Investigation of iminosulfuranes as novel transdermal penetration enhancers: Enhancement activity and cytotoxicity

Pharmaceutical Research

Volumn 22, Issue 11, 2005, Pages 1918-1925

  Song, Yifan ^a,f   Xiao, Chunhong ^b   Mendelsohn, Richard ^b   Zheng, Tao ^c   Strekowski, Lucjan ^d   Michniak, Bozena ^a,e  

^a RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

^b RUTGERS UNIVERSITY   (United States)

^c Georgia State University ^*  (United States)

^d GEORGIA STATE UNIVERSITY   (United States)

^e RUTGERS UNIVERSITY   (United States)

^f MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Chemical enhancers; Dimethyl sulfoxide; Iminosulfuranes; Percutaneous penetration; Transdermal drug delivery

Indexed keywords

CAFFEINE; FURAN DERIVATIVE; HYDROCORTISONE; IMINOSULFURANE; LIPID; N (4 BUTYLBENZOYL) S,S DIMETHYLIMINOSULFURANE; N (4 FLUOROBENZOYL) S,S DIMETHYLIMINOSULFURANE; N (4 HEXYLBENZOYL) S,S DIMETHYLIMINOSULFURANE; N (4 IODOBENZOYL) S,S DIMETHYLIMINOSULFURANE; PROTEIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONFOCAL MICROSCOPY; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG MECHANISM; DRUG PENETRATION; DRUG SYNTHESIS; EPIDERMIS CELL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; HYDROGEN BOND; KERATINOCYTE; MALE; MOLECULAR SIZE; MOUSE; NONHUMAN; PARTITION COEFFICIENT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAMAN SPECTROMETRY; SKIN FIBROBLAST; SKIN PERMEABILITY; STRATUM CORNEUM; TOXICITY TESTING;

ADMINISTRATION, CUTANEOUS; ANIMALS; DIMETHYL SULFOXIDE; DRUG DELIVERY SYSTEMS; EPIDERMIS; HYDROCORTISONE; MALE; MICE; MICE, INBRED HRS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SKIN; SKIN ABSORPTION; SULFONES; SULFUR COMPOUNDS;

EID: 27144507787     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-005-7416-4     Document Type: Article

References (28)

1. C. S. Asbill A. F. El-Kattan B. Michniak 2000 Enhancement of transdermal drug delivery: chemical and physical approaches Crit. Rev. Ther. Drug Carrier Syst. 17 621 658
2. R. H. Guy 1998 Iontophoresis-recent developments J. Pharm. Pharmacol. 50 371 374
3. S. Henry D. V. McAllister M. G. Allen M. R. Prausnitz 1998 Microfabricated microneedles: a novel approach to transdermal drug delivery J. Pharm. Sci. 87 922 925
4. S. Mitragotri D. A. Edwards D. Blankschtein R. Langer 1995 A mechanistic study of ultrasonically-enhanced transdermal drug delivery J. Pharm. Sci. 84 697 706
5. J. C. Weaver T. E. Vaughan Y. Chizmadzhev 1999 Theory of electrical creation of aqueous pathways across skin transport barriers Adv. Drug Deliv. Rev. 35 21 39
6. R. B. Stoughton W. Fritsch 1964 Influence of dimethylsulfoxide (DMSO) on human percutaneous absorption Arch. Dermatol. 90 512 517
7. T. Kurihara-Bergstrom G. L. Flynn W. I. Higuchi 1986 Physicochemical study of percutaneous absorption enhancement by dimethyl sulfoxide: kinetic and thermodynamic determinants of dimethyl sulfoxide mediated mass transfer of alkanols J. Pharm. Sci. 75 479 486
8. B. W. Barry 1987 Mode of action of penetration enhancers in human skin J. Control. Release 6 85 97
9. A. M. Kligman 1965 Topical pharmacology and toxicology of dimethyl sulfoxide. 1 JAMA 193 796 804
10. T. M. Sweeney A. M. Downes A. G. Matoltsy 1966 The effect of dimethyl sulfoxide on the epidermal water barrier J. Invest. Dermatol. 46 300 302
11. E. Skog J. E. Wahlberg 1967 Effect of dimethyl sulfoxide on skin. A macroscopic and microscopic investigation on human skin Acta Derm.-Venereol. 47 426 434
12. L. F. Montes J. L. Day C. J. Wand L. Kennedy 1967 Ultrastructural changes in the horny layer following local application of dimethyl sulfoxide J. Invest. Dermatol. 48 184 196
13. J. M. Shackleford K. L. Yielding 1984 Ultrastructural studies of barrier restoration in epidermis of hairless mice following dimethyl sulfoxide application J. Cutaneous Pathol. 11 259 268
14. N. Kim M. El-Khalili M. M. Henary L. Strekowski B. B. Michniak 1999 Percutaneous penetration enhancement activity of aromatic S,S- dimethyliminosulfuranes Int. J. Pharm. 187 219 229
15. L. Strekowski M. Henary N. Kim B. B. Michniak 1999 N-(4-Bromobenzoyl)-S, S-dimethyliminosulfurane, a potent dermal penetration enhancer Bioorg. Med. Chem. Lett. 9 1033 1034
16. T. Mossman 1983 Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 55 63
17. T. Watanabe T. Hasegawa H. Takahashi T. Ishibashi H. Itagaki K. Sugibayashi 2002 Utility of MTT assay in three-dimensional cultured human skin model as an alternative for draize skin irritation test: approach using diffusion law of irritant in skin and toxicokinetics-toxicodynamics correlation Pharm. Res. 19 669 675
18. R. C. Wester H. I. Maibach L. Sedik J. Melendres S. DiZio M. Wade 1992 In vitro percutaneous absorption of cadmium from water and soil into human skin Fundam. Appl. Toxicol. 19 1 5
19. A. M. Kligman E. Christophers 1963 Preparation of isolated sheets of human stratum corneum Arch. Dermatol. 88 70 73
20. H. K. Vaddi P. C. Ho S. Y. Chan 2002 Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry J. Pharm. Sci. 91 1639 1651
21. 2 Molecular Simulation Users Guide, Version 4.6, San Diego, 2001.
22. D. Rogers A. J. Hopfinger 1994 Applications of genetic function approximation to quantitative structure-activity relationships and quantitative structure-property relationships J. Chem. Inf. Comput. Sci. 34 854 866
23. D. Rogers 1994 WOLF 6.2 GFA Program Molecular Simulation Inc. San Diego
24. J. Friedman 1988 Multivariate Adaptive Regression Splines Stanford University Stanford
25. L. C. Fuhrman B. Michniak C. R. Behl A. W. Malick 1997 Effect of novel penetration enhancers on the transdermal delivery of hydrocortisone: an in vitro species comparison J. Control. Release 45 199 206
26. A. K. Ghose V. N. Viswanadhan J. J. Wendoloski 1998 Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: an analysis of ALOGP and CLOGP methods J. Phys. Chem. 102 3762 3772
27. E. W. Smith H. I. Maibach 1995 Percutaneous Penetration Enhancers CRC Press Boca Raton
28. A. N. C. Anigbogu A. C. Williams B. W. Barry H. G. M. Edwards 1995 Fourier transform Raman spectroscopy of interactions between the penetration enhancer dimethylsulfoxide and human SC Int. J. Pharm. 125 265 282