Alkaloid-metal based anticancer agents

Current Topics in Medicinal Chemistry

Volumn 13, Issue 17, 2013, Pages 2104-2115

  Chen, Zhen Feng ^a   Liu, Yan Cheng ^a   Huang, Ke Bin ^a   Liang, Hong ^a  

^a GUANGXI NORMAL UNIVERSITY   (China)

Author keywords

carboline alkaloid; Alkaloid; Anticancer agents; Liriodenine; Metal complexes; Quinolinoline

Indexed keywords

8 QUINOLINOL DERIVATIVE; ALKALOID DERIVATIVE; ALKALOID METAL COMPLEX; AMINOQUINOLINE DERIVATIVE; ANTINEOPLASTIC METAL COMPLEX; BETA CARBOLINE; CAMPTOTHECIN; CARBOPLATIN; CISPLATIN; CLIOQUINOL; DICENTRINE; GOLD DERIVATIVE; HARMALINE; HARMAN; HARMINE; IRINOTECAN; LIRIODEINE; LIRIODENINE; LOBAPLATIN; NEDAPLATIN; OXALIPLATIN; OXOGLAUCINE; PALLADIUM COMPLEX; QUINOLINOLINE; RUTHENIUM DERIVATIVE; SINOMENINE; TOPOTECAN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINBLASTINE; VINCRISTINE;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; AUTOPHAGY; CANCER INHIBITION; CELL CYCLE ARREST; CELL DEATH; CHINESE MEDICINE; CYTOTOXICITY; FLUORESCENCE ACTIVATED CELL SORTING; HUMAN; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS; COORDINATION COMPLEXES; HUMANS; MOLECULAR STRUCTURE; NEOPLASMS;

EID: 84887961756     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/15680266113139990146     Document Type: Article

References (75)

1. Dembistky, V. M. Astonishing diversity of natural surfactants. 5. Biological active glycosides of aromatic metabolites, Lipids, 2005, 40, 1081-1105.
2. Dembitsky, V. M. Astonishing diversity of natural surfactants. 5. Biological active glycosides of aromatic metabolites, Lipids, 2005, 40, 869-900.
3. Raffauf, R. F. (1996) Plant Alkaloids: A Guide To Their Discovery and Distribution, 298 pp., Food Products Press, Binghamton, NY.
4. Harborne, J. B., Baxter, H., and Moss, G. (1998) Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants, 976 pp., CRC Press, Boca Raton, FL.
5. Pelletier, S. W. (2001) (ed.), Alkaloids: Chemical and Biological Perspectives, Vol. 15, Pergamon, London.
6. Roberts, M. F., and Wink, M. (1998) Alkaloids: Biochemistry, Ecology, and Medicinal Applications, 486 pp., Kluwer Academic, Dordrecht.
7. Cordell, G. A. (ed.) (1998) Alkaloids: Chemistry and Biology, Vol. 51, 439 pp., Academic Press, London.
8. Hesse, M. (2002) Alkaloids: Nature's Curse or Blessing? 400 pp., Wiley-VCH Press, Weinheim.
9. Daly, J. W. (2004) Marine toxins and nonmarine toxins: Convergence or symbiotic organisms? J. Nat. Prod. 67, 1211-1215.
10. Daly, J. W. (1998) Thirty years of discovering arthropod alkaloids in amphibian skin, J. Nat. Prod. 61, 162-172.
11. Pommier, Y. Topoisomerase I inhibitors: camptothecins and beyond. Nat. Rev. Cancer, 2006, 6, 789, 802.
12. Duflos, A.; Kruczynski, A.; Barret, J.-M. Novel aspectes of natural and modified vinca alkaloids. Curr. Med. Chem. Anticancer Agents, 2002, 2, 55, 70.
13. Zhang, C. H.; Mei, X. G.; Liu L. And Yu, L. J. Enhanced paclitaxel production induced by the combination of elicitors in cell suspension cultures of Taxus chinensis. Biotechnol. Lett, 2000, 22, 156111564.
14. Konkimalla, V. B.; Suhas, V. L.; Chandra, N. R.; Gebhart, E.; Efferth, T. Diagnosis and therapy of oral squamous cell carcinoma. Expert. Rev. Anticancer Ther, 2007, 7, 317, 329.
15. Wet, H.; Heerden, F. R.; Wyk, B. E. Alkaloidal variation in cissampelos capensis (menispermaceae). Molecules, 2011, 16, 300133009.
16. Kok, T. W. The anti-angiogenic effect of sinomenine. Angiogenesis, 2005, 8, 3, 12.
17. Rosenberg, B.; Camp, L. V.; Trosko, J. E.; Mansour, V. H. Platinum compounds: a new class of potent antitumour agents. Nature, 1969, 222, 385, 386.
18. Zhu, G.; Myint, M.; Ang, W. H.; Song, L.; Lippard, S. J. Monofunctional platinum-DNA adducts are strong inhibitors of transcription and substrates for nucleotide excision repair in live mammalian cells. Cancer Research, 2012, 72, 790, 800.
19. Kabolizadeh, P.; Engelmann, B. J.; Pullen, N.; Stewart, J. K.; Ryan, J. J.; Farrell, N. P. Platinum anticancer agents and antidepressants: desipramine enhances platinum-based cytotoxicity in human colon cancer cells. J. Biol. Inorg. Chem, 2012, 17, 123, 132.
20. Wong, E.; Giandomenico, C. M. Current status of platinum-based antitumor drugs. Chem. Rev, 1999, 99, 2451, 2466.
21. Jamieson, E. R.; Lippard, S. J. Structure, recognition, and processing of cisplatin-DNA adducts Chem. Rev, 1999, 99, 2467, 2498.
22. Jung, Y.; Lippard, S. J. Direct cellular responses to platinuminduced DNA damage. Chem. Rev, 2007, 107, 1387, 1407.
23. Wataru, S.; Swisher, E. M.; Karlan, B. Y.; Agarwal, M. K.; Higgins, J.; Friedman, C.; Villegas, E.; Jacquemont, C.; Farrugia, D. J.; Couch, F. J.; Nicole Urban, N.; Taniguchi, T. Secondary mutations as a mechanism of cisplatin resistance in BRCA2-mutated cancers. Nature, 2008, 451, 1116, 1121.
24. Zutphen, S.; Reedijk, J. Targeting platinum anti-tumour drugs: Overview of strategies employed to reduce systemic toxicity. Coord. Chem. Rev, 2005, 249, 2845, 2853.
25. Alt, A.; Lammens, K.; Chiocchini, C.; Alfred Lammens, A.; Pieck, J. C.; Kuch, D.; Karl-Peter Hopfner, K.-P.; Carell, T. Bypass of DNA lesions generated during anticancer treatment with cisplatin by DNA polymerase eta. Science, 2007, 318, 967, 970.
26. Lovejoy, K. S. and Lippard, S. J. Non-traditional platinum compounds for improved accumulation, oral bioavailability, and tumor targeting. Dalton Trans, 2009, 10651, 10659.
27. Kelland, L. The resurgence of platinum-based cancer chemotherapy. Nature Rev, 2007, 7, 573, 583.
28. Ho, Y.-P.; To, K. K. W.; Au-Yeung, S. C. F.; Wang, X.; Lin, G.; Han, X. Potential new antitumor agents from an innovative combination of demethylcantharidin, a modified traditional Chinese medicine, with a platinum moiety. J. Med. Chem, 2001, 44, 206522068.
29. Chen, Z.-F.; Liang, H. Progresses in TCM metal-based antitumour agents. Anti-Cancer Agents in Medicinal Chemistry, 2010, 10, 4124423.
30. http://www. intechopen. com/books/recent-advances-in-theoriesand-practice-of-chinese-medicine/traditional-chinese-medicineactive-ingredient-metal-based-anticancer-agents.
31. Hambley, T. W. Metal-based therapeutics. Science, 2007, 318, 139211393.
32. Walker, S. R.; Carter, E. J.; Huff, B. C.; Morris J. C. Variolins and related alkaloids. Chem. Rev, 2009, 109, 3080, 3098.
33. Stévigny, C.; Bailly C. and Quetin-Leclercq J. Cytotoxic and antitumor potentialities of aporphinoid alkaloids. Curr. Med. Chem.-Anti-Cancer Agents, 2005, 5, 173, 182.
34. Woo, S. H.; Sun, N.-J.; Cassady J. M. and Snapka, R. M. Topoisomerase II inhibition by aporphine alkaloids. Biochem. Pharmacol, 1999, 57, 1141, 1145.
35. Tang, H.; Wei, Y.-B.; Zhang, C.; Ning, F.-X.; Qiao, W.; Huang, S.-L.; Ma, L.; Huang, Z.-S.; Gu, L.-Q. Synthesis, biological evaluation and molecular modeling of oxoisoaporphine and oxoaporphine derivatives as new dual inhibitors of acetylcholinesterase/butyrylcholinesterase. Eur. J. Med. Chem, 2009, 44, 252322532.
36. Zhang, A.; Zhang, Y.; Branfman, A. R.; Baldessarini, R. J.; Neumeyer J. L. Advances in development of dopaminergic aporphinoids. J. Med. Chem, 2007, 50, 171, 181.
37. Costa, E. V.; Pinheiro, M. L. B.; Souza, A. D. L.; Barison, A.; Campos, F. R.; Valdez, R. H.; Ueda-Nakamura, T.; Filho, B. P. D.; Nakamura, C. V. Trypanocidal activity of oxoaporphine and pyrimidine-β-carboline alkaloids from the branches of Annona foetida Mart. (Annonaceae). Molecules, 2011, 16, 971419720.
38. Chen, Z.-F.; Liu, Y.-C.; Liu, L.-M.; Wang, H.-S.; Qin, S.-H.; Wang, B.-L.; Bian, H.-D.; Yang, B.; Fun, H.-K.; Liu, H.-G.; Liang, H.; Orvig, C. Potential new inorganic antitumour agents from combining the anticancer traditional Chinese medicine (TCM) liriodenine with metal ions, and DNA binding studies. Dalton Trans, 2009, 262, 272.
39. Liu, Y.-C.; Chen, Z.-F.; Liu, L.-M.; Peng, Y.; Hong, X.; Yang, B.; Liu, H.-G.; Liang, H. and Orvig, C. Divalent later transition metal complexes of the traditional Chinese medicine (TCM) liriodenine: coordination chemistry, cytotoxicity and DNA binding studies. Dalton Trans, 2009, 10813, 10823.
40. Chen, Z.-F.; Liu, Y.-C.; Peng, Y.; Hong, X.; Wang, H.-H.; Zhang, M.-M.; Liang, H. Synthesis, characterization, and in vitro antitumor properties of gold(III) compounds with the traditional Chinese medicine (TCM) liriodenine. J. Biol. Inorg. Chem, 2012, 17, 2472261.
41. Chen, Z.-F.; Shi, Y.-F.; Liu, Y.-C.; Hong, X.; Geng, B.; Peng, Y.; Liang, H. TCM active ingredient oxoglaucine metal complexes: crystal structure, cytotoxicity and interaction with DNA. Inorg. Chem, 2012, 51, 1998, 2009.
42. Cao, R. H.; Peng, W. L.; Wang, Z. H.; Xu, A. L. α-Carboline alkaloids: biochemical and pharmacological functions. Curr. Med. Chem, 2007, 14, 479-500.
43. Funayama, Y.; Nishio, K.; Wakabayashi, K.; Nagao, M.; Shimoi, K.; Ohira, T.; Hasegawa, S.; Saijo, N. Effects of α-and α-carboline derivatives on DNA topoisomerase activities. Mutat. Res. Fundam. Mol. Mech. Mutagen, 1996, 349, 183-191.
44. Li, Y.; Liang, F. S.; Jiang, W.; Yu, F. S.; Cao, R. H.; Ma, Q. H.; Da, X. Y.; Jiang, J. D.; Wang, Y. C.; So, S. DH334, a α-carboline anti-cancer drug, inhibits the CDK activity of budding yeast. Cancer Biol. Ther, 2007, 6, 1193-1199.
45. Castro, A. C.; Dang, L. C.; Soucy, F.; Grenier, L.; Mazdiyasni, H.; Hottelet, M.; Parent, L.; Pien, C.; Palombella, V.; Adams, J. Novel IKK inhibitors: α-carbolines. Bioorg. Med. Chem. Lett, 2003, 13, 2419-2422.
46. Xiao, S. L.; Lin, W.; Wang, C.; Yang, M. Synthesis and biological evaluation of DNA targeting flexible side-chain substituted betacarboline derivatives. Bioorg. Med. Chem. Lett, 2001, 11, 437-441.
47. Kostova, I. Ruthenium complexes as anticancer agents. Curr. Med. Chem, 2006, 13, 1085, 1107.
48. Antonarakis, E. S.; Emadi, A. Ruthenium-based chemotherapeutics: are they ready for prime time? Cancer Chemother. Pharmacol, 2010, 66, 1, 9.
49. Rademaker-Lakhai, J. M.; Van Den Bongard, D.; Pluim, D.; Beijnen, J. H.; Schellens, J. H. M. A phase I and pharmacological study with imidazolium-trans-DMSO-imidazole-tetrachlororuthenate, an ovel ruthenium anticancer agent. Clin. Cancer Res, 2004, 10, 3717, 3727.
50. Hartinger, C. G.; Jakupec, M. A.; Zorbas-Seifried, S.; Groessl, M.; Egger, A.; Berger, W.; Zorbas, H.; Dyson, P. J.; Keppler, B. K. KP1019, a new redox-active anticancer agent-preclinical development and results of a clinical phase I study in tumor patients. Chem. Biodiversity, 2008, 5, 2140, 2155.
51. Levina, A.; Mitra, A.; Lay, P. A. Recent developments in ruthenium anticancer drugs. Metallomics, 2009, 1, 458, 470.
52. Novakova, O.; Malina, J.; Suchankova, T.; Kasparkova, J.; Bugaric, T.; Sadler, P. J.; Brabec, V. Energetics, conformation, and recognition of DNA duplexes modified by monodentate Ru(II) complexes containing terphenyl arense. Chem. Eur. J, 2010, 16, 574455754.
53. Bugaric, T.; Novakova, O.; Halamikova, A.; Zerzankova, L.; Vrana, O.; Kasparkova, J.; Habtemariam, A.; Parson S.; Sadler, P. J.; Brabec, V. Cytotoxicity, cellular uptake, and DNA interactions of new monodentate ruthenium(II) complexes containing terphenyl arenes. J. Med. Chem, 2008, 51, 5310, 5319.
54. Kou, J.-F., Chen, Q.; Wang, J.-Q.; Chen, X.; Wang, L.-L.; Chao, H.; Ji, L.-N. Chiral ruthenium(II) anthraquinone complexes as dual inhibitors of topoisomerases I and II. J. Biol. Inorg. Chem, 2012, 17, 81, 96.
55. Tan, C.; Lai, S.; Wu, S.; Hu, S.; Zhou, l.; Chen, Y.; Wang, M.; Zhu, Y.; Lian, W.; Peng, W.; Ji, L.; Xu, A. Nuclear permeable ruthenium(II) I-carboline complexes induced autophagy to antagonize mitochondrial-mediated apoptosis. J. Med. Chem, 2010, 53, 761377624.
56. Tan, C.; Wu, S.; Lai, S.; Wang, M.; Chen, Y.; Zhou, l.; Zhu, Y.; Lian, W.; Peng, W.; Ji, L.; Xu, A. Synthesis, structures, cellular uptake and apoptosis-inducing properties of highly cytotoxic ruthenium-Norharman complexes. Dalton Trans, 2011, 40, 8611, 8621.
57. New, E. J.; Roche, C.; Madawala, R.; Zhang, J. Z.; Hambley, T. W. Fluorescent analogues of quinoline reveal amine ligand loss from cis and trans platinum(II) complexes in cancer cells. J. Inorg. Biochem., 2009, 103, 112011125.
58. Ma, E. S. F.; Bates, W. D.; Edmunds, A.; Kelland, L. R.; Fojo, T.; Farrell, N. Enhancement of aqueous solubility and stability employing a trans acetate axis in trans planar amine platinum compounds while maintaining the biological profile. J. Med. Chem, 2005, 48, 5651, 5654.
59. Chen, Z.-F.; Song, X.-Y.; Peng, Y.; Hong, X.; Liu, Y.-C.; Liang, H. High cytotoxicity of dihalo-substituted 8-quinolinolato-lanthanides. Dalton Trans, 2011, 40, 1684, 1692.
60. Liu, Y.-C.; Chen, Z.-F.; Song, X.-Y.; Peng Y.; Qin, Q.-P.; Liang H. Synthesis, crystal structure, cytotoxicity and DNA interaction of 5, 7-dibromo-8-quinolinolato-lanthanides. Eur. J. Med. Chem, 2013, 59, 168, 175.
61. Chen, Z.-F.; Gu, Y.-Q.; Song, X.-Y.; Liu, Y.-C.; Peng, Y.; Liang H. Synthesis, crystal structure, cytotoxicity and DNA interaction of 5, 7-dichloro-8-quinolinolato-lanthanides. Eur. J. Med. Chem, 2013, 59, 194, 202.
62. Chen, Z.-F.; Wei, J.-H.; Liu, Y.-C.; Liu, M.; Gu, Y.-Q.; Huang, K.-B.; Wang, M.; Liang H. High antitumor activity of 5, 7-dihalo-8-quinolinolato cerium complexes. Eur. J. Med. Chem, 2013, 68, 4544462.
63. Liu, Y.-C.; Wei, J.-H.; Chen, Z.-F.; Liu, M.; Gu, Y.-Q.; Huang, K.-B.; Li, Z.-Q.; Liang H. The antitumor activity of zinc(II) and copper(II) complexes with 5, 7-dihalo-substituted-8-quinolinoline. Eur. J. Med. Chem, 2013, in press.
64. Chen, Z.-F.; Peng, Y.; Gu, Y.-Q.; Liu, Y.-C.; Liu, M.; Huang, K.-B.; Hu, K.; Liang H. High antitumor activity of 5, 7-dihalo-8-quinolinolato tin(IV) complexes. Eur. J. Med. Chem, 2013, 62, 51558.
65. Tardito, S.; Barilli, A.; Bassanetti, I.; Tegon, M.; Bussolati, O.; Franchi-Gazzola, R.; Mucchino, C.; Marchio, L. Copper-dependent cytotoxicity of 8-hydroxyquinoline derivatives correlates with theri hydrophobicity and does not require caspase activation. J. Med. Chem, 2012, 55, 10448, 10459.
66. Milbank, J. B. J.; Stevenson, R. J.; Ware, D. C.; Chang, J. Y. C.; Tercel, M.; Ahn, G-O.; Wilson, W. R.; Denny, W. A. Synthesis and evaluation of stable bidentate transition metal complexes of 1-(chloromethyl)-5-hydroxy-3-(5, 6, 7-trimethoxyindol-2-ylcarbonyl)-2, 3-dihydro-1H-pyrrolo[3, 2-f]quinoline (seco-6-azaCBI-TMI) as hypoxia selective cytotoxins. J. Med. Chem, 2009, 52, 6822, 6834.
67. Jia, X.; Yang, F.-F.; Li, J.; Liu, J.-Y.; Xu, J.-P. Synthesis and in vitro photodynamic activity of oligomeric ethylene glycol-quinoline substituted zinc(II) phthalocyanine derivatives. J. Med. Chem, 2013, 56, 5797, 5805.
68. Adsule, S.; Barve, V.; Chen, D.; Ahmed, F.; Dou, Q. P.; Padhye, S.; Sarkar, F. Novel Schiff base copper complexes of quinoline-2-carboxaldehyde as proteasome inhibitors in human prostate cancer cells. J. Med. Chem, 2009, 52, 6822, 6834.
69. Gligorijevic, N.; Todorovic, T.; Radulovic, S.; Sladic, D.; Filipovic, N.; GoCevac, D.; Jeremic, D.; AnCelkovic, K. Synthesis and characterization of new Pt(II) and Pd(II) complexes with 2-quinolinecarboxaldehyde selenosemicarbazone: Cytotoxic activity evaluation of Cd(II), Zn(II), Ni(II), Pt(II) and Pd(II) complexes with heteroaromatic selenosemicarbazones. Eur. J. Med. Chem, 2009, 44, 1623, 1629.
70. Yang, T.; Tu, C.; Zhang, J.; Lin, L.; Zhang, X.; Liu, Q.; Ding, J.; Xu, Q.; Guo, Z. Novel Au(III) complexes of aminoquinoline derivatives: crystal structure, DNA binding and cytotoxicity against melanoma and lung tumor cells. Dalton Trans, 2003, 3419, 3424.
71. Hope, J. M.; Wilson, J. J.; Lippard, S. J. Photoluminescent DNA binding and cytotoxic activity of a platinum(II) complex bearing a tetradentate t-diketiminate ligand. Dalton Trans, 2013, 42, 317633180.
72. Huang, K.-B.; Chen, Z.-F.; Liu, Y.-C.; Li, Z.-Q.; Wei, J.-H.; Wang, M.; Xie, X.-L.; Liang, H. Platinum(II) complexes containing aminophosphonate esters: synthsis, characterization, cytotoxicity and action mechanism. Eur. J. Med. Chem, 2013, 64, 554, 561.
73. Juribasic, M.; Molcanov, K.; Kojic-prodic, B.; Bellotto, L.; Kralj, M.; Zani, F.; Tusek-Bozic, L. Palladium(II) complexes of quinolinylaminophosphonates: Synthesis, structural characterization, antitumor and antimicrobial activity. J. Inorg. Biochem, 2011, 105, 8678879.
74. Saturnino, C.; Napoli, M.; Paolucci, G.; Bortoluzzi, M.; Popolo, A.; Pinto, A.; Longo, P. Synthesis and cytotoxic activities of group 3 metal complexes having monoanionic tridentate ligands. Eur. J. Med. Chem, 2010, 45, 4169, 4174.
75. Csermely, P.; Ágoston, V.; Pongor, S. The efficiency of multitarget drugs: the network approach might help drug design. Trends Pharmacol. Sci, 2005, 26, 178, 182.