Synthesis of a new bis(indolyl)methane that inhibits growth and induces apoptosis in human prostate cancer cells

Mariangela Marrelli, Xavier Cachet, Filomena Conforti, Rosa Sirianni, Adele Chimento, Vincenzo Pezzi, Sylvie Michel, Giancarlo A. Statti, Francesco Menichini

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The synthesis and the antiproliferative activity against the human breast MCF-7, SkBr3 and the prostate LNCaP cancer cell lines of a series of bis(indolyl)methane derivatives are reported. The synthesis of new compounds was first accomplished by the reaction of different indoles with trimethoxyacetophenone in the presence of catalytic amounts of hydrochloric acid. A second procedure involving the use of oxalic acid dihydrate [(CO 2H)2·2H2O] and N-cetyl-N,N,N- trimethylammonium bromide in water was carried out and led to better yields. Compound 5b significantly reduced LNCaP prostate cancer cell viability in a dose-dependent manner, with an IC50 of 0.64 ± 0.09 M. To determine whether the growth inhibition was associated with the induction of apoptosis, treated cells were stained using DAPI. LNCaP cells treated with 1 M of 5b showed the morphological changes characteristic of apoptosis after 24 h of incubation.

Original languageEnglish (US)
Pages (from-to)2039-2045
Number of pages7
JournalNatural Product Research
Volume27
Issue number21
DOIs
StatePublished - Nov 1 2013

Fingerprint

Methane
prostatic neoplasms
methane
Prostatic Neoplasms
apoptosis
Cells
Apoptosis
Indoles
Oxalic Acid
synthesis
Hydrochloric Acid
oxalic acid
hydrochloric acid
indoles
Carbon Monoxide
Growth
bromides
Bromides
Human Activities
growth retardation

Keywords

  • antiproliferative activity
  • apoptosis
  • bis(indolyl)methane
  • indole

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Marrelli, M., Cachet, X., Conforti, F., Sirianni, R., Chimento, A., Pezzi, V., ... Menichini, F. (2013). Synthesis of a new bis(indolyl)methane that inhibits growth and induces apoptosis in human prostate cancer cells. Natural Product Research, 27(21), 2039-2045. https://doi.org/10.1080/14786419.2013.824440

Synthesis of a new bis(indolyl)methane that inhibits growth and induces apoptosis in human prostate cancer cells. / Marrelli, Mariangela; Cachet, Xavier; Conforti, Filomena; Sirianni, Rosa; Chimento, Adele; Pezzi, Vincenzo; Michel, Sylvie; Statti, Giancarlo A.; Menichini, Francesco.

In: Natural Product Research, Vol. 27, No. 21, 01.11.2013, p. 2039-2045.

Research output: Contribution to journalArticle

Marrelli, M, Cachet, X, Conforti, F, Sirianni, R, Chimento, A, Pezzi, V, Michel, S, Statti, GA & Menichini, F 2013, 'Synthesis of a new bis(indolyl)methane that inhibits growth and induces apoptosis in human prostate cancer cells', Natural Product Research, vol. 27, no. 21, pp. 2039-2045. https://doi.org/10.1080/14786419.2013.824440
Marrelli, Mariangela ; Cachet, Xavier ; Conforti, Filomena ; Sirianni, Rosa ; Chimento, Adele ; Pezzi, Vincenzo ; Michel, Sylvie ; Statti, Giancarlo A. ; Menichini, Francesco. / Synthesis of a new bis(indolyl)methane that inhibits growth and induces apoptosis in human prostate cancer cells. In: Natural Product Research. 2013 ; Vol. 27, No. 21. pp. 2039-2045.
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