Details

Autor(en) / Beteiligte

• Imperatore, Concetta
• Scuotto, Maria
• Valadan, Mohammadhassan
• Rivieccio, Elisa
• Saide, Assunta
• Russo, Annapina
• Altucci, Carlo
• Menna, Marialuisa
• Ramunno, Anna
• Mayol, Luciano
• Russo, Giulia
• Varra, Michela

Titel

Photo-control of cancer cell growth by benzodiazo N-substituted pyrrole derivatives

Ist Teil von

• Journal of photochemistry and photobiology. A, Chemistry., 2019-05, Vol.377, p.109-118

Ort / Verlag

Lausanne: Elsevier B.V

Erscheinungsjahr

2019

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• [Display omitted] •The new reported compounds easily switch from the trans to the cis form after LED irradiation.•The UV spectra reveal the reversibility of trans↔cis isomerisation and the cis isomers are detectable in 1H NMR spectra.•Kinetics of the trans↔cis isomerisations were evaluated by UV and fast UV experiments.•The compounds differently affect the dynamic of MT polymerization after UV irradiation.•Under irradiation the compounds affect HCT-116 p53-/- cell viability. In order to expand the class of diazocompounds able to act as photo-activable microtubule inhibitors the potential of azo-heteroarenes has been explored. In this paper we focus on the synthesis, physical properties and biological effects of methyl rac-2-(2-((E)-(4-((R)-2,3-dihydroxypropoxy)phenyl) diazenyl)-1H-pyrrol-1-yl)-3-hydroxypropanoate (1a) and methyl rac-2-(2-((E)-(4-((S)-2,3-dihydroxypropoxy)phenyl) diazenyl)-1H-pyrrol-1-yl)-3-hydroxypropanoate (1b). Preliminary biological studies on the HCT-116 p53-/- cancer cell line have shown that the weak antiproliferative action of the trans isomers of these molecules, especially of 1a, is enhanced upon LED light irradiation at 435 nm. On A375 cells the molecules have not shown any effect on cell viability either in the dark or under irradiation. Moreover, the two diastereomeric components of 1a as pure stereomers have been synthesized and characterized for their chemical-physical properties. Interestingly, upon irradiation, 1a has shown an antiproliferative activity on the HCT-116 p53-/- cells greater than that of the pure stereomers, 1RR and 1RS. Tubulin polymerization assay has also demonstrated that 1a, 1RR and 1RS inhibit tubulin aggregation mostly after exposure of the samples to LED light irradiation.