中文
Earlier issues
Announcement
More
Progress in Chemistry 2018, Vol. 30 Issue (6): 831-846 DOI: 10.7536/PC171212 Previous Articles   Next Articles

• Review •

Small Molecular Platinum(Ⅳ) Compounds as Antitumor Agents

Xiaoxiao Tan1,2, Guoshuai Li1, Qingpeng Wang1*, Bingquan Wang1, Dacheng Li1,2*, Peng George Wang3   

  1. 1. Institute of Biopharmaceutical Research, Liaocheng University, Liaocheng 252059, China;
    2. Department of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China;
    3. College of Pharmacy, Nankai University, Tianjin 300071, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the Natural Science Foundation of Shandong (No.ZR2017BH092,ZR2014HL105),the Open Project of Shandong Collaborative Innovation Center for Antibody Drugs (No.CIC-AD1835,CIC-AD1836),the Doctoral Foundation of Liaocheng University (No.318051635),and the Taishan Scholar Research Foundation of Shandong.
PDF ( 2967 ) Cited
Export

EndNote

Ris

BibTeX

Platinum(Ⅳ) compounds which exert unique advantages as antitumor drugs,have aroused wide attention of researchers in pharmaceutical area. A great deal of efforts have been devoted to this field, and many remarkable results are achieved. The investigation on platinum(Ⅳ) compounds has become an active and hot topic. Large numbers of complexes with high activity, low toxicity, low drug-resistance, high bioavailability, satisfactory pharmacokinetic property and remarkable tumor targeting property have been prepared and evaluated in recent years. The current work is mainly focused on the following two aspects:(1) Platinum(Ⅳ) compounds based on classical platinum drugs. Various functional axial ligands are incorporated to platinum system to construct novel multi-functional platinum(Ⅳ) compounds with effective activities. (2) Platinum(Ⅳ) compounds based on non-classical platinum compounds are obtained by modifying the transverse ligands to prepare platinum(Ⅳ) complexes with non-classical platinum(Ⅱ) cores, and these target compounds have shown great competence in overcoming drug resistance of platinum drugs. Moreover, photosensitive platinum(Ⅳ) compounds have good performance in photodynamic therapy which is a new trend of clinical cancer treatment. Platinum(Ⅳ) compounds are of great potentials to be developed as the next generation of approved platinum anticancer drugs with oral administration. Herein, by combining authors' research and referring to the works from literatures in recent five years, the research progress of small molecular platinum(Ⅳ) compounds as antitumor agents is systematically reviewed, and the perspectives of the foreseeable future of platinum(Ⅳ) compounds as medicinal drugs are also presented.
Contents
1 Introduction
2 Platinum (Ⅳ) compounds based on classical platinum drugs
2.1 Lipid/water tuning
2.2 Membrane protein targeting
2.3 Energy metabolism enzyme targeting
2.4 Mitochondrial targeting
2.5 HSA targeting
2.6 Inflammatory factor targeting
2.7 DNA targeting
2.8 HDAC targeting
2.9 Others
3 Platinum (Ⅳ) compounds based on non-classical platinum compounds
3.1 Modification of stable ligands
3.2 Modification of leaving ligands
3.3 Photosensitive platinum (Ⅳ) compounds with azido ligands
4 Conclusion
Key words: platinum drug, platinum (Ⅳ), antitumor, prodrug, multi-targeting drug

CLC Number: 

[1] Wheate N J, Walker S, Craig G E, Oun R. Dalton Trans., 2010, 39(35):8113.
[2] Johnstone T C, Suntharalingam K, Lippard S J. Chem. Rev., 2016, 116(5):3436.
[3] Kenny R G, Su W C, Crawford A, Marmion C J. Eur. J. Inorg. Chem., 2017, 2017(12):1596.
[4] Gabano E, Ravera M, Osella D. Dalton Trans., 2014, 43(26):9813.
[5] Song Y, Suntharalingam K, Yeung J S, Royzen M, Lippard S J. J. Inorg. Biochem., 2013, 24(10):1733.
[6] Bai L K, Gao C Z, Liu Q H, Yu C T, Zhang Z X, Cai L X, Yang B, Qian Y X, Yang J, Liao X L. Eur. J. Med. Chem., 2017, 140:349.
[7] Schreiber-Brynzak E, Pichler V, Heffeter P, Hanson B, Theiner S, Lichtscheidl-Schultz I, Kornauth C, Bamonti L, Dhery V, Groza D, Berry D, Berger, Galanski M, Jakupec M A, Keppler B K. Metallomics, 2016, 8(4):422.
[8] Mccormick M C, Schult F A, Baik M H. Polyhedron, 2016, 103:28.
[9] Shi Y, Liu S A, Kerwood D J, Goodisman J, Dabrowiak J C. J. Inorg. Biochem., 2012, 107(1):6.
[10] Lippert B, Miguel P J S. Coordin. Chem. Rev., 2016, 327/328:333.
[11] Misic M M, Jakovljevic V L, Bugarcic Z D, Zivkovic V I, Srejovic I M, Barudzic N S, Djuric D M, Novokmet S S. Cardiovasc. Toxicol., 2015, 15(3):261.
[12] Tetko I V, Varbanov H P, Galanski M, Talmaciu M, Platts J A, Ravera M, Gabano E. J. Inorg. Biochem., 2016, 156:1.
[13] Ratzon E, Najajreh Y, Salem R, Khamaisie H, Ruthardt M, Mahajna J. BMC Cancer, 2016, 16(1):140.
[14] Goschl S, Schreiber-Brynzak E, Pichler V, Cseh K, Heffeter P, Jungwirth U, Jakupec M A, Berger W, Keppler B K. Metallomics, 2017, 9(3):309.
[15] Ravera M, Gabano E, Zanellato I, Fregonese F, Pelosi G, Platts J A, Osella D. Dalton Trans., 2016, 45(12):5300.
[16] Pelosi G, Ravera M, Gabano E, Fregonese F, Osella D. Chem. Commun., 2015, 51(38):8051.
[17] Yap S Q, Chin C F, Thng A H H, Pang Y Y, Hom H K, Ang W H. ChemMedChem, 2017, 12(4):300.
[18] Gabano E, Ravera M, Tinello S, Osell D. Eur. J. Inorg. Chem., 2015, 32:5335.
[19] Xu Z F, Wang Z G, Yiu S M, Zhu G Y. Dalton Trans., 2015, 44(46):19918.
[20] Deng D, Xu C, Sun P C, Wu J D, Yan C Y, Hu M X, Yan N E. Nature, 2014, 510(7503):121.
[21] Szablewski L. Biochim. Biophys. Acta Rev. Cancer, 2013, 1835(2):164.
[22] Liu P X, Lu Y H, Gao X Q, Liu R, Zhang-Negrerie D, Shi Y, Wang Y Q, Wang S Q, Gao Q Z. Chem. Commun., 2013, 49(24):2421.
[23] Li H, Gao X Q, Liu R, Wang Y, Zhang M H, Fu Z, Mi Y, Wang Y Q, Yao Z, Gao Q Z. Eur. J. Med. Chem., 2015, 101:400.
[24] Patra M, Johnstone T C, Suntharalingam K, Lippard S J. Angew. Chem., 2016, 128:1.
[25] Wang Q P, Huang Z L, Ma J, Lu X L, Zhang L, Wang X, Wang P G. Dalton Trans., 2016, 45:10366.
[26] Ma J, Wang Q P, Yang X D, Hao W P, Huang Z L, Zhang J B, Wang X, Wang P G. Dalton Trans., 2016, 45:11830.
[27] Ma J, Yang X D, Hao W P, Huang Z L, Wang X, Wang P G. Eur. J. Med. Chem., 2017, 128:45.
[28] Ma J, Wang Q P, Huang Z L, Yang X D, Nie Q D, Hao W P, Wang P G, Wang X. J. Med. Chem., 2017, 60:5736.
[29] Ravera M, Gabano E, Tinello S, Zanellato I, Osella D. J. Inorg. Biochem., 2017, 167:27.
[30] Huang X C, Huang R Z, Gou S H, Wang Z M, Wang H S. Bioconjugate Chem., 2017, 28:1305.
[31] 刘伟平(Liu W P), 楼丽广(Lou L G), 侯树谦(Hou S Q), 高安丽(Gao A L), 谢成英(Xie C Y), 全海天(Quan H T), 姜婧(Jiang J). CN 105481902A, 2016.
[32] Mayr J, Hager S, Koblmuller B, Klose M H M, Holste K, Fischer B, Pelivan K, Berger W, Heffeter P, Kowol C R, Keppler B K. J. Biol. Inorg. Chem., 2017, 22:591.
[33] Wong D Y Q, Lim J H, Ang W H. Chem. Sci., 2015, 6:3051.
[34] Yuan Y Y, Chen Y L, Tang B Z, Liu B. Chem. Commun., 2014, 50:3868.
[35] Xu Z C, Zhao J, Gou S H, Xu G. Chem. Commun., 2017, 53:3749.
[36] Wexselblatt E, Yavin E, Gibson D. Angew. Chem. Int. Ed., 2013, 52:6059.
[37] Johnstone T C, Kulak N, Pridgen E M, Farokhzad O C, Langer R, Lippard S J. ACS Nano, 2013, 7:5675.
[38] Zajac J, Kostrhunova H, Novohradsky V, Vrana O, Raveendran R, Gibson D, Kasparkova J, Brabec V. J. Inorg. Biochem., 2016, 156:89.
[39] Wexselblatt E, Raveendran R, Salameh S, Friedman-Ezra A, Yavin E, Gibson D. Chem. Eur. J., 2015, 21:3108.
[40] Ritacco I, Mazzone G, Russo N, Sicilia E. Inorg. Chem., 2016, 55:1580.
[41] Nosova Y N, Foteeva L S, Zenin I V, Fetisov T I, Kirsanov K I, Yakubovskaya M G, Antonenko T A, Tafeenko V A, Aslanov L A, Lobas A A, Gorshkov M V, Galanski M, Keppler B K, Timerbaev A R, Milaeva E R, Nazarov A A. Eur. J. Inorg. Chem., 2017, 2017(12):1785.
[42] Suntharalingam K, Song Y, Lippard S J. Chem. Commun., 2014, 50:2465.
[43] Feldhaeusser B, Platt S R, Marrache S, Kolishetti N, Pathak R, Montgomery D J, Reno L R, Howerth E, Dhar S. Nanoscale, 2015, 7:13822.
[44] Dhar S, Pathak R, Marrache S. US 20170037071A1, 2017.
[45] Zheng Y R, Suntharalingam K, Johnstone T C, Yoo H, Lin W, Brooks J G, Lippard S J. J. Am. Chem. Soc., 2014, 136:8790.
[46] Mayr J, Heffeter P, Groza D, Galvez L, Koellensperger G, Roller A, Alte B, Haider M, Berger W, Kowol C R, Keppler B K. Chem. Sci., 2017, 8:2241.
[47] Bilodeau M T, Moreau B. WO 2015102928A1, 2015.
[48] Pichler V, Mayr J, Heffeter P, Dömötör O, Enyedy É A, Hermann G, Groza D, Köllensperger G, Galanksi M, Berger W, Keppler B K, Kowol C R. Chem. Commun., 2013, 49:2249.
[49] Sommerfeld N S, Strohhofer D, Cseh K, Theiner S, Jakupec M A, Koellensperger G, Galanski M, Keppler B K. Eur. J. Inorg. Chem., 2017, 34:4049.
[50] Cheng Q Q, Shi H D, Wang H X, Min Y Z, Wang J, Liu Y Z. Chem. Commun., 2014, 50:7427.
[51] Pathak R, Marrache S, Choi J H, Berding T B, Dhar S. Angew. Chem. Int. Ed., 2014, 126:1994.
[52] Dhar S, Pathak R. WO 2015089389A1, 2015.
[53] Neumann W, Crews B C, Sarosi M B, Daniel C M, Ghebreselasie K, Scholz M S, Marnett L J, Hey-Hawkins E. ChemMedChem, 2015, 10:183.
[54] Qin X D, Xu G, Chen F H, Fang L, Gou S H. Bioorg. Med. Chem., 2017, 25:2507.
[55] Chen F H, Qin X D, Xu G, Gou S H, Jin X F. Biochem. Pharmaclo., 2017, 135:50.
[56] Wong D Y Q, Yeo C H F, Ang W H. Ang. Angew. Chem. Int. Ed., 2014, 53:6752.
[57] Qin X D, Fang L, Chen F H, Gou S H. Eur. J. Med. Chem., 2017, 137:167.
[58] Wang Z G, Xu Z F, Zhu G Y. Angew. Chem., 2016, 55:15564.
[59] Novohradsky V, Zerzankova L, Stepankova J, Vrana O, Raveendran R, Gibson D, Kasparkova J, Brabec V. J. Inorg. Biochem., 2014, 140:72.
[60] Gabano E, Ravera M, Zanellato I, Tinello S, Gallina A, Rangone B, Gandin V, Marzano C, Bottone M G, Osella D. Dalton Trans., 2017, 46:14174.
[61] Gou S H. WO 2017148193A1, 2017.
[62] Ma L L, Ma R, Wang Y P, Zhu X Y, Zhang J L, Chan H C, Chen X F, Zhang W J, Chiu S K, Zhu G Y. Chem. Commun., 2015, 51:6301.
[63] Huang X C, Huang R Z, Gou S H, Wang Z M, Liao Z X, Wang H S. Bioconjugate Chem., 2016, 27:2132.
[64] Sharma P, Allison J P. Science, 2015, 348(6230):56.
[65] Awuah S G, Zheng Y R, Bruno P M, Hemann M T, Lippard S J. J. Am. Chem. Soc., 2015, 137:14854.
[66] 黄宇彬(Huang Y B), 周东方(Zhou D F), 景遐斌(Jing X B), 谢志刚(Xie Z G). CN 105906667A, 2016.
[67] Qi R G, Xiao H H, Wu S H, Li Y X, Zhang Y, Jing X B. J. Mater. Chem. B, 2015, 3:176.
[68] Ma L L, Ma R, Wang Z G, Yiu S M, Zhu G Y. Chem. Commun., 2016, 52:10735.
[69] Thiabaud G, Arambula J F, Siddik Z H, Sessler J L. Chem. Eur. J., 2014, 20:8942.
[70] Sessler J L, Arambula J, Siddik Z H, Thiabaud G. WO 2015191797A1, 2015.
[71] Kysilka V, Mengler J, Havlovic K, Kacer P, Cerveny L. WO 2016034214A1, 2016.
[72] Margiotta N, Savino S, Marzano C, Pacifico C, Hoeschele J D, Gandin V, Natile G. J. Inorg. Biochem., 2016, 160:85.
[73] Hamilton G, Olszewski U. Expert Opin. Drug Delivery, 2013, 9:1381.
[74] Massaguer A, Gonzalez-Canto A, Escribano E, Barrabes S, Artigas G, Moreno V, Marchan V. Dalton Trans., 2015, 44:202.
[75] Lana F, Sandra A, Ana K, Radmila J, Biljana D, Siniša R. Anti-Cancer Agents Med. Chem., 2016, 16:1628.
[76] Shahraki S, Saeidifar M, Shiri F, Heidari A. J. Biomol. Struct. Dyn., 2017, 35:3098.
[77] Bhowmik P K, Spangelo B L, Vo V, Han H, Tanthmanatham O. WO 2016025742A1, 2016.
[78] Abedi A, Amani V, Safari N, Ostad S N, Notash B. J. Organomet. Chem., 2015, 799-800:30.
[79] Navas F, Mendes F, Santos I, Navarro-Ranninger C, Cabrera S, Quiroga A G. Inorg. Chem., 2017, 56:6175.
[80] Harper B W J, Petruzzella E, Sirota R, Faccioli F F, Aldrich-Wright J R, Gandin V, Gibson D. Dalton Trans., 2017, 46:7005.
[81] Macias F J, Deo K M, Pages B J, Wormell P, Clegg J K, Zhang Y J, Li F, Zheng G, Sakoff J, Gilbert J, Aldrich-Wright J R. Chem. Eur. J., 2015, 21:16990.
[82] Liang B B, Huo S Y, Ren Y L, Sun S J, Cao Z Q, Shen S G. Transition Met. Chem., 2014, 40:31.
[83] Karmakar S, Chatterjee S, Purkait K, Mukherjee A. Dalton Trans., 2016, 45:11710.
[84] Cetraz M, Sen V, Schoch S, Streule K, Golubev V, Hartwig A, Koberle B. Arch. Toxicol., 2017, 91:785.
[85] Komleva N V, Lapshina M A, Kostyuk G V, Ivanov A V, Parkhomenko Ⅱ, Papina R I, Sen V D, Terentiev A A. Russ. Chem. Bull., 2015, 64:1178.
[86] Escolà A, Crespo M, López C, Quirante J, Jayaraman A, Polat I H, Badía J, Baldomà L, Cascante M. Bioorg. Med. Chem., 2016, 24:5804.
[87] Bauer E, Domingo X, Balcells C, Polat I H, Crespo M, Quirante J, Badía J, Baldomà L, Mercè F, Cascante M. Dalton Trans., 2017, 46:14973.
[88] Bouche M, Dahm G, Wantz M, Fournel S, Achard T, Bellemin-Laponnaz S. Dalton Trans., 2016, 45:11362.
[89] Perfahl S, Bodtke A, Pracharova J, Kasparkova J, Brabec V, Cuadrado J, Stürup S, Schulzke C, Bednarski P J. Inorg. Chim. Acta, 2017, 456:86.
[90] Bakalova A, Buyukliev R, Momekov G. J. Mol. Struct., 2015, 1091:118.
[91] Bose R N, Moghaddas S, Belkacemi L, Tripathi S, Adams N R, Majmudar P, McCall K, Dezvareh H, Nislow C. J. Med. Chem., 2015, 58:8387.
[92] Hofer D, Varbanov H P, Legin A, Jakupec M A, Roller A, Galanski M, Keppler B K. J. Inorg. Biochem., 2015, 153:259.
[93] Hoffmeister B R, Hejl M, Jakupec M A, Galanski M, Keppler B K. Eur. J. Inorg. Chem., 2015, 2015(10):1700.
[94] Hoffmeister B R, Hejl M, Adib-Razavi M S, Jakupec M A, Galanski M, Keppler B K. Chem. Biodivers., 2015, 12:559.
[95] Zhao Y, Woods J A, Farrer N J, Robinson K S, Pracharova J, Kasparkova J, Novakova O, Li H L, Salassa L, Pizarro A M, Clarkson G J, Song L J, Brabec V, Sadler P J. Chem. Eur. J., 2013, 19:9578.
[96] Zhao Y, Farrer N J, Li H L, Butler J S, McQuitty R J, Habtemariam A, Wang F Y, Sadler P J. Angew. Chem. Int. Ed., 2013, 52:13633.
[97] Vernooij R R, Joshi T, Shaili E, Kubeil M, Appadoo D R, Izgorodina E I, Graham B, Sadler P J, Wood B R, Spiccia L. Inorg. Chem., 2016, 55(12):5983.
[98] Shaili E, Fernandez-Gimenez M, Rodriguez-Astor S, Gandioso A, Sandin L, Garcia-Velez C, Massaguer A, Clarkson G J, Woods J A, Sadler P J, Marchan V. Chem. Eur. J., 2015, 21:18474.
[99] Venkatesh V, Wedge C J, Romero-Canelon I, Habtemariam A, Sadler P J. Dalton Trans., 2016, 45:13034.
[100] Gandioso A, Shaili E, Massaguer A, Artigas G, Gonzalez-Canto A, Woods J A, Sadler P J, Marchan V. Chem. Commun., 2015, 51:9169.
[101] Kasparkova J, Kostrhunova H, Novakova O, Krikavova R, Vanco J, Travnicek Z, Brabec V. Angew. Chem., 2015, 54:14478.
[1] Shunxin Gu, Qin Jiang, Pengfei Shi. Antitumor Activity and Application of Luminescent Iridium(Ⅲ) Complexes [J]. Progress in Chemistry, 2022, 34(9): 1957-1971.
[2] Zhihua Gong, Sha Hu, Xueping Jin, Lei Yu, Yuanyuan Zhu, Shuangxi Gu. Synthetic Methods and Application of Phosphoester Prodrugs [J]. Progress in Chemistry, 2022, 34(9): 1972-1981.
[3] Zi-Yue Xu, Yun-Chang Zhang, Jia-Le Lin, Hui Wang, Dan-Wei Zhang, Zhan-Ting Li. Supramolecular Self-Assembly Applied for the Design of Drug Delivery Systems [J]. Progress in Chemistry, 2019, 31(11): 1540-1549.
[4] Yuewen Sun, Suxing Jin, Xiaoyong Wang, Zijian Guo. Application Prospect of Metal Complexes in Chemoimmunotherapy of Tumors [J]. Progress in Chemistry, 2018, 30(10): 1573-1583.
[5] Wang Yian, You Ming. Chemoprevention of Oral Cancer by a Mixture of Chinese Herbs (Anti-Tumor Mixture B) [J]. Progress in Chemistry, 2013, 25(09): 1594-1600.
[6] Ren Tianbin, Xia Wenjuan, Wu Wei, Li Yongyong*. Stimuli-Responsive and Polymeric Prodrugs [J]. Progress in Chemistry, 2013, 25(05): 775-784.
[7] Lang Xuliang, Luan Xudong, Gao Chunmei, Jiang Yuyang. Recent Progress of Acridine Derivatives with Antitumor Activity [J]. Progress in Chemistry, 2012, 24(08): 1497-1505.
[8] Zhang Jianjun, Gao Yuan, Sun Wanjin. Albumin as Drug Carriers [J]. Progress in Chemistry, 2011, 23(8): 1747-1754.
[9] Chen Zhenfeng Peng Yan Tan Mingxiong Liu Yancheng Wang Hengshan Liang Hong. Preliminary Studies on the Antitumor Metal-Based Drugs Basing on TCM Active Ingredients [J]. Progress in Chemistry, 2009, 21(05): 929-933.
[10] Chen Yu Du Kejie Chao Hui Ji Liangnian. New Trends for Ruthenium Complexes with Anticancer Activity [J]. Progress in Chemistry, 2009, 21(05): 836-844.
[11] . Antitumor Au(III) Complexes [J]. Progress in Chemistry, 2009, 21(04): 644-653.
[12] Zhu Xingyong1 Zhang Wenping2 You Qidong1* Zhang Cang2 Zuo Lijuan2. Antitumor Platinum(Ⅱ) Drugs [J]. Progress in Chemistry, 2008, 20(09): 1324-1334.
[13] Ping Qu Hua He Xuhui Liu . Antitumor Activity and the Mechanism of Rhodium Complexes [J]. Progress in Chemistry, 2006, 18(12): 1646-1651.
[14] Gang Xu,Yubo Cui,Kai Cui,Shaohua Gou**. Progress on the Study of Non-Platinum Metallic Drugs in Antitumor [J]. Progress in Chemistry, 2006, 18(01): 107-113.
[15] Wang Lianhong1,2,Liu Yun2,You Qidong*1,Gou Shaohua*2. Progress in Non-classical Antitumor Platinum Drugs [J]. Progress in Chemistry, 2004, 16(03): 456-.