Synthesis and spectral properties of cholesterol- and FTY720-containing boron dipyrromethene dyes.
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 (approximately 70-80 nm) compared with those derived from 5 (in which a phenylethynyl moiety is bonded to C-8 of BODIPY).
Li
Zaiguo
Z
Department of Chemistry and Biochemistry, Queens College of City University of New York, Flushing, New York 11367-1597, USA.
Bittman
Robert
R
D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002784:Cholesterol / Q000737:chemistry*; D000068876:Fingolimod Hydrochloride; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011162:Porphobilinogen / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011409:Propylene Glycols / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D001896:Boron Compounds; D005456:Fluorescent Dyes; D011409:Propylene Glycols; C507544:dipyrromethene; D011162:Porphobilinogen; D002784:Cholesterol; D000068876:Fingolimod Hydrochloride; D013110:Sphingosine