Novel Ferrocenic Steroidal Drug Derivatives and Their Bioactivities

Abstract

Seven novel ferrocenic derivatives, compounds 1-7, were synthesized from steroidal drugs by Aldol condensation reaction. The derivatives were purified by chromatography, and their structures were determined on the basis of HR-ESI-MS and two-dimensional NMR spectroscopy. The purity of all derivatives was more than 95%. Compounds 1-5 demonstrated anti-proliferative activity on HeLa cell line by SRB assay more than their parent compounds. All seven derivatives showed anti-oxidative activities evaluated by DPPH scavenging and metal ion chelating, while their parent compounds gave no activity. Compound 1 indicated the most potent anti-proliferative activity similar to doxorubicin, with the GI(50) at 0.223 +/- 0.014 microg/mL. Compounds 6 and 7 demonstrated similar potent in vivo anti-inflammatory to their parent compounds (prednisolone and hydrocortisone) at 80.99 +/- 13.5 and 68.24 +/- 10.4% edema inhibition, respectively. This study has suggested that the novel compound 1 was the most potential derivative that can be further developed for cancer treatment.

The essential oils chemical compositions and antimicrobial, antioxidant activities and toxicity of threeHyptisspecies

“…All the determinations were performed in triplicate. The SC 50 was determined as the sample concentration that resulted in a 50% reduction of total free radical (Manosroi et al, 2008;Wu & Wang, 2008).…”

Synthesis of a DNA-targeting nickel (II) complex with testosterone thiosemicarbazone which exhibits selective cytotoxicity towards human prostate cancer cells (LNCaP)

“…Androgens (e.g., testosterone) are sex hormones that are required for normal growth and functional activities of the human prostate. These hormones are able to interact with the androgen receptors and form a stable receptor-ligand complex [14][15][16]. Several organometallic steroidal complexes containing ferrocenyl were synthesized by Top et al and the reported antiproliferative effect of these compounds on the hormone-independent prostate cancer cells PC-3 is stronger compared to the ferrocenyl derivative of the nonsteroidal antiandrogen nilutamide [17].…”

Metallocenes as target specific drugs for cancer treatment

“…Mansroi and coworkers published a series ferrocenyl vectorized with steroidal derivatives of estrogens and androgens, Chart 6 [51]. …”

“…These ferrocenic steroidal compounds ( 10–14 ) were screened in human cervical adenocarcinoma cell line (HeLa) and compared to doxorubicin, Table 6 [51]. Ferrocenic testosterone and methyl testosterone derivatives 10 and 11 showed GI 50 (50% cell growth inhibition) values corresponding that of doxorubicin, 0.223, 0.271 and 0.250 μg/mL respectively.…”