Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine
In comparison with pristine sinomenine and carborane precursors, the calculations of molecular docking with matrix metalloproteinases (MMPs) and methylcarboranyl-<i>n</i>-butyl sinomenine showed improved interactions. Accordingly, methylcarboranyl-<i>n</i>-butyl sinomenine sh...
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MDPI AG
2020-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/20/4697 |
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| author | Jianghong Cai Narayan S. Hosmane Masao Takagaki Yinghuai Zhu |
| author_facet | Jianghong Cai Narayan S. Hosmane Masao Takagaki Yinghuai Zhu |
| author_sort | Jianghong Cai |
| collection | DOAJ |
| description | In comparison with pristine sinomenine and carborane precursors, the calculations of molecular docking with matrix metalloproteinases (MMPs) and methylcarboranyl-<i>n</i>-butyl sinomenine showed improved interactions. Accordingly, methylcarboranyl-<i>n</i>-butyl sinomenine shows a high potential in the treatment of rheumatoid arthritis (RA) in the presence of slow neutrons. The reaction of potassium salt of sinomenie, which is generated from the deprotonation of sinomenine (<b>1</b>) using potassium carbonate in a solvent of <i>N</i>,<i>N</i>-dimethyl formamide, with 4-methylcarboranyl-<i>n</i>-butyl iodide, (<b>2</b>) forms methylcarboranyl-<i>n</i>-butyl sinomenine (<b>3</b>) in 54.3% yield as a new product. This new compound was characterized by <sup>1</sup>H, <sup>13</sup>C, and <sup>11</sup>B NMR spectroscopy, FT-IR spectroscopy, and elemental analyses to confirm its molecular composition. In addition to molecular docking interactions with MMPs, the in vitro killing effects of <b>3</b>, along with its toxicity measurements, exhibited its potential to be the new drug delivery agent for boron neutron capture synovectomy (BNCS) and boron neutron capture therapy (BNCT) for the treatment of rheumatoid arthritis (RA) and cancers in the presence of slow neutrons, respectively. |
| first_indexed | 2024-03-10T15:38:22Z |
| format | Article |
| id | doaj.art-455fe40097f94a37938b50332f2c7eb6 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T15:38:22Z |
| publishDate | 2020-10-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-455fe40097f94a37938b50332f2c7eb62023-11-20T17:01:53ZengMDPI AGMolecules1420-30492020-10-012520469710.3390/molecules25204697Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl SinomenineJianghong Cai0Narayan S. Hosmane1Masao Takagaki2Yinghuai Zhu3School of Pharmacy, Macau University of Science and Technology, Avenida Wai Long, Taipa, Macau 999078, ChinaDepartment of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USAGraduate School of Human and Environmental Studies, Kyoto University, Kyoto 604-8232, JapanSchool of Pharmacy, Macau University of Science and Technology, Avenida Wai Long, Taipa, Macau 999078, ChinaIn comparison with pristine sinomenine and carborane precursors, the calculations of molecular docking with matrix metalloproteinases (MMPs) and methylcarboranyl-<i>n</i>-butyl sinomenine showed improved interactions. Accordingly, methylcarboranyl-<i>n</i>-butyl sinomenine shows a high potential in the treatment of rheumatoid arthritis (RA) in the presence of slow neutrons. The reaction of potassium salt of sinomenie, which is generated from the deprotonation of sinomenine (<b>1</b>) using potassium carbonate in a solvent of <i>N</i>,<i>N</i>-dimethyl formamide, with 4-methylcarboranyl-<i>n</i>-butyl iodide, (<b>2</b>) forms methylcarboranyl-<i>n</i>-butyl sinomenine (<b>3</b>) in 54.3% yield as a new product. This new compound was characterized by <sup>1</sup>H, <sup>13</sup>C, and <sup>11</sup>B NMR spectroscopy, FT-IR spectroscopy, and elemental analyses to confirm its molecular composition. In addition to molecular docking interactions with MMPs, the in vitro killing effects of <b>3</b>, along with its toxicity measurements, exhibited its potential to be the new drug delivery agent for boron neutron capture synovectomy (BNCS) and boron neutron capture therapy (BNCT) for the treatment of rheumatoid arthritis (RA) and cancers in the presence of slow neutrons, respectively.https://www.mdpi.com/1420-3049/25/20/4697boron neutron capture synovectomy (BNCS)boron neutron capture therapy (BNCT)anti-rheumatoid arthritiscarboranyl sinomeninemolecular docking |
| spellingShingle | Jianghong Cai Narayan S. Hosmane Masao Takagaki Yinghuai Zhu Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine Molecules boron neutron capture synovectomy (BNCS) boron neutron capture therapy (BNCT) anti-rheumatoid arthritis carboranyl sinomenine molecular docking |
| title | Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine |
| title_full | Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine |
| title_fullStr | Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine |
| title_full_unstemmed | Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine |
| title_short | Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine |
| title_sort | synthesis molecular docking and in vitro boron neutron capture therapy assay of carboranyl sinomenine |
| topic | boron neutron capture synovectomy (BNCS) boron neutron capture therapy (BNCT) anti-rheumatoid arthritis carboranyl sinomenine molecular docking |
| url | https://www.mdpi.com/1420-3049/25/20/4697 |
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