title: Aza-BODIPY dyes with enhanced hydrophilicity.
abstract: Attempts to make a diamino disulfonic acid derivative of an aza-BODIPY showed it was difficult to add BF2 to a disulfonated azadipyrromethene, and sulfonation of an aza-BODIPY resulted in loss of the BF2 fragment. We conclude the electron-deficient character of aza-BODIPY dyes destabilizes them relative to BODIPY dyes. Consequently, sulfonation of the aza-BODIPY core is not a viable strategy to increase water solubility. This assertion was indirectly supported via stability studies of a BODIPY and an aza-BODIPY in aqueous media. To afford the desired compound type, an aza-BODIPY with two amino and two sulfonic acid groups was prepared via modification of the aryl substituents with cysteic acid.
authors.affiliation: Department of Chemistry, Texas A&M University, Box 30012, College Station, TX 77842, USA. burgess@tamu.edu.
authors.forename: Anyanee
authors.initials: A
authors.lastname: Kamkaew
authors.forename: Kevin
authors.initials: K
authors.lastname: Burgess
mesh_terms: D000818:Animals; D001372:Aza Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D045744:Cell Line, Tumor; D003544:Cysteic Acid / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D057927:Hydrophobic and Hydrophilic Interactions; D051379:Mice; D008856:Microscopy, Fluorescence; D013451:Sulfonic Acids / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001372:Aza Compounds; D001896:Boron Compounds; D005456:Fluorescent Dyes; D013451:Sulfonic Acids; C579460:boron difluoride; D014867:Water; D003544:Cysteic Acid