Citation: GAO An-Li, XIONG Qing-Feng, JIANG Jing, YU Juan, LOU Li-Guang, LIU Wei-Ping. Design, Syntheses and Anticancer Activities of Platinum(Ⅳ) Prodrugs with Dihydrogen Phosphate as an Axial Ligand[J]. Chinese Journal of Inorganic Chemistry, ;2018, 34(9): 1649-1654. doi: 10.11862/CJIC.2018.211 shu

Design, Syntheses and Anticancer Activities of Platinum(Ⅳ) Prodrugs with Dihydrogen Phosphate as an Axial Ligand

1.
Platinum-Based Drug Lab, Kunming Institute of Precious Metals, Kunming 650106, China
2.
Tumor Pharmacology Lab, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

Corresponding author: JIANG Jing, dianaair@126.com LIU Wei-Ping, liuweiping1963@126.com
Received Date: 3 May 2018
Revised Date: 15 June 2018

Figures(5)

CPL-1501 and CPL-1504, two platinum(Ⅳ) prodrugs with dihydrogen phosphate as one axial ligand, were synthesized from cisplatin and oxaliplatin, respectively, as the starting material, and characterized by elemental analysis, IR as well as ¹³C and ³¹P NMR. Their reduction potential was measured via the cyclic voltammetry. The standard MTT was used to evaluate anticancer activity of the two prodrugs against several human cancer cell lines. CPL-1501 has a good water-solubility (10 mg·mL^-1) and water-stability. With the favorable E_p values, it can be readily reduced to an active prototype cisplatin in the oxygen-deprived micro-environment of cancer cells. The biological tests reveal that CPL-1501 is able to inhibit the growth of cancer cells and its anticancer activity is comparable to that of cisplatin but much greater than that of carboplatin, whereas CPL-1504 does not show significant activity, probably due to its lower E_p values.
- platinum(Ⅳ) complexes,
- synthesis,
- characterization,
- anticancer activity
1. [1]
  Dasari S, Tchounwou P B. Eur. J. Pharmacol., 2014, 740:364-378 doi: 10.1016/j.ejphar.2014.07.025
2. [2]
  Johnstone T C, Suntharalingam K, Lippard S J. Chem. Rev., 2016, 116(5):3436-3486 doi: 10.1021/acs.chemrev.5b00597
3. [3]
  Dilruba S, Kalayda G V. Cancer Chemother. Pharmacol., 2016, 77(6):1103-1124 doi: 10.1007/s00280-016-2976-z
4. [4]
  Thiabaud G, McCall R, He G G, et al. Angew. Chem., 2016, 128(41):12816-12821 doi: 10.1002/ange.201604236
5. [5]
  Han X P, Sun J, Wang Y J, et al. Med. Res. Rev., 2015, 35(6):1268-1299 doi: 10.1002/med.21360
6. [6]
  Zhang P Y, Sadler P J. Eur. J. Inorg. Chem., 2017, 2017(12):1541-1548 doi: 10.1002/ejic.v2017.12
7. [7]
  Wang X Y, Guo Z J. Chem. Soc. Rev., 2013, 42:202-224 doi: 10.1039/C2CS35259A
8. [8]
  Muhammad N, Sadia N, Zhu C C, et al. Chem. Commun., 2017, 53(72):9971-9974 doi: 10.1039/C7CC05311H
9. [9]
  Sun Y Y, Liu F, Gou S H, et al. Eur. J. Med. Chem., 2012, 55(17):297-306
10. [10]
  Chen H, Chen F H, Hu W W, et al. J. Inorg. Biochem., 2018, 180:119-128 doi: 10.1016/j.jinorgbio.2017.11.017
11. [11]
  Wang J T, Li Y, Tan J H, et al. Dalton Trans., 2011, 40(3):564-566 doi: 10.1039/C0DT01161D
12. [12]
  Jiang J, Lei J, Chen X Z, et al. Res. Chem. Intermed., 2015, 41(9):6149-6155 doi: 10.1007/s11164-014-1728-0
13. [13]
  Liu W P, Jiang J, Xie C Y, et al. J. Inorg. Biochem., 2014, 140:126-130 doi: 10.1016/j.jinorgbio.2014.07.013
14. [14]
  GAO An-Li, QIU Jie, HOU Shu-Qian, et al. Chinese J. Inorg. Chem., 2017, 33(5):837-842
15. [15]
  Curci A, Gandin V, Marzano C, et al. Inorg. Chem., 2017, 56(13):7482-7493 doi: 10.1021/acs.inorgchem.7b00931
16. [16]
  Zhang S F, Gangal G, Uludag H. Chem. Soc. Rev., 2007, 36:507-531 doi: 10.1039/B512310K
17. [17]
  Nakatake H, Ekimoto H, Aso M, et al. Chem. Pharm. Bull., 2011, 59(6):710-713 doi: 10.1248/cpb.59.710
18. [18]
  Shi Y, Liu S A, Kerwood D J, et al. J. Inorg. Biochem., 2012, 107(1):6-14 doi: 10.1016/j.jinorgbio.2011.10.012
19. [19]
  Zhang J Z, Bonnitcha P, Wexselblatt E, et al. Chem. Eur. J., 2013, 19(5):1672-1676 doi: 10.1002/chem.201203159
20. [20]
  Wilson J J, Lippard S J. Inorg. Chem., 2011, 50(7):3103-3115 doi: 10.1021/ic2000816
21. [21]
  Hambley T W, Battle A R, Deacon G B, et al. J. Inorg. Biochem., 1999, 77(1/2):3-12
22. [22]
  Choi S, Filotto C, Bisanzo M, et al. Inorg. Chem., 1998, 37(10):2500-2504 doi: 10.1021/ic971047x
23. [23]
  Kratochwil N A, Bednarski P J. Arch. Pharm. Pharm. Med. Chem., 1999, 332(8):279-285 doi: 10.1002/(ISSN)1521-4184
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沈阳化工大学材料科学与工程学院沈阳 110142