Squaramides with cytotoxic activity against human gastric carcinoma cells HGC-27: synthesis and mechanism of action

被引:17
|
作者
Quintana, Mireia [1 ]
Alegre-Requena, Juan V. [1 ,2 ]
Marques-Lopez, Eugenia [2 ]
Herrera, Raquel P. [2 ]
Triola, Gemma [1 ]
机构
[1] CSIC, Inst Adv Chem Catalonia IQAC, Biomed Chem Dept, E-08034 Barcelona, Spain
[2] Univ Zaragoza, CSIC, Lab Organocatalisis Asimetr, Dept Quim Organ,ISQCH, E-50009 Zaragoza, Spain
关键词
ENANTIOSELECTIVE MICHAEL ADDITION; BIOLOGICAL EVALUATION; KINASE INHIBITORS; APOPTOSIS; DEATH; DERIVATIVES; DISCOVERY; AUTOPHAGY; TOXICITY; POTENT;
D O I
10.1039/c5md00515a
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of squaramates and squaramides have been synthesized and their cytotoxic activity has been investigated in different cancer cell lines. Among the studied compounds, squaramide 34 showed a potent and selective cytotoxicity against the human gastric cancer cell line HGC-27. Studies directed to elucidate the mechanism of induced cell death were performed. Cell cycle distribution analysis and cell death studies showed that compound 34 induces cell cycle arrest at the G(1) phase and caspase-dependent apoptosis. In conclusion, squaramide 34 can be considered a potential anticancer agent for gastric carcinoma.
引用
收藏
页码:550 / 561
页数:12
相关论文
共 50 条
  • [41] Semi-synthetic salinomycin analogs exert cytotoxic activity against human colorectal cancer stem cells
    Klose, Johannes
    Kattner, Sarah
    Borgstrom, Bjorn
    Volz, Claudia
    Schmidt, Thomas
    Schneider, Martin
    Oredsson, Stina
    Strand, Daniel
    Ulrich, Alexis
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2018, 495 (01) : 53 - 59
  • [42] Synthesis of Novel Xanthone Analogues and Their Growth Inhibitory Activity Against Human Lung Cancer A549 Cells
    Wu, Junqi
    Dai, Jinwei
    Zhang, Yuyang
    Wang, Jing
    Huang, Lei
    Ding, Hongmei
    Li, Tiejun
    Zhang, Yuefan
    Mao, Junqin
    Yu, Shichong
    DRUG DESIGN DEVELOPMENT AND THERAPY, 2019, 13 : 4239 - 4246
  • [43] Cytotoxic activity of soy phytoestrogen coumestrol against human breast cancer MCF-7 cells: Insights into the molecular mechanism
    Zafar, Atif
    Singh, Swarnendra
    Naseem, Imrana
    FOOD AND CHEMICAL TOXICOLOGY, 2017, 99 : 149 - 161
  • [44] Synthesis and selective cytotoxic activity of novel hybrid chalcones against prostate cancer cells
    Nagaraju, M.
    Deepthi, E. Gnana
    Ashwini, C.
    Vishnuvardhan, M. V. P. S.
    Nayak, V. Lakshma
    Chandra, Rajesh
    Ramakrishna, S.
    Gawali, B. B.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (13) : 4314 - 4317
  • [45] In vitro cytotoxic data on Se-methylselenocysteine conjugated to dendritic poly(glycerol) against human squamous carcinoma cells
    Goncalves Correa, Nicoli Dolores
    Silva, Felipe Douglas
    Vieira, Daniel Perez
    Soares, Carlos Roberto Jorge
    de Queiroz, Alvaro Antonio Alencar
    JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION, 2022, 33 (05) : 651 - 667
  • [46] Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin
    Liu, Jian-Fei
    Sang, Chun-Yan
    Xu, Xiao-Hui
    Zhang, Lin-Lin
    Yang, Xuan
    Hui, Lin
    Zhang, Jin-Bang
    Chen, Shi-Wu
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 64 : 621 - 628
  • [47] Cytotoxic activity of hydrolyzable tannins against human oral tumor cell lines - A possible mechanism
    Sakagami, H
    Jiang, Y
    Kusama, K
    Atsumi, T
    Ueha, T
    Toguchi, M
    Iwakura, I
    Satoh, K
    Ito, H
    Hatano, T
    Yoshida, T
    PHYTOMEDICINE, 2000, 7 (01) : 39 - 47
  • [48] Synthesis and X-ray study of dispiro 8-nitroquinolone analogues and their cytotoxic properties against human cervical cancer HeLa cells
    Shyamsivappan, Selvaraj
    Vivek, Raju
    Saravanan, Arjunan
    Arasakumar, Thangaraj
    Subashini, Gopalan
    Suresh, Thangaraj
    Shankar, Ramasamy
    Mohan, Palathurai Subramaniam
    MEDCHEMCOMM, 2019, 10 (03) : 439 - 449
  • [49] An In Vitro Study on the Cytotoxic, Antioxidant, and Antimicrobial Properties of Yamogenin-A Plant Steroidal Saponin and Evaluation of Its Mechanism of Action in Gastric Cancer Cells
    Stefanowicz-Hajduk, Justyna
    Graczyk, Piotr
    Hering, Anna
    Gucwa, Magdalena
    Nowak, Anna
    Halasa, Rafal
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2024, 25 (09)
  • [50] Structure-activity relationships and the cytotoxic effects of novel diterpenoid alkaloid derivatives against A549 human lung carcinoma cells
    Wada, Koji
    Hazawa, Masaharu
    Takahashi, Kenji
    Mori, Takao
    Kawahara, Norio
    Kashiwakura, Ikuo
    JOURNAL OF NATURAL MEDICINES, 2011, 65 (01) : 43 - 49