The 9-(bromoalkyl)-1,4-dimethyl-9H-carbazoles (2a-d) derivatives, characterized by the presence of five or seven methylenic spacer groups bonded to the carbazolic nitrogen, have been synthesized from the corresponding 1,4-dimethyl-9H-carbazole and appropriate dibromoalkyl by following a general synthetic method. All the prepared species have been fully characterized by means of IR, and 1H and 13C NMR spectroscopy, GC-MS and Elemental analysis. Good crystals of the 2c have been obtained and the crystal structure has been solved by means of X-ray diffractometry. In order to study the cytotoxic effect of 2a, 2b, 2c, 2d carbazole derivatives on A2780 ovarian cancer cells, we performed MTT assay after exposure of this cell population to those compounds in a concentration range from 1 to 10μM. Finally, we want to verify whether the cytotoxic effect of the 2c carbazole is mediated by apoptotic mechanisms, by performing chromatin condensation assay on the A2780 cell cultures upon the carbazole treatment at concentration of 10 μM for 72h. All together our data demonstrate that carbazole derivatives exert inhibitory effects on ovarian cancer cell growth, highlighting a stronger and a dose-dependent anti proliferative activity displayed by 2c carbazole, designating this compound, as a better candidate in the treatment of human ovarian cancer.

Crystallographic study and biological evaluation of 1,4-dimethyl-N-alkyl-carbazoles.

Caruso A.;Pingitore A.;Caroleo M. C.;Cione E.;Perri M.;Sinicropi M. S.
;
2015

Abstract

The 9-(bromoalkyl)-1,4-dimethyl-9H-carbazoles (2a-d) derivatives, characterized by the presence of five or seven methylenic spacer groups bonded to the carbazolic nitrogen, have been synthesized from the corresponding 1,4-dimethyl-9H-carbazole and appropriate dibromoalkyl by following a general synthetic method. All the prepared species have been fully characterized by means of IR, and 1H and 13C NMR spectroscopy, GC-MS and Elemental analysis. Good crystals of the 2c have been obtained and the crystal structure has been solved by means of X-ray diffractometry. In order to study the cytotoxic effect of 2a, 2b, 2c, 2d carbazole derivatives on A2780 ovarian cancer cells, we performed MTT assay after exposure of this cell population to those compounds in a concentration range from 1 to 10μM. Finally, we want to verify whether the cytotoxic effect of the 2c carbazole is mediated by apoptotic mechanisms, by performing chromatin condensation assay on the A2780 cell cultures upon the carbazole treatment at concentration of 10 μM for 72h. All together our data demonstrate that carbazole derivatives exert inhibitory effects on ovarian cancer cell growth, highlighting a stronger and a dose-dependent anti proliferative activity displayed by 2c carbazole, designating this compound, as a better candidate in the treatment of human ovarian cancer.
A2780 ovarian cancer cells, Apoptosis, Carbazole derivatives, X-Ray structure, Heterocycles, MTT.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/20.500.11770/137278
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? 5
  • Scopus 19
  • ???jsp.display-item.citation.isi??? 19
social impact