Presence of antigenotoxic and anticytotoxic effects of the chalcone 1E,4E-1-(4-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one using in vitro and in vivo assays

被引:8
|
作者
Lemes, Susy Ricardo [1 ]
eSilva, Carolina Ribeiro [1 ]
Veras, Jefferson Holanda [1 ]
Chen-Chen, Lee [1 ]
Lima, Rosa Silva [2 ]
Perez, Caridad Noda [2 ]
Montes de Sousa, Maria Alice [3 ]
de Melo Reis, Paulo Roberto [3 ]
da Silva Junior, Nelson Jorge [4 ]
机构
[1] Univ Fed Goias, Inst Ciencias Biol, Goiania, Go, Brazil
[2] Univ Fed Goias, Inst Quim, Goiania, Go, Brazil
[3] Pontificia Univ Catolica Goias, Lab Estudos Expt & Biotecnol, Goiania, Go, Brazil
[4] Pontificia Univ Catolica Goias, Escola Med Farm & Biomed, Goiania, Go, Brazil
关键词
Ames test; anticytotoxic; antigenotoxic; chalcone; micronucleus test; DNA-DAMAGE; DOXORUBICIN; ANTIOXIDANT; DERIVATIVES; CYTOTOXICITY; INHIBITORS; AGENTS;
D O I
10.1080/01480545.2018.1497046
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chalcones are chemically defined as alpha,beta-unsaturated ketones with a 1,3-diphenyl-2-propen-1-one nucleus. These compounds occur naturally in plants and are considered precursors of flavonoids. Given that evaluating genetic toxicology tests is essential in investigating the safe use and chemopreventive potential of different natural and synthetic compounds, this study aimed to assess the genotoxic, cytotoxic, antigenotoxic, and anticytotoxic activity of the chalcone 1E,4E-1-(4-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one (CAB7 beta). The CAB7 beta was synthesized via Claisen-Schmidt reaction. The Ames test was applied using the co-treatment model as well as a micronucleus assay of mouse bone marrow with co-, pre- and post-treatment models. Our results indicate no genotoxic effect for CAB7 beta in any of the tests applied. At all the concentrations used, CAB7 beta showed a significant DNA protective effect against the mutagenic action of 4-nitroquinoline-1-oxide and sodium azide according to the Ames test, and against doxorubicin in the co-, pre- and post-treatment models of the micronucleus assay. CAB7 beta alone displayed cytotoxic activity in the micronucleus test. At concentrations of 12,5 and 50 mu g/plate, CAB7 beta showed a moderate cytotoxic profile only in Salmonella typhimurium strain TA98. However, an anticytotoxic effect was observed against S. typhimurium strain TA100 for all the concentrations tested and during co-, pre- and post-treatment in the micronucleus assay. It was concluded that CAB7 beta exhibited a slightly cytotoxic effect in S. typhimurium strain TA98 and significant antigenotoxic and anticytotoxic effects in cells of mouse, making it a promising candidate in chemoprevention and possibly in the development of new cancer treatments.
引用
收藏
页码:383 / 390
页数:8
相关论文
共 50 条
  • [31] (2E)-1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)-3-(4-chlorophenyl)prop-2en-1-one
    Sarveswari, S.
    Vijayakumar, V.
    Ng, Seik Weng
    Tiekink, Edward R. T.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O624 - U1770
  • [32] A Novel Monocarbonyl Analogue of Curcumin, (1E,4E)-1,5-Bis(2,3-dimethoxyphenyl)penta-1,4-dien-3-one, Induced Cancer Cell H460 Apoptosis via Activation of Endoplasmic Reticulum Stress Signaling Pathway
    Wang, Yi
    Xiao, Jian
    Zhou, Huiping
    Yang, Shulin
    Wu, Xiaoping
    Jiang, Chengxi
    Zhao, Yunjie
    Liang, Donglou
    Li, Xiaokun
    Liang, Guang
    JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (11) : 3768 - 3778
  • [33] (5S)-1,4-Bis{[(1E)-4-methylbenzylidene]amino}-5-(thien-2-yl)pyrrolidin-2-one
    Chopra, Deepak
    Venugopala, K. N.
    Rao, G. K.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O2840 - U2041
  • [34] ss-NMR and single-crystal X-ray diffraction in the elucidation of a new polymorph of bischalcone (1E, 4E)-1,5-bis(4-fluorophenyl) penta-1,4-dien-3one
    Ferreira, Livia O. A.
    Valdo, Ana Karoline S. M.
    Nascimento Neto, Jose Antonio
    Ribeiro, Leandro
    da Silva, Jefferson R. D.
    Queiroz, Luiz H. K., Jr.
    Perez, Caridad N.
    Martins, Felipe T.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2019, 75 : 694 - +
  • [35] (E)-3-(4-Chlorophenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1one
    Tang, Jie
    Chen, Jin-ying
    Jiang, Ling-qun
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O278 - U1626
  • [36] The synthesis, crystal structure and spectroscopic analysis of (E)-3-(4-chlorophenyl)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)prop-2-en-1-one
    Vinaya
    Richard, Austin S.
    Murthy, Subbiah M.
    Basavaraju, Yeriyur B.
    Yathirajan, Hemmige S.
    Parkin, Sean
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2023, 79 : 674 - +
  • [37] A New Cyclooxygenase-2 Inhibitor, (1E,4E)-1,5-Bis(2-bromophenyl)penta-1,4-dien-3-one (GL63) Suppresses Cyclooxygenase-2 Gene Expression in Human Lung Epithelial Cancer Cells: Coupled mRNA Stabilization and Posttranscriptional Inhibition
    Xiao, Jian
    Tan, Yi
    Pan, Yunbao
    Liang, Guang
    Qu, Changju
    Zhang, Xie
    Zhang, Yi
    Li, Xiaokun
    Yang, Huiling
    BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2010, 33 (07) : 1170 - 1175
  • [38] Synthesis and Antiviral Bioactivity of Novel 3-((2-(1E,4E)-3-Oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-quinazolinone Derivatives
    Ma, Juan
    Li, Pei
    Li, Xiangyang
    Shi, Qingcai
    Wan, Zhihua
    Hu, Deyu
    Jin, Linhong
    Song, Baoan
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (36) : 8928 - 8934
  • [39] Crystal structure of (E)-5-((4-chlorophenyl) diazenyl)-2-(5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole, C23H17ClFN5S2
    El-Hiti, Gamal A.
    Abdel-Wahab, Bakr F.
    Baashen, Mohammed
    Hegazy, Amany S.
    Kariuki, Benson M.
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2017, 232 (01): : 157 - 158
  • [40] The chemical reactivity and antimalarial investigation of crystal structure (2E)-3-(biphenyl-4-yl)-1-(4-chlorophenyl)prop-2-en-1-one and hydroxyphenyl, nitrophenyl substituted chalcone derivative molecules
    Thamarai, A.
    Raja, M.
    Sakthivel, S.
    Kumaran, S.
    Muthu, S.
    Narayana, B.
    Ramesh, P.
    Sevvanthi, S.
    Javed, Saleem
    Naick, B. Nagaraja
    Irfan, Ahmad
    JOURNAL OF MOLECULAR STRUCTURE, 2023, 1280