title: Monoalkoxy BODIPYs--a fluorophore class for bioimaging.
abstract: Small molecule fluorophores are indispensable tools for modern biomedical imaging techniques. In this report, we present the development of a new class of BODIPY dyes based on an alkoxy-fluoro-boron-dipyrromethene core. These novel fluorescent dyes, which we term MayaFluors, are characterized by good aqueous solubility and favorable in vitro physicochemical properties. MayaFluors are readily accessible in good yields in a one-pot, two-step approach starting from well-established BODIPY dyes, and allow for facile modification with functional groups of relevance to bioconjugate chemistry and bioorthogonal labeling. Biological profiling in living cells demonstrates excellent membrane permeability, low nonspecific binding, and lack of cytotoxicity.
authors.affiliation: Center for Systems Biology and ∥Center for Human Genetic Research, Massachusetts General Hospital , 185 Cambridge Street, Boston, Massachusetts 02114, United States.
authors.forename: Alexandra M
authors.initials: AM
authors.lastname: Courtis
authors.forename: Sofia A
authors.initials: SA
authors.lastname: Santos
authors.forename: Yinghua
authors.initials: Y
authors.lastname: Guan
authors.forename: J Adam
authors.initials: JA
authors.lastname: Hendricks
authors.forename: Balaram
authors.initials: B
authors.lastname: Ghosh
authors.forename: D Miklos
authors.initials: DM
authors.lastname: Szantai-Kis
authors.forename: Surya A
authors.initials: SA
authors.lastname: Reis
authors.forename: Jagesh V
authors.initials: JV
authors.lastname: Shah
authors.forename: Ralph
authors.initials: R
authors.lastname: Mazitschek
mesh_terms: D001896:Boron Compounds / Q000032:analysis* / Q000138:chemical synthesis / Q000737:chemistry; D002463:Cell Membrane Permeability; D002470:Cell Survival; D005260:Female; D005456:Fluorescent Dyes / Q000032:analysis* / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D061986:MCF-7 Cells; D057054:Molecular Imaging / Q000379:methods*; D015394:Molecular Structure; D012995:Solubility; D014407:Tumor Cells, Cultured
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes