Synthesis and Anticancer Activity Comparison of Phenylalkyl Isoselenocyanates with Corresponding Naturally Occurring and Synthetic Isothiocyanates

Journal of Medicinal Chemistry
2008.0

Abstract

Synthesis and identification of novel phenylalkyl isoselenocyanates (ISCs), isosteric selenium analogues of naturally occurring phenylalkyl isothiocyanates (ITCs), as effective cytotoxic and antitumor agents are described. The structure-activity relationship comparison of ISCs with ITCs and effect of the increasing alkyl chain length in inhibiting cancer cell growth were evaluated on melanoma, prostate, breast, glioblastoma, sarcoma, and colon cancer cell lines. IC(50) values for ISC compounds were generally lower than their corresponding ITC analogues. Similarly, in UACC 903 human melanoma cells, the inhibition of cell proliferation and induction of apoptosis were more pronounced with ISCs compared to ITCs. Further, ISCs and ITCs effectively inhibited melanoma tumor growth in mice following intraperitoneal xenograft. A similar reduction in tumor size was observed at 3 times lower doses of ISCs compared to corresponding ITCs.

Knowledge Graph

Similar Paper

Synthesis and Anticancer Activity Comparison of Phenylalkyl Isoselenocyanates with Corresponding Naturally Occurring and Synthetic Isothiocyanates
Journal of Medicinal Chemistry 2008.0
Synthesis and antiproliferative activity of novel α- and β-dialkoxyphosphoryl isothiocyanates
Bioorganic & Medicinal Chemistry Letters 2011.0
Enhanced in Vitro Biological Activity of Synthetic 2-(2-Pyridyl) Ethyl Isothiocyanate Compared to Natural 4-(Methylsulfinyl) Butyl Isothiocyanate
Journal of Medicinal Chemistry 2012.0
Novel phosphonate analogs of sulforaphane: Synthesis, in vitro and in vivo anticancer activity
European Journal of Medicinal Chemistry 2017.0
Phosphorus-containing isothiocyanate-derived mercapturic acids as a useful alternative for parental isothiocyanates in experimental oncology
Bioorganic & Medicinal Chemistry Letters 2018.0
Synthesis and structure–activity relationships of aliphatic isothiocyanate analogs as antibiotic agents
Medicinal Chemistry Research 2013.0
In vitro and in vivo antifungal activity of synthetic pure isothiocyanates against Sclerotinia sclerotiorum
Pest Management Science 2011.0
Synthesis and antiproliferative activity of novel symmetrical alkylthio- and alkylseleno-imidocarbamates
European Journal of Medicinal Chemistry 2011.0
Natural Product-Derived Antitumor Compound Phenethyl Isothiocyanate Inhibits mTORC1 Activity via TSC2
Journal of Natural Products 2012.0
Selective Depletion of Mutant p53 by Cancer Chemopreventive Isothiocyanates and Their Structure−Activity Relationships
Journal of Medicinal Chemistry 2011.0