DETERMINATION OF THREE ULTRAVIOLET FILTERS IN SUNSCREEN FORMULATIONS AND FROM SKIN PENETRATION STUDIES BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY
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1 Quim. Nov, Vol. 34, No. 5, , 2011 DETERMINATION OF THREE ULTRAVIOLET FILTERS IN SUNSCREEN FORMULATIONS AND FROM SKIN PENETRATION STUDIES BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY Fernnd Mri Pinto Vilel, Yris Mri Fonsec, Fbin T. M. C. Vicentini e Mri José Vieir Fonsec * Deprtmento de Ciêncis Frmcêutics, Fculdde de Ciêncis Frmcêutics de Ribeirão Preto, Universidde de São Pulo, Av. do Cfé, s/n, Ribeirão Preto - SP, Brsil Mri d Penh Henriques do Amrl Deprtmento Frmcêutico, Fculdde de Frmáci e Bioquímic, Universidde Federl de Juiz de For, Cmpus Universitário, Juiz de For - MG, Brsil Not Técnic Recebido em 2/8/10; ceito em 11/11/10; publicdo n web em 25/2/11 An nlyticl procedure to quntify 3-benzophenone, octylmethoxycinnmte nd octylslicylte ws vlidted nd employed to ssess these ultrviolet filters in sunscreen formultions nd from skin penetrtion studies. The effect of the vehicle on the skin retention of these filters ws investigted. HPLC nd extrction procedure were found to be relible when obtining dt for the sunscreen formultions nd for evlution skin penetrtion. The results demonstrted tht crem gel generted higher epiderml concentrtions of these filters thn lotion or crem-bsed formultion. Additionlly, when compring the skin retentions of ech filter using the sme formultion, 3-benzophenone showed the highest skin retention. Keywords: 3-benzophenone; octylmethoxycinnmte; octylslicylte. INTRODUCTION Oxidtive stress nd inflmmtory responses induced by ultrviolet (UV) rdition cn cuse vriety of hrmful effects in skin, including premture photoging nd the induction of immunosuppression nd skin crcinogenesis. 1-3 To limit sun exposure, the government dvises one to wer loose fitting, tightly woven clothing, to sty in the shde between 11.m. nd 3 p.m. nd to use sunscreen with sun protection fctor (SPF) of 15 or higher liberlly repplying every 2 h or fter working, swimming, plying or exercising outdoors. 4,5 The necessity to provide high SPF nd screening efficiency ginst both ultrviolet A (UVA) nd ultrviolet B (UVB) wvelengths hs led to the development of sunscreen formultions with multiple dded sunscreen chemicls. 6 Of the pproved sunscreen chemicls, 3-benzophenone (3-BZ), octylmethoxycycinnmte (OMC), nd octylslicylte (OS) re some of the most common ctive ingredients used in sunscreen formultions. 7 Benzophenones efficiently bsorb both UVA nd UVB rys, nd 3-BZ is the most commonly used in sunscreen formultions. Among the cinnmtes, OMC is the most widely used UVB filter in the world. It is often used in combintion with other filters to chieve high SPF in the finl product. Slicyltes, such s OS, bsorb UVB rdition, re very stble, nd re insoluble in wter. They re commonly used to improve the substntivity of the formultion nd reduce the photodegrdtion of some sunscreens. 8 When formulting sunscreens, the sunscreen gents should remin on the surfce of the skin, ccumulte in the strtum corneum, nd crete brrier ginst UV rdition without trnsdermlly penetrting systemic circultion. 9 Unfortuntely, severl studies hve demonstrted tht some UV filters, such s 3-BZ, OMC, nd OS, cn penetrte the epidermis. 7,10-13 Additionlly, recent reports *e-mil: mgik@fcfrp.usp.br hve shown tht when the filters, 3-BZ, OMC nd octocrylene, penetrte into these nucleted lyers, the levels of rective oxygen species produced nturlly by the epiderml chromophores under UV illumintion increse. 14 It is importnt to consider tht sunscreen formultions re pplied to lrge re of the body nd for long periods of time, producing constnt nd high input of the chemicl into the vible skin lyer nd into systemic circultion. 3 The development of formultions nd the synthesis of new sunscreen molecules with good substntivity hve been of gret interest to decrese bsorption nd to improve the sfety nd effectiveness of the topicl sunscreen formultions In this context, it is of gret importnce to develop dequte, relible nd sensitive new techniques to extrct nd quntify the sunscreens in the formultions nd from the skin smples. These techniques cn then id in the sfety of sunscreen formultions becuse studies hve lso demonstrted tht UV filters cn be found in the deeper lyers of the skin, in urine, in plsm, nd even in brestmilk. 7,10-13,18 First in this study, reverse phse-high-performnce liquid chromtogrphy (RP-HPLC) technique nd n extrction procedure for simultneous determintion of the three UV filters in the sunscreen formultions, nd from skin smples were developed nd vlidted. Second, the pplicbility of this method for determining skin penetrtion ws investigted. Lst, the effects of the three different sunscreen formultions were investigted by testing the skin penetrtion of 3-BZ, OMC, nd OS in vitro. EXPERIMENTAL Regents 3-benzophenone (99.9%, Eusolex 4360), octylmethoxycinnmte (99.9%, Eusolex 2292), nd octylslicylte (99.8%, Eusolex OS) were purchsed from Merck (Drmstdt, Germny). Acetic cid (chromtogrphic grde) ws supplied by Merck (Drmstdt, Germny) nd methyl
2 880 Vilel et l. Quim. Nov lcohol (MeOH) for use in the chromtogrph ws purchsed from J. T. Bker (USA). The wter used to prepre the solutions nd the mobile phse ws purified by Milli-Q-plus System (Millipore, Bedford, MA, USA). Ethyl lcohol ws supplied from Synth (So Pulo, Brzil). All of the rw mterils used for the formultions were purchsed from Glen (Cmpins, SP, Brzil) or Clrint (So Pulo, SP, Brzil). All other chemicls were of regent grde nd were used without further purifiction. Sunscreen formultions The study ws performed using 3 model formultions of sunscreen: crem, lotion nd crem gel, ech contining mixture of the 3 orgnic UV filters. 3-BZ (4.0%, w/w), OMC (7.5%, w/w), nd OS (5.0%, w/w) were incorported into the formultions t room temperture 24 h fter their preprtion, nd the ph ws djusted to 6.0 using minomethylpropnol. 3-BZ ws first solubilized in propylene glycol nd ws then incorported into the formultions. Blnk formultions were prepred contining ll of the components without the UV filters. The percent composition of ech formultion is described in Tble 1. Tble 1. Percent composition (w/w) of the formultions Component Crem Lotion Crem gel Polwx Crbopol 940 b Cetyl lcohol Steric cid Gliceryl monosterte Propylprben Methylprben EDTA Propylene glycol Distilled wter Self-emulsifying wx (cetosteryl lcohol nd polyoxyethylene derived from ftty cid ester sorbitn 2OE). b Anionic hydrophilic colloid (crboxypolymethylene). Determintion of 3-benzophenone, octylmethoxycinnmte nd octylslicylte by HPLC Chromtogrphic conditions The presence of the UV filters 3-BZ, OMC, nd OS, ws determined using Shimdzu (Kyoto, Jpn) liquid chromtogrph system equipped with n LC-10 AT VP solvent pump unit nd n SPD-10A VP UV-Visible detector operting t 305 nm. Seprtion ws performed on Supelcosil TM LC-18 (25 cm x 4.6 mm, 5 µm) column equipped with C-18 (4 x 4 mm, 5 µm, Merck) precolumn. This procedure ws dpted from previously described techniques. 19,20 The mobile phse ws MeOH/wter (84:16, v/v) mixture contining 0.1% (v/v) cetic cid. The flow rte ws 1 mlmin -1, nd the system ws run t room temperture. Dt were collected using Chromtopc C-R6A integrtor (Shimdzu, Kyoto, Jpn). All solutions nd solvents were filtered through Millipore filter membrne (pore size = 0.45 µm) nd were vcuum degssed by soniction before use. Stndrd solution Stndrd solutions of the UV filters were prepred dily. The individul solutions of ll of the UV filters were prepred by dissolving g of smples in 25 ml of mobile phse followed by ultrsoniction t room temperture for 15 min. This solution ws further diluted (10x) in mobile phse. Stndrd solutions with concentrtions of t 4 mg/ml for 3-BZ, 7.5 mg/ml for OMC, nd 5 mg/ ml for OS were prepred. All smples were quntified by compring the pek res of the smples with the pek res of the reference substnces present in the stndrd solution. Method vlidtion Vlidtion ws performed following the ICH guidelines. 21 The method ws vlidted considering the prmeters of linerity, ccurcy, precision, specificity nd the limits of detection nd quntittion. Linerity ws tested using the stndrd solutions of 3-BZ, OMC, nd OS. Clibrtion curves were prepred using 5 different concentrtions of ech of the UV filters ( mg/ml) nd were nlyzed by the liner regression of the pek res versus the UV filter concentrtions. Precision ws expressed s reltive stndrd devition (RSD%) nd ws determined by repetbility (intr-dy) nd intermedite precision (inter-dy). Repetbility ws evluted by the nlysis of six replictes of ech experiment during the sme dy nd under the sme experimentl conditions. The intermedite precision ws tested by ssying six replictes on three different dys. The concentrtions used were 4.0 mg/ml for 3-BZ, 7.5 mg/ml for OMC, nd 5.0 mg/ml for OS. Accurcy ws determined bsed on recovery tests performed by dding known mounts of the UV filters to blnk formultions. Smples of 0.05 g of the formultions contining ll three UV filters were dissolved into 50 ml of ethnol. For the preprtion of smples of the low, medium nd high concentrtion, 0.8, 1.0, nd 1.2 ml, respectively, of these solutions were diluted with mobile phse in 10-mL volumetric flsk. Ech of the solutions were filtered nd injected into the HPLC system. Accurcy ws expressed s percent of recovery, which ws estimted from the reltionship between the experimentl nd theoreticl concentrtions ((C e /C t ) x 100). The detection limit (LD) nd quntittion limit (LQ) were determined from the stndrd devition of the response nd from the slope of the constructed clibrtion curve. The LD ws expressed s (3.3 x ơ)/s nd, the LQ ws expressed s (10 x ơ)/s, where ơ is the stndrd devition of the response nd S is the slope of clibrtion curve. The specificity ws determined by compring the results obtined by the nlyses of the stndrd solution, of the blnk formultion nd of the formultions contining the three UV filters. Applicbility of the technique In this study, the pplicbility of the HPLC technique for the nlysis of the in vitro retention studies of the topicl formultions spiked with 3-BZ, OMC, nd OS ws investigted by treting the pig er skin sections (re of 1.77 cm 2 ) with methnolic solutions of the UV filters, prepred s described below. These methnolic solutions consisted of 0.5, 0.1 or 0.02% of the UV filters contined in 300 mg of the formultion in every 100 µl of smple. The treted skin sections were llowed to rest for 30 min before they were submitted to the extrction process (procedure described below). The UV filters extrcted from these skin sections were quntified by HPLC, nd the pig skin sections without ddition of ny solution were lso nlyzed. In vitro skin penetrtion To conduct this study the skin from the outer surfce of n excised porcine er ws used. Pig ers were obtined within 2 h fter the
3 Vol. 34, No. 5 Determintion of three ultrviolet filters in sunscreen formultions 881 slughter of the nimls. The whole skin membrne ws crefully removed from the underlying crtilge with sclpel. Additionlly, the subcutneous tissues were removed, nd the skin ws stored t -20 C for mximum period of 30 d before use. 22,23 A Frnz diffusion cell (diffusion res of 1.77 cm 2 ) ws used to perform the study, with the strtum corneum fcing the donor comprtment (where the formultion ws pplied) nd the dermis fcing the receptor comprtment. The receptor chmber contined 150 mm of phosphte buffer (ph 7.2) in polyoxyethylene (20) sorbitn monolurte (Tween 20 ) (0.5%, v/v), nd the fluid ws mntined under constnt stirring nd temperture (37 ± 0.5 o C). 24 The formultions crem, lotion, nd crem gel, contining UV filters nd unloded formultions (300 mg of ech) were pplied to the surfce of the strtum corneum, while voiding light exposure. Six hours post-ppliction of the formultions, the skin surfces were wiped with cotton swb to remove ny excess formultion. To seprte the strtum corneum from the remining epidermis nd dermis, the skin sections were subjected to tpe stripping with 15 pieces of dhesive tpe. The remining epidermis nd dermis were cut in smll pieces, bth sonicted for 30 min in 2.5 ml of MeOH, vortex mixed for 1 min nd centrifuged for 15 min t rpm. The superntnt ws trnsferred to 5 ml volumetric flsk. To the remining precipitte, 2.5 ml of methnol ws dded, nd the extrction procedure ws repeted. The superntnt of the second extrction ws dded to the previous smple in the volumetric flsk, nd these smples were diluted with methnol to fill the flsk. The resulting mixture ws filtered using 0.45-µm membrne, nd the sunscreens were ssyed by HPLC, s described previously. Sttisticl nlysis Dt were sttisticlly nlyzed by one-wy ANOVA, followed by Bonferroni s multiple comprison t-tests. The level of significnce ws set to p-vlue < RESULTS Determintion of 3-benzophenone, octylmethoxycinnmte nd octylslicylte by HPLC The chromtogrphic nlysis for the quntittive determintion of the UV filters ws vlidted ccording to ICH guidelines 21 to obtin reproducible nlyses with high ccurcy nd precision in the rnge of the concentrtions investigted. The proposed HPLC technique enbled the seprtion nd quntittive determintion of the three UV filters present in the sunscreen formultions nd from the porcine skin smples. Isocrtic elution with MeOH/wter (84:16, v/v) contining 0.1% (v/v) cetic cid ws found to be simple in comprison to other studies tht used grdient elution techniques. 7 As demonstrted in Figure 1, 3-BZ, OMC, nd OS hd reten tion times of pproximtely 6, 17, nd 19 min, respectively, llowing for the rpid determintion of these UV filters, which is essentil for routine nlysis. Furthermore, the specificity study showed tht the blnk formultions did not disply interference with regrd to the chromtogrphic chrcteristics. Additionlly, in the presence of the different formultion components, the chromtogrphic profiles of 3-BZ, OMC, nd OS (retention times nd res) were not ffected (dt not shown). The clibrtion curves were liner within the concentrtion rnge of µg/ml for ech of the UV filters, nd the regression nlyses gve the following representtive liner equtions: y = 41490x for 3-BZ, y = 60800x for OMC, nd y = 15350x for OS. The correltion coefficients (r) were ll bove Figure 1. Chromtogrm of the stndrd solution for (A) 3-benzophenone (4.0 µg/ml), (B) octylmethoxycinnmte (7.5 µg/ml), nd (C) octylslicylte (5.0 µg/ml) The detection limits of 3-BZ, OMC, nd OS were 0.36, 0.38, nd 0.27 µg/ml, respectively, nd the quntittion limits were 1.12, 1.15, nd 0.81 µg/ml, respectively. The precision of the method ws determined by repetbility (intr-ssy) nd intermedite precision (inter-ssy), nd is shown s the reltive stndrd devition (R.S.D%). The repetbility nd intermedite precision for the three sunscreens were ll less thn 5% which cn be considered stisfctory for the purpose of this nlysis (Tble 2). Tble 2. Precision of the HPLC technique for the quntifiction of the UV filters in the sunscreen formultions The ccurcy for the detection of the UV filters in the formultions vried from % for the crem, % for the lotion, nd % for the crem gel (Tble 3). These results cn be ccepted due to the complexity of the cosmetic formultion determintion. 25 Applicbility of the technique The recoveries of 3-BZ, OMC, nd OS from the skin smples were ll bove 70% (Tble 4). Therefore, the combined procedures for the extrction nd HPLC ssying of these sunscreen gents in the skin smples re efficient in terms of recovery nd fst mnipultion. In vitro skin penetrtion Inter-dy vrition RSD RSD RSD% 3-BZ (4 µg/ml) OMC (7.5 µg/ml) OS (5 µg/ml) Intr-dy vrition b 3-BZ (4 µg/ml) OMC (7.5 µg/ml) OS (5 µg/ml) The results re presented s the men ± the stndrd devition (SD). Six replictes were ssyed on three different dys. b Six replictes were ssyed on the sme dy. As demonstrted by Figure 2 nd Tble 5, 3-BZ, OMC, nd OS showed potentil for skin penetrtion in the crem, lotion, nd crem gel formultions.
4 882 Vilel et l. Quim. Nov Tble 3. Accurcy of the HPLC technique for the quntifiction of the UV filters in the sunscreen formultions Theoreticl concentrtion 3-BZ Experimentl concentrtion Experimentl concentrtion Experimentl concentrtion ± ± ± ± ± ± ± ± ± OMC ± ± ± ± ± ± ± ± ± OS ± ± ± ± ± ± ± ± ± The results re the men ± SD of three experiments. Tble 4. Recoveries of 3-benzophenone, octylmethoxycinnmte, nd octylslicylte extrcted from the vible epidermis nd dermis The crem gel formultion provided the highest retention of the sunscreens in the epidermis nd dermis, while the skin retentions of the crem nd lotion emulsions were not significntly different. The skin retention of 3-BZ in the crem gel ws 1.9- nd 1.8-fold higher thn in the crem nd lotion, respectively. The skin retention of OMC when the crrier ws crem gel ws 2.86 nd 3.66 higher thn when the crem nd lotion, respectively, were used. Finlly, the skin retention of OS in the crem gel ws 2.53 nd 3.22 higher thn in the crem nd lotion formultions, respectively. DISCUSSION Theoreticl concentrtion (µg) Experimentl concentrtion (µg) 3-BZ ± ± ± OMC ± ± ± OS ± ± ± BZ, OMC, nd OS, ech in 100 µl methnolic solution dded to the skin smples. The results re the men ± SD of three experiments. Considering the gret necessity for the development of dequte, relible nd sensitive techniques to extrct nd quntify the sunscreens in the formultions nd from the skin smples s well s to ensure the sfety of the sunscreen formultions, the present study imed to develop nd vlidte RP-HPLC technique for the nlysis of three UV filters found in sunscreen formultions nd skin smples. In ddition, the in vitro skin penetrtion effects of three different sunscreen formultions contining UV filters were investigted. The vlues obtined for linerity, precision, ccurcy, detection limit nd quntittion limit were in ccordnce with the ICH guidelines, 21 which indicte tht the chromtogrphic conditions used re relible to quntify 3-BZ, OMC, nd OS in the rnge evluted. Figure 2. HPLC chromtogrms of the skin retentions for the three sunscreen formultions crem gel (A), crem (B), nd lotion (C) contining the UV filters Moreover, no interference from the formultions nd the extrcted skin endogenous compounds were observed, indicting the pplicbility of this technique with the in vitro retention studies of the topicl formultions contining the UV filters. Considering the significnt difference between the retention vlues of the sunscreen incorported into the crem gel in comprison with the other formultions, it might be suggested tht the ffinities of the sunscreens to the vehicles differed. The crem nd lotion formultions hve higher oil contents thn the crem gel; therefore, the UV filters, which hve high lipophilic chrcteristics, most likely remin in the crem nd lotion formultions. Thus, the UV filter in these formultions would not s redily penetrte the skin. Studies hve shown tht emulsion-gel provides greter retention of 3-BZ, OMC, nd OS in the epidermis compred to the petroleum jelly. 13 Additionlly, the penetrtions nd strtum corneum retentions of the UV filters re formultion dependent. 10 Therefore, corroborting with Treffel nd Gbrd 13 nd Gupt et l., 10 the formultiondependent skin penetrtions of the investigted UV filters were detected in the present study. Also for these resons, the vehicle should be crefully chosen to prevent the skin penetrtion of the cosmetic formultions contining the sunscreen gents. In compring the skin retentions of ech UV filter in the sme formultion, expressed s percentges of the pplied doses, 3-BZ showed higher skin retention thn the other two filters. This difference in the 3-BZ retention, when compred to those of OMC
5 Vol. 34, No. 5 Determintion of three ultrviolet filters in sunscreen formultions 883 Tble 5. Amount of UV filters retined in the epidermis nd dermis for the three formultions fter 6 Retention Retention b Retention Retention b Retention Retention b 3-BZ ± 5.97 * 0.41 ± 0.09 * ± ± ± ± 0.02 OMC ± 9.91 * 0.26 ± 0.07 * ± ± ± ± 0.03 OS ± 5.85 * 0.22 ± 0.06* 7.24 ± ± ± ± 0.02 The UV filter retentions re expressed s µg/cm 2. b The UV filter retentions re expressed s percentges of the pplied doses. Results re represented s mens ± SD (n =6). Sttisticl nlysis ws performed by one-wy ANOVA followed by Bonferroni s test of the multiple comprisons. *Significnt sttisticl difference compred to the crem nd lotion formultions (p < 0.05). nd OS, ws pproximtely 1.7-, 2.6-, nd 3.3-fold higher in the crem gel, crem, nd lotion formultions, respectively. These results my be ttributed to the different physicl chrcteristics nd chemicl properties of ech UV filter; these properties ffect the penetrbility of the compounds into the strtum corneum nd into the deeper lyers of skin. 3-BZ is chrcterized by reltively low moleculr weight (228.25) nd log P of which suggest tht 3-BZ hs good bility to penetrte the skin. 26 Comprtively, the oil-wter prtition coefficients (octnol/wter prtition) for OMC nd OS re 5.96 nd 6.02, respectively, indicting they re both highly lipophilic. Due to these high lipophilicities, it is likely tht the compounds re cpble of ccumulting nd forming reservoirs within the lipid phses of the strtum corneum. Additionlly, these gents would hve difficulty penetrting the vible epidermis becuse of the hydrophilic nture of this lyer. 27 In other words, these chrcteristics explin the superior penetrting cpbility of 3-BZ into the skin when compred to OMC nd OS. Furthermore, Gupt et l. 10 showed tht 3-BZ presented higher penetrtion into the vible epidermis nd dermis, wheres the OMC showed better retention in the strtum corneum. CONCLUSION The results demonstrte tht the proposed chromtogrphic technique is useful nd relible tool for the nlysis of sunscreens in formultions nd from skin smples. It not only provided the detection nd quntifiction of the microquntities in the smples, but it lso eliminted most of the interference problems cused by the formultions nd the skin in the smples. In other words, this technique should enble the development of studies nd qulity controls of the sunscreen formultions. Furthermore, crem gel formultion generted the highest epiderml concentrtion of the studied UV filters, nd by compring the skin retention mounts of ech sunscreen in the sme formultion, 3-BZ showed the highest skin retention bility. Therefore, formultions must be developed to minimize the penetrtion of these UV filters into the deeper lyers of skin, nd they must tke into ccount the physicl nd chemicl properties of the sunscreen formultion components nd of the UV filters. Additionlly, it is indispensble tht penetrtion studies of the sunscreens into the skin be developed to ensure the sfety of the sunscreen formultions. ACKNOWLEDGMENTS The uthors re grteful to Fundção de Ampro à Pesquis do Estdo de São Pulo (FAPESP, Brzil), Conselho Ncionl de Desenvolvimento Científico e Tecnológico (CNPq, Brzil) nd Coordenção de Aperfeiçomento de Pessol de Nível Superior (CAPES, Brzil) for finncil support nd for grnting reserch fellowship. F. M. P. Vilel ws the recipient of FAPESP fellowship (process # 2009/ ). REFERENCES 1. Hllidy, G. M.; Mutt. Res. 2005, 571, Hnson, K. M.; Clegg, R. M.; Photochem. Photobiol. 2002, 76, Touitou, E.; Godin, B.; Clin. Dermtol. 2008, 26, cessed in Februry Rmpul, A.; Prkin, I. P.; Crmer, L. P.; J. Photochem. Photobiol., A 2007, 191, Flor, J.; Dvolos, M. R.; Corre, M. A.; Quim. Nov 2007, 30, Srveiy, V.; Risk, S.; Benson, H. A. E.; J. Chromtogr., B: Anl. Technol. Biomed. Life Sci. 2004, 803, Antoniou, C.; Kosmdki, M. G.; Strtigos, A. J.; Ktsmbs, A. D.; J. Eur. Acd. Dermtol. Venereol. 2008, 22, Klinubol, P.; Aswnond, P.; Wnichwechrungrung, S. P.; Skin Phrmcol. Physiol. 2008, 21, Gupt, V. K.; Ztz, J. L.; Rerek, M.; Phrm. Res. 1999, 16, Jnju, N. R.; Mogensen, B.; Andreson, A. M.; Petersen, J. H.; Henriksen, M.; Skkkebek, N. E.; Wulf, H. C.; J. Invest. Dermtol. 2004, 123, Jing, R.; Roberts, M. S.; Collins, D. M.; Benson, H. A. E.; Br. J. Clin. Phrmcol. 1999, 4, Treffel, P.; Gbrd, B.; Phrm. Res. 1996, 13, Hnson, K. M.; Grtton, E.; Brdeen, C. J.; Free Rdicl Biol. Med. 2006, 41, Anselmi, C.; Centini, M.; Rossi, C.; Ricci, M.; Rstrelli, A.; Andressi, M.; Buonocore, A.; L Ros, C.; Int. J. Phrm. 2002, 242, Brry, B. W.; Dermtologicl formultions: percutneous bsorption, M. Dekker: New York, Monti, D.; Settone, M. F.; Centini, M.; Anselmi, C.; Int. J. Cosmet. Sci. 1993, 15, Hny, J.; Ngel, R.; Dtsch. Lebensmitt. Rundsch. 1991, 91, Gspr, L. R.; Mi Cmpos, P. M. B. G.; Int. J. Phrm. 2006, 307, Sntoro, M. I. R. M.; Oliveir, D. A. G. C. E.; Kedor-Hckmnn, E. R. M.; Singh, A. K.; Int. J. Phrm. 2005, 297, Interntionl Conference on Hrmoniztion (ICH), ICH Hrmonized triprtite guideline, Topic Q2B; Note for guidelines on Vlidtion of Anlyticl Procedures: Methodology, Csgrnde, R.; Georgetti, S. R.; Verri Jr, W. A.; Borin, M. F.; Lopez, R. F. V.; Fonsec, M. J. V.; Int. J. Phrm. 2007, 328, Fonsec, Y. M.; Vicentini, F. T. M. C.; Ctini, C. D.; Fonsec, M. J. V.; Quim. Nov 2010, 33, Vicentini, F. T. M. C.; Simi, T. R. M.; Cimpo, J. O. D.; Wolg, N. O.; Pitol, K. L.; Iyoms, M. M.; Bentley, M. V. L. B.; Fonsec, M. J. V.; Eur. J. Phrm. Biophrm. 2008, 69, Schkel, D. J.; Klsbeek, D.; Boer, K.; J. Chromtogr., A 2004, 1049, Fernndez, C.; Nielloud, F.; Fortuné, R.; Vin, L.; Mrti-Mestres, G.; J. Phrm. Biomed. Anl. 2002, 28, Wlters, K. A.; Brin, K. R.; Howes, D.; Jmes, V. J.; Krus, A. L.; Teetsel, N. M.; Toulon, M.; Wtkinson, A. C.; Gettings, S. D.; Food Chem. Toxicol. 1997, 35, 1219.
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