Abstract
Drug delivery systems especially stimulus-responsive ones play an important role in medicinal chemistry because most of the cancer drugs have various side effects. In the present research, amine groups bonded to β-cyclodextrin (βCD) were used as a pH-sensitive cap for the cavities of magnetic mesoporous silica nanoparticles. In order to insert βCD cap on the cavities of magnetic mesoporous silica nanoparticles, a host which makes host–guest interaction with βCD was needed. Ethylene diamine chain was used as a host for βCD. Doxorubicin was loaded on Fe3O4@mSiO2@NH2 nanoparticles and then functionalized by βCD. In acidic media, the nitrogens of amine groups were protonated and the repellence among the chains gave rise to more and controlled drug release while in neutral media βCD all of the nitrogens had positive charge and these positive charges gave rise to repellence among chains. These interactions caused to open the chains, and βCD was released which in turn gave rise to the delivery of DOX. The amount of DOX loaded on the Fe3O4@mSiO2@NH2 nanoparticles surface was estimated by thermal gravimetric analysis. The results of drug delivery experiments were interesting which were investigated by ultraviolet–visible spectroscopy. To obtain the hydrodynamic diameter of Fe3O4@mSiO2@βCD, dynamic light scattering technique was used. Furthermore, the cytotoxicity of Fe3O4@mSiO2@βCD was also investigated.
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M.K. Gök, S. Özgümüş, K. Demir, Ü. Cirit, S. Pabuccuoğlu, E. Cevher, Y. Özsoy, S. Bacınoğlu, Development of starch based mucoadhesive vaginal drug delivery systems for application in veterinary medicine. Carbohydr. Polym. 136, 63–70 (2016)
F. Shakeel, M. Iqbal, E. Ezzeldin, Bioavailability enhancement and pharmacokinetic profile of an anticancer drug ibrutinib by self-nanoemulsifying drug delivery system. J. Pharm. Pharmacol. 68, 772–780 (2016)
Y. Qiu, S. Tong, L. Zhang, Y. Sakurai, D.R. Myers, L. Hong, W.A. Lam, G. Bao, Magnetic forces enable controlled drug delivery by disrupting endothelial cell-cell junctions. Nat. Commun. 8, 15594 (2017)
R. Davidson, A. Scott, M. Maini, A. Bryceson, S. Croft, Liposomal amphotericin B in drug-resistant visceral leishmaniasis. Lancet 337, 1061–1062 (1991)
J. Vandooren, G. Opdenakker, P.M. Loadman, D.R. Edwards, Proteases in cancer drug delivery. Adv. Drug Deliv. Rev. 97, 144–155 (2016)
L.S. Arias, J.P. Pessan, A.P.M. Vieira, T.M.T. de Lima, A.C.B. Delbem, D.R. Monteiro, Iron oxide nanoparticles for biomedical applications: a perspective on synthesis, drugs, antimicrobial activity, and toxicity. Antibiotics. 7, 1–32 (2018)
K.J. McCullagh, R.C. Perlingeiro, Coaxing stem cells for skeletal muscle repair. Adv. Drug Deliv. Rev. 84, 198–207 (2015)
F. Ye, Å. Barrefelt, H. Asem, M. Abedi-Valugerdi, I. El-Serafi, M. Saghafian, K. Abu-Salah, S. Alrokayan, M. Muhammed, M. Hassan, Biodegradable polymeric vesicles containing magnetic nanoparticles, quantum dots and anticancer drugs for drug delivery and imaging. Biomaterials 35, 3885–3894 (2014)
J. Nicolas, S. Mura, D. Brambilla, N. Mackiewicz, P. Couvreur, Design, functionalization strategies and biomedical applications of targeted biodegradable/biocompatible polymer-based nanocarriers for drug delivery. Chem. Soc. Rev. 42, 1147–1235 (2013)
J. Zhang, Z.-F. Yuan, Y. Wang, W.-H. Chen, G.-F. Luo, S.-X. Cheng, R.-X. Zhuo, X.-Z. Zhang, Multifunctional envelope-type mesoporous silica nanoparticles for tumor-triggered targeting drug delivery. J. Am. Chem. Soc. 135, 5068–5073 (2013)
E.M. Cahill, E.D. O’Cearbhaill, Toward biofunctional microneedles for stimulus responsive drug delivery. Bioconjug. Chem. 26, 1289–1296 (2015)
M. Karimi, A. Ghasemi, P.S. Zangabad, R. Rahighi, S.M.M. Basri, H. Mirshekari, M. Amiri, Z.S. Pishabad, A. Aslani, M. Bozorgomid, Smart micro/nanoparticles in stimulus-responsive drug/gene delivery systems. Chem. Soc. Rev. 45, 1457–1501 (2016)
R. Vasani, D. Losic, A. Cavallaro, N. Voelcker, Fabrication of stimulus-responsive diatom biosilica microcapsules for antibiotic drug delivery. J. Mater. Chem. B 3, 4325–4329 (2015)
W.N. Lee, G. Davey, Chinese visitors’ experiences of nature and wild macaques: inspiration and personal growth for living in Hong Kong. Hum. Dimens. Wildl. 20, 206–219 (2015)
G.A. Hughes, Nanostructure-mediated drug delivery, in Nanomedicine in Cancer, ed. by L.P. Balogh (Pan Stanford, Massachusetts, USA, 2017), p. 47–72. https://doi.org/10.4032/9781315114361
S. Mura, J. Nicolas, P. Couvreur, Stimuli-responsive nanocarriers for drug delivery. Nat. Mater. 12, 991 (2013)
K. Ulbrich, K. Hola, V. Subr, A. Bakandritsos, J. Tucek, R. Zboril, Targeted drug delivery with polymers and magnetic nanoparticles: covalent and noncovalent approaches, release control, and clinical studies. Chem. Rev. 116, 5338–5431 (2016)
S.-H. Wu, C.-Y. Mou, H.-P. Lin, Synthesis of mesoporous silica nanoparticles. Chem. Soc. Rev. 42, 3862–3875 (2013)
S. Goenka, V. Sant, S. Sant, Graphene-based nanomaterials for drug delivery and tissue engineering. J. Control. Release 173, 75–88 (2014)
T.M. Allen, P.R. Cullis, Liposomal drug delivery systems: from concept to clinical applications. Adv. Drug Deliv. Rev. 65, 36–48 (2013)
V.P. Torchilin, Multifunctional, stimuli-sensitive nanoparticulate systems for drug delivery. Nat. Rev. Drug Discov. 13, 813 (2014)
B. Pourbadiei, R. Pyadar, F. Mansouri, pH-sensitive nanoscale polymers: highly efficient systems for DOX delivery in cancer treatment. J. Nanomed. Res 5, 1–6 (2017)
X. Cai, Y. Luo, W. Zhang, D. Du, Y. Lin, pH-Sensitive ZnO quantum dots–doxorubicin nanoparticles for lung cancer targeted drug delivery. ACS Appl. Mater. Interfaces 8, 22442–22450 (2016)
J.-Z. Du, X.-J. Du, C.-Q. Mao, J. Wang, Tailor-made dual pH-sensitive polymer–doxorubicin nanoparticles for efficient anticancer drug delivery. J. Am. Chem. Soc. 133, 17560–17563 (2011)
M. Hrubý, Č. Koňák, K. Ulbrich, Polymeric micellar pH-sensitive drug delivery system for doxorubicin. J. Control. Release 103, 137–148 (2005)
S. Kayal, R. Ramanujan, Doxorubicin loaded PVA coated iron oxide nanoparticles for targeted drug delivery. Mater. Sci. Eng. C 30, 484–490 (2010)
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The authors gratefully acknowledge partial support from Research Council of Payame Noor University, Tehran 19395–3697, Iran.
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Shahmoradi, S., Bahram, M. & Hoseinpour, F. Magnetic mesoporous silica nanoparticles functionalized by pH-sensitive caps for DOX release. J IRAN CHEM SOC 16, 1801–1808 (2019). https://doi.org/10.1007/s13738-019-01652-z
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DOI: https://doi.org/10.1007/s13738-019-01652-z