Skip to main content
Erschienen in: Journal of Nanoparticle Research 5/2015

01.05.2015 | Research Paper

Carboxylic acid functionalization of halloysite nanotubes for sustained release of diphenhydramine hydrochloride

verfasst von: S. Sh. Zargarian, V. Haddadi-Asl, H. Hematpour

Erschienen in: Journal of Nanoparticle Research | Ausgabe 5/2015

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Halloysite nanotubes (HNT) (cylindrical shape with external diameter and length in the range of 30–80 nm and 0.2–1 µm, respectively) were functionalized with 3-aminopropyltriethoxysilane (APTES) from hydroxyl groups by a coupling reaction. Subsequently, maleic anhydride was attached to the APTES moieties to yield carboxylic acid-functionalized HNT. Loading and subsequent release of a model drug molecule diphenhydramine hydrochloride (DPH) on modified and unmodified nanotubes were investigated. Morphology of HNT was studied by electron microscopy. Successful attachment of APTES and carboxylic acid groups to halloysite and drug loading were evaluated by Fourier transform infrared spectroscopy. The amount of surface modification and drug adsorption capacity were calculated via thermogravimetric analysis. The ordered crystal structure of loaded drug was evaluated by X-ray diffraction. UV–Visible spectrophotometer was used to study drug release from modified and unmodified samples. Carboxylated halloysite exhibits higher loading capacity and prolonged release of DPH as compared to that of the natural halloysite.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
Zurück zum Zitat Aguzzi C, Viseras C, Cerezo P, Salcedo I, Sanchez-Espejo R, Valenzuela C (2013) Release kinetics of 5-aminosalicylic acid from halloysite. Colloids Surf B Biointerfaces 105:75–80CrossRef Aguzzi C, Viseras C, Cerezo P, Salcedo I, Sanchez-Espejo R, Valenzuela C (2013) Release kinetics of 5-aminosalicylic acid from halloysite. Colloids Surf B Biointerfaces 105:75–80CrossRef
Zurück zum Zitat Ali MS, Ghori M, Rafiuddin S, Khatri AR (2007) A new hydrophilic interaction liquid chromatographic (HILIC) procedure for the simultaneous determination of pseudoephedrine hydrochloride (PSH), diphenhydramine hydrochloride (DPH) and dextromethorphan hydrobromide (DXH) in cough-cold formulations. J Pharm Biomed Anal 43:158–167CrossRef Ali MS, Ghori M, Rafiuddin S, Khatri AR (2007) A new hydrophilic interaction liquid chromatographic (HILIC) procedure for the simultaneous determination of pseudoephedrine hydrochloride (PSH), diphenhydramine hydrochloride (DPH) and dextromethorphan hydrobromide (DXH) in cough-cold formulations. J Pharm Biomed Anal 43:158–167CrossRef
Zurück zum Zitat Ambrogi V, Fardella G, Grandolini G, Perioli L (2001) Intercalation compounds of hydrotalcite-like anionic clays. Int J Pharm 220:23–32CrossRef Ambrogi V, Fardella G, Grandolini G, Perioli L (2001) Intercalation compounds of hydrotalcite-like anionic clays. Int J Pharm 220:23–32CrossRef
Zurück zum Zitat Choy J, Choi S, Oh J, Park T (2007) Clay minerals and layered double hydroxides for novel biological applications. Appl Clay Sci 36:122–132CrossRef Choy J, Choi S, Oh J, Park T (2007) Clay minerals and layered double hydroxides for novel biological applications. Appl Clay Sci 36:122–132CrossRef
Zurück zum Zitat Emami SH, Pirbasti ZH, Hasani-Sadrabadi MM, Kordestani SS (2011) The effect of isopropanol addition on enhancement of transdermal controlled release of ibuprofen from ethylene vinyl acetate copolymer membranes. J Appl Polym Sci 122:3048–3054CrossRef Emami SH, Pirbasti ZH, Hasani-Sadrabadi MM, Kordestani SS (2011) The effect of isopropanol addition on enhancement of transdermal controlled release of ibuprofen from ethylene vinyl acetate copolymer membranes. J Appl Polym Sci 122:3048–3054CrossRef
Zurück zum Zitat Eslami H, Solati-Hashjin M, Tahriri M (2009) Effect of fluorine ion addition on structural, thermal, mechanical, solubility and biocompatibility characteristics of hydroxyapatite nanopowders. Adv Appl Ceram 000:1–13 Eslami H, Solati-Hashjin M, Tahriri M (2009) Effect of fluorine ion addition on structural, thermal, mechanical, solubility and biocompatibility characteristics of hydroxyapatite nanopowders. Adv Appl Ceram 000:1–13
Zurück zum Zitat Fejer I, Kata M, Eros I, Dekani I (2002) Interaction of monovalent cationic drugs with montmorillonite. Colloid Polym Sci 280:372–379 Fejer I, Kata M, Eros I, Dekani I (2002) Interaction of monovalent cationic drugs with montmorillonite. Colloid Polym Sci 280:372–379
Zurück zum Zitat Forsgren J, Jämstorp E, Bredenberg S, Engqvist H, Strømme M (2010) A ceramic drug delivery vehicle for oral administration of highly potent opioids. J Pharm Sci 99:219–226CrossRef Forsgren J, Jämstorp E, Bredenberg S, Engqvist H, Strømme M (2010) A ceramic drug delivery vehicle for oral administration of highly potent opioids. J Pharm Sci 99:219–226CrossRef
Zurück zum Zitat Ghebaur A, Garea SA, Iovu H (2012) New polymer-halloysite hybrid materials—potential controlled drug release system. Int J Pharm 436:568–573CrossRef Ghebaur A, Garea SA, Iovu H (2012) New polymer-halloysite hybrid materials—potential controlled drug release system. Int J Pharm 436:568–573CrossRef
Zurück zum Zitat He Q, Yang D, Deng X, Wu Q, Li R, Zhai Y, Zhang L (2013) Preparation, characterization and application of N-2-Pyridylsuccinamic acid-functionalized halloysite nanotubes for solid-phase extraction of Pb(II). Water Res 47:3976–3983CrossRef He Q, Yang D, Deng X, Wu Q, Li R, Zhai Y, Zhang L (2013) Preparation, characterization and application of N-2-Pyridylsuccinamic acid-functionalized halloysite nanotubes for solid-phase extraction of Pb(II). Water Res 47:3976–3983CrossRef
Zurück zum Zitat Jinhua W, Xiang Z, Bing Z, Yafei Z, Rui Z, Jindun L, Rongfeng C (2010) Rapid adsorption of Cr (VI) on modified halloysite nanotubes. Desalination 259:22–28CrossRef Jinhua W, Xiang Z, Bing Z, Yafei Z, Rui Z, Jindun L, Rongfeng C (2010) Rapid adsorption of Cr (VI) on modified halloysite nanotubes. Desalination 259:22–28CrossRef
Zurück zum Zitat Joo Y, Jeon Y, Lee SU, Sim JH, Ryu J, Lee S, Lee H, Sohn D (2012) Aggregation and stabilization of carboxylic acid functionalized halloysite nanotubes (HNT-COOH). J Phys Chem C 116:18230–18235CrossRef Joo Y, Jeon Y, Lee SU, Sim JH, Ryu J, Lee S, Lee H, Sohn D (2012) Aggregation and stabilization of carboxylic acid functionalized halloysite nanotubes (HNT-COOH). J Phys Chem C 116:18230–18235CrossRef
Zurück zum Zitat Joshi GV, Patel HA, Kevadiya BD, Bajaj HC (2009) Montmorillonite intercalated with vitamin B1 as drug carrier. Appl Clay Sci 45:248–253CrossRef Joshi GV, Patel HA, Kevadiya BD, Bajaj HC (2009) Montmorillonite intercalated with vitamin B1 as drug carrier. Appl Clay Sci 45:248–253CrossRef
Zurück zum Zitat Kelly HM, Deasy PB, Ziaka E, Claffey N (2004) Formulation and preliminary in vivo dog studies of a novel drug delivery system for the treatment of periodontitis. Int J Pharm 274:167–183CrossRef Kelly HM, Deasy PB, Ziaka E, Claffey N (2004) Formulation and preliminary in vivo dog studies of a novel drug delivery system for the treatment of periodontitis. Int J Pharm 274:167–183CrossRef
Zurück zum Zitat Kim H, Fassihi R (1997) Application of binary polymer system in drug release rate modulation. 2. Influence of formulation variables and hydrodynamic conditions on release kinetics. J Pharm Sci 86:323–328CrossRef Kim H, Fassihi R (1997) Application of binary polymer system in drug release rate modulation. 2. Influence of formulation variables and hydrodynamic conditions on release kinetics. J Pharm Sci 86:323–328CrossRef
Zurück zum Zitat Levis SR, Deasy PB (2002) Characterisation of halloysite for use as a microtubular drug delivery. Int J Pharm 243:125–134CrossRef Levis SR, Deasy PB (2002) Characterisation of halloysite for use as a microtubular drug delivery. Int J Pharm 243:125–134CrossRef
Zurück zum Zitat Levis SR, Deasy PB (2003) Use of coated microtubular halloysite for the sustained release of diltiazem hydrochloride and propranolol hydrochloride. Int J Pharm 253:145–157CrossRef Levis SR, Deasy PB (2003) Use of coated microtubular halloysite for the sustained release of diltiazem hydrochloride and propranolol hydrochloride. Int J Pharm 253:145–157CrossRef
Zurück zum Zitat Lvov YM, Price RR (2008) Halloysite nanotubules, a novel substrate for the controlled delivery of bioactive molecules. In: Ruiz-Hitzky E, Ariga K, Lvov YM (eds) Bio-inorganic hybrid nanomaterials. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, pp 419–442 Lvov YM, Price RR (2008) Halloysite nanotubules, a novel substrate for the controlled delivery of bioactive molecules. In: Ruiz-Hitzky E, Ariga K, Lvov YM (eds) Bio-inorganic hybrid nanomaterials. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, pp 419–442
Zurück zum Zitat Lvov YM, Shchukin DG, Mohwald HM, Price RR (2008) Halloysite clay nanotubes for controlled release of protective agents. ACS Nano 2:814–820CrossRef Lvov YM, Shchukin DG, Mohwald HM, Price RR (2008) Halloysite clay nanotubes for controlled release of protective agents. ACS Nano 2:814–820CrossRef
Zurück zum Zitat Mitchell MJ, Chen CS, Ponmudi V, Hughes AD, King MR (2012) E-selectin liposomal and nanotube-targeted delivery of doxorubicin to circulating tumor cells. J Control Release 160:609–617CrossRef Mitchell MJ, Chen CS, Ponmudi V, Hughes AD, King MR (2012) E-selectin liposomal and nanotube-targeted delivery of doxorubicin to circulating tumor cells. J Control Release 160:609–617CrossRef
Zurück zum Zitat Nandgude TD, Bhise KS, Gupta VB (2008) Characterization of hydrochloride and tannate salts of diphenhydramine. Indian Journal of Pharmaceutical Sciences 70:482-486 Nandgude TD, Bhise KS, Gupta VB (2008) Characterization of hydrochloride and tannate salts of diphenhydramine. Indian Journal of Pharmaceutical Sciences 70:482-486  
Zurück zum Zitat Pan J, Yao H, Xu L, Ou H, Huo P, Li X, Yan Y (2011) Selective recognition of 2,4,6-trichlorophenol by molecularly imprinted polymers based on magnetic halloysite nanotubes composites. J Phys Chem C 115:5440–5449CrossRef Pan J, Yao H, Xu L, Ou H, Huo P, Li X, Yan Y (2011) Selective recognition of 2,4,6-trichlorophenol by molecularly imprinted polymers based on magnetic halloysite nanotubes composites. J Phys Chem C 115:5440–5449CrossRef
Zurück zum Zitat Papadopoulou V, Kosmidis K, Vlachou M, Macheras P (2006) On the use of the Weibull function for the discernment of drug release mechanisms. Int J Pharm 309:44–50CrossRef Papadopoulou V, Kosmidis K, Vlachou M, Macheras P (2006) On the use of the Weibull function for the discernment of drug release mechanisms. Int J Pharm 309:44–50CrossRef
Zurück zum Zitat Peppas N (1985) Analysis of Fickian and non-Fickian drug release from polymers. Pharm Acta Helv 60:110 Peppas N (1985) Analysis of Fickian and non-Fickian drug release from polymers. Pharm Acta Helv 60:110
Zurück zum Zitat Qi R, Guo R, Zheng F, Liu H, Yu J, Shi X (2013) Controlled release and antibacterial activity of antibiotic-loaded electrospun halloysite/poly(lactic-co-glycolic acid) composite nanofibers. Colloids Surf B Biointerfaces 110:148–155CrossRef Qi R, Guo R, Zheng F, Liu H, Yu J, Shi X (2013) Controlled release and antibacterial activity of antibiotic-loaded electrospun halloysite/poly(lactic-co-glycolic acid) composite nanofibers. Colloids Surf B Biointerfaces 110:148–155CrossRef
Zurück zum Zitat Siepmann J, Peppas N (2012) Modeling of drug release from delivery systems based on hydroxypropyl methylcellulose (HPMC). Adv Drug Deliv Rev 64:163–174CrossRef Siepmann J, Peppas N (2012) Modeling of drug release from delivery systems based on hydroxypropyl methylcellulose (HPMC). Adv Drug Deliv Rev 64:163–174CrossRef
Zurück zum Zitat Singh B, Mackinnon IDR (1996) Experimental transformation of kaolinite to halloysite. Clays Clay Miner 44:825–834CrossRef Singh B, Mackinnon IDR (1996) Experimental transformation of kaolinite to halloysite. Clays Clay Miner 44:825–834CrossRef
Zurück zum Zitat Tan D, Yuan P, Annabi-Bergaya F, Yu H, Liu D, Liu H, He H (2013) Natural halloysite nanotubes as mesoporous carriers for the loading of ibuprofen. Microporous Mesoporous Mater 179:89–98CrossRef Tan D, Yuan P, Annabi-Bergaya F, Yu H, Liu D, Liu H, He H (2013) Natural halloysite nanotubes as mesoporous carriers for the loading of ibuprofen. Microporous Mesoporous Mater 179:89–98CrossRef
Zurück zum Zitat Tan D, Yuan P, Annabi-Bergaya F, Liu D, Wang L, Liu H, He H (2014a) Loading and in vitro release of ibuprofen in tubular halloysite. Appl Clay Sci 96(SI):50–55CrossRef Tan D, Yuan P, Annabi-Bergaya F, Liu D, Wang L, Liu H, He H (2014a) Loading and in vitro release of ibuprofen in tubular halloysite. Appl Clay Sci 96(SI):50–55CrossRef
Zurück zum Zitat Tan D, Yuan P, Annabi-Bergaya F, Liu D, Wang L, Liu H, He H (2014b) Loading and in vitro release of ibuprofen in tubular halloysite. Appl Clay Sci 96:50–55CrossRef Tan D, Yuan P, Annabi-Bergaya F, Liu D, Wang L, Liu H, He H (2014b) Loading and in vitro release of ibuprofen in tubular halloysite. Appl Clay Sci 96:50–55CrossRef
Zurück zum Zitat Veerabadran NG, Price RR, Lvov YM (2007) Clay nanotubes for encapsulation and sustained release of drugs. NANO 2:115–120CrossRef Veerabadran NG, Price RR, Lvov YM (2007) Clay nanotubes for encapsulation and sustained release of drugs. NANO 2:115–120CrossRef
Zurück zum Zitat Vergaro V, Abdullayev E, Lvov YM, Zeitoun A, Cingolani R, Rinaldi R, Zeitoun A, Leporatti S (2010) Cytocompatibility and uptake of halloysite clay nanotubes. Biomacromolecules 11:820–826CrossRef Vergaro V, Abdullayev E, Lvov YM, Zeitoun A, Cingolani R, Rinaldi R, Zeitoun A, Leporatti S (2010) Cytocompatibility and uptake of halloysite clay nanotubes. Biomacromolecules 11:820–826CrossRef
Zurück zum Zitat Viseras MT, Aguzzi C, Cerezo P, Viseras C, Valenzuela C (2008) Equilibrium and kinetics of 5-aminosalicylic acid adsorption by halloysite. Microporous Mesoporous Mater 108:112–116CrossRef Viseras MT, Aguzzi C, Cerezo P, Viseras C, Valenzuela C (2008) Equilibrium and kinetics of 5-aminosalicylic acid adsorption by halloysite. Microporous Mesoporous Mater 108:112–116CrossRef
Zurück zum Zitat Wang Q, Zhang J, Wang A (2013) Alkali activation of halloysite for adsorption and release of ofloxacin. Appl Surf Sci 287:54–61CrossRef Wang Q, Zhang J, Wang A (2013) Alkali activation of halloysite for adsorption and release of ofloxacin. Appl Surf Sci 287:54–61CrossRef
Zurück zum Zitat Wang Q, Zhang J, Zheng Y, Wang A (2014) Adsorption and release of ofloxacin from acid- and heat-treated halloysite. Colloids Surf B Biointerfaces 113:51–58CrossRef Wang Q, Zhang J, Zheng Y, Wang A (2014) Adsorption and release of ofloxacin from acid- and heat-treated halloysite. Colloids Surf B Biointerfaces 113:51–58CrossRef
Zurück zum Zitat Yah WO, Takahara A, Lvov YM (2012a) Selective modification of halloysite lumen with octadecylphosphonic acid: new inorganic tubular micelle. J Am Chem Soc 134:1853–1859CrossRef Yah WO, Takahara A, Lvov YM (2012a) Selective modification of halloysite lumen with octadecylphosphonic acid: new inorganic tubular micelle. J Am Chem Soc 134:1853–1859CrossRef
Zurück zum Zitat Yah WO, Xu H, Soejima H, Ma W, Lvov Y, Takahara A (2012b) Biomimetic dopamine derivative for selective polymer modification of halloysite nanotube lumen. J Am Chem Soc 134:12134–12137CrossRef Yah WO, Xu H, Soejima H, Ma W, Lvov Y, Takahara A (2012b) Biomimetic dopamine derivative for selective polymer modification of halloysite nanotube lumen. J Am Chem Soc 134:12134–12137CrossRef
Zurück zum Zitat Yuan P, Southon PD, Liu Z, Green MER, Hook JM, Antill SJ, Kepert CJ (2008) Functionalization of halloysite clay nanotubes by grafting with γ-aminopropyltriethoxysilane. J Phys Chem C 112:15742–15751CrossRef Yuan P, Southon PD, Liu Z, Green MER, Hook JM, Antill SJ, Kepert CJ (2008) Functionalization of halloysite clay nanotubes by grafting with γ-aminopropyltriethoxysilane. J Phys Chem C 112:15742–15751CrossRef
Zurück zum Zitat Yuan P, Southon PD, Liu Z, Kepert CJ (2012) Organosilane functionalization of halloysite nanotubes for enhanced loading and controlled release. Nanotechnology 23:375705CrossRef Yuan P, Southon PD, Liu Z, Kepert CJ (2012) Organosilane functionalization of halloysite nanotubes for enhanced loading and controlled release. Nanotechnology 23:375705CrossRef
Zurück zum Zitat Zheng JP, Luan L, Wang HY, Xi LF, Yao KD (2007) Study on ibuprofen/montmorillonite intercalation composites as drug release system. Appl Clay Sci 36:297–301CrossRef Zheng JP, Luan L, Wang HY, Xi LF, Yao KD (2007) Study on ibuprofen/montmorillonite intercalation composites as drug release system. Appl Clay Sci 36:297–301CrossRef
Metadaten
Titel
Carboxylic acid functionalization of halloysite nanotubes for sustained release of diphenhydramine hydrochloride
verfasst von
S. Sh. Zargarian
V. Haddadi-Asl
H. Hematpour
Publikationsdatum
01.05.2015
Verlag
Springer Netherlands
Erschienen in
Journal of Nanoparticle Research / Ausgabe 5/2015
Print ISSN: 1388-0764
Elektronische ISSN: 1572-896X
DOI
https://doi.org/10.1007/s11051-015-3032-3

Weitere Artikel der Ausgabe 5/2015

Journal of Nanoparticle Research 5/2015 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.