Molecular dynamics and partitioning of di-tert-butyl nitroxide in stratum corneum membranes: Effect of terpenes

Lipids

Volumn 45, Issue 5, 2010, Pages 419-427

  Camargos, Heverton Silva ^a   Silva, Adolfo Henrique Moraes ^a   Anjos, Jorge Luiz Vieira ^a   Alonso, Antonio ^a  

^a FEDERAL UNIVERSITY OF GOIÁS   (Brazil)

Author keywords

EPR; Lipid dynamics; Spin label; Stratum corneum; Terpene

Indexed keywords

CARVONE; CINEOLE; DI TERT BUTYL NITROXIDE; DIMYRISTOYLPHOSPHATIDYLCHOLINE; DIPALMITOYLPHOSPHATIDYLCHOLINE; HYDROCARBON; LIMONENE; NITROXIDE; TERPENE DERIVATIVE; TERPINEOL; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; AQUEOUS SOLUTION; ARTICLE; CELL POLARITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTRON SPIN RESONANCE; HYDROGEN BOND; HYDROPHOBICITY; INFRARED SPECTROSCOPY; LIPID SOLUBILITY; MOLECULAR DYNAMICS; NITROGEN PARTITIONING; NONHUMAN; PARTITION COEFFICIENT; PHASE TRANSITION; RAT; SPIN LABELING; STRATUM CORNEUM;

ANIMALS; ANIMALS, NEWBORN; BUTANES; CELL MEMBRANE; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROCARBONS; MOLECULAR DYNAMICS SIMULATION; MOLECULAR STRUCTURE; RATS; RATS, WISTAR; SKIN; SKIN ABSORPTION; TERPENES; WATER;

EID: 77953232187     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-010-3407-2     Document Type: Article

References (32)

1. MA Yamane AC Williams BW Barry 1995 Effects of terpenes and oleic acid as skin penetration enhancers towards 5-fluorouracil as assessed with time, permeation, partitioning and differential scanning calorimetry Int J Pharm 116 237 251 10.1016/0378-5173(94)00312-S 1:CAS:528:DyaK2MXjs1Gis74%3D
2. S Gao J Singh 1998 In vitro percutaneous absorption enhancement of a lipophilic drug tamoxifen by terpenes J Control Release 51 193 199 10.1016/S0168-3659(97)00168-5 1:CAS:528:DyaK1cXot12ltw%3D%3D 9685917 (Pubitemid 28252871)
3. HK Vaddi PC Ho SY 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 10.1002/jps.10160 1:CAS:528:DC%2BD38XltVyitLo%3D 12115825 (Pubitemid 34680226)
4. SM Al-Saidan 2004 Transdermal self-permeation enhancement of ibuprofen J Control Release 100 199 209 10.1016/j.jconrel.2004.08.011 1:CAS:528: DC%2BD2cXps1Oru7s%3D 15544868 (Pubitemid 39491272)
5. PA Cornwell BW Barry JA Bouwstra GS Gooris 1996 Modes of action of terpene penetration enhancers in human skin; differential scanning calorimetry, small-angle X-ray diffraction and enhancer uptake studies Int J Pharm 127 9 26 10.1016/0378-5173(95)04108-7 1:CAS:528:DyaK28XhtVCgsLw%3D (Pubitemid 26069150)
6. A Alonso NC Meirelles M Tabak 1995 Effect of hydration upon the fluidity of intercellular membranes of stratum corneum: an EPR study Biochim Biophys Acta 1237 6 15 10.1016/0005-2736(95)00069-F 7619844
7. A Alonso NC Meirelles VE Yushmanov M Tabak 1996 Water increases the fluidity of intercellular membranes of stratum corneum: correlation with water permeability, elastic, and electrical properties J Invest Dermatol 106 1058 1063 10.1111/1523-1747.ep12338682 1:CAS:528:DyaK28Xjs1Shtbc%3D 8618039
8. A Alonso NC Meirelles M Tabak 2000 Lipid chain dynamics in stratum corneum studied by spin label electron paramagnetic resonance Chem Phys Lipids 104 101 111 10.1016/S0009-3084(99)00090-0 1:CAS:528:DC%2BD3cXotVKi 10669304 (Pubitemid 30009873)
9. WP De Queiros DD Neto A Alonso 2005 Dynamics and partitioning of spin-labeled stearates into the lipid domain of stratum corneum J Control Release 106 374 385 10.1016/j.jconrel.2005.05.009 16006000 (Pubitemid 41187446)
10. JLV Dos Anjos DD Neto A Alonso 2007 Effects of ethanol/l-menthol on the dynamics and partitioning of spin-labeled lipids in the stratum corneum Eur J Pharm Biopharm 67 406 412 10.1016/j.ejpb.2007.02.004 17350812 (Pubitemid 47211894)
11. JLV Dos Anjos DD Neto A Alonso 2007 Effects of 1,8-cineole on the dynamics of lipids and proteins of stratum corneum Int J Pharm 345 81 87 10.1016/j.ijpharm.2007.05.041 (Pubitemid 350087544)
12. JLV Dos Anjos A Alonso 2008 Terpenes increase the partitioning and molecular dynamics of an amphipathic spin label in stratum corneum membranes Int J Pharm 350 103 112 10.1016/j.ijpharm.2007.08.024 17950546
13. A Alonso JG Dos Santos M Tabak 2000 Stratum corneum protein mobility as evaluated by a spin label maleimide derivative Biochim Biophys Acta 1478 89 101 1:CAS:528:DC%2BD3cXhslals78%3D 10719178
14. A Alonso WP Dos Santos SJ Leonor M Tabak 2001 Stratum corneum protein dynamics as evaluated by a spin-label maleimide derivative: effect of urea Biophys J 81 3566 3576 10.1016/S0006-3495(01)75987-5 1:CAS:528: DC%2BD3MXovVels7w%3D 11721017
15. A Alonso JV Da Silva M Tabak 2003 Hydration effects on the protein dynamics in stratum corneum as evaluated by EPR spectroscopy Biochim et Biophys Acta 1646 32 41 1:CAS:528:DC%2BD3sXhvFGqtLw%3D
16. SG Do Couto MD Oliveira A Alonso 2005 Dynamics of proteins and lipids in the stratum corneum: effects of percutaneous permeation enhancers Biophys Chem 116 23 31 10.1016/j.bpc.2005.01.009 15911079 (Pubitemid 40725821)
17. XY Liu C Nakamura Q Yang N Kamo J Miyake 2002 Immobilized liposome chromatography to study drug-membrane interactions J Chromatogr A 961 113 118 10.1016/S0021-9673(02)00505-8 1:CAS:528:DC%2BD38XltFWjtrg%3D 12186381 (Pubitemid 34765534)
18. P Tammela L Laitinen A Galkin T Wennberg R Heczko H Vuorela JP Slotte P Vuorela 2004 Permeability characteristics and membrane 52 affinity of flavonoids and alkyl gallates in Caco-2 cells and in phospholipids vesicles Arch Biochem Biophys 425 193 199 10.1016/j.abb.2004.03.023 1:CAS:528:DC%2BD2cXjsVWmsLs%3D 15111127 (Pubitemid 38542811)
19. Z Arsov M Schara J Strancar 2002 Quantifying the lateral lipid domain properties in erythrocyte ghost membranes using EPR-spectra decomposition J Magn Reson 157 52 60 10.1006/jmre.2002.2575 1:CAS:528:DC%2BD38XmtlWms7k%3D 12202132
20. D Stopar J Strancar RB Spruijt MA Hemminga 2006 Motional restrictions of membrane proteins: a site-directed spin labeling study Biophys J 91 3341 3348 10.1529/biophysj.106.090308 1:CAS:528:DC%2BD28XhtFensLbI 16905615 (Pubitemid 44788267)
21. Nordio PL (1976) General magnetic resonance theory. In: Berliner LJ (ed) Spin labeling, theory and application. Academic Press, New York, pp 5-51
22. M Tabak A Alonso OR Nascimento 1983 Single-crystal electron-spin- resonance studies of a nitroxide spin label. 1. Determination of the g and A tensors J Chem Phys 79 1176 1184 10.1063/1.445921 1:CAS:528:DyaL3sXkvVWgsb8%3D
23. A Finkelstein 1976 Water and nonelectrolyte permeability of lipid bilayer membranes J Gen Physiol 68 127 135 10.1085/jgp.68.2.127 1:CAS:528: DyaE28XkvVyru7Y%3D 956767
24. PW Wertz DT Downing 1987 Covalently bound v-hydroxyacylsphingosine in the stratum corneum Biochim Biophys Acta 917 108 111 1:CAS:528:DyaL2sXotF2qtw%3D%3D 3790600
25. JA Rogers A Wong 1980 The temperature dependence and thermodynamics of partitioning of phenols in the n-octanol-water system Int J Pharm 6 339 348 10.1016/0378-5173(80)90117-9 1:CAS:528:DyaL3MXnt1Crtg%3D%3D
26. Y-Z Da K Ito H Fujiwara 1992 Energy aspects of oil/water partition leading to the novel hydrophobic parameters for the analysis of quantitative structure activity relationships J Med Chem 35 3382 3387 10.1021/jm00096a014 1:CAS:528:DyaK38XlsFSntbc%3D 1527790
27. EJ Shimshick HM McConnell 1973 Lateral phase separation in phospholipid membranes Biochemistry 12 2351 2360 10.1021/bi00736a026 1:CAS:528: DyaE3sXkt1yltL4%3D 4351059
28. D-C Wang TF Taraschi E Rubin N Janes 1993 Configuration entropy is the driving force of ethanol action on membrane architecture Biochim Biophys Acta 1145 141 148 10.1016/0005-2736(93)90391-C 1:CAS:528:DyaK3sXhtFyktbc%3D 8380716 (Pubitemid 23026363)
29. D Kurad G Jeschke D Marsh 2003 Lipid membrane polarity profiles by high-field EPR Biophys J 85 1025 1033 10.1016/S0006-3495(03)74541-X 1:CAS:528:DC%2BD3sXmtVyks7o%3D 12885649
30. D Marsh C Toniolo 2008 Polarity dependence of EPR parameters for TOAC and MTSSL spin labels: correlation with DOXYL spin labels for membrane studies J Magn Reson 190 211 221 10.1016/j.jmr.2007.11.005 1:CAS:528: DC%2BD1cXosFSlug%3D%3D 18042415
31. B Ongpipattanakul ML Francoeur RO Potts 1994 Polymorphism in stratum corneum lipids Biochim Biophys Acta 1190 115 122 10.1016/0005-2736(94)90040-X 1:CAS:528:DyaK2cXitFWju7k%3D 8110804 (Pubitemid 24066266)
32. STK Narishetty R Panchagnula 2005 Effect of l-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine J Control Release 102 59 70 10.1016/j.jconrel.2004.09.016 1:CAS:528:DC%2BD2MXktVGjtA%3D%3D 15653134 (Pubitemid 40093776)