Synthesis and Spectral Properties of Cholesterol- and FTY720-Containing Boron Dipyrromethene Dyes

• Published in: Journal of organic chemistry 2007-10, Vol.72 (22), p.8376-8382
• Main Authors: Li, Zaiguo, Bittman, Robert
• Format: Article
• Language: English
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Boron Compounds - chemical synthesis; Boron Compounds - chemistry; Chemistry; Cholesterol - chemistry; Exact sciences and technology; Fingolimod Hydrochloride; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Lipids; Molecular Structure; Organic chemistry; Porphobilinogen - analogs & derivatives; Porphobilinogen - chemical synthesis; Porphobilinogen - chemistry; Preparations and properties; Propylene Glycols - chemistry; Spectrophotometry, Ultraviolet - methods; Sphingosine - analogs & derivatives; Sphingosine - chemistry; Stereoisomerism; Steroids
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo701475q

Two analogues (1, 2) of free cholesterol and one analogue (3) of the immunosuppressive sphingolipid FTY720 containing a boron dipyrromethene chromophore (BODIPY) were synthesized. The synthetic routes involved preparation of boron dipyrromethene moieties (5, 11), bearing a phenylethynyl group at different positions of the chromophore, and lipids (13, 20) bearing an azido group. The dye was tethered to the lipid via a 1,2,3-triazole in the linker by the click reaction. Analogues derived from 11 [in which an (E)-styrylethynyl moiety is bonded to C-5 of BODIPY] exhibited a marked red shift (∼70−80 nm) compared with those derived from 5 (in which a phenylethynyl moiety is bonded to C-8 of BODIPY).