Development of Vizantin, a Safe Immunostimulant, Based on the Structure–Activity Relationship of Trehalose-6,6′-dicorynomycolate

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, a...

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Veröffentlicht in:Journal of medicinal chemistry 2013-01, Vol.56 (1), p.381-385
Hauptverfasser: 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
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm3016443