Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine
Author ORCID Identifier
Z. Nicolazzo:https://orcid.org/0000-0002-6470-5080
Publication Title
Molecules
E-ISSN
14203049
Document Type
Article
Abstract
In comparison with pristine sinomenine and carborane precursors, the calculations of molecular docking with matrix metalloproteinases (MMPs) and methylcarboranyl-n-butyl sinomenine showed improved interactions. Accordingly, methylcarboranyl-n-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 (1) using potassium carbonate in a solvent of N,N-dimethyl formamide, with 4-methylcarboranyl-n-butyl iodide, (2) forms methylcarboranyl-n-butyl sinomenine (3) in 54.3% yield as a new product. This new compound was characterized by 1H, 13C, and 11B 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 3, 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.
Publication Date
10-1-2020
DOI
10.3390/molecules25204697
PubMed ID
33066470
Keywords
Anti-rheumatoid arthritis, Boron neutron capture synovectomy (BNCS), Boron neutron capture therapy (BNCT), Carboranyl sinomenine, Molecular docking
Recommended Citation
Cai, Jianghong; Hosmane, Narayan S.; Takagaki, Masao; and Zhu, Yinghuai, "Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine" (2020). NIU Bibliography. 594.
https://huskiecommons.lib.niu.edu/niubib/594
Department
Department of Chemistry and Biochemistry
