title: Synthesis of protein-reactive (aminostyryl)pyridinium dyes.
abstract: The synthesis of two protein reactive (aminostyryl)pyridinium fluorescent dyes, N-ethyl-N-[4-[2-[4-(1-methylpyridinio)]ethyl]phenyl]glycine chloride N-hydroxysuccinimide ester (SuASP, 2) and 4-[4-[2-[4-(N,N- dimethylamino)phenyl]ethenyl]pyridinio]butyrate N-hydroxysuccinimide ester (ASPSu, 3), is reported. Both form amide linkage through the activated succinimidyl ester with primary amines. The two analogues differ by the position of the pyridinium positive change relative to the activated ester. SuASP forms an amide linkage that positions the positive charge distal to the protein surface, while ASPSu places the positive charge proximal. The synthesis of SuASP utilizes a palladium coupling reaction for the arylation of 4-vinylpyridine, while the major connection for ASPSu is accomplished through an aldol condensation between 4-(N,N-dimethylamino)benzaldehyde and picoline. Both reagents are shown to label covalently bovine serum albumin.
authors.affiliation: Department of Chemistry and Cancer Center, University of California, San Diego, La Jolla 92093-0506.
authors.forename: A C
authors.initials: AC
authors.lastname: Stevens
authors.forename: R P
authors.initials: RP
authors.lastname: Frutos
authors.forename: D F
authors.initials: DF
authors.lastname: Harvey
authors.forename: A A
authors.initials: AA
authors.lastname: Brian
mesh_terms: D000588:Amines / Q000378:metabolism*; D004563:Electrochemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011506:Proteins / Q000378:metabolism*; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D012710:Serum Albumin, Bovine / Q000378:metabolism; D013053:Spectrophotometry; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
chemical_list: D000588:Amines; D005456:Fluorescent Dyes; D011506:Proteins; D011726:Pyridinium Compounds; D013343:Styrenes; C079700:N-ethyl-N-(4-(2-(4-(1-methylpyridino))ethenyl)phenyl)glycine N-hydroxysuccinimide ester; C079701:4-(4-(2-(4-(N,N-dimethylamino)phenyl)ethenyl)pyridinio)butyrate N-hydroxysuccinimide ester; D012710:Serum Albumin, Bovine