• 中国中文核心期刊
  • 中国科学引文数据库核心期刊
  • 中国科技核心期刊
  • 中国高校百佳科技期刊
高级检索

四价铂前药研究现状与进展

朱杰, 张宸, 吴建兵, 张奕华, 黄张建

朱杰, 张宸, 吴建兵, 张奕华, 黄张建. 四价铂前药研究现状与进展[J]. 中国药科大学学报, 2022, 53(5): 613-622. DOI: 10.11665/j.issn.1000-5048.20220512
引用本文: 朱杰, 张宸, 吴建兵, 张奕华, 黄张建. 四价铂前药研究现状与进展[J]. 中国药科大学学报, 2022, 53(5): 613-622. DOI: 10.11665/j.issn.1000-5048.20220512
ZHU Jie, ZHANG Chen, WU Jianbing, ZHANG Yihua, HUANG Zhangjian. Status and progress of tetravalent platinum prodrugs[J]. Journal of China Pharmaceutical University, 2022, 53(5): 613-622. DOI: 10.11665/j.issn.1000-5048.20220512
Citation: ZHU Jie, ZHANG Chen, WU Jianbing, ZHANG Yihua, HUANG Zhangjian. Status and progress of tetravalent platinum prodrugs[J]. Journal of China Pharmaceutical University, 2022, 53(5): 613-622. DOI: 10.11665/j.issn.1000-5048.20220512

四价铂前药研究现状与进展

基金项目: 国家自然科学基金资助项目(No. 81822041,No.21977116,No.82173681)

Status and progress of tetravalent platinum prodrugs

Funds: This study was supported by the National Natural Science Foundation of China (No.81822041, No.21977116, No.82173681)
  • 摘要: 以顺铂为代表的二价铂[Pt(Ⅱ)]类药物是现在活跃于一线的抗肿瘤药物,但Pt(Ⅱ)类药物存在不良反应大、生物利用度不佳以及耐药性等问题。四价铂[Pt(Ⅳ)]络合物是Pt(Ⅱ)在轴向位置进行不同取代的衍生物,在肿瘤还原性物质的作用下Pt(Ⅳ)可被还原为Pt(Ⅱ),因此Pt(Ⅳ)可作为Pt(Ⅱ)的前药。Pt(Ⅳ)中轴向取代基的引入可改善Pt(Ⅱ)类药物的药代动力学性质、选择性和生物活性,以及实现除DNA交联之外的附加细胞毒机制,可一定程度上克服Pt(Ⅱ)类药物的耐药性。本文归纳总结了铂类药物的耐药机制,包括铂转运增加、解毒能力增加、自噬增强和DNA修复增强等方面;综述了Pt(Ⅳ)前药的构效关系、主要类型及研究进展,并提出了克服铂类药物耐药性的可能途径。
    Abstract: Bivalent platinum drugs [Pt(II)] represented by cisplatin are the first-line drugs in clinical application, but they have defects such as severe side-effects, poor bioavailability and drug resistance.Tetravalent platinum [Pt(IV)] complexes, derivatives of Pt(II) with different substitutions in axial positions, can be reduced to Pt(II) under the action of reductants in tumor, and can therefore act as a prodrug of Pt(II).Axial substituents can improve platinum drugs'' pharmacokinetics, selectivity and bioactivity, as well as achieve anti-tumor effect by additional cytotoxic mechanisms other than DNA damage, which can overcome the drug resistance to Pt(II).This review outlines the resistance mechanisms of platinum drugs, including platinum transport, detoxification, autophagy, and DNA repair, etc.It also summarizes the structure-activity relationship, main types and advances of tetravalent platinum prodrugs, as well as possible approach to solve platinum drug resistance.
  • [1] . Nature,1969,222(5191):385-386.
    [2] Wheate NJ,Walker S,Craig GE,et al. The status of platinum anticancer drugs in the clinic and in clinical trials[J]. Dalton Trans,2010,39(35):8113-8127.
    [3] Cleare MJ,Hoeschele JD. Studies on the antitumor activity of group VIII transition metal complexes. Part I. Platinum (II) complexes[J]. Bioinorg Chem,1973,2(3):187-210.
    [4] Shimada M,Itamochi H,Kigawa J. Nedaplatin:a cisplatin derivative in cancer chemotherapy[J]. Cancer Manag Res,2013,5:67-76.
    [5] McKeage MJ. Lobaplatin:a new antitumour platinum drug[J]. Expert Opin Investig Drugs,2001,10(1):119-128.
    [6] Gately D,Howell S. Cellular accumulation of the anticancer agent cisplatin:a review[J]. Br J Cancer,1993,67(6):1171-1176.
    [7] Safaei R,Katano K,Samimi G,et al. Cross-resistance to cisplatin in cells with acquired resistance to copper[J]. Cancer Chemother Pharmacol,2004,53(3):239-246.
    [8] Todd RC,Lippard SJ. Inhibition of transcription by platinum antitumor compounds[J]. Metallomics,2009,1(4):280-291.
    [9] Zimmermann T,Zeizinger M,Burda JV. Cisplatin interaction with cysteine and methionine,a theoretical DFT study[J]. J Inorg Biochem,2005,99(11):2184-2196.
    [10] Fuertes MA,Alonso C,Pérez JM. Biochemical modulation of cisplatin mechanisms of action:enhancement of antitumor activity and circumvention of drug resistance[J]. Chem Rev,2003,103(3):645-662.
    [11] Ginson D. Platinum(iv) anticancer prodrugs:hypotheses and facts[J]. Dalton Trans,2016,45(33):12983-12991.
    [12] Pendyala L,Krishnan BS,Walsh JR,et al. Studies on the human metabolism of iproplatin[J]. Cancer Chemother Pharmacol,1989,25(1):10-14.
    [13] Awuah SG,Zheng YR,Bruno PM,et al. A Pt(IV) pro-drug preferentially targets indoleamine-2,3-dioxygenase,providing enhanced ovarian cancer immuno-chemotherapy[J]. J Am Chem Soc,2015,137(47):14854-14857.
    [14] Gandioso A,Shaili E,Massaguer A,et al. An integrin-targeted photoactivatable Pt(IV) complex as a selective anticancer pro-drug:synthesis and photoactivation studies[J]. Chem Commun (Camb),2015,51(44):9169-9172.
    [15] Perland E,Fredriksson R. Classification systems of secondary active transporters[J]. Trends Pharmacol Sci,2017,38(3):305-315.
    [16] Yonezawa A,Masuda S,Yokoo S,et al. Cisplatin and oxaliplatin,but not carboplatin and nedaplatin,are substrates for human organic cation transporters (SLC22A1-3 and multidrug and toxin extrusion family)[J]. J Pharmacol Exp Ther,2006,319(2):879-886.
    [17] Gao J,Wang WY. Knockdown of galectin-1 facilitated cisplatin sensitivity by inhibiting autophagy in neuroblastoma cells[J]. Chem Biol Interact,2019,297:50-56.
    [18] Aguilar A. Kidney cancer:OCT2 demethylation cracks open oxaliplatin resistance[J]. Nat Rev Nephrol,2016,12(10):581.
    [19] Lasorsa A,Nardella MI,Rosato A,et al. Mechanistic and structural basis for inhibition of copper trafficking by platinum anticancer drugs[J]. J Am Chem Soc,2019,141(30):12109-12120.
    [20] Zimmermann T,Burda JV. Cisplatin interaction with amino acids cysteine and methionine from gas phase to solutions with constant pH[J]. Interdiscip Sci Comput Life Sci,2010,2(1):98-114.
    [21] Liang S,Han LQ,Mu WW,et al. Carboplatin-loaded SMNDs to reduce GSH-mediated platinum resistance for prostate cancer therapy[J]. J Mater Chem B,2018,6(43):7004-7014.
    [22] Kimura T,Kambe T. The functions of metallothionein and ZIP and ZnT transporters:an overview and perspective[J]. Int J Mol Sci,2016,17(3):336.
    [23] Kawahara B,Ramadoss S,Chaudhuri G,et al. Carbon monoxide sensitizes cisplatin-resistant ovarian cancer cell lines toward cisplatin via attenuation of levels of glutathione and nuclear metallothionein[J]. J Inorg Biochem,2019,191:29-39.
    [24] Fukuda T,Oda K,Wada-Hiraike O,et al. The anti-malarial chloroquine suppresses proliferation and overcomes cisplatin resistance of endometrial cancer cells via autophagy inhibition[J]. Gynecol Oncol,2015,137(3):538-545.
    [25] Zhao L,Li W,Zhou YX,et al. The overexpression and nuclear translocation of Trx-1 during hypoxia confers on HepG2 cells resistance to DDP,and GL-V9 reverses the resistance by suppressing the Trx-1/Ref-1 axis[J]. Free Radic Biol Med,2015,82:29-41.
    [26] Ayers PW,Parr RG,Pearson RG. Elucidating the hard/soft acid/base principle:a perspective based on half-reactions[J]. J Chem Phys,2006,124(19):194107.
    [27] Chen J,Gao CZ,Zhang Y,et al. Inorganic nano-targeted drugs delivery system and its application of platinum-based anticancer drugs[J]. J Nanosci Nanotechnol,2017,17(1):1-17.
    [28] Browning RJ,Reardon PJT,Parhizkar M,et al. Drug delivery strategies for platinum-based chemotherapy[J]. ACS Nano,2017,11(9):8560-8578.
    [29] Du J,Cullen JJ,Buettner GR. Ascorbic acid:chemistry,biology and the treatment of cancer[J]. Biochim Biophys Acta,2012,1826(2):443-457.
    [30] Michelet F,Gueguen R,Leroy P,et al. Blood and plasma glutathione measured in healthy subjects by HPLC:relation to sex,aging,biological variables,and life habits[J]. Clin Chem,1995,41(10):1509-1517.
    [31] Gamcsik MP,Kasibhatla MS,Teeter SD,et al. Glutathione levels in human tumors[J]. Biomarkers,2012,17(8):671-691.
    [32] Kennedy L,Sandhu JK,Harper ME,et al. Role of glutathione in cancer:from mechanisms to therapies[J]. Biomolecules,2020,10(10):E1429.
    [33] Choi S,Filotto C,Bisanzo M,et al. Reduction and anticancer activity of platinum(IV) complexes[J]. Inorg Chem,1998,37(10):2500-2504.
    [34] Gibbons GR,Wyrick S,Chaney SG. Rapid reduction of tetrachloro(D,L-trans)1,2-diaminocyclohexaneplatinum(IV) (tetraplatin) in R/MINI 1640 tissue culture medium[J]. Cancer Res,1989,49(6):1402-1407.
    [35] Perez RP,O''Dwyer PJ,Handel LM,et al. Comparative cytotoxicity of CI-973,cisplatin,carboplatin and tetraplatin in human ovarian carcinoma cell lines[J]. Int J Cancer,1991,48(2):265-269.
    [36] Schilder RJ,LaCreta FP,Perez RP,et al. Phase I and pharmacokinetic study of ormaplatin (tetraplatin,NSC 363812) administered on a day 1 and day 8 schedule[J]. Cancer Res,1994,54(3):709-717.
    [37] Bramwell VH,Crowther D,O''Malley S,et al. Activity of JM9 in advanced ovarian cancer:a phase I-II trial[J]. Cancer Treat Rep,1985,69(4):409-416.
    [38] Clavel M,Monfardini S,Gundersen S,et al. Phase II study of iproplatin (CHIP,JM-9) in advanced testicular cancers progressing after prior chemotherapy[J]. Eur J Cancer Clin Oncol,1988,24(8):1345-1348.
    [39] Petrelli NJ,Creaven PJ,Herrera L,et al. Phase II trial of continuous-infusion iproplatin (CHIP) and 5-fluorouracil (5-FU) in advanced colorectal carcinoma[J]. Cancer Chemother Pharmacol,1989,23(1):61-62.
    [40] Anderson H,Wagstaff J,Crowther D,et al. Comparative toxicity of cisplatin,carboplatin (CBDCA) and iproplatin (CHIP) in combination with cyclophosphamide in patients with advanced epithelial ovarian cancer[J]. Eur J Cancer Clin Oncol,1988,24(9):1471-1479.
    [41] Bouchal P,Jarkovsky J,Hrazdilova K,et al. The new platinum-based anticancer agent LA-12 induces retinol binding protein 4 in vivo[J]. Proteome Sci,2011,9(1):68.
    [42] Zheng YR,Suntharalingam K,Johnstone TC,et al. Pt(IV) prodrugs designed to bind non-covalently to human serum albumin for drug delivery[J]. J Am Chem Soc,2014,136(24):8790-8798.
    [43] Zanellato I,Bonarrigo I,Sardi M,et al. Evaluation of platinum-ethacrynic acid conjugates in the treatment of mesothelioma[J]. ChemMedChem,2011,6(12):2287-2293.
    [44] Kasparkova J,Kostrhunova H,Novakova O,et al. A photoactivatable platinum(IV) complex targeting genomic DNA and histone deacetylases[J]. Angew Chem Int Ed Engl,2015,54(48):14478-14482.
    [45] Johnson SW,Swiggard PA,Handel LM,et al. Relationship between platinum-DNA adduct formation and removal and cisplatin cytotoxicity in cisplatin-sensitive and-resistant human ovarian cancer cells[J]. Cancer Res,1994,54(22):5911-5916.
    [46] Wang ZG,Xu ZF,Zhu GY. A platinum(IV) anticancer prodrug targeting nucleotide excision repair to overcome cisplatin resistance[J]. Angew Chem Int Ed Engl,2016,55(50):15564-15568.
    [47] Becherel OJ,Jakob B,Cherry AL,et al. CK2 phosphorylation-dependent interaction between aprataxin and MDC1 in the DNA damage response[J]. Nucleic Acids Res,2010,38(5):1489-1503.
    [48] Chen FH,Pei SN,Wang X,et al. Emerging JWA-targeted Pt(IV) prodrugs conjugated with CX-4945 to overcome chemo-immune-resistance[J]. Biochem Biophys Res Commun,2020,521(3):753-761.
    [49] Xue X,You S,Zhang Q,et al. Mitaplatin increases sensitivity of tumor cells to cisplatin by inducing mitochondrial dysfunction[J]. Mol Pharm,2012,9(3):634-644.
    [50] Neumann W,Crews BC,Sárosi MB,et al. Conjugation of cisplatin analogues and cyclooxygenase inhibitors to overcome cisplatin resistance[J]. ChemMedChem,2015,10(1):183-192.
    [51] Oliveira BL,Stenton BJ,Unnikrishnan VB,et al. Platinum-triggered bond-cleavage of pentynoyl amide and N-propargyl handles for drug-activation[J]. J Am Chem Soc,2020,142(24):10869-10880.
    [52] Sun T,Lv T,Wu JB,et al. General strategy for integrated bioorthogonal prodrugs:Pt(II)-triggered depropargylation enables controllable drug activation in vivo[J]. J Med Chem,2020,63(22):13899-13912.
  • 期刊类型引用(4)

    1. 宋永真,李雅静,张振凌,王胜超. 曼地亚红豆杉酒炙工艺及质量标准研究. 中医学报. 2024(05): 1068-1075 . 百度学术
    2. 剡槿熙,臧明伍,刘贺,徐晨晨,史宇璇,白京,赵燕,郝静怡,张亚茹. 二萜类化合物在肉类食品保鲜防腐中的应用研究进展. 食品科学. 2024(13): 282-291 . 百度学术
    3. 王楠楠,蔡婷婷,童晔玲,刘霞,朱婉萍,江石平,赵桂芝. 基于NF-κB信号通路的HTRF法筛选红豆杉中抗气道炎症有效活性成分研究. 浙江中医杂志. 2023(08): 553-556 . 百度学术
    4. 傅贵江. 杉木人工林抚育间伐对套种南方红豆杉的影响. 武夷科学. 2022(01): 39-43 . 百度学术

    其他类型引用(5)

计量
  • 文章访问数:  1062
  • HTML全文浏览量:  14
  • PDF下载量:  1219
  • 被引次数: 9
出版历程
  • 收稿日期:  2022-02-11
  • 修回日期:  2022-04-30
  • 刊出日期:  2022-10-24

目录

    /

    返回文章
    返回
    x 关闭 永久关闭