Anthracene-Derived Bis-Aminophosphonates: Crystal Structure,In Vitro Antitumor Activity,and Genotoxicity In Vivo |
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| Authors: | I Kraicheva E Vodenicharova B Shivachev R Nikolova A Kril M Topashka-Ancheva |
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| Institution: | 1. Institute of Polymers, Bulgarian Academy of Sciences , 1113 , Sofia , Bulgaria;2. Institute of Mineralogy and Crystallography, Bulgarian Academy of Sciences , 1113 , Sofia , Bulgaria;3. Institute of Experimental Morphology, Pathology and Anthropology with Museum, Bulgarian Academy of Sciences , 1113 , Sofia , Bulgaria;4. Institute of Biodiversity and Ecosystems Research, Bulgarian Academy of Sciences , 1113 , Sofia , Bulgaria |
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| Abstract: | Abstract The X-ray crystal structures of the anthracene-derived bis-aminophosphonates 4.4′-bisN-methyl(diethoxyphosphonyl)-1-(9-anthryl)]diaminodiphenylmethane (1) and 1,3-bis N-methyl(diethoxyphosphonyl)-1-(9-anthryl)]diaminobenzene (3) are reported. The X-ray analyses demonstrated that both compounds crystallize in a centrosymmetric manner containing a meso-form (1) and a pair of enantiomers (3). The cytotoxic potential, genotoxicity, and antiproliferative activity of bis-aminophosphonates 1 and bisN-methyl(diethoxyphosphonyl)-1-(9-anthryl)]benzidine (2), as well as their subcellular distribution in a tumor cell culture system, are also discussed. Compounds 1 and 2 showed optimal antiproliferative activity to human tumor cells from colon carcinoma line HT-29. In vitro and in vivo safety testing revealed that the compounds exert lower toxicity to normal cells as compared with well-known anticancer and cytotoxic agents. Supplemental materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfur, and Silicon and the Related Elementsto view the free supplemental file. |
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| Keywords: | Aminophosphonic acids single crystal antitumor activity in vitro cytotoxicity genotoxicity |
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