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Synthesis and Anticancer Activity Comparison of Phenylalkyl Isoselenocyanates with Corresponding Naturally Occurring and Synthetic Isothiocyanates
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    Synthesis and Anticancer Activity Comparison of Phenylalkyl Isoselenocyanates with Corresponding Naturally Occurring and Synthetic Isothiocyanates
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    Department of Pharmacology, H072, Chemical Carcinogenesis and Chemoprevention Program of Penn State Hershey Cancer Institute, and Penn State Melanoma Therapeutics Program, Penn State Hershey College of Medicine, Hershey, Pennsylvania 17033
    * To whom correspondence should be addressed. Address: Department of Pharmacology, H072, Penn State Milton S. Hershey Medical Center, Penn State College of Medicine, 500 University Drive, Hershey, PA 17033. Phone: 717-531-0003, extension 285016. Fax: 717-531-0244. E-mail: [email protected]
    †Department of Pharmacology.
    ‡Chemical Carcinogenesis and Chemoprevention Program of Penn State Hershey Cancer Institute.
    §Penn State Melanoma Therapeutics Program.
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2008, 51, 24, 7820–7826
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    https://doi.org/10.1021/jm800993r
    Published November 18, 2008
    Copyright © 2008 American Chemical Society

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    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. IC50 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.

    Copyright © 2008 American Chemical Society

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    1H NMR spectra for compounds 1c, 1d, 2ad, 4bd, 5, and 6 and 1H NMR data for compounds 1c and 1d. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2008, 51, 24, 7820–7826
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm800993r
    Published November 18, 2008
    Copyright © 2008 American Chemical Society

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