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o-Carboranylalkoxy-1,3,5-Triazine Derivatives: Synthesis, Characterization, X-ray Structural Studies, and Biological

Guo Fan Jin1, Hyun Seung Ban2, Hiroyuki Nakamura3

  • 1School of Pharmacy, Jiangsu University, Zhenjiang 212013, Jiangsu, China. 1000004770@ujs.edu.cn.

Molecules (Basel, Switzerland)
|September 12, 2018
PubMed
Summary

New triazine derivatives with alkoxy-o-carboranes were synthesized. These compounds show high accumulation and cytotoxicity in melanoma cells, outperforming p-boronophenylalanine in vitro.

Keywords:
1,3,5-triazineboron neutron capture therapyheterocyclic systemmorpholineo-Carborane

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Boron Neutron Capture Therapy

Background:

  • 1,3,5-triazine derivatives are versatile scaffolds in medicinal chemistry.
  • Carboranes, particularly o-carboranes, are of interest for their unique properties and potential in targeted therapies.
  • Developing novel boron-containing compounds for cancer treatment is an active area of research.

Purpose of the Study:

  • To synthesize novel morpholine- and bis(2-methoxyethyl)amine-substituted 1,3,5-triazine derivatives incorporating an alkoxy-o-carborane.
  • To investigate the in vitro cytotoxicity and cellular accumulation of these novel carboranyl-triazine compounds.
  • To compare their efficacy against B16 melanoma cells with a known boron delivery agent, p-boronophenylalanine.

Main Methods:

  • Chemical synthesis of substituted 1,3,5-triazine derivatives.
  • X-ray crystallography for molecular structure elucidation.
  • In vitro cell culture studies using B16 melanoma cells.

Main Results:

  • Successful synthesis of target morpholine- and bis(2-methoxyethyl)amine-substituted alkoxy-o-carboranyl-1,3,5-triazines.
  • Confirmation of molecular structures via X-ray crystallography.
  • Demonstrated high accumulation of methylene-bridged derivatives in B16 melanoma cells.
  • Exhibited superior in vitro cytotoxicity compared to p-boronophenylalanine.

Conclusions:

  • Novel carboranyl-triazine conjugates were effectively synthesized and characterized.
  • The synthesized compounds show promising selective accumulation and potent cytotoxicity in melanoma cells.
  • These findings support the potential of these novel triazine derivatives as therapeutic agents, possibly for boron neutron capture therapy.