• 中国精品科技期刊
  • 中国高校百佳科技期刊
  • 中国中文核心期刊
  • 中国科学引文数据库核心期刊
Advanced Search
ZHANG Danfeng, JIAO Yu, LIU Yong, ZHANG Yanmin, ZHANG Zhimin, LU Tao. Progress of small molecule anti-tumor covalent drugs[J]. Journal of China Pharmaceutical University, 2017, 48(1): 1-7. DOI: 10.11665/j.issn.1000-5048.20170101
Citation: ZHANG Danfeng, JIAO Yu, LIU Yong, ZHANG Yanmin, ZHANG Zhimin, LU Tao. Progress of small molecule anti-tumor covalent drugs[J]. Journal of China Pharmaceutical University, 2017, 48(1): 1-7. DOI: 10.11665/j.issn.1000-5048.20170101
shu

Progress of small molecule anti-tumor covalent drugs

More Information
    Graphical Abstract
    • Abstract
  • Covalent drugs are a type of inhibitors which exert their biological functions by irreversibly binding to the target through covalent bonds. With the marketing of kinase inhibitor covalent drugs against tumor, covalent drugs have regained the attention for drug discovery and have become a recent hotspot of anti-tumor drugs. In this paper, the action mechanisms, pharmacological advantages and the development strategies of modern covalent drugs are discussed and the recent research progress of anti-tumor covalent inhibitors is summarized, which provides a reference for the design of new anti-tumor covalent drugs.
    • FullText(HTML)
    • References (29)
  • [1]
    Robertson JG.Enzymes as a special class of therapeutic target:clinical drugs and modes of action[J].Curr Opin Struct Biol,2007,17(6):674-679.
    [2]
    Robertson JG.Mechanistic basis of enzyme-targeted drugs[J].Biochemistry,2005,44(15):5561-5571.
    [3]
    Singh J,Petter RC,Baillie TA,et al. The resurgence of covalent drugs[J].Nat Rev Drug Discov,2011,10(4):307-317.
    [4]
    Johnson DS,Weerapana E,Cravatt BF.The synthesis of possible transition state analogue inhitors of thymidine phosphorylase[J].Future Med Chem,2015(56):406-409.
    [5]
    Kwak EL,Sordella R,Bell DW, et al.Irreversible inhibitors of the EGF receptor may circumvent acquired resistance to gefitinib[J].Proc Natl Acad Sci U S A,2005,102(21):7665-7670.
    [6]
    Butterworth S,Finlay MRV,Ward RA,et al.2-(2,4,5-Substituted-anilino)pyrimidine derivatives as EGFR modulators useful for treating cancer:WO,2013014448A[P].2012-01-31[2016-01-06] .
    [7]
    U. S. Food and Drug Administration. Osimertinib[EB/OL].http://www.fda.gov/Drugs/InformationOnDrugs/ApprovedDrugs/ucm472565.htm.
    [8]
    Ou SH. Second-generation irreversible epidermal growth factor receptor(EGFR)tyrosine kinase inhibitors(TKIs):a better mousetrap? A review of the clinical evidence[J].Crit Rev Oncol Hematol,2012,83(3):407-421.
    [9]
    Honigberg LA,Smith AM,Sirisawad M,et al.The Bruton tyrosine kinase inhibitor PCI-32765 blocks B-cell activation and is efficacious in models of autoimmune disease and B-cell malignancy[J].Proc Natl Acad Sci U S A,2010,107(29):13075-13080.
    [10]
    Liu Q,Sabnis Y,Zhao Z,et al.Developing irreversible inhibitors of the protein kinase cysteinome[J].Chem Biol,2013,20(2):146-159.
    [11]
    Huang F, Zhu HJ, Zhou X, et al. Progress of bruton′s tyrosine kinase(BTK)and its inhibitors[J].J China Pharm Univ(中国药科大学学报),2014,45(6):617-624.
    [12]
    Li D,Ambrogio L,Shimamura T,et al.BIBW2992,an irreversible EGFR/HER2 inhibitor highly effective in preclinical lung cancer models[J].Oncogene,2008,27(34):4702-4711.
    [13]
    Giordano P,Manzo A,Montanino A,et al.Afatinib:an overview of its clinical development in non-small-cell lung cancer and other tumors[J].Crit Rev Oncol Hematol,2016,97:143-151.
    [14]
    Rabindran SK,Discafani CM,Rosfjord EC,et al.Antitumor activity of HKI-272,an orally active,irreversible inhibitor of the HER-2 tyrosine kinase[J].Cancer Res,2004,64(11):3958-3965.
    [15]
    Schwab CL,English DP,Black J,et al.Neratinib shows efficacy in the treatment of HER2 amplified carcinosarcoma in vitro and in vivo[J].Gynecol Oncol,2015,139(1):112-117.
    [16]
    Korfage IJ,Essink-Bot ML,Westenberg SM,et al.How distressing is referral to colposcopy in cervical cancer screening[J]?Gynecol Oncol,2014,132(1):142-148.
    [17]
    Becker D,Walters Haygood CL,Smith B,et al.Survival and toxicity of a modified GOG 172 IP chemotherapy regimen in patients with ovarian,fallopian tube or primary peritoneal carcinoma[J].Gynecol Oncol,2015,137(1):176-177.
    [18]
    Engelman JA, Zejnullahu K, Gale CM, et al. PF00299804,an irreversible pan-erbB inhibitor,is effective in lung cancer models with EGFR and ERBB2 mutations that are resistant to gefitinib[J].Cancer Res,2007,67(24):11924-11932.
    [19]
    Gonzales AJ,Hook KE,Althaus IW,et al.Antitumor activity and pharmacokinetic properties of PF-00299804,a second-generation irreversible pan-erbB receptor tyrosine kinase inhibitor[J].Mol Cancer Ther,2008,7(7):1880-1889.
    [20]
    Matsuyama A,Arai R,Yashiroda Y,et al.ORFeome cloning and global analysis of protein localization in the fission yeast Schizosaccharomyces pombe[J].Nat Biotechnol,2006,24(7):841-847.
    [21]
    Evans E,Ponader S,Karp R,et al.Covalent inhibition of btk with clinical development compound AVL-292 disrupts signaling that maintains the microenvironment necessary for chronic lymphocytic leukemia growth[J].Cl Lymph Myelom Leuk,2011,11(2):S173-S174.
    [22]
    Wu H,Wang WC,Liu FY,et al.Discovery of a potent,covalent BTK inhibitor for B-cell lymphoma[J].ACS Chem Biol,2014,9(5):1086-1091.
    [23]
    Janssen I.A study to investigate the effects of itraconazole on the pharmacokinetics of JNJ-42165279 in healthy male participants [EB/OL].https://www.clinicaltrials.gov/ct2/show/NCT02065739.
    [24]
    Fouqué A,Delalande O,Jean M,et al. A novel covalent mTOR inhibitor,DHM25,shows in vivo antitumor activity against triple-negative breast cancer cells[J].J Med Chem,2015,58(16):6559-6573.
    [25]
    Peto R,Davies C,Godwin,et al.Comparisons between different polychemotherapy regimens for early breast cancer:meta-analyses of long-term outcome among 100,000 women in 123 randomised trials[J].Lancet,2012,379(9184):432-444.
    [26]
    Malleter M,Tauzin S,Bessede A,et al.CD95L cell surface cleavage triggers a prometastatic signaling pathway in triple-negative breast cancer[J].Cancer Res,2013,73(22):6711-6721.
    [27]
    Zhou W, Hur W, McDermott U, et al. A structure-guided approach to creating covalent FGFR inhibitors[J].Chem Biol,2010,17(3):285-295.
    [28]
    Zhang T,Inesta-vaquera F,Niepel M,et al.Discovery of potent and selective covalent inhibitors of JNK[J].Chem Biol,2010,19(1):140-154.
    [29]
    Leproult E,Barluenga S,Moras D,et al.Cysteine mapping in conformationally distinct kinase nucleotide binding sites:application to the design of selective covalent inhibitors[J].J Med Chem,2011,54(5):1347-1355.
    • Related Articles

  • Related Articles

    [1]ZHU Song, JIANG Jing, LIU Yang, ZOU Wenyu, HU Pengwei, LU Yuting, SONG Min, HANG Taijun. Structural identification of the related substances of lorazepam tablets by LC-MS[J]. Journal of China Pharmaceutical University, 2021, 52(5): 555-565. DOI: 10.11665/j.issn.1000-5048.20210507
    [2]LIANG Fangmei, NI Yueling, WANG Lu, HANG Taijun, SONG Min. Structural identification of the related substances of fusidic acid by LC-MS[J]. Journal of China Pharmaceutical University, 2018, 49(3): 322-332. DOI: 10.11665/j.issn.1000-5048.20180311
    [3]YIN Xiaoya, WANG Cheng, MING Guojun, HANG Taijun. Identification of the related substances in pioglitazone hydrochloride by hyphenated LC-MS techniques[J]. Journal of China Pharmaceutical University, 2017, 48(6): 701-710. DOI: 10.11665/j.issn.1000-5048.20170611
    [4]XU Guijun, LI Zhijun, WANG Qi, TAN Jiejun, SHI Guoshan, QI Wei, LI Di, WANG Youpeng. Isolation and identification of anti-inflammatory constituents from Houttuynia cordata[J]. Journal of China Pharmaceutical University, 2016, 47(3): 294-298. DOI: 10.11665/j.issn.1000-5048.20160308
    [5]CHEN Wenhua, ZOU Limin, ZHANG Fei, ZHANG Liandi, LIAO Mingyi, DING Li. Identification of the related substances in bendamustine hydrochloride[J]. Journal of China Pharmaceutical University, 2015, 46(3): 333-338. DOI: 10.11665/j.issn.1000-5048.20150312
    [6]ZHOU Yongmei, SHI Xianming, MA Lei, ZHANG Sifang. Isolation and identification of Withaphysalins from Physalis minima[J]. Journal of China Pharmaceutical University, 2015, 46(1): 62-65. DOI: 10.11665/j.issn.1000-5048.20150107
    [7]RAO Ya-kun, DING Li, YU Yong. Structural identification of two major impurities in sodium levofolinate[J]. Journal of China Pharmaceutical University, 2012, 43(4): 350-354.
    [8]WANG Ying, YIN Hong-ping, CHEN Tao, WANG Min. Preliminary structural identification and protection on renal cell injury of acidic polysaccharide from Cordyceps sinensis[J]. Journal of China Pharmaceutical University, 2009, 40(6): 559-564.
    [9]Structure Studies of N-(4-chlorobenzyl)-2,3-methylenedio-xyl-9-acetoxyl-10-methoxy-7,8,13,13a-tetrahydro-8H-dibenzo-quinolizine chloride[J]. Journal of China Pharmaceutical University, 2002, (1): 72-74.
    [10]IDENTIFICATION OF SYNTHETIC BY-PRODUCT N-(4-CHLOROBENZOYL)-DICYCLOHEXANYLUREA BY FOURIER TRANSFORM MASS SPECTROMETRY[J]. Journal of China Pharmaceutical University, 1989, (6): 367-369.

Catalog

    Get Citation
    PDF
    XML
    Article views (1595) PDF downloads (5371) Cited by()
    Turn off MathJax
    Article Contents
    Abstract
    References
    Related Articles

    Copyright © Journal of China Pharmaceutical University苏ICP备12050101号-2

    Address：24 Tongjia Lane, Nanjing City, Jiangsu Province （210009）Tel: 025-83271566E-mail: xuebao@cpu.edu.cn

    Supported by: Beijing Renhe Information Technology Co., Ltd.  Baidu Analytics

    Total visits：302635

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return