Synthesis and characterization of a new retinoic acid ECPIRM as potential chemotherapeutic agent for human cutaneous squamous carcinoma

Anticancer Agents Med Chem. 2015;15(9):1204-12. doi: 10.2174/1871520615666150520142719.

Abstract

Cutaneous squamous cell carcinoma (CSCC) is one of the most common cancers worldwide, requiring effective therapeutic interventions. Retinoids are important chemopreventive and therapeutic agents for a variety of human cancers including CSCC. In this study we synthesized a novel retinoic derivative N-(4-ethoxycarbonylphenyl) isoretinamide (ECPIRM) and evaluated its biological activities and possible mechanisms in human cutaneous squamous cell lines. ECPIRM had better inhibitory effect on the proliferation of squamous carcinoma cells SCL-1 and colo-16, compared with All-trans retinoic acid and 13-cis retinoic acid. ECPIRM had less toxicity to normal keratinocyte cell line HaCaT. Mechanistically, ECPIRM induced G1 cell cycle arrest in SCL-1 cells, via the downregulation of CDK2, CDK4, cycling D1 and cyclin E expression and upregulation of p21. In addition, these effects were at least partially due to the inhibition of JNK/ ERK-AP-1 signaling pathway by ECPIRM. Importantly, these effects of ECPIRM are independent of the classical retinoid receptor pathway, suggesting that the novel compound will have less side-effects in chemotherapy. These findings demonstrate that ECPIRM is a potential inhibitor of MPAK-AP-1 pathway, and is a potential therapeutic agent against CSCC.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Antineoplastic Agents / therapeutic use
  • Carcinoma, Squamous Cell / drug therapy*
  • Cell Cycle Checkpoints / drug effects
  • Cell Cycle Proteins / metabolism
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Humans
  • Isotretinoin / chemical synthesis*
  • Isotretinoin / pharmacology
  • Isotretinoin / therapeutic use
  • MAP Kinase Signaling System
  • Phosphorylation
  • Receptors, Retinoic Acid / drug effects
  • Skin Neoplasms / drug therapy*
  • Skin Neoplasms / metabolism
  • Transcription Factor AP-1 / antagonists & inhibitors

Substances

  • Antineoplastic Agents
  • Cell Cycle Proteins
  • N-(4-ethoxycarbonylphenyl)isoretinamide
  • Receptors, Retinoic Acid
  • Transcription Factor AP-1
  • Isotretinoin