PRODRUGS; QUERCETIN; SKIN; SKIN ABSORPTION; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34247616686     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2006.12.003     Document Type: Article

References (34)

1. Anderson B.D. Prodrugs and their topical use. In: Shah V.P., and Maibach H.I. (Eds). Topical Drug Bioavailability, Bioequivalence and Penetration (1993), Plenum press, New York 69-89
2. Baumann J., Bruchhausen F.V., and Wurm G. Flavonoids and related compounds as inhibitors of arachidonic acid peroxidation. Prostaglandins 20 (1980) 627-639
3. Bickers D.R., and Kappas A. The skin as a site of chemical metabolism. In: Gram T.E. (Ed). Extrahepatic Metabolism of Drugs and other Foreign Compounds (1980), MTP, Lancaster 295-318
4. Bonina F.P., Montenegro L., De Capraris P., Bousquet E., and Tirendi S. 1-Alkylazacycloalkan-2one esters as prodrugs of indomethacin for improved delivery through human skin. Int. J. Pharm. 77 (1991) 21-29
5. Bonina F., Lanza M., Montenegro L., Puglisi C., Tomaino A., Trombetta D., Castelli F., and Saija A. Flavonoids as potential protective agents against photo-oxidative skin damage. Int. J. Pharm. 145 (1996) 87-94
6. Bronaugh R.L., and Stewart R.F. Methods for in vitro percutaneous absorption studies. III. Hydrophobic compounds. J. Pharm. Sci. 73 (1984) 1255-1258
7. Bundgaard H., Mork N., and Hoelgaard A. Enhanced delivery of nalidixic acid through human skin via acyloxymethyl ester prodrugs. Int. J. Pharm. 55 (1989) 91-97
8. Chan S.Y., and Li Wan Po A. Prodrugs for dermal delivery. Int. J. Pharm. 55 (1989) 1-16
9. Crozier A., Jensen E., Lean M.E.J., and McDonald M.S. Quantitative analysis of flavonoids by reversed-phase high performance liquid chromatography. J. Chromatogr. 761 (1997) 315-321
10. Formica J.V., and Regelson W. Review of the biology of quercetin and related flavonoids. Fd. Chem. Toxic. 33 (1995) 1061-1080
11. Guy R.H., and Hadgraf J. Percutaneous penetration enhancement: physicochemical considerations and implications for prodrug design. In: Sloan K.B. (Ed). Prodrugs: Topical and Ocular Delivery (1992), Dekker, New York 1-16
12. Hormann H.P., and Korting H.C. Evidence for the efficacy and safety of topical herbal drugs in dermatology: part I: anti-inflammatory agents. Phytomedicine 1 (1994) 161-171
13. Johansen M., Mollgaard B., Wotton P.K., Larsen C., and Hoelggard A. In vitro evaluation of dermal prodrug delivery-transport and bioconversion of a series of aliphatic esters of metronidazole. Int. J. Pharm. 32 (1986) 199-206
14. Kasting G.B., Smith R.L., and Anderson B.D. Prodrug for dermal delivery: solubility, molecular size and functional group effects. In: Sloan K.B. (Ed). Prodrugs: Topical and Ocular Delivery (1992), Dekker, New York 117-161
15. Katsarou A., Davoy E., Xenos K., Armenaka M., and Theoharides T.C. Effect of an antioxidant (quercetin) on sodium-lauryl-sulfate-induced skin irritation. Contact Dermatitis 42 (2000) 85-89
16. Kligman A.M., and Christophers E. Preparation of isolated sheets of human skin. Arch. Dermatol. 88 (1963) 702-705
17. Kligman A.M. A biological brief on percutaenous absorption. Drug Dev. Ind. Pharm. 70 (1983) 52-56
18. Lambusta D., Nicolosi G., Patti A., and Piattelli M. Enzyme-mediated regioprotection deprotection of hydroxyl-groups in (β)-catechin. Synthesis-Stuttgart 11 (1993) 1155-1158
19. Middleton Jr. E., and Kandswami C. The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer. In: Harborne J.B. (Ed). The Flavonoids. Advances in Research Since 1986 (1994), Chapman and Hall, Cambridge 619-652
20. Morel I., Lescoat G., Cogrel P., Sergent O., Pasdeloup N., Brissot P., Cillard P., and Cillard J. Antioxidant and iron-chelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures. Biochem. Pharmacol. 4 (1993) 13-19
21. Mueller, L.G., 1988. Novel anti-inflammatory esters, pharmaceutical compositions and methods for reducing inflammation. UK Patent GB 2 204 869 A, 23 November.
22. Pannatier A., Jenner P., Testa B., and Etter J.C. The skin as drug-metabolizing organ. Drug Metab. Rev. 8 (1978) 319-343
23. Pignatello R., Montenegro L., Stancampiano A.H.S., Puleo A., and Puglisi G. Synthesis and in vitro skin permeation of naproxen conjugates with α-alkylamino acids. Curr. Drug Deliv. 2 (2005) 185-189
24. Roberts W.J., and Sloan K.B. Correlation of aqueous and lipid solubilities with flux for prodrugs of 5-fluorouracil, theophylline, and 6-mercaptopurine: a Potts-Guy approach. J. Pharm. Sci. 88 (1999) 515-532
25. Roberts W.J., and Sloan K.B. Prediction of transdermal flux of prodrugs of 5-fluorouracil, theophylline, and 6-mercaptopurine with a series/parallel model. J. Pharm. Sci. 89 (2000) 1415-1431
26. Saija A., Tomaino A., Trombetta D., Pellegrino M.L., Tita B., Messina C., Bonina F.P., Rocco C., Nicolosi G., and Castelli F. In vitro antioxidant and photoprotective properties and interaction with model membranes of three new quercetin esters. Eur. J. Pharm. Biopharm. 56 (2003) 167-174
27. Sardone L., Pignataro B., Castelli F., Sampietro M.G., Nicolosi G., and Marletta G. Temperature and pressure dependence of quercetin-3-O-palmitate interaction with a model phospholipid membrane: film balance and scanning probe microscopy study. J. Colloid Inter. Sci. 271 (2004) 329-335
28. Scheuplein R.J., and Blank I.H. Permeability of the skin. Physiol. Rev. 51 (1971) 703-723
29. Sloan K.B. Prodrugs for dermal delivery. Adv. Drug Del. Rev. 3 (1989) 67-101
30. Sloan K.B., Scott W., Ezike-Mkparu U., Murray T., Nickels D., Singh S., Shanks T., Tovar J., Ulmer K., and Waranis R. Topical delivery of 5-fluorouracil and 6-mercaptopurine by their alkylcarbonyloxymethyl prodrugs from water: vehicle effects on design of prodrugs. Pharm. Res. 4 (2003) 639-645
31. Touitou E., and Fabin B. Altered skin permeation of a highly lipophilic molecule: tetrahydrocannabinol. Int. J. Pharm. 43 (1988) 17-22
32. Van Acker S.A.B.E., Van den Berg D.J., Tromp M.N.J.L., Griffoen D.H., van Bennekom W.P., van der Vijgh W.J.F., and Bast A. Structural aspects of antioxidant activity of flavonoids. Free Radic. Biol. Med. 20 (1996) 331-342
33. Wasdo S.C., and Sloan K.B. Topical delivery of a model phenolic drug: alkyloxycarbonyl prodrugs of acetaminophen. Pharm. Res. 21 (2004) 940-946
34. Yano T., Nakagawa A., and Tsuji M. Skin permeability of various non-steroidal antiinflammatory drugs. Life Sci. 39 (1986) 1043-1050