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
[21]   Dextran-based nanoparticles with 5-FU-conjugated polymethacrylate segments for drug delivery: Synthesis of amphiphilic graft copolymers by mechanochemical solid-state polymerization and characterization [J].
Doi, Naoki ;
Yamauchi, Yukinori ;
Sasai, Yasushi ;
Suzuki, Kaho ;
Kuzuya, Masayuki ;
Kondo, Shin-ichi .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2024, 274
[22]   Surface modification of garnet fillers with a polymeric sacrificial agent enables compatible interfaces of composite solid-state electrolytes [J].
Luo, Bin ;
Wu, Jintian ;
Zhang, Ming ;
Zhang, Zhihao ;
Zhang, Xingwei ;
Fang, Zixuan ;
Xu, Ziqiang ;
Wu, Mengqiang .
CHEMICAL SCIENCE, 2023, 14 (45) :13067-13079
[23]   Novel hydrophilic N-halamine polymer with enhanced antibacterial activity synthesized by inverse emulsion polymerization [J].
Wang, Xiao ;
Hao, Xiufeng ;
Chang, Dan ;
Zhu, Chongyi ;
Chen, Lili ;
Dong, Alideertu ;
Gao, Ge .
JOURNAL OF APPLIED POLYMER SCIENCE, 2019, 136 (17)
[24]   Synthesis and Solid-State Polymerization of Butadiyne Derivatives with Trialkoxyphenylurethane Groups [J].
Takahashi, Rintaro ;
Nunokawa, Tatsuya ;
Shibuya, Tadahiro ;
Tomita, Ryohei ;
Tatewaki, Yoko ;
Okada, Shuji ;
Kimura, Tatsumi ;
Shimada, Satoru ;
Matsuda, Hiro .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2012, 85 (02) :236-244
[25]   Solid-State Form Characterization of Riparin I [J].
de Moura, Elisana Afonso ;
Cahino Terto, Marcio Vinicius ;
de Moura Mendonca, Elisangela Afonso ;
Virgulino Procopio, Jose Valdilanio ;
Costa, Vicente Carlos de O. ;
Barbosa Filho, Jose Maria ;
Chavez Gutierrez, Stanley Juan ;
Tavares, Josean Fechine ;
Macedo, Rui Oliveira ;
da Silva, Marcelo Sobral .
MOLECULES, 2017, 22 (10)
[26]   Novel perchlorate and phosphate salts of vinpocetine: Characterization, relative solid-state stability evaluation and Hirshfeld surface analysis [J].
Ma, Yu-heng ;
Ge, Shu-wang ;
Wang, Wei ;
Zheng, Qiang ;
Zuo, Yun-wei ;
Zhong, Chang-jiang ;
Sun, Bai-wang .
JOURNAL OF MOLECULAR STRUCTURE, 2016, 1105 :1-10
[27]   Glass-ionomer dental cements as novel solid-state buffers [J].
Klos, Jacek ;
Nicholson, John W. ;
Czarnecka, Beata .
JOURNAL OF MATERIALS RESEARCH AND TECHNOLOGY-JMR&T, 2021, 15 :3570-3574
[28]   Synthesis of DNA conjugate by mechanochemical solid-state polymerization and its affinity separation of oligonucleotides having single-base difference by capillary electrophoresis [J].
Kondo, S ;
Shichijyou, D ;
Sasai, Y ;
Yamauchi, Y ;
Kuzuya, M .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (07) :863-865
[29]   Photo-responsive polymer micelles fromo-nitrobenzyl ester-based amphiphilic block copolymers synthesized by mechanochemical solid-state copolymerization [J].
Doi, Naoki ;
Yamauchi, Yukinori ;
Ikegami, Ryo ;
Kuzuya, Masayuki ;
Sasai, Yasushi ;
Kondo, Shin-ichi .
POLYMER JOURNAL, 2020, 52 (12) :1375-1385
[30]   A solid-state NMR method for characterization of pharmaceutical eutectics [J].
Hareendran, Chaithanya ;
Shaligram, Parth S. ;
Gonnade, Rajesh ;
Ajithkumar, T. G. .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2024, 26 (05) :3800-3803