Sinteza borovog kompleksa dipirometena za konjugaciju s proteinima

Borov kompleks dipirometena (BODIPY®) predstavlja razred fluorescentnih boja koje se mogu koristiti u medicinske i biološke svrhe. Fluorescentno obilježavanje molekula nastaje konjugacijom, odnosno vezanjem fluorescentnih boja za određene proteine i peptide, s ciljem praćenja njihovih interakcija, konformacijskih promjena i lokalizacije pojedinih peptida i dijelova proteina. BODIPY molekule su prilično neosjetljive na polarnost i pH okoliša te vrlo stabilne u fiziološkim uvjetima. Jezgra BODIPY fluorescentnih boja je dovoljno snažna da izdrži niz kemijskih promjena, a male promjene u strukturi omogućuju aktivaciju fluorescentnih svojstava. U ovom radu uspješno je sintetiziran N,N'-difluoroboril-2,8-dietil-1,3,7,9-tetrametil- 5-(4-izotiocijanatofenil)-dipirometen, BODIPY derivat koji koristi za konjugaciju s proteinima. Opisan je alternativan put sinteze u odnosu na literaturni. Iako je prilikom sinteze došlo do gubitka fluorescentne skupine, na kraju se uspio dobiti željeni BODIPY te su raspravljeni mogući putevi sinteze u kojima bi fluorescentna skupina ostala očuvana.The boron complexes of dipyrromethene (BODIPY®) comprise a class of fluorescent dyes that can be used in medical and biological studies. Fluorescent molecular labeling can be obtained by conjugation, or linking fluorescent dyes to certain proteins and peptides, in order to detect interactions, conformational changes and localization of specific peptides and parts of a protein. BODIPY molecules are relatively insensitive to the polarity and pH of their environment and are very stable to physiological conditions. The BODIPY core is strong enough to withstand a series of chemical reactions, and even the smallest changes to their structures enable the activation of their fluorescent properties. Herein, we have successfully synthesized N, N'-difluoroboryl-2,8-diethyl-1,3,7,9-tetramethyl-5-(4-isothiocyanatophenyl)-dipyrromethene, BODIPY derivative that is used for conjugation to proteins. Alternative pathway of synthesis is described with regard to literature. During the synthesis, a fluorescent group was lost in one step, however, desired BODIPY has been synthesized, thus possible pathways of synthesis in which fluorescent group can be preserved are discussed