Trends of Platinum and Metal-Arene Anticancer Drugs Based on Natural Products
- Corresponding author: XUE Xu-Ling, xuexuling87@163.com QIAN Yong, yongqian@njnu.edu.cn
Citation: GE Chao, Lü Meng-Di, ZHANG Zi-You, CHEN Jun, WANG Meng-Meng, XUE Xu-Ling, QIAN Yong, LIU Hong-Ke. Trends of Platinum and Metal-Arene Anticancer Drugs Based on Natural Products[J]. Chinese Journal of Inorganic Chemistry, ;2020, 36(4): 597-606. doi: 10.11862/CJIC.2020.086
Galanski M.. Recent Pat. Anticancer Drug Discov., 2006, 1(2):285-295
doi: 10.2174/157489206777442287
Reed E.. Cancer Treat. Rev., 1998, 24(5):331-344
doi: 10.1016/S0305-7372(98)90056-1
Xue X L, Zhu C C, Guo Z J, et al.. Inorg. Chem., 2017, 56(7):3754-3762
doi: 10.1021/acs.inorgchem.6b02148
Xue X L, Qian C G, Guo Z J, et al.. Angew. Chem. Int. Ed., 2019, 58:12661-12666
doi: 10.1002/anie.201906203
Hall M D, Mellor H R, Hambley T W, et al.. J. Med. Chem., 2007, 50(15):3403-3411
doi: 10.1021/jm070280u
Rijt S V, Sadler P J.. Drug Discovery Today, 2009, 14:1089-1097
doi: 10.1016/j.drudis.2009.09.003
Johnstone T C, Suntharalingam K, Lippard S J.. Chem. Rev., 2016, 116(5):3436-3486
doi: 10.1021/acs.chemrev.5b00597
Wang X Y, Wang X H, Guo Z J.. Acc. Chem. Res., 2015, 48(9):2622-2631
doi: 10.1021/acs.accounts.5b00203
Wang X Y, Guo Z J.. Chem. Soc. Rev., 2013, 42(1):202-224
doi: 10.1039/C2CS35259A
Huang X C, Huang R Z, Wang Z M, et al.. Bioconjugate Chem., 2016, 27:2132-2148
doi: 10.1021/acs.bioconjchem.6b00353
Parveen S, Arjmand F, Tabassum S.. Eur. J. Med. Chem., 2019, 175:269-286
doi: 10.1016/j.ejmech.2019.04.062
Abid M, Shamsi F, Azam A.. Mini-Rev. Med. Chem., 2016, 16(10):772-786
doi: 10.2174/1389557515666151001142012
Adam A M A.. J. Mol. Struct., 2019, 1195:43-57
doi: 10.1016/j.molstruc.2019.05.097
Liu H K, Sadler P J.. Acc. Chem. Res., 2011, 44:349-359
doi: 10.1021/ar100140e
Li J J, Tian Z Z, Liu Z, et al.. Appl. Organometal. Chem., 2019, 33(4):4685-4695
doi: 10.1002/aoc.4685
Kelman A D, Clarke M J, Peresie H J, et al.. J. Clin. Hematol. Oncol., 1977, 7:274-288
Alessio E, Mestroni G, Sava G, et al.. Metal Ions in Biological Systems. Florida:CRC Press, 2004:323-351
Mestroni G, Pacor S, Zorzet S, et al.. Chemical, Biological and Antitumor Properties of Ruthenium(Ⅱ) Complexes with Dimethyl Sulfoxide. Berlin, New York:Springer-Verlag, 1989:71-87
Alessio E, Sava G, Beijnen J H, et al.. Invest. New Drugs, 2015, 33:201-214
doi: 10.1007/s10637-014-0179-1
Alessio E, Mestroni G, Bergamo A, et al.. Curr. Top. Med. Chem., 2004, 4:1525-1535
doi: 10.2174/1568026043387421
Alessio E, Messori L.. Met. Ions Life Sci., 2018, 18:141-170
Clarke M J, Bitler S, Kelman A D, et al.. J. Inorg. Biochem., 1980, 12:79-87
doi: 10.1016/S0162-0134(00)80045-8
Antonarakis E S, Emadi A.. Cancer Chemother. Pharmacol., 2010, 66(1):1-9
doi: 10.1007/s00280-010-1293-1
Reisner E, Arion V B, Pombeiro A J L, et al.. Inorg. Chem., 2004, 43:7083-7093
doi: 10.1021/ic049479c
Jakupec M A, Hartinger C G, Keppler B K, et al.. J. Med. Chem., 2005, 48:2831-2837
doi: 10.1021/jm0490742
Habtemariam A, Melchart M, Sadler P J, et al.. J. Med. Chem., 2006, 49:6858-6868
doi: 10.1021/jm060596m
Chen H, Parkinson J A, Sadler P J, et al.. J. Am. Chem. Soc., 2002, 124(12):3064-3082
doi: 10.1021/ja017482e
Coverdale J P C, Bridgewater H E, Sadler P J, et al.. J. Med. Chem., 2018, 61(20):9246-9255
doi: 10.1021/acs.jmedchem.8b00958
Liu H K, Habtemariam A, Sadler P J, et al.. Dalton Trans., 2016, 45:18676-18688
doi: 10.1039/C6DT03356C
Yan Y K, Habtemariam A, Sadler P J, et al.. Chem. Commun., 2005, 38:4764-4776
Wang H Y, Sadler P J, Liu H K, et al.. Eur. J. Inorg. Chem., 2017, 12:1792-1799
Banerjee S, Soldevila-Barreda J J, Sadler P J, et al.. Chem. Sci., 2018, 9(12):3177-3185
doi: 10.1039/C7SC05058E
Hartinger C G, Dyson P J.. Chem. Soc. Rev., 2009, 38:391-401
doi: 10.1039/B707077M
Aird R E, Cummings J, Sadler P J, et al.. Br. J. Cancer, 2002, 86(10):1652-1657
doi: 10.1038/sj.bjc.6600290
Liu H K, Parkinson J A, Sadler P J, et al.. Chem. Sci., 2010, 1:258-270
doi: 10.1039/c0sc00175a
Liu H K, Bella J, P.. J. Sadler, et al. Angew. Chem. Int. Ed., 2006, 45:8153-8156
doi: 10.1002/anie.200602873
Liu H K, Wang F Y, Sadler P J, et al.. Chem. Eur. J., 2006, 12:6151-6165
doi: 10.1002/chem.200600110
Wootton C A, Liu H K, Sadler P J, et al.. Dalton Trans., 2015, 44:3624-3632
doi: 10.1039/C4DT03819C
Li J, Sadler P J, Liu H K, et al.. Dalton Trans., 2017, 46:16205-16215
doi: 10.1039/C7DT03374E
Wu Q, Mao Z W, Liu H K, et al.. J. Inorg. Biochem., 2018, 189:30-39
doi: 10.1016/j.jinorgbio.2018.08.013
HAO Yuan-Yuan, GE Chao, LIU Hong-Ke, et al.. Chem. J. Chinese Universities, 2018, 39(4):614-622
GE Chao, QIAN Yong, LIU Hong-Ke, et al.. Chinese J. Inorg. Chem., 2018, 34(6):1079-1085
Cragg G M, Grothaus P G, Newman D J, et al.. Chem. Rev., 2009, 109:3012-3043
doi: 10.1021/cr900019j
Robinson S L, Christensonab J K, Wackett L P.. Nat. Prod. Rep., 2019, 36:458-475
doi: 10.1039/C8NP00052B
Lefranc F, Koutsaviti A, Kornienko A, et al.. Nat. Prod. Rep., 2019, 36:810-841
doi: 10.1039/C8NP00057C
Gao Z, Huang K, Yang X, et al.. Biochim. Biophys. Acta, 1999, 1472:643-650
doi: 10.1016/S0304-4165(99)00152-X
Liu Z L, Tanaka S, Horigome H, et al.. Biol. Pharm. Bull., 2002, 25:37-41
doi: 10.1248/bpb.25.37
Qin X D, Xu G, Gou S H, et al.. Biol. Med. Chem., 2017, 25:2507-2517
doi: 10.1016/j.bmc.2017.03.007
Middleton E, Kandaswami C, Theoharides T C.. Pharmacol. Rev., 2000, 52:673-751
Kurzwernhart A, Kandioller W, Hartinger C G, et al.. Chem. Commun., 2012, 48:4839-4841
doi: 10.1039/c2cc31040f
Kurzwernhart A, Kandioller W, Hartinger C G.. J. Med. Chem., 2012, 55:10512-10522
doi: 10.1021/jm301376a
Kurzwernhart A, Keppler B K, Hartinger C G, et al.. Eur. J. Inorg. Chem., 2016, 2:240-246
Aggarwal B B, Kumar A, Bharti A C.. Anticancer Res., 2003, 23:363-398
Zhang Y N, Fu M F, Zhai G X, et al.. Future Med. Chem., 2019, 11(9):1035-1056
doi: 10.4155/fmc-2018-0190
Valentini A, Conforti F, Crispini A, et al.. J. Med. Chem., 2009, 52:484-491
doi: 10.1021/jm801276a
Anand P, Kunnumakkara A B, Newman R A, et al.. Mol. Pharm., 2007, 4(6):807-818
doi: 10.1021/mp700113r
Kunnumakkara A B, Diagaradjane P, Guha S, et al.. Clin. Cancer Res., 2008, 14(7):2128-2136
doi: 10.1158/1078-0432.CCR-07-4722
Odot J, Albert P, Carlier A, et al.. Int. J. Cancer, 2004, 111(3):381-387
Cao J, Liu Y, Jia L, et al.. Free Radical Biol. Med., 2007, 43(6):968-975
doi: 10.1016/j.freeradbiomed.2007.06.006
Kumar A, Dhawan S, Hardegen N J, et al.. Biochem. Pharmacol., 1998, 55:775-783
doi: 10.1016/S0006-2952(97)00557-1
Singh S, Aggarwal B B.. J. Biol. Chem., 1995, 270(42):24995-25000
doi: 10.1074/jbc.270.42.24995
Schwertheim S, Wein F, Lennartz K, et al.. J. Cancer Res. Clin. Oncol., 2017, 143(7):1143-1154
doi: 10.1007/s00432-017-2380-z
Zhang H H, Zhang Y, Cheng Y N, et al.. Mol. Carcinog., 2018, 57(1):44-56
Gururaj A E, Belakavadi M, Venkatesh D A, et al.. Biochem. Biophys. Res. Commun., 2002, 297(4):934-942
doi: 10.1016/S0006-291X(02)02306-9
Mitra K, Gautam S, Chakravarty A R, et al.. Angew. Chem. Int. Ed., 2015, 54:13989-13993
doi: 10.1002/anie.201507281
Censi V, Caballero A B, Gamez P, et al.. J. Inorg. Biochem., 2019, 198:110749-110761
doi: 10.1016/j.jinorgbio.2019.110749
Bonfili L, Pettinari R, Cuccioloni M, et al.. ChemMedChem, 2012, 7:2010-2020
doi: 10.1002/cmdc.201200341
Caruso F, Rossi M, Pettinari C.. J. Med. Chem., 2012, 55:1072-1081
doi: 10.1021/jm200912j
Pettinari R, Marchetti F, Dyson P J, et al.. Organometallics, 2014, 33:3709-3715
doi: 10.1021/om500317b
(a) Pettinari R, Marchetti F, Dyson P J, et al.. Dalton Trans., 2015, 44: 20523-20531 (b)Pettinari R, Marchetti F, Dyson P J, et al.. Inorg. Chem. Front., 2019, 6: 2448-2457
Kandioller W, Hartinger C G, Keppler B K, et al.. Organometallics, 2009, 28:4249-4251
doi: 10.1021/om900483t
Hironishi M, Kordek R, Yanagihara R, et al.. Neurodegenera-tion, 1996, 5:325-329
doi: 10.1006/neur.1996.0044
Verma S, Cam M C, McNeill J H.. J. Am. Coll. Nutr., 1998, 17:11-18
doi: 10.1080/07315724.1998.10718730
Melchior M, Rettig S J, Liboiron B D, et al.. Inorg. Chem., 2001, 40:4686-4690
doi: 10.1021/ic000984t
Carland M, Tan K J, Denny W A, et al.. J. Inorg. Biochem., 2005, 99:1738-1743
doi: 10.1016/j.jinorgbio.2005.06.003
Peacock A F A, Melchart M, Sadler P J, et al.. Chem. Eur. J., 2007, 13:2601-2613
doi: 10.1002/chem.200601152
Kandioller W F, Hartinger C G, Dyson P J, et al.. J. Organomet. Chem., 2009, 694:922-929
doi: 10.1016/j.jorganchem.2008.10.016
Cao R H, Peng W L, Wang Z H, et al.. Curr. Med. Chem., 2007, 14:479-500
doi: 10.2174/092986707779940998
Xiao S L, Lin W, Wang C, et al.. Bioorg. Med. Chem. Lett., 2001, 11:437-441
doi: 10.1016/S0960-894X(00)00679-X
Funayama Y, Nishio K, Wakabayashi K, et al.. Mutat. Res., 1996, 349:183-191
doi: 10.1016/0027-5107(95)00176-X
Li Y, Liang F S, Jiang W, et al.. Cancer Biol. Ther., 2007, 6:1193-1199
Castro A C, Dang L C, Soucy F, et al.. Bioorg. Med. Chem. Lett., 2003, 13:2419-2422
doi: 10.1016/S0960-894X(03)00408-6
Cao R, Chen Q, Hou X, et al.. Bioorg. Med. Chem., 2004, 12:4613-4623
doi: 10.1016/j.bmc.2004.06.038
He L, Liao S Y, Mao Z W, et al.. Chem. Eur. J., 2013, 19:12152-12160
doi: 10.1002/chem.201301389
Dzubak P, Hajduch M, Vydra D, et al.. Nat. Prod. Rep., 2006, 33:394-411
Park H Y, Park S H, Yoon H K, et al.. Arch. Pham. Res., 2004, 27:57-60
doi: 10.1007/BF02980047
You R, Long W, Lai Z, et al.. J. Med. Chem., 2013, 56:1984-1995
doi: 10.1021/jm301652t
Kalani K, Kushwaha V, Verma R, et al.. Bioorg. Med. Chem. Lett., 2013, 33:2566-2570
Kuo R Y, Qian K, Lee H K, et al.. Nat. Prod. Rep., 2009, 26:1321-1344
doi: 10.1039/b810774m
Lin K W, Huang A M, Hour T C, et al.. Bioorg. Med. Chem., 2011, 19:4274-4285
doi: 10.1016/j.bmc.2011.05.054
Mahmoud A M, Hussein O E, Hozayen W G, et al.. Chem. Biol. Interact., 2017, 270:59-72
doi: 10.1016/j.cbi.2017.04.009
Liu Y, Qian K, Wang C Y, et al.. Bioorg. Med. Chem. Lett., 2012, 22:7530-7533
doi: 10.1016/j.bmcl.2012.10.041
Song J, Ko H, Sohn E J, et al.. Bioorg. Med. Chem. Lett., 2014, 24:1188-1191
doi: 10.1016/j.bmcl.2013.12.111
Vicker N, Su X, Lawrence H, et al.. Bioorg. Med. Chem. Lett., 2004, 14:3263-3267
Su X, Lawrence H, Ganeshapillai D, et al.. Bioorg. Med. Chem., 2004, 12:4439-4457
doi: 10.1016/j.bmc.2004.06.008
Kong Y Q, Chen F, Liu H K, et al.. J. Inorg. Biochem., 2018, 182:194-199
doi: 10.1016/j.jinorgbio.2018.02.004
Kapadia N S, Isarani S A, Shah M B.. Pharm. Biol., 2005, 43:551-553
doi: 10.1080/13880200500220888
Pile J E, Navalta J W, Davis C D, et al.. J. Nat. Prod., 2013, 76:1001-1006
doi: 10.1021/np3008792
Subramaniya B R, Srinivasan G, Sadullah S S M, et al.. PloS One, 2011, 6:1-11
Padhye S, Dandawate P, Yusufi M, et al.. Med. Res. Rev., 2010, 32:1131-1158
Sreelatha T, Hymavathi A, Babu K S, et al.. J. Agric. Food Chem., 2009, 57:6090-6094
doi: 10.1021/jf901760h
Chen Z F, Tan M X, Liu L M, et al.. Dalton Trans., 2009, 48:10824-10833
Likhitwitayawuid K, Kaewamatawong R, Ruangrungsi N, et al.. Planta Med., 1998, 64:237-241
doi: 10.1055/s-2006-957417
Prasad K R, Babu K S, Rao R R, et al.. Med. Chem. Res., 2012, 21:578-583
doi: 10.1007/s00044-011-9559-7
Mahal K, Schobert R, Biersack B, et al.. J. Inorg. Biochem., 2014, 138:64-72
doi: 10.1016/j.jinorgbio.2014.04.020
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