title: Bright oligothiophene N-succinimidyl esters for efficient fluorescent labeling of proteins and oligonucleotides.
abstract: The synthesis of multicolor fluorescent oligothiophene N-succinimidyl esters (TSEs) is reported, and their optical properties are discussed with the aid of ab initio calculations. The esters were coupled to proteins and to 3'-amino-modified oligonucleotides in mild conditions and with similar modalities. A comparative study of the bioconjugate of IgG1 anti-CD3 antibody labeled with a blue fluorescent TSE and with fluorescein isothiocyanate (FITC) is reported, showing that the former achieves higher photoluminescence intensity and optical stability than the latter. Fluorescence resonance energy transfer experiments with TSE-labeled oligonucleotides and examples of cellular imaging via TSE-labeled proteins are reported.
authors.affiliation: Consiglio Nazionale Ricerche (ISOF), Mediteknology srl, Area Ricerca CNR, Via Gobetti 101, I-40129 Bologna, Italy. barbarella@isof.cnr.it
authors.forename: Giovanna
authors.initials: G
authors.lastname: Barbarella
authors.forename: Massimo
authors.initials: M
authors.lastname: Zambianchi
authors.forename: Alfredo
authors.initials: A
authors.lastname: Ventola
authors.forename: Eduardo
authors.initials: E
authors.lastname: Fabiano
authors.forename: Fabio
authors.initials: F
authors.lastname: Della Sala
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Gigli
authors.forename: Marco
authors.initials: M
authors.lastname: Anni
authors.forename: Andrea
authors.initials: A
authors.lastname: Bolognesi
authors.forename: Letizia
authors.initials: L
authors.lastname: Polito
authors.forename: Marina
authors.initials: M
authors.lastname: Naldi
authors.forename: Massimo
authors.initials: M
authors.lastname: Capobianco
mesh_terms: D000911:Antibodies, Monoclonal / Q000378:metabolism; D017252:CD3 Complex / Q000378:metabolism; D004705:Endocytosis; D004952:Esters / Q000138:chemical synthesis* / Q000378:metabolism*; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000378:metabolism*; D006367:HeLa Cells; D006801:Humans; D000922:Immunotoxins / Q000378:metabolism; D019169:Jurkat Cells; D009699:N-Glycosyl Hydrolases / Q000378:metabolism; D009841:Oligonucleotides / Q000378:metabolism; D010940:Plant Proteins / Q000378:metabolism; D011485:Protein Binding; D054789:Ribosome Inactivating Proteins, Type 1; D000076985:Saporins; D013876:Thiophenes / Q000138:chemical synthesis* / Q000378:metabolism*
chemical_list: D000911:Antibodies, Monoclonal; D017252:CD3 Complex; D004952:Esters; D005456:Fluorescent Dyes; D000922:Immunotoxins; D009841:Oligonucleotides; D010940:Plant Proteins; D054789:Ribosome Inactivating Proteins, Type 1; D013876:Thiophenes; D009699:N-Glycosyl Hydrolases; D000076985:Saporins