Biophysical and biological properties of newly synthesized dioxinocoumarin derivatives. II. Dark and photoinduced effects on T7 phage, yeast and HeLa cells

G. Csík, G. Rontó, Silvano Nocentini, Simone Averbeck, Dietrich Averbeck, Thierry Besson, Gérard Coudert, Gérald Guillaumet

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The dioxinocoumarin derivatives 5H-[2]benzopyrano-[3,4-g][1,4]benzodioxin-5-one (I), 5H-[2]benzopyrano-[3,4-g] [2,3]-dihydro-[1,4]benzodioxin-5-one (II), 6H-[2]benzopyrano[3,4-f]-1,4-benzodioxin-6-one (III) and 6H-[2] benzopyrano[3,4-f]-2,3-dihydro-1,4-benzodioxin-6-one (IV) were synthesized. Their biological effect was studied in the presence and absence of UVA radiation, and compared with that of 8-methoxypsoralen (8-MOP) and angelicin derivatives on T7 phage, diploid yeast (Saccharomyces cerevisiae) and HeLa cells. The photobiological activities of compounds I and III were stronger than that of 8-MOP in phage inactivation and DNA synthesis inhibition in HeLa cells, whereas compounds II and IV, with a saturated dioxin ring, showed very poor activity. The photosensitizing activity of dioxinocoumarins on phage inactivation decreased by a factor of two to three in the absence of oxygen. Treatments with compound I and UVA in the presence of oxygen modified the helical structure and stability of phage DNA and proteins. Compounds I and II were more active than IV for photoinduced cell killing in yeast, although always less active than 8-MOP. At comparable photocytotoxic levels, compounds I and III were as strong inducers of cytoplasmic "petite" mutants in yeast as angelicin, suggesting a possible monofunctional mode of action with cellular DNA.

Original languageEnglish
Pages (from-to)129-139
Number of pages11
JournalJournal of Photochemistry and Photobiology, B: Biology
Volume24
Issue number2
DOIs
Publication statusPublished - 1994

Fingerprint

Bacteriophage T7
Methoxsalen
Bacteriophages
yeast
methoxsalen
HeLa Cells
bacteriophages
Yeast
deoxyribonucleic acid
Yeasts
chemical derivatives
yeasts
Derivatives
deactivation
DNA
cells
Oxygen
saccharomyces
inactivation
Dioxins

Keywords

  • Cytoplasmic "petite" mutants
  • Dark effect
  • Dioxinocoumarins
  • DNA synthesis inhibition
  • HeLa cell
  • Photosensitization
  • T7 phage
  • Yeast

ASJC Scopus subject areas

  • Plant Science
  • Bioengineering
  • Physical and Theoretical Chemistry

Cite this

Biophysical and biological properties of newly synthesized dioxinocoumarin derivatives. II. Dark and photoinduced effects on T7 phage, yeast and HeLa cells. / Csík, G.; Rontó, G.; Nocentini, Silvano; Averbeck, Simone; Averbeck, Dietrich; Besson, Thierry; Coudert, Gérard; Guillaumet, Gérald.

In: Journal of Photochemistry and Photobiology, B: Biology, Vol. 24, No. 2, 1994, p. 129-139.

Research output: Contribution to journalArticle

Csík, G. ; Rontó, G. ; Nocentini, Silvano ; Averbeck, Simone ; Averbeck, Dietrich ; Besson, Thierry ; Coudert, Gérard ; Guillaumet, Gérald. / Biophysical and biological properties of newly synthesized dioxinocoumarin derivatives. II. Dark and photoinduced effects on T7 phage, yeast and HeLa cells. In: Journal of Photochemistry and Photobiology, B: Biology. 1994 ; Vol. 24, No. 2. pp. 129-139.
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AU - Csík, G.

AU - Rontó, G.

AU - Nocentini, Silvano

AU - Averbeck, Simone

AU - Averbeck, Dietrich

AU - Besson, Thierry

AU - Coudert, Gérard

AU - Guillaumet, Gérald

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