Development of vizantin, a safe immunostimulant, based on the structure-activity relationship of trehalose-6,6'-dicorynomycolate

J Med Chem. 2013 Jan 10;56(1):381-5. doi: 10.1021/jm3016443. Epub 2012 Dec 19.

Abstract

Vizantin, 6,6'-bis-O-(3-nonyldodecanoyl)-α,α'-trehalose, was developed as a safe immunostimulator on the basis of a structure-activity relationship (SAR) study with trehalose 6,6'-dicorynomycolate (TDCM). It was possible to synthesize vizantin on a large scale more easily than in the case of TDCM, and the compound exhibited more potent prophylactic effect on experimental lung metastasis of B16-F0 melanoma cells. Because vizantin stimulated human macrophages, it is a promising candidate for clinical application.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis*
  • Adjuvants, Immunologic / chemistry
  • Adjuvants, Immunologic / pharmacology
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cord Factors / chemical synthesis*
  • Cord Factors / chemistry
  • Cord Factors / pharmacology
  • Glycolipids / chemical synthesis*
  • Glycolipids / chemistry
  • Glycolipids / pharmacology
  • Humans
  • In Vitro Techniques
  • Lung Neoplasms / prevention & control
  • Lung Neoplasms / secondary
  • Macrophages / drug effects
  • Macrophages / immunology
  • Melanoma, Experimental / pathology
  • Mice
  • Mice, Inbred C57BL
  • Phagocytosis / drug effects
  • Stereoisomerism
  • Structure-Activity Relationship
  • Trehalose / analogs & derivatives*
  • Trehalose / chemical synthesis
  • Trehalose / chemistry
  • Trehalose / pharmacology
  • Xenograft Model Antitumor Assays

Substances

  • 6,6'-bis-O-(3-nonyldodecanoyl)-alpha,alpha'-trehalose
  • Adjuvants, Immunologic
  • Antineoplastic Agents
  • Cord Factors
  • Glycolipids
  • 6,6'-dicorynomycolyl trehalose
  • Trehalose