Synthesis and in vitro anti-tumor activity of carboranyl levodopa

Yinghuai Zhu; Yongxiang Lin; Narayan S Hosmane

doi:10.1016/j.bioorg.2019.103090

Synthesis and in vitro anti-tumor activity of carboranyl levodopa

Bioorg Chem. 2019 Sep:90:103090. doi: 10.1016/j.bioorg.2019.103090. Epub 2019 Jun 26.

Authors

Yinghuai Zhu¹, Yongxiang Lin², Narayan S Hosmane³

Affiliations

¹ School of Pharmacy, Macau University of Science and Technology, Avenida Wai Long, Taipa 999078, Macau. Electronic address: yhzhu@must.edu.mo.
² Institute of Chemical and Engineering Sciences, No. 1 Pesek Road, Jurong Island 627833, Singapore.
³ Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USA. Electronic address: hosmane@niu.edu.

PMID: 31260876
DOI: 10.1016/j.bioorg.2019.103090

Abstract

Reactions of closo-1-Me-2-Iodobutyl-1,2-closo-dicarborane, 1-Me-2-I(CH₂)₄-C₂B₁₀H₁₀, with l-dopa methyl ester can produce carboranyl l-dopa methyl esters in 54% yield in the presence of sodium hydroxide. The appended closo-carboranes can be decapitated with sodium hydroxide in a mixed solvent of ethanol and deionized water to produce highly water-soluble carboranyl levodopa in 64% yield. All the new compounds were characterized by ¹H, ¹³C, ¹¹B NMR, FT-IR spectroscopy and elemental analysis. The highly water soluble carboranyl levodopa 4 shows promising efficacy of anti-tumors in vitro in the presence of slow neutron beams.

Keywords: Anti-tumor; Bio-assessment; Drug delivery; Levodopa; Neutron capture therapy (NCT).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology*
Apoptosis
Cell Proliferation
Dopamine Agents / chemistry*
Gliosarcoma / drug therapy*
Gliosarcoma / pathology
Humans
In Vitro Techniques
Levodopa / chemistry*
Tumor Cells, Cultured

Substances

Antineoplastic Agents
Dopamine Agents
Levodopa