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Preliminary Study of the Anticancer Applications of Mesoporous Materials Functionalized with the Natural Product Betulinic Acid
Author(s) -
SánchezMuñoz Sergio,
GómezRuiz Santiago,
PérezQuintanilla Damián,
MoranteZarcero Sonia,
Sierra Isabel,
Prashar Sanjiv,
Paschke Reinhard,
Kaluđerović Goran N.
Publication year - 2012
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201100588
Subject(s) - thermogravimetry , chemistry , nuclear chemistry , mesoporous material , betulinic acid , sorption , triethylamine , nitrogen , fluorescence spectroscopy , toluene , adsorption , organic chemistry , fluorescence , inorganic chemistry , catalysis , physics , quantum mechanics , biology , genetics
Dehydrated MCM‐41 ( S 1 ) was functionalized under nitrogen with 3‐chloropropyltriethoxysilane (CPTS) and 3‐aminopropyltriethoxysilane (APTS) by grafting in toluene at 80 °C over 48 h to give the corresponding materials S 2 and S 3 , respectively. Subsequently, S 2 and S 3 were suspended in methanol and reacted in a nitrogen atmosphere with betulinic acid (BA) for 48 h at 65 °C (in the presence of the triethylamine of S 2 ) to give the BA‐functionalized materials S 4 and S 5 . All materials studied were characterized by powder X‐ray diffraction, X‐ray fluorescence, nitrogen gas sorption, multinuclear MAS NMR spectroscopy, thermogravimetry, UV spectroscopy, IR, SEM, and TEM. To study the release of BA, S 4 and S 5 were suspended in solutions simulating various body pH conditions (pH 7.4, 5.5, and 3.0). Results of the quantification of BA release by HPLC for S 4 show a pH‐dependent and very slow BA release following a logarithmic tendency, while S 5 behaves differently, also pH‐dependent but, in this case, fast release of BA which requires only days for total release of the therapeutic compound. In addition, the cytotoxic activity of all synthesized materials against various cancer cell lines was studied. The results show the absence of an antiproliferative effect on the surfaces without BA S 1 – S 3, while an antiproliferative effect was observed with S 4 and S 5 and was attributed to the release of BA in the medium.