New inhibitors of matrix metalloproteinases 9 (MMP-9): Lignans from Selaginella moellendorffii

被引:15
|
作者
Zhu, Yuan [1 ]
Huang, Ri-Zhen [2 ,3 ]
Wang, Chun-Gu [1 ]
Ouyang, Xi-Lin [1 ]
Jing, Xiao-Teng [1 ]
Liang, Dong [1 ]
Wang, Heng-Shan [1 ]
机构
[1] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, State Key Lab Chem & Mol Engn Med Resources, 15 Yucai Rd, Guilin 541004, Guangxi, Peoples R China
[2] Southeast Univ, Pharmaceut Res Ctr, Nanjing, Jiangsu, Peoples R China
[3] Southeast Univ, Sch Chem & Chem Engn, Nanjing, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Lignans; Selaginella moellendorffii; Matrix metalloproteinase; Migration; Anticancer activity; CANCER PROGRESSION; NEOLIGNANS; INVASION; HIERON; CELLS; METASTASIS; MIGRATION; INSIGHTS;
D O I
10.1016/j.fitote.2018.09.008
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Matrix metalloproteinase 9 (MMP-9) is one of the structurally related zinc-dependent endopeptidases families and provides a new target for cancer therapy owing to its pivotal role in metastatic tumors. In this paper, fourteen lignans, including three novel lignans, named selamoellenin B-D (1-3), and eleven known lignan derivatives (4-14) were isolated from the plant of Selaginella moellendorffii. Among them, compound 3 is optically active, which was enantiomerically seperated to afford a pair of enantiomers, ( - )-3 and ( + )-3. Their structures were elucidated by extensive spectroscopic analyses. Their cytotoxic activities were evaluated against four human cancer cell lines. Among them, five compounds (4, 5, 6, 11 and 13) exhibited great potent cytotoxicity and their structure-activity relationships were also discussed. All compounds except for 3 lignan analogues with low cytotoxicity were selected for further in vitro enzyme inhibition, surface plasmon resonance (SPR), and molecular docking assays based on the MMPs target. The results shown that, compound 11 have the best inhibitory effect and can be considered as a potential drug candidate targeting at MMP-9 for cancer therapy.
引用
收藏
页码:281 / 289
页数:9
相关论文
共 50 条
  • [21] Opioids and matrix metalloproteinases: the influence of morphine on MMP-9 production and cancer progression
    Khabbazi, Samira
    Hassanshahi, Mohammadhossein
    Hassanshahi, Alireza
    Peymanfar, Yaser
    Su, Yu-Wen
    Xian, Cory J.
    NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 2019, 392 (02) : 123 - 133
  • [22] Serum levels of matrix metalloproteinases MMP-2 and MMP-9 and their inhibitors in women with glucose intolerance in pregnancy and normal controls
    Stojanovic, Nemanja
    Lewandowski, Krzysztof
    Salata, Ireneusz
    Bienkiewicz, Malgorzata
    Tuck, Susan
    Prelevic, Gordana
    Press, Martin
    GYNECOLOGICAL ENDOCRINOLOGY, 2010, 26 (03) : 201 - 207
  • [23] Temporomandibular inflammation regulates the matrix metalloproteinases MMP-2 and MMP-9 in limbic structures
    Nascimento, Glauce C.
    De Paula, Bruna B.
    Gerlach, Raquel F.
    Leite-Panissi, Christie R. A.
    JOURNAL OF CELLULAR PHYSIOLOGY, 2021, 236 (09) : 6571 - 6580
  • [24] The differences of Matrix Metalloproteinases (MMP-9 and MMP-13) in chronic inflammatory rheumatic diseases
    Eser, Burcu
    Tecer, Duygu
    Dincel, Aylin S.
    ROMANIAN JOURNAL OF MILITARY MEDICINE, 2022, 125 (02) : 325 - 329
  • [25] Matrix metalloproteinases (MMP-8, MMP-9) and the tissue inhibitors of metalloproteinases (TIMP-1, TIMP-2) in patients with fungal keratitis
    Rohini, Gomathinayagam
    Murugeswari, Ponnalagu
    Prajna, Namperumalsamy Venkatesh
    Lalitha, Prajna
    Muthukkaruppan, Veerappan
    CORNEA, 2007, 26 (02) : 207 - 211
  • [26] Opioids and matrix metalloproteinases: the influence of morphine on MMP-9 production and cancer progression
    Samira Khabbazi
    Mohammadhossein Hassanshahi
    Alireza Hassanshahi
    Yaser Peymanfar
    Yu-Wen Su
    Cory J. Xian
    Naunyn-Schmiedeberg's Archives of Pharmacology, 2019, 392 : 123 - 133
  • [27] MMP-9 directed shRNAs as relevant inhibitors of matrix metalloproteinase 9 activity and signaling
    Nowak, Ewa
    Galilejczyk, Anna
    Sypniewski, Daniel
    Bednarek, Ilona
    POSTEPY HIGIENY I MEDYCYNY DOSWIADCZALNEJ, 2013, 67 : 742 - 749
  • [28] Matrix Metalloproteinase-9 (MMP-9) as a Cancer Biomarker and MMP-9 Biosensors: Recent Advances
    Huang, Hao
    SENSORS, 2018, 18 (10)
  • [29] Assessment of serum matrix metalloproteinases MMP-2 and MMP-9 after human liver transplantation: Increased serum MMP-9 level in acute rejection
    Kuyvenhoven, JP
    Verspaget, HW
    Gao, Q
    Ringers, J
    Smit, VTHBM
    Lamers, CBHW
    Van Hoek, B
    TRANSPLANTATION, 2004, 77 (11) : 1646 - 1652
  • [30] DIFFERENTIAL EXPRESSION OF TISSUE INHIBITORS OF MATRIX METALLOPROTEINASES (TIMPS) AND MATRIX METALLOPROTEINASES (MM9-2, MMP-9) IN CELLS OF B-CELL AND T-CELL ORIGIN
    STETLERSTEVENSON, M
    WANG, J
    LEVY, A
    STETLERSTEVENSON, WG
    LABORATORY INVESTIGATION, 1993, 68 (01) : A100 - A100