Citation: Zhang Kailong, Yu Zhijian, Qiu Jiaqing, Ke Zhiwei, Huang Chao, Jiang Jianzhong, Yu Qunying. Pharmaceutical Research on Small Ruthenium Complexes[J]. Chemistry, ;2019, 82(11): 972-981. shu

Pharmaceutical Research on Small Ruthenium Complexes

School of Pharmacy and Life Sciences, Jiujiang University, Jiujiang 332005

Corresponding author: Yu Qunying, qunyingyu@qq.com
Received Date: 6 August 2019
Accepted Date: 30 August 2019

Figures(9)

Ruthenium complexes are not only a novel class of antineoplastic agents, but also an active photosensitizers which can be used as probes for detecting structural and functional aspects of nucleic acid chemistry, biological imaging of reactive carbonyl species, sensing amyloid β aggregation in Alzheimer's disease (AD), and so on. In light of these, we summarize the recent advances of pharmaceutical research in small molecule ruthenium complexes.
- Ruthenium complexes,
- Imaging,
- Anticancer agents,
- Aβ aggregates
1. [1]
  E Alessio. Eur. J. Inorg. Chem., 2017, 2017: 1549~1560.
2. [2]
  I Kostova. Curr. Med. Chem., 2006, 13: 1085~1107.
3. [3]
  C Artner, H U Holtkamp, C G Hartinger et al. J. Inorg. Biochem., 2017, 177: 322~327.
4. [4]
  F E Poynton, S A Bright, S Blasco et al. Chem. Soc. Rev., 2017, 46: 7706~7756.
5. [5]
  A Notaro, G Gasser. Chem. Soc. Rev., 2017, 46: 7317~7337.
6. [6]
  C S Allardyce, P J Dyson. Platinum Met. Rev., 2001, 45: 62~69.
7. [7]
  M J Clarke, F Zhu, D R Frasca. Chem. Rev., 1999, 99: 2511~2534.
8. [8]
  S Thota, D A Rodrigues, D C Crans et al. J. Med. Chem., 2018, 61: 5805~5821.
9. [9]
  E Alessio, G Mestroni, A Bergamo et al. Curr. Top. Med. Chem., 2004, 4: 1525~1535.
10. [10]
  C G Hartinger, M A Jakupec, S Zorbas-Seifried et al. Chem. Biodivers., 2008, 5: 2140~2155.
11. [11]
  C G Hartinger, S Zorbas-Seifried, M A Jakupec et al. J. Inorg. Biochem., 2006, 100: 891~904.
12. [12]
  L Zeng, P Gupta, Y Chen et al. Chem. Soc. Rev., 2017, 46: 5771~5804.
13. [13]
  D A Smithen, H Yin, M H R Beh et al. Inorg. Chem., 2017, 56: 4121~4132.
14. [14]
  L Zeng, Y Chen, J Liu et al. Sci. Rep., 2016, 6: 19449.
15. [15]
  C M Clavel, E Paunescu, P Nowak-Sliwinska et al. J. Med. Chem., 2015, 58: 3356~3365.
16. [16]
  L Zhang, P Carroll, E Meggers. Org. Lett., 2004, 6: 521~523.
17. [17]
  P J Sadler, R F Lainez, H Abraba et al. US: 20060058270A1.
18. [18]
  M Wenjie. US: 8357678B2.
19. [19]
  G Mestroni, E Alessio, G Sava. WO: 1998000431A1.
20. [20]
  A J Gamble, J M Lynam, P H Walton. WO: 2013038134A1.
21. [21]
  R E Morris, P J Sadler, H Chen et al. US: 20050239765A1.
22. [22]
  R E Morris, P J Sadler, D Jodrell et al. US: 6936634B2.
23. [23]
  B K Keppler. WO: 1997036595A3.
24. [24]
  G Mestroni, E Alessio, G Sava et al. US: 6921824B1.
25. [25]
  R E Morris, R E Aird, P J Sadler et al. J. Med. Chem., 2001, 44: 3616~3621.
26. [26]
  Z Adhireksan, G E Davey, P Campomanes et al. Nat. Commun., 2014, 5: 3462.
27. [27]
  R L Hayward, Q C Schornagel, R Tente et al. Cancer Chemother. Pharmacol., 2005, 55: 577~583.
28. [28]
  X Meng, M L Leyva, M Jenny et al. Cancer Res., 2009, 69: 5458~5466.
29. [29]
  J E' Debreczeni, A N Bullock, G E Atilla et al. Angew. Chem. Int. Ed., 2006, 45: 1580~1585.
30. [30]
  R Trondl, P Heffeter, C R Kowol et al. Chem. Sci., 2014, 5: 2925~2932.
31. [31]
  E S Antonarakis, A Emadi. Cancer Chemother. Pharmacol., 2010, 66: 1~9.
32. [32]
  S Chatterjee, S Kundu, A Bhattacharyya et al. J. Biol. Inorg. Chem., 2008, 13: 1149~1155.
33. [33]
  R F S Lee, S Escrig, C Maclachlan et al. Int. J. Mol. Sci., 2017, 18: 1869.
34. [34]
  M Montani, G V B Pazmay, A Hysi et al. Pharmacol. Res., 2016, 107: 282~290.
35. [35]
36. [36]
  N P Cook, V Torres, D Jain et al. J. Am. Chem. Soc. 2011, 133: 11121~11123.
37. [37]
  C de la Torre, A Toscani, C Marín-Hernández et al. J. Am. Chem. Soc., 2017, 139: 18484~18487.
38. [38]
  Y H Tang, Y Y Ma, J Yin et al. Chem. Soc. Rev., 2019, 48: 4036~4048.
39. [39]
  C L Liu, R Zhang, W Z Zhang et al. J. Am. Chem. Soc., 2019, 141: 8462~8472.
40. [40]
  K Arora, M Herroon, M H Al-Afyouni et al. J. Am. Chem. Soc., 2018, 140: 14367~14380.
41. [41]
  S Chakrabortty, B K Agrawalla, A Stumper et al. J. Am. Chem. Soc., 2017, 139: 2512~2519.
42. [42]
  S Balasubramanian, L H Hurley, S Neidle. Nat. Rev. Drug Discov., 2011, 10: 261~275.
43. [43]
  N Hosoya, K Miyagawa. Cancer Sci., 2014, 105: 370~388.
44. [44]
  P Kumar, S Dasari, A K Patra. Eur. J. Med. Chem., 2017, 136: 52~62.
45. [45]
  G Sathyaraj, T Weyhermüller, B U Nair. Eur. J. Med. Chem., 2010, 45: 284~291.
46. [46]
  D L Arockiasamy, S Radhika, R Parthasarathi et al. Eur. J. Med. Chem., 2009, 44: 2044~2051.
47. [47]
  W Su, Q Qian, P Li et al. Inorg. Chem., 2013, 52: 12440~12449.
48. [48]
  T S Kamatchi, N Chitrapriya, S K Kim et al. Eur. J. Med. Chem., 2013, 59: 253~264.
49. [49]
  N Busto, J Valladolid, M Martinez-Alonso et al. Inorg. Chem., 2013, 52: 9962~9974.
50. [50]
  P Lincoln, B Norden. J. Phys. Chem. B, 1998, 102: 9583~9594.
51. [51]
  H Chen, J A Parkinson, R E Morris et al. J. Am. Chem. Soc., 2003, 125: 173~186.
52. [52]
  N Besker, C Coletti, A Marrone et al. J. Phys. Chem. B, 2007, 111: 9955~9964.
53. [53]
  F Caruso, E Monti, J Matthews et al. Inorg. Chem., 2014, 53: 3668~3677.
54. [54]
  S P Foxon, C Green, M G Walker et al. Inorg. Chem., 2012, 51: 463~471.
55. [55]
  M Frik, A Martinez, B T Elie et al. J. Med. Chem., 2014, 57: 9995~10012.
56. [56]
  S Shi, T Xie, T M Yao et al. Polyhedron, 2009, 28: 1355~1361.
57. [57]
  H Huang, P Zhang, B Yu et al. J. Med. Chem., 2014, 57: 8971~8983.
58. [58]
  S H Lai, W Li, J H Yao et al. J. Photochem. Photobiol. B, 2016, 158: 39~48.
59. [59]
  P Čanovic, A R Simovic, S Radisavljevic et al. J. Biol. Inorg. Chem., 2017, 22: 1007~1028.
60. [60]
  P Heffeter, K Böck, B Atil et al. J. Biol. Inorg. Chem., 2010, 15: 737~748.
61. [61]
  A Casini, C Gabbiani, F Sorrentino et al. J. Med. Chem., 2008, 51: 6773~6781.
62. [62]
  I M Ghobrial, T E Witzig, A A Adjei. CA-Cancer J. Clin., 2005, 55: 178~194.
63. [63]
  S Elmore. Toxicol. Pathol., 2007, 35, 495~516.
64. [64]
  K Zheng, Q Wu, C Wang et al. Anti-Cancer Agents Med. Chem., 2017, 17: 29~39.
65. [65]
  D Wan, B Tang, Y J Wang et al. Eur. J. Med. Chem., 2017, 139: 180~190.
66. [66]
  T Chen, Y Liu, W J Zheng et al. Inorg. Chem., 2010, 49: 6366~6368.
67. [67]
  W Li, G W Jiang, J H Yao et al. J. Photochem. Photobiol. B, 2014, 140: 94~104.
68. [68]
  A Castonguay, C Doucet, M Juhas et al. J. Med. Chem., 2012, 55: 8799~8806.
69. [69]
  C Tan, S Lai, S Wu et al. J. Med. Chem., 2010, 53: 7613~7624.
70. [70]
  Z Luo, L Yu, F Yang et al. Metallomics, 2014, 6: 1480~1490.
71. [71]
  Z F Chen, Q P Qin, J L Qin et al. J. Med. Chem., 2015, 58: 4771~4789.
72. [72]
  A Bergamo, C Gaiddon, J H Schellens et al. J. Inorg. Biochem., 2012, 106, 90~99.
73. [73]
  H Bregman, P J Carroll, E Meggers. J. Am. Chem. Soc., 2006, 128: 877~884.
74. [74]
  J Maksimoska, L Feng, K Harms et al. J. Am. Chem. Soc., 2008, 130: 15764~15765.
75. [75]
  E Meggers. Curr. Opin. Chem. Biol., 2007, 11: 287~292.
76. [76]
77. [77]
  Y K Yan, M Melchart, A Habtemariam et al. Chem. Commun., 2005, 4764~4776.
78. [78]
  C G Hartinger, N Metzler-Nolte, P J Dyson. Organometallics, 2012, 31(16): 5677~5685.
79. [79]
  F Schmitt, J Freudenreich, N P Barry et al. J. Am. Chem. Soc., 2012, 134(2): 754~757.
80. [80]
  J E Debreczeni, A N Bullock, G E Atilla et al. Angew. Chem. Int. Ed., 2006, 45: 1580~1585.
81. [81]
  G Shi, S Monro, R Hennigar et al. Coord. Chem. Rev., 2015, 282: 127~138.
82. [82]
  S J Dougan, M Melchart, A Habtemariam et al. Inorg. Chem., 2006, 45: 10882~10894.
83. [83]
  Y Fu, A Habtemariam, A M B H Basri et al. Dalton Transac., 2011, 40: 10553~10562.
84. [84]
  Y Fu, M J Romero, A Habtemariam et al. Chem. Sci., 2012, 3: 2485~2494.
85. [85]
  M Hanif, P Schaaf, W Kandioller et al. Aust. J. Chem., 2010, 63: 1521~1528.
86. [86]
  S H Van Rijt, A Mukherjee, A M Pizarro et al. J. Med. Chem., 2010, 53: 840~849.
87. [87]
  M J McKeage, S J Berners-Price, P Galettis et al. Cancer Chemother. Pharmacol., 2000, 46: 343~350.
88. [88]
  L Di, P V Fish, T Mano. Drug Discov. Today, 2012, 17(9~10): 486~495.
89. [89]
  S J Dougan, A Habtemariam, S E McHale et al. PNAS, 2008, 105, 11628~11633.
90. [90]
  M G Mendoza-Ferri, C G Hartinger, A A Nazarov et al. Organometallics, 2009, 28: 6260~6265.
91. [91]
  A L Noffke, A Habtemariam, A M Pizarro et al. Chem. Commun., 2012, 48: 5219~5246.
92. [92]
  B Serli, E Zangrando, T Gianferrara et al. Eur. J. Inorg. Chem., 2005, (17): 3423~3434.
93. [93]
  D N Akbayeva, L Gonsalvi, W Oberhauser et al. Chem. Commun., 2003, (2): 264~265.
94. [94]
  R E Morris, R E Aird, P D Murdoch et al. J. Med. Chem., 2001, 44(22): 3616~3621.
95. [95]
  C Scolaro, A Bergamo, L Brescacin et al. J. Med. Chem., 2005, 48(12): 4161~4171.
96. [96]
  A Dorcier, W H Ang, S Bolano et al. Organometallics, 2006, 25(17): 4090~4096.
97. [97]
  A F A Peacock, A Habtemariam, S A Moggach et al. Inorg. Chem., 2007, 46(10): 4049~4059.
98. [98]
  M Hanif, A A Nazarov, C G Hartinger et al. Dalton Transac., 2010, 39(31): 7345~7352.
99. [99]
  I Berger, M Hanif, A A Nazarov et al. Chem. Eur. J., 2008, 14: 9046~9057.
100. [100]
  M Hanif, S M Meier, W Kandioller et al. J. Inorg. Biochem., 2011, 105(2): 224~231.
101. [101]
  A F Peacock, M Melchart, R J Deeth et al. Chem. Eur. J., 2007, 13: 2601~2613.
102. [102]
  J H Kasser, W Kandioller, C G Hartinger et al. Organomet. Chem., 2010, 695(6): 875~881.
103. [103]
  M Hanif, H Henke, S M Meier et al. Inorg. Chem., 2010, 49(17): 7953~7963.
104. [104]
  W Kandioller, C G Hartinger, A A Nazarov et al. Organometallics, 2009, 28(15): 4249~4251.
105. [105]
  W Kandioller, C G Hartinger, A A Nazarov et al. J. Organomet. Chem., 2009, 694(6): 922~929.
106. [106]
  W Kandioller, C G Hartinger, A A Nazarov et al. Chem. Eur. J., 2009, 15: 12283~12291.
107. [107]
  A Habtemariam, M Melchart, R Fernandez et al. J. Med. Chem., 2006, 49(23): 6858~6868.
108. [108]
  A F A Peacock, S Parsons, P J Sadler. J. Am. Chem. Soc., 2007, 129(11): 3348~3357.
109. [109]
  S H Van Rijt, A J Hebden, T Amaresekera et al. J. Med. Chem., 2009, 52(23): 7753~7764.
110. [110]
111. [111]
  S M Meier, M Novak, W Kandioller et al. Chem. Eur. J., 2013, 19: 9297~9307.
112. [112]
  M Schmidlehner, L S Flocke, A Roller et al. Dalton Transac., 2016, 45: 724~733.
113. [113]
  S M Meier, M Hanif, Z Adhireksan et al. Chem. Sci., 2013, 4: 1837~1846.
114. [114]
  C A Riedl, L S Flocke, M Hejl et al. Inorg. Chem., 2017, 56: 528~541.
115. [115]
  R E Aird, J Cummings, A A Ritchie et al. Br. J. Cancer, 2002, 86: 1652~1657.
116. [116]
  L K Filak, G Muhlgassner, F Bacher et al. Organometallics, 2011, 30(2): 273~283.
117. [117]
  L K Filak, G Muhlgassner, M A Jakupec et al. J. Biol. Inorg. Chem., 2010, 15(6): 903~918.
118. [118]
  W F Schmid, R O John, V B Arion et al. Organometallics, 2007, 26(26): 6643-6652.
119. [119]
  W Ginzinger, G Muhlgassner, V B Arion et al. J. Med. Chem., 2012, 55: 3398-3413.
120. [120]
  S Betanzos-Lara, O Novakova, R J Deeth et al. J. Biol. Inorg. Chem., 2012, 17(7): 1033-1051.
121. [121]
  C M Hackl, M S Legina, V Pichler et al. Chem. Eur. J., 2016, 22: 17269-17281.
122. [122]
  C A Puckett, R J Ernst, J K Barton. Dalton Transac., 2010, 39: 1159-1170.
123. [123]
  G Hartinger, S Zorbas-Seifried, M A Jakupec. J. Inorg. Biochem., 2006, 100: 891-904.
124. [124]
  P D W Eckford, F J Sharom. Chem. Rev., 2009, 109: 2989-3011.
125. [125]
  R E Aird, J Cummings, A A Ritchie et al. Br. J. Cancer, 2002, 86, 1652-1657.
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
3. [3]
  Huilin ZHENG , Tao WANG , Ruilin GAO , Mengke ZHOU , Xinyue LI , Hui WANG , Xiaoxia GU . Antitumor and antibacterial activities of transition metal complexes incorporating pyridyl salicylaldehyde Schiff base. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 897-905. doi: 10.11862/CJIC.20250358
4. [4]
  Rui WU , Yankun ZHANG , Jiufu LU , Pengfei ZHANG , Yang WANG . Research process on radioactive ¹⁸F-labelled chemical agents as positron emission tomography imaging probes for tumour detection. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1702-1718. doi: 10.11862/CJIC.20240387
5. [5]
  Dingwen CHEN , Siheng YANG , Haiyan FU , Hua CHEN , Xueli ZHENG , Weichao XUE , Jiaqi XU , Ruixiang LI . NiOOH-mediated synthesis of gold nanoaggregates for electrocatalytic performance for selective oxidation of glycerol to glycolate. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2317-2326. doi: 10.11862/CJIC.20250053
6. [6]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
7. [7]
  Hao WANG , Kun TANG , Jiangyang SHAO , Kezhi WANG , Yuwu ZHONG . Electro-copolymerized film of ruthenium catalyst and redox mediator for electrocatalytic water oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2193-2202. doi: 10.11862/CJIC.20240176
8. [8]
  Huihua GONG , Tianhua CUI , Li JI , Liyuan ZHANG , Xueli ZHENG , Haiyan FU , Hua CHEN , Jiawei MAO , Ruixiang LI . Efficient hydrogenation of CO₂ realized by Ru-NNN complex. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 1085-1095. doi: 10.11862/CJIC.20250321
9. [9]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
10. [10]
  Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
11. [11]
  Renyi Shao , Khurram Abbas , Vladimir Yu. Osipov , Haimei Zhu , Yuan Li , Usama , Hong Bi . Red-emitting carbon dots prepared from Epipremnum Aureum leaves extract for biological imaging. Acta Physico-Chimica Sinica, 2026, 42(2): 100134-0. doi: 10.1016/j.actphy.2025.100134
12. [12]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
13. [13]
  Zhengqi SHEN , Hanxue LIU , Lin HOU , Meng REN , Xiangyu DAI , Yating ZHANG , Zhi SU , Chao GE , Xuling XUE , Hongke LIU . A dual-pathway synergistic inhibition strategy based on ruthenium/iridium metal complexes targeting GPX4 and DHODH: Mechanism of directly activating ferroptosis in leukemia cells. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 271-283. doi: 10.11862/CJIC.20250230
14. [14]
  Fa Wang , Yu Chen , Hui Chao . Ruthenium(II) Complexes as Photoactivated Chemo-Prodrugs for Hypoxic Tumor Therapy. University Chemistry, 2025, 40(7): 200-212. doi: 10.12461/PKU.DXHX202410024
15. [15]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
16. [16]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . Highly Efficient, Targeted, and Traceable Perovskite Nanocrystals for Photoelectrocatalytic Oncotherapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-0. doi: 10.1016/j.actphy.2024.100042
17. [17]
  Anbang Du , Yuanfan Wang , Zhihong Wei , Dongxu Zhang , Li Li , Weiqing Yang , Qianlu Sun , Lili Zhao , Weigao Xu , Yuxi Tian . Photothermal Microscopy of Graphene Flakes with Different Thicknesses. Acta Physico-Chimica Sinica, 2024, 40(5): 2304027-0. doi: 10.3866/PKU.WHXB202304027
18. [18]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
19. [19]
  Huiru Sheng , Rui Qi , Chao Shen , Hao Xu , Jiabin Shen , Pengfei Zhang . Green synthesis of pyrrolo[1,2-a]quinoxaline derivatives as antineoplastic agents: a comprehensive chemistry laboratory teaching exploration. University Chemistry, 2026, 41(7): 266-273. doi: 10.12461/PKU.DXHX202505015
20. [20]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093

Get Citation

PDF

XML

Metrics

PDF Downloads(25)
Abstract views(3496)
HTML views(464)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142