Azobenzene functionalized mesoporous AlMCM-41-type support for drug release applications

Walter de Gruyter GmbH - Tập 12 Số 7 - Trang 788-795 - 2014
Raul−Augustin Mitran, Daniela Berger1, Laura Băjenaru1, Silviu Năstase1, Cristian Andronescu2, Cristian Matei1
1University “Politehnica” of Bucharest
23Romanian Academy of Sciences

Tóm tắt

AbstractA light-responsive material, aminoazobenzene functionalized AlMCM-41, was synthesized and characterized in order to be used as carrier for drug delivery devices. The light-induced hydrophobic-hydrophilic switching effect of azobenzene functionalized aluminosilicate was exploited in the release of irinotecan, a cytostatic drug. To obtain the functionalized mesoporous support, an azobenzene-silane precursor was synthesized by coupling 4-(4′-aminophenylazo) benzoic acid with 3-aminopropyl triethoxysilane and further grafted on AlMCM-41. The azobenzene functionalized mesoporous aluminosilicate exhibited no significant toxicity towards murine fibroblast healthy cells and a reduced toxicity towards murine melanocyte cells. The hybrid materials obtained by loading irinotecan on AlMCM-41 (wt. 35.4%) and aminoazobenzene modified AlMCM-41 (wt. 22%), respectively were characterized by FTIR, small and wide angle XRD, N2 adsorption-desorption isotherms and DSC analyses. A two-fold increase in the drug release rate from azobenzene functionalized aluminosilicate in phosphate buffer solution under UV irradiation was noticed, as compared with dark conditions. Moreover, the azobenzene functionalization of AlMCM-41 significantly increased the irinotecan delivery rate and total cumulative release in comparison with the pristine AlMCM-41 in similar conditions.

Từ khóa


Tài liệu tham khảo

M. Colilla, B. Gonzalez, M. Vallet-Regi, Biomat. Sci. 1, 114 (2013)

Z. Li, J.C. Barnes, A. Bosoy, J.F. Stoddart, J.I. Zink, Chem. Soc. Rev. 41, 2590 (2012)

A. Popat, S.B. Hartono, F. Stahr, J. Liu, S.Z. Qiao, G. Qing Lu, Nanoscale 3, 2801 (2011)

J.L. Vivero-Escoto, I.I. Slowing, B.G. Trewyn, V.S.Y. Lin, Small 6, 1952 (2010)

F. Tang, L. Li, D. Chen, Adv. Mater. 24, 1504 (2012)

M. Vallet-Regí, F. Balas, D. Arcos, Angew. Chem. Int. Edit. 46, 7548 (2007)

T. Tanaka, H. Ogino, M. Iwamoto, Langmuir 23, 11417 (2007)

N. Liu, Z. Chen, D.R. Dunphy, Y.-B. Jiang, R.A. Assink, C.J. Brinker, Angew. Chem. Int. Edit. 42, 1731 (2003)

J. Lu, E. Choi, F. Tamanoi, J.I. Zink, Small 4, 421 (2008)

S. Angelos, E. Choi, F. Vögtle, L. De Cola, J.I. Zink, J. Phys. Chem. C 111, 6589 (2007)

M. Alvaro, M. Benitez, D. Das, H. Garcia, E. Peris, Chem. Mater. 17, 4958 (2005)

Y. Zhu, M. Fujiwara, Angew. Chem. Int. Edit. 46, 2241 (2007)

Q. Yuan, Y. Zhang, T. Chen, D. Lu, Z. Zhao, X. Zhang, Z. Li, C.-H. Yan, W. Tan, ACS Nano 6, 6337 (2012)

D.P. Ferris, Y.-L. Zhao, N.M. Khashab, H.A. Khatib, J.F. Stoddart, J.I. Zink, J. Am. Chem. Soc. 131, 1686 (2009)

Y.-W. Yang, Med. Chem. Comm. 2, 1033 (2011)

R.H. El Halabieh, O. Mermut, C.J. Barrett, Pure Appl. Chem. 76, 1445 (2004)

X. Pei, A. Fernandes, B. Mathy, X. Laloyaux, B. Nysten, O. Riant, A.M. Jonas, Langmuir 27, 9403 (2011)

C. Song, R. Griffin, H. Park, In: B. Teicher (Ed.), Cancer Drug Resistance (Humana Press, Totowa, New Jersey, 2006) 21

K.H. Schündehütte, Houben-Weyl Methoden der Organischen Chemie (Thieme, Stuttgart, 196510/3 (in German)

G.B. Demirel, N. Dilsiz, M. Cakmak, T. Caykara, J. Mater. Chem. 21, 3189 (2011)

F. Laduron, V. Tamborowski, L. Moens, A. Horvath, D. De Smaele, S. Leurs, Org. Process. Res. Dev. 9, 102 (2005)

G. Maria, D. Berger, S. Nastase, I. Luta, Micropor. Mesopor. Mat. 149, 25 (2012)

A.H. Janssen, A.J. Koster, K.P. de Jong, J. Phys. Chem. B 106, 11905 (2002)

M.J.B. Souza, A.S. Araujo, A.M.G. Pedrosa, B.A. Marinkovic, P.M. Jardim, E. Morgado Jr, Mater. Lett. 60, 2682 (2006)

S. Nastase, L. Bajenaru, C. Matei, R. A. Mitran, D. Berger, Micropor. Mesopor. Mat. 182, 32 (2013)

D. Arcos, A. López-Noriega, E. Ruiz-Hernández, O. Terasaki, M. Vallet-Regí, Chem. Mater. 21, 1000 (2009)

Q. He, J. Shi, F. Chen, M. Zhu, L. Zhang, Biomater. 31, 3335 (2010)

Thông tin
Thông tin xuất bản

Walter de Gruyter GmbH

Tập 12 Số 7

788-795

Thông tin tác giả