title: Efficient synthesis of an indoloquinolizinium alkaloid selective DNA-binder by ring-closing metathesis.
abstract: Two total syntheses of the indolo[2,3-a]quinolizinium cation have been accomplished through the application of two ring-closing metathesis reactions to form the pyridinium ring. One of these approaches provides the tetracyclic cation in only five steps from commercially available harmane. Fluorescence-based thermal denaturation experiments, as well as spectrofluorimetric titration, circular dichroism measurements, and theoretical simulations, showed a consistent DNA-binding capacity by intercalation with a marked preference for AT-rich sequences.
authors.affiliation: Departamento de Química Orgánica y Química Inorgánica, ‡Departamento de Biología de Sistemas, §Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá , 28871-Alcalá de Henares, Madrid, Spain.
authors.forename: Beatriz
authors.initials: B
authors.lastname: Abarca
authors.forename: Raul
authors.initials: R
authors.lastname: Custodio
authors.forename: Ana M
authors.initials: AM
authors.lastname: Cuadro
authors.forename: David
authors.initials: D
authors.lastname: Sucunza
authors.forename: Alberto
authors.initials: A
authors.lastname: Domingo
authors.forename: Francisco
authors.initials: F
authors.lastname: Mendicuti
authors.forename: Julio
authors.initials: J
authors.lastname: Alvarez-Builla
authors.forename: Juan J
authors.initials: JJ
authors.lastname: Vaquero
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D005453:Fluorescence; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D007211:Indoles; D011807:Quinolizines; D004247:DNA