Department of Chemistry of Functional Molecule (Imagawa Lab.)


J Med Chem (2013) 56, 381-385

Development of Vizantin, a Safe Immunostimulant, based on the Structure-Activity Relationship of Trehalose-6,6’-Dicorynomycolate

Yamamoto, Hirofumi; Oda, Masataka; Nakano, Mayo; Watanabe, Naoyuki; Yabiku, Kenta; Shibutani, Masahiro; Inoue, Masahisa; Imagawa, Hiroshi; Nagahama, Masahiro; Himeno, Seiichiro ; Setsu, Kojun; Sakurai, Jun; Nishizawa, Mugio


Bacterial components, including Trehalose 6,6’-dimycolates (TDMs), have attracted considerable attention as lead compounds for adjuvant development. However, these compounds can result in clinical symptoms of septic shock, making it imperative to design suitable ‘safe’ immunostimulants that can activate the immune response without causing toxicity. In this article, we describe the development of Vizantin, 6,6’-bis-O-(3-nonyldodecanoyl)-α,α’-trehalose, on the basis of a structure-activity relationship study (SARs) with trehalose 6,6’-dicorynomycolate (TDCM). Our results show that it was easier to synthesize Vizantin on a large scale. Further it exhibited a more potent prophylactic effect on experimental lung metastasis of B16-F0 melanoma cells and could also stimulate human macrophages, making it a promising candidate as an adjuvant in clinical applications.