Characterization of a novel polymeric prodrug of an antibacterial agent synthesized by mechanochemical solid-state polymerization

被引:3
作者
Yamauchi, Yukinori [1 ]
Doi, Naoki [2 ]
Kondo, Shin-ichi [2 ]
Sasai, Yasushi [2 ]
Kuzuya, Masayuki [3 ]
机构
[1] Matsuyama Univ, Dept Pharmaceut Phys Chem, Coll Pharmaceut Sci, 4-2 Bunkyo Cho, Matsuyama, Ehime 7908578, Japan
[2] Gifu Pharmaceut Univ, Dept Drug Delivery Technol & Sci, Lab Pharmaceut Phys Chem, Gifu, Japan
[3] Chubu Gakuin Univ, Fac Human Welf, Dept Hlth & Welf, Gifu, Japan
关键词
acid anhydride bond; antibacterial agent; controlled release; mechanochemical polymerization; polymeric prodrug; ANTIINFLAMMATORY DRUGS NSAIDS; PHARMACOLOGICAL-ACTIVITY; HYDROLYTIC DEGRADATION; RELEASE; COPOLYMERS; STABILITY; ESTERS; ACID);
D O I
10.1002/ddr.21700
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Polycrystalline methacryloyl monomers of the antibacterial drug nalidixic acid with an anhydride bond to the drug carboxyl group were prepared. The physicochemical properties of the synthesized vinyl monomer were characterized using X-ray powder diffraction, thermal analysis, and polarized light microscopy measurements. Mechanochemical solid-state polymerization of the resulting monomers was carried out to yield a novel polymeric prodrug. The in vitro hydrolysis behavior of the polymeric prodrug indicated that the release rate of drug from the polymeric prodrug was clearly dependent on the pH value of the hydrolysis solution. Moreover, sustained release of the drug at an almost constant rate for more than 10 hr was shown in both neutral and alkaline solutions. The results suggest that anhydride-based polymeric prodrugs could be potentially useful in colon targeted drug delivery systems.
引用
收藏
页码:867 / 874
页数:8
相关论文
共 50 条
[31]   Irreversible exchange of potassium with thallium in coordination polymer nanostructures upon solid-state Mechanochemical process [J].
Mirzadeh, Elham ;
Akhbari, Kamran ;
White, Jonathan .
INORGANIC CHEMISTRY COMMUNICATIONS, 2018, 92 :95-100
[32]   Synthesis, characterization polymerization and antibacterial properties of novel thiophene substituted acrylamide [J].
Elsabee, Maher Z. ;
Ali, Eman A. ;
Mokhtar, Samia M. ;
Eweis, Mohamed .
REACTIVE & FUNCTIONAL POLYMERS, 2011, 71 (12) :1187-1194
[33]   A silver complex with ibuprofen: Synthesis, solid state characterization, DFT calculations and antibacterial assays [J].
Pereira e Silva, Irlene Maria ;
Profirio, Daniel de Moraes ;
Ferraz de Paiva, Raphael Enoque ;
Lancellotti, Marcelo ;
Barboza Formiga, Andre Luiz ;
Corbi, Pedro Paulo .
JOURNAL OF MOLECULAR STRUCTURE, 2013, 1049 :1-6
[34]   A LLZO Fibers/ PPO polymeric matrix solid electrolyte for high voltage solid-state lithium batteries [J].
Zhong, Liang ;
Li, Jie ;
Chen, Zhi-xiong ;
Zhou, Li-ping ;
Liu, Hai-xia ;
Shen, Xiang-qian ;
Jing, Mao-xiang .
APPLIED PHYSICS A-MATERIALS SCIENCE & PROCESSING, 2024, 130 (09)
[35]   Solid-state graft polymerization of styrene in spherical polypropylene particles in the presence of montmorillonite [J].
Fu, Zhisheng ;
Sun, Fangli ;
Fan, Zhiqiang .
JOURNAL OF APPLIED POLYMER SCIENCE, 2012, 126 (05) :1497-1504
[36]   Direct quantification of the degree of polymerization of hydrolyzed cellulose by solid-state NMR spectroscopy [J].
Yuan, Shichen ;
Tyufekchiev, Maksim, V ;
Timko, Michael T. ;
Schmidt-Rohr, Klaus .
CELLULOSE, 2022, 29 (04) :2131-2144
[37]   Structural Characterization of a Cyclodextrin/l-menthol Inclusion Complex in the Solid-state by Solid-state NMR and Vibrational Circular Dichroism [J].
Sakai, Takahiro ;
Akagi, Yumiko ;
Suzuki, Hisashi ;
Irie, Mitsuki ;
Nakamura, Tetsuya ;
Sato, Hisako ;
Kawamura, Izuru .
ANALYTICAL SCIENCES, 2020, 36 (11) :1337-1343
[38]   Solid-state characterization of poly(ethylene glycol) samples prepared by solvent cast technique [J].
Dinc, C. Ozdemir ;
Guner, A. .
BULGARIAN CHEMICAL COMMUNICATIONS, 2017, 49 :15-20
[39]   Direct thermodynamic characterization of solid-state reactions by isothermal calorimetry [J].
Cvetnic, Marija ;
Splajt, Robert ;
Topic, Edi ;
Rubcic, Mirta ;
Bregovic, Nikola .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2023, 26 (01) :67-75
[40]   Solid-state characterization and solubility of a genistein-caffeine cocrystal [J].
Sowa, Michal ;
Slepokura, Katarzyna ;
Matczak-Jon, Ewa .
JOURNAL OF MOLECULAR STRUCTURE, 2014, 1076 :80-88