A stability-indicating high performance liquid chromatography method to determine apocynin in nanoparticles
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摘要
In this study, we developed and validated a fast, specific, sensitive, precise and stability-indicating high performance liquid chromatography(HPLC) method to determine the drug apocynin in bovine serum albumin(BSA) nanoparticles. Chromatographic analyses were performed on an RP C18 column and using a photodiode array detector at a wavelength of 276 nm. Mobile phase consisted of a mixture of acetonitrile and 1% acetic acid(60:40, v/v), and it was eluted isocratically at a flow rate of 0.8 mL/min. The retention time of apocynin chromatographic peak was 1.65 min. The method was linear, precise, accurate and specific in the range of 5–100 μg/mL. The intra-and inter-day precisions presented relative standard deviation(RSD) values lower than 2%. The method was robust regarding changes in mobile phase proportion, but not for flow rate. Limits of detection and quantitation were 78 ng/mL and 238 ng/mL, respectively. Apocynin was exposed to acid and alkali hydrolysis, oxidation and visible light. The drug suffered mild degradation under acid and oxidation conditions and great degradation under alkali conditions. Light exposure did not degrade the drug. The method was successfully applied to determine the encapsulation efficiency of apocynin in BSA nanoparticles.
In this study, we developed and validated a fast, specific, sensitive, precise and stability-indicating high performance liquid chromatography(HPLC) method to determine the drug apocynin in bovine serum albumin(BSA) nanoparticles. Chromatographic analyses were performed on an RP C18 column and using a photodiode array detector at a wavelength of 276 nm. Mobile phase consisted of a mixture of acetonitrile and 1% acetic acid(60:40, v/v), and it was eluted isocratically at a flow rate of 0.8 mL/min. The retention time of apocynin chromatographic peak was 1.65 min. The method was linear, precise, accurate and specific in the range of 5–100 μg/mL. The intra-and inter-day precisions presented relative standard deviation(RSD) values lower than 2%. The method was robust regarding changes in mobile phase proportion, but not for flow rate. Limits of detection and quantitation were 78 ng/mL and 238 ng/mL, respectively. Apocynin was exposed to acid and alkali hydrolysis, oxidation and visible light. The drug suffered mild degradation under acid and oxidation conditions and great degradation under alkali conditions. Light exposure did not degrade the drug. The method was successfully applied to determine the encapsulation efficiency of apocynin in BSA nanoparticles.
In this study, we developed and validated a fast, specific, sensitive, precise and stability-indicating high performance liquid chromatography(HPLC) method to determine the drug apocynin in bovine serum albumin(BSA) nanoparticles. Chromatographic analyses were performed on an RP C18 column and using a photodiode array detector at a wavelength of 276 nm. Mobile phase consisted of a mixture of acetonitrile and 1% acetic acid(60:40, v/v), and it was eluted isocratically at a flow rate of 0.8 mL/min. The retention time of apocynin chromatographic peak was 1.65 min. The method was linear, precise, accurate and specific in the range of 5–100 μg/mL. The intra-and inter-day precisions presented relative standard deviation(RSD) values lower than 2%. The method was robust regarding changes in mobile phase proportion, but not for flow rate. Limits of detection and quantitation were 78 ng/mL and 238 ng/mL, respectively. Apocynin was exposed to acid and alkali hydrolysis, oxidation and visible light. The drug suffered mild degradation under acid and oxidation conditions and great degradation under alkali conditions. Light exposure did not degrade the drug. The method was successfully applied to determine the encapsulation efficiency of apocynin in BSA nanoparticles.
引文
[1]F.Engels,B.F.Renirie,B.A.Hart,et al.,Effects of apocynin,a drug isolated from the roots of Picrorhiza kurroa,on arachidonic acid metabolism,FEBS Lett.305(1992)254–256.
[2]S.Hougee,A.Hartog,A.Sanders,et al.,Oral administration of the NADPH-oxidase inhibitor apocynin partially restores diminished cartilage proteoglycan synthesis and reduces inflammation in mice,Eur.J.Pharmacol.531(2006)264–269.
[3]K.R.Houser,D.K.Johnson,F.T.Ishmael,Anti-inflammatory effects of methoxyphenolic compounds on human airway cells,J.Inflamm.9(2012)1–12.
[4]J.M.Li,N.P.Gall,D.J.Grieve,et al.,Activation of NADPH oxidase during progression of cardiac hypertrophy to failure,Hypertension 40(2002)477–484.
[5]M.M.El-Sawalhi,L.A.Ahmed,Exploring the protective role of apocynin,a specific NADPH oxidase inhibitor,in cisplatin-induced cardiotoxicity in rats,Chem.Biol.Interact.207(2014)58–66.
[6]D.K.Miller,C.E.Oelrichs,G.Y.Sun,et al.,Subchronic apocynin treatment attenuates methamphetamine-induceddopamine release and hyperactivity in rats,Life Sci.98(2014)6–11.
[7]R.F.Klees,P.C.De Marco,R.M.Salasznyk,et al.,Apocynin derivatives interrupt intracellular signaling resulting in decreased migration in breast cancer cells,J.Biomed.Biotechnol.2006(2006)1–10.
[8]K.Lirdprapamongkol,J.P.Kramb,T.Suthiphongchai,et al.,Vanillin suppresses metastatic potential of human cancer cells through PI3K inhibition and decreases angiogenesis in vivo,J.Agric.Food Chem.57(2009)3055–3063.
[9]S.Suzuki,P.Pitchakarn,S.Sato,et al.,Apocynin,an NADPH oxidase inhibitor,suppresses progression of prostate cancer via Rac1 dephosphorylation,Exp.Toxicol.Pathol.65(2013)1035–1041.
[10]H.Kinoshita,T.Matsumura,N.Ishii,et al.,Apocynin suppresses the progression of atherosclerosis in apo E-deficient mice by inactivation of macrophages,Biochem.Biophys.Res.Commun.431(2013)124–130.
[11]X.N.Tang,B.Cairns,N.Cairns,et al.,Apocynin improves outcome in experimental stroke with a narrow dose range,Neuroscience 154(2008)556–562.
[12]J.D.Lambeth,K.H.Krause,R.A.Clark,NOX enzymes as novel targets for drug development,Semin.Immunopathol.30(2008)339–363.
[13]K.Wang,L.Li,Y.Song,et al.,Improvement of pharmacokinetics behavior of apocynin by nitrone derivatization:comparative pharmacokinetics of nitroneapocynin and its parent apocynin in rats,PLo S One 8(2013)e70189.
[14]B.J.Connell,M.C.Saleh,B.V.Khan,et al.,Apocynin may limit total cell death following cerebral ischemia and reperfusion by enhancing apoptosis,Food Chem.Toxicol.9(2011)43063–43069.
[15]V.J.Mohanraj,Y.Chen,Nanoparticles–a review,Trop.J.Pharm.Res.5(2006)561–573.
[16]N.M.Khalil,E.Carraro,L.F.Cótica,et al.,Potential of polymeric nanoparticles in AIDS treatment and prevention,Expert Opin.Drug Deliv.8(2011)95–112.
[17]N.M.Khalil,T.C.do Nascimento,D.M.Casa,et al.,Pharmacokinetics of curcuminloaded PLGA and PLGA-PEG blend nanoparticles after oral administration in rats,Colloids Surf.B 101(2013)353–360.
[18]C.D.Rodrigues,D.Meza Casa,L.F.Dalmolin,et al.,Amphotericin b-loaded poly(lactide)-poly(ethylene glycol)-blend nanoparticles:characterization and in vitro efficacy and toxicity,Curr.Nanosci.9(2013)594–598.
[19]A.Frank,E.Pridgen,L.K.Molnar,et al.,Factors affecting the clearance and biodistribution of polymeric nanoparticles,Mol.Pharm.5(2008)505–515.
[20]N.M.Khalil,R.M.Mainardes,Colloidal polymeric nanoparticles and brain drug delivery,Curr.Drug Deliv.6(2009)261–273.
[21]A.Kumari,S.K.Yadav,S.C.Yadav,Biodegradable polymeric nanoparticles based drug delivery systems,Colloids Surf.B 75(2010)1–18.
[22]G.Barratt,Colloidal drug carriers:achievements and perspectives,Cell.Mol.Life Sci.60(2003)21–37.
[23]M.Ulbricht,Advanced functional polymer membranes,Polymer 47(2006)2217–2262.
[24]Z.Dongmei,Z.Xiuhua,Z.Yuangang,et al.,Preparation,characterization,and in vitro targeted delivery of folate-decorated paclitaxel-loaded bovine serum albumin nanoparticles,Int.J.Nanomed.5(2010)669–677.
[25]A.O.Elzoghby,W.M.Samy,N.A.Elgindy,Albumin-based nanoparticles as potential controlled release drug delivery systems,J.Control.Release 157(2012)168–182.
[26]M.Rahimnejad,G.Najafpour,G.Bakeri,Investigation and modeling effective parameters influencing the size of BSA protein nanoparticles as colloidal carriers,Colloids Surf.A 412(2012)96–100.
[27]Q.Wang,R.E.Smith,R.Luchtefeldc,et al.,Bioavailability of apocynin through its conversion to lycoconjugate but not to diapocynin,Phytomedicine 15(2008)496–503.
[28]K.A.Trumbull,D.Mc Allister,M.M.Gandelman,et al.,Diapocynin and apocynin administration fails to significantly extend survival in G93A SOD1 ALS mice,Neurobiol.Dis.45(2012)137–144.
[29]H.Chandasana,Y.S.Chhonker,V.Bala,et al.,Pharmacokinetic,bioavailability,metabolism and plasma protein binding evaluation of NADPH-oxidase inhibitor apocynin using LC–MS/MS,J.Chromatogr.B 985(2015)180–188.
[30]ICH–International Conference on Harmonization of Technical Requeriments for Registration of Pharmaceuticals for Human Use:Q2B–Validation of Analytical Procedures:Methodology,2005.
[31]N.M.Khalil,J.Ascari,D.V.Ronik,et al.,Processo de formula??o de nanopartículas de apocinina revestidas com o polímero natural BSA e reticuladas com glutaraldeído pelo método de coacerva??o e fármaco 2014,Patente:Número Do registro:BR 10 2014 029625-5 A2,2014,Brasil.
[32]G.da Rocha Lindner,N.M.Khalil,R.M.Mainardes,Resveratrol-loaded polymeric nanoparticles:validation of an HPLC-PDA method to determine the drug entrapment and evaluation of its antioxidant activity,Sci.World J.2013(2013)1–9.
[33]J.das Neves,B.Sarmento,M.M.Amiji,et al.,Development and validation of a rapid reversed-phase HPLC method for the determination of the non-nucleoside reverse transcriptase inhibitor dapivirine from polymeric nanoparticles,J.Pharm.Biomed.Anal.52(2010)167–172.
[2]S.Hougee,A.Hartog,A.Sanders,et al.,Oral administration of the NADPH-oxidase inhibitor apocynin partially restores diminished cartilage proteoglycan synthesis and reduces inflammation in mice,Eur.J.Pharmacol.531(2006)264–269.
[3]K.R.Houser,D.K.Johnson,F.T.Ishmael,Anti-inflammatory effects of methoxyphenolic compounds on human airway cells,J.Inflamm.9(2012)1–12.
[4]J.M.Li,N.P.Gall,D.J.Grieve,et al.,Activation of NADPH oxidase during progression of cardiac hypertrophy to failure,Hypertension 40(2002)477–484.
[5]M.M.El-Sawalhi,L.A.Ahmed,Exploring the protective role of apocynin,a specific NADPH oxidase inhibitor,in cisplatin-induced cardiotoxicity in rats,Chem.Biol.Interact.207(2014)58–66.
[6]D.K.Miller,C.E.Oelrichs,G.Y.Sun,et al.,Subchronic apocynin treatment attenuates methamphetamine-induceddopamine release and hyperactivity in rats,Life Sci.98(2014)6–11.
[7]R.F.Klees,P.C.De Marco,R.M.Salasznyk,et al.,Apocynin derivatives interrupt intracellular signaling resulting in decreased migration in breast cancer cells,J.Biomed.Biotechnol.2006(2006)1–10.
[8]K.Lirdprapamongkol,J.P.Kramb,T.Suthiphongchai,et al.,Vanillin suppresses metastatic potential of human cancer cells through PI3K inhibition and decreases angiogenesis in vivo,J.Agric.Food Chem.57(2009)3055–3063.
[9]S.Suzuki,P.Pitchakarn,S.Sato,et al.,Apocynin,an NADPH oxidase inhibitor,suppresses progression of prostate cancer via Rac1 dephosphorylation,Exp.Toxicol.Pathol.65(2013)1035–1041.
[10]H.Kinoshita,T.Matsumura,N.Ishii,et al.,Apocynin suppresses the progression of atherosclerosis in apo E-deficient mice by inactivation of macrophages,Biochem.Biophys.Res.Commun.431(2013)124–130.
[11]X.N.Tang,B.Cairns,N.Cairns,et al.,Apocynin improves outcome in experimental stroke with a narrow dose range,Neuroscience 154(2008)556–562.
[12]J.D.Lambeth,K.H.Krause,R.A.Clark,NOX enzymes as novel targets for drug development,Semin.Immunopathol.30(2008)339–363.
[13]K.Wang,L.Li,Y.Song,et al.,Improvement of pharmacokinetics behavior of apocynin by nitrone derivatization:comparative pharmacokinetics of nitroneapocynin and its parent apocynin in rats,PLo S One 8(2013)e70189.
[14]B.J.Connell,M.C.Saleh,B.V.Khan,et al.,Apocynin may limit total cell death following cerebral ischemia and reperfusion by enhancing apoptosis,Food Chem.Toxicol.9(2011)43063–43069.
[15]V.J.Mohanraj,Y.Chen,Nanoparticles–a review,Trop.J.Pharm.Res.5(2006)561–573.
[16]N.M.Khalil,E.Carraro,L.F.Cótica,et al.,Potential of polymeric nanoparticles in AIDS treatment and prevention,Expert Opin.Drug Deliv.8(2011)95–112.
[17]N.M.Khalil,T.C.do Nascimento,D.M.Casa,et al.,Pharmacokinetics of curcuminloaded PLGA and PLGA-PEG blend nanoparticles after oral administration in rats,Colloids Surf.B 101(2013)353–360.
[18]C.D.Rodrigues,D.Meza Casa,L.F.Dalmolin,et al.,Amphotericin b-loaded poly(lactide)-poly(ethylene glycol)-blend nanoparticles:characterization and in vitro efficacy and toxicity,Curr.Nanosci.9(2013)594–598.
[19]A.Frank,E.Pridgen,L.K.Molnar,et al.,Factors affecting the clearance and biodistribution of polymeric nanoparticles,Mol.Pharm.5(2008)505–515.
[20]N.M.Khalil,R.M.Mainardes,Colloidal polymeric nanoparticles and brain drug delivery,Curr.Drug Deliv.6(2009)261–273.
[21]A.Kumari,S.K.Yadav,S.C.Yadav,Biodegradable polymeric nanoparticles based drug delivery systems,Colloids Surf.B 75(2010)1–18.
[22]G.Barratt,Colloidal drug carriers:achievements and perspectives,Cell.Mol.Life Sci.60(2003)21–37.
[23]M.Ulbricht,Advanced functional polymer membranes,Polymer 47(2006)2217–2262.
[24]Z.Dongmei,Z.Xiuhua,Z.Yuangang,et al.,Preparation,characterization,and in vitro targeted delivery of folate-decorated paclitaxel-loaded bovine serum albumin nanoparticles,Int.J.Nanomed.5(2010)669–677.
[25]A.O.Elzoghby,W.M.Samy,N.A.Elgindy,Albumin-based nanoparticles as potential controlled release drug delivery systems,J.Control.Release 157(2012)168–182.
[26]M.Rahimnejad,G.Najafpour,G.Bakeri,Investigation and modeling effective parameters influencing the size of BSA protein nanoparticles as colloidal carriers,Colloids Surf.A 412(2012)96–100.
[27]Q.Wang,R.E.Smith,R.Luchtefeldc,et al.,Bioavailability of apocynin through its conversion to lycoconjugate but not to diapocynin,Phytomedicine 15(2008)496–503.
[28]K.A.Trumbull,D.Mc Allister,M.M.Gandelman,et al.,Diapocynin and apocynin administration fails to significantly extend survival in G93A SOD1 ALS mice,Neurobiol.Dis.45(2012)137–144.
[29]H.Chandasana,Y.S.Chhonker,V.Bala,et al.,Pharmacokinetic,bioavailability,metabolism and plasma protein binding evaluation of NADPH-oxidase inhibitor apocynin using LC–MS/MS,J.Chromatogr.B 985(2015)180–188.
[30]ICH–International Conference on Harmonization of Technical Requeriments for Registration of Pharmaceuticals for Human Use:Q2B–Validation of Analytical Procedures:Methodology,2005.
[31]N.M.Khalil,J.Ascari,D.V.Ronik,et al.,Processo de formula??o de nanopartículas de apocinina revestidas com o polímero natural BSA e reticuladas com glutaraldeído pelo método de coacerva??o e fármaco 2014,Patente:Número Do registro:BR 10 2014 029625-5 A2,2014,Brasil.
[32]G.da Rocha Lindner,N.M.Khalil,R.M.Mainardes,Resveratrol-loaded polymeric nanoparticles:validation of an HPLC-PDA method to determine the drug entrapment and evaluation of its antioxidant activity,Sci.World J.2013(2013)1–9.
[33]J.das Neves,B.Sarmento,M.M.Amiji,et al.,Development and validation of a rapid reversed-phase HPLC method for the determination of the non-nucleoside reverse transcriptase inhibitor dapivirine from polymeric nanoparticles,J.Pharm.Biomed.Anal.52(2010)167–172.