期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 22, 页码 8376-8382出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo701475q
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资金
- NHLBI NIH HHS [HL-083187, R24 HL083187, R24 HL083187-02] Funding Source: Medline
Two analogues (1, 2) of free cholesterol and one analogue (3) of the immunosuppressive sphingolipid FrY720 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 (similar to 70-80 nm) compared with those derived from 5 (in which a phenylethynyl moiety is bonded to C-8 of BODIPY).
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