Naphthoquinone fused diazepines targeting hyperamylasemia: potential therapeutic agents for diabetes and cancer

Future Med Chem. 2024;16(21):2231-2245. doi: 10.1080/17568919.2024.2400968. Epub 2024 Sep 20.

Abstract

Aim: Elevated levels of amylase in the blood, known as hyperamylasemia, have been correlated with diabetes and cancer. To investigate the impact of hyperamylasemia on cellular proliferation, it is imperative to design dual inhibitors targeting both α-amylase activity and cancer progression.Materials & methods: Naphthoquinone fused diazepines have been synthesized using multicomponent reaction with high Eco-score of 87 and evaluated for bio efficacy using antioxidant and α-amylase inhibition assay. A correlation between diabetes and cancer has been established via preliminary screening against A549 based lung cancer cell line at 5 μM.Results & conclusion: Compound 4b exhibited superior anti-oxidant and α-amylase inhibitory potential over butylated hydroxytoluene (BHT) and acarbose, respectively with uncompetitive mode of inhibition. Compounds possessing more than 50 % inhibition were then investigated for their IC50 against A549 (Lung cancer), and Breast cancer (MCF-7 and MDA-MB-231) cells. Among all, compound 4p has been selected for further studies, as it demonstrated significant cytotoxicity, while compound 4b showed no effect on AKT gene expression but upregulated IGF-1R gene expression, suggesting a role in managing diabetes. Compound 4p exhibited the ability to decrease AKT expression and increase IGF-1R expression, indicating its potential for treating both diabetes and cancer.

Keywords: anti-cancer; anti-oxidant; benzodiazepines; hyperamylasemia; molecular docking; multicomponent reaction; α-amylase.

Plain language summary

[Box: see text].

MeSH terms

  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation* / drug effects
  • Diabetes Mellitus / drug therapy
  • Diabetes Mellitus / metabolism
  • Drug Screening Assays, Antitumor
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Molecular Structure
  • Naphthoquinones* / chemical synthesis
  • Naphthoquinones* / chemistry
  • Naphthoquinones* / pharmacology
  • Neoplasms / drug therapy
  • Neoplasms / pathology
  • Structure-Activity Relationship
  • alpha-Amylases* / antagonists & inhibitors
  • alpha-Amylases* / metabolism

Substances

  • Naphthoquinones
  • alpha-Amylases
  • Antineoplastic Agents
  • Antioxidants
  • Enzyme Inhibitors