Perspectives on the synthesis and use of ageladine A. Issue 29 (15th July 2015)

• Record Type: Journal Article
• Authors: Mordhorst, Thorsten; Bickmeyer, Ulf
• Is Part Of: Tetrahedron letters. Volume 56:Issue 29(2015)
• Page Start: 4363
• Page End: 4366
• Publication Date: 2015-07-15
• Subjects: QAKGJAQGTQLMFN-UHFFFAOYSA-N; Natural product -- Focused synthesis -- Stokes shift -- Life imaging -- Macrostomum lignano -- Fluorescence; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.081
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A modified synthesis to reveal gram-scales of ageladine A is demonstrated. An increased Stokes shift of ageladine A in living transparent animals is demonstrated. The Stokes shift in flatworms matches DAPI filter settings. Abstract: Focusing on the marine-derived alkaloid ageladine A ([4-(4, 5-dibromo-1 H -pyrrol-2-yl)]-1 H -imidazo[4, 5- c ]pyridin-2-amine trifluoroacetate), we combined and modified published strategies to develop a synthesis method with easily managed reaction steps that allows gram-scale batch synthesis. On exploration additional features of the fluorescent properties of the compound were revealed. In tissues and cells of a marine flatworm, the emission profile shifted to longer wavelengths than in water. The fluorescence emission maximum shifted around 30–450 nm and the profile showed sufficient intensity at approximately 550 nm and above.