Login Register Cart 0
Generic placeholder image

Anti-Cancer Agents in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1871-5206
ISSN (Online): 1875-5992

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Advancements in the Use of Platinum Complexes as Anticancer Agents

Author(s): Rajiv Sharma, Vikram Jeet Singh and Pooja A. Chawla*

Volume 22, Issue 5, 2022

Published on: 05 August, 2021

Page: [821 - 835] Pages: 15

DOI: 10.2174/1871520621666210805150705

Price: $65

Abstract

Background: The platinum (II) complexes as anticancer agents have been well explored for the development of novel analogs. Yet, none of them achieved clinical importance in oncology. At present, anticancer compounds containing platinum (II) complexes have been employed in the treatment of colorectal, lung, and genitourinary tumors. Among the platinum-based anticancer drugs, Cisplatin (cis-diamine dichloroplatinum (II), cis-[Pt(NH3)2Cl2]) is one of the most potent components of cancer chemotherapy. The nephrotoxicity, neurotoxicity and ototoxicity, and platinum compounds associated resistant cancer are some major disadvantages.

Objective: With the rapidly growing interest in platinum (II) complexes in tumor chemotherapy, researchers have synthesized many new platinum analogs as anticancer agents that show better cytotoxicity, and less off-target effects with less cellular resistance. This follows the introduction of oxaliplatin, water-soluble carboplatin, multinuclear platinum and newly synthesized complexes, etc.

Methods: This review emphasizes recent advancements in drug design and development, the mechanism of platinum (II) complexes, their stereochemistry, current updates, and biomedical applications of platinum-based anticancer agents.

Conclusion: In the last few decades, the popularity of platinum complexes as potent anti-cancer agents has risen as scientists have synthesized many new platinum complexes that exhibit better cytotoxicity coupled with less off-target effects.

Keywords: Platinum complexes, cisplatin, chemotherapeutic agents, analogues, anticancer agents, cellular resistance.

« Previous Next »
Graphical Abstract

[1]
Giaccone, G. Clinical perspectives on platinum resistance. Drugs, 2000, 59(4)(Suppl. 4), 9-17.
[http://dx.doi.org/10.2165/00003495-200059004-00002] [PMID: 10864226]
[2]
Kelland, L.R.; Sharp, S.Y.; O’Neill, C.F.; Raynaud, F.I.; Beale, P.J.; Judson, I.R. Mini-review: discovery and development of platinum complexes designed to circumvent cisplatin resistance. J. Inorg. Biochem., 1999, 77(1-2), 111-115.
[http://dx.doi.org/10.1016/S0162-0134(99)00141-5] [PMID: 10626362]
[3]
Wang, K.; Lu, J.; Li, R. The events that occur when cisplatin encounters cells. Coord. Chem. Rev., 1996, 151, 53-88.
[4]
Reedijk, J.; Fichtinger-Schepman, A.M.J.; van Oosterom, A.T.; van de Putte, P. Platinum amine coordination compounds as anti-tumor drugs. Molecular aspects of the mechanism of action. Coordination Compounds: Synthesis and Medical Application; Springer, 1987, pp. 53-89.
[http://dx.doi.org/10.1007/3-540-17881-3_2]
[5]
Sherman, S.E.; Lippard, S.J. Structural aspects of platinum anticancer drug interactions with DNA. Chem. Rev., 1987, 87(5), 1153-1181.
[http://dx.doi.org/10.1021/cr00081a013]
[6]
Jamieson, E.R.; Lippard, S.J. Structure, recognition, and processing of cisplatin- DNA adducts. Chem. Rev., 1999, 99(9), 2467-2498.
[http://dx.doi.org/10.1021/cr980421n] [PMID: 11749487]
[7]
Abu-Surrah, A.S.; Kettunen, M. Platinum group antitumor chemistry: design and development of new anticancer drugs complementary to cisplatin. Curr. Med. Chem., 2006, 13(11), 1337-1357.
[http://dx.doi.org/10.2174/092986706776872970] [PMID: 16712474]
[8]
Hambley, T.W. The influence of structure on the activity and toxicity of Pt anti-cancer drugs. Coord. Chem. Rev., 1997, 166, 181-223.
[http://dx.doi.org/10.1016/S0010-8545 (97)00023-4]
[9]
Calvert, A.H.; Harland, S.J.; Newell, D.R.; Siddik, Z.H.; Jones, A.C.; McElwain, T.J.; Raju, S.; Wiltshaw, E.; Smith, I.E.; Baker, J.M.; Peckham, M.J.; Harrap, K.R. Early clinical studies with cis-diammine-1,1-cyclobutane dicarboxylate platinum II. Cancer Chemother. Pharmacol., 1982, 9(3), 140-147.
[http://dx.doi.org/10.1007/BF00257742] [PMID: 6761010]
[10]
Allan, S.G.; Smyth, J.F. Small intestinal mucosal toxicity of cis-platinum--comparison of toxicity with platinum analogues and dexamethasone. Br. J. Cancer, 1986, 53(3), 355-360.
[http://dx.doi.org/10.1038/bjc.1986.59] [PMID: 3516192]
[11]
Akaza, H.; Togashi, M.; Nishio, Y.; Miki, T.; Kotake, T.; Matsumura, Y.; Yoshida, O.; Aso, Y. chemotherapy, S.U.C.S.G. Phase II study of cis-diammine (glycolato) platinum, 254-S, in patients with advanced germ-cell testicular cancer, prostatic cancer, and transitional-cell carcinoma of the urinary tract. Cancer Chemother. Pharmacol., 1992, 31(3), 187-192.
[http://dx.doi.org/10.1007/BF00685546] [PMID: 1334448]
[12]
Kelland, L.R. New platinum antitumor complexes. Crit. Rev. Oncol. Hematol., 1993, 15(3), 191-219.
[http://dx.doi.org/10.1016/1040-8428(93)90042-3] [PMID: 8142057]
[13]
Evans, B.D.; Raju, K.S.; Calvert, A.H.; Harland, S.J.; Wiltshaw, E. Phase II study of JM8, a new platinum analog, in advanced ovarian carcinoma. Cancer Treat. Rep., 1983, 67(11), 997-1000.
[PMID: 6315233]
[14]
Weiss, R.B.; Christian, M.C. New cisplatin analogues in development. A review. Drugs, 1993, 46(3), 360-377.
[http://dx.doi.org/10.2165/00003495-199346030-00003] [PMID: 7693428]
[15]
Bitha, P.; Carvajal, S.G.; Citarella, R.V.; Child, R.G.; Delos Santos, E.F.; Dunne, T.S.; Durr, F.E.; Hlavka, J.J.; Lang, S.A., Jr; Lindsay, H.L. Water-soluble third generation antitumor platinum complexes, [2,2-bis (aminomethyl)-1,3-propanediol-N,N′]-[1,1-cyclobutanedicarboxylato (2-)-O,O′]platinum(II) and [1,1-cyclobutanedicarboxylato(2-)-O,O′] [tetrahydro-4H-pyran-4,4-dimethanamine-N,N′]platinum(II). J. Med. Chem., 1989, 32(8), 2015-2020.
[http://dx.doi.org/10.1021/jm00128a052] [PMID: 2754720]
[16]
Kobayashi, H.; Takemura, Y.; Miyachi, H.; Ogawa, T. Antitumor activities of new platinum compounds, DWA2114R, NK121 and 254-S, against human leukemia cells sensitive or resistant to cisplatin. Invest. New Drugs, 1991, 9(4), 313-319.
[http://dx.doi.org/10.1007/BF00183571] [PMID: 1804804]
[17]
Kraker, A.J.; Moore, C.W.; Roberts, B.J.; Leopold, W.R.; Elliott, W.L. Preclinical antitumor activity of CI-973,[SP-4-3-(R)]-[1,1- cyclobutanedicarboxylato(2-)](2 methyl-1,4-butane-diamine-N,N′) platinum. Invest. New Drugs, 1991, 9(1), 1-7.
[http://dx.doi.org/10.1007/BF00194538] [PMID: 2026477]
[18]
Perez, R.P.; O’Dwyer, P.J.; Handel, L.M.; Ozols, R.F.; Hamilton, T.C. Comparative cytotoxicity of CI-973, cisplatin, carboplatin and tetraplatin in human ovarian carcinoma cell lines. Int. J. Cancer, 1991, 48(2), 265-269.
[http://dx.doi.org/10.1002/ijc.2910480219] [PMID: 2019469]
[19]
Cleare, M.J.; Hoeschele, J.D. Studies on the antitumor activity of group VIII transition metal complexes. Part I. Platinum (II) complexes. Bioinorg. Chem., 1973, 2(3), 187-210.
[http://dx.doi.org/10.1016/S0006-3061(00)80249-5]
[20]
Lebwohl, D.; Canetta, R. Clinical development of platinum complexes in cancer therapy: an historical perspective and an update. Eur. J. Cancer, 1998, 34(10), 1522-1534.
[http://dx.doi.org/10.1016/S0959-8049(98)00224-X] [PMID: 9893623]
[21]
Rečnik, L-M.; Cantelli, C.; Fersing, C.; Gongora, C.; Pouget, J-P.; Lisowski, V. Synthesis and in vitro antitumour activity of carboplatin analogues containing functional handles compatible for conjugation to drug delivery systems. Bioorg. Med. Chem. Lett., 2020, 30(22)127527
[http://dx.doi.org/10.1016/j.bmcl.2020.127527] [PMID: 32890684]
[22]
Hadian Rasanani, S.; Eslami Moghadam, M.; Soleimani, E.; Divsalar, A.; Ajloo, D.; Tarlani, A.; Amiri, M. J. J. o. B. S. Dynamics, Anticancer activity of new imidazole derivative of 1R, 2Rdiaminocyclohexane palladium and platinum complexes as DNA fluorescent probes. 2018, 36(12), 3058-3076.
[23]
Khokhar, A.R.; al-Baker, S.; Krakoff, I.H.; Perez-Soler, R. Toxicity and antitumor activity of cis-bis-carboxylato(trans-R,R-1,2-diaminocyclohexane) platinum(II) complexes entrapped in liposomes. Cancer Chemother. Pharmacol., 1989, 23(4), 219-224.
[http://dx.doi.org/10.1007/BF00451645] [PMID: 2647311]
[24]
Burchenal, J.H.; Kalaher, K.; O’Toole, T.; Chisholm, J. Lack of cross-resistance between certain platinum coordination compounds in mouse leukemia. Cancer Res., 1977, 37(9), 3455-3457.
[PMID: 884687]
[25]
Lyu, A.; Qin, X.; Fang, L.; Gou, S. Synthesis, cytotoxicity, and interaction with DNA of platinum (II) complexes of (1 R, 2 R)-N1-2-amyl-1, 2-diaminocyclohexane. J. Coord. Chem., 2016, 69(10), 1653-1662.
[http://dx.doi.org/10.1080/00958972.2016.1180373]
[26]
Xu, G.; Lin, J.; Li, W.; Zhao, J.; Gou, S. Design, synthesis and biological evaluation of demethylcantharidate-linked platinum (II) complexes of N-monoalkyl-1R, 2R-diaminocyclohexane derivatives. Inorg. Chim. Acta, 2017, 462, 188-194.
[http://dx.doi.org/10.1016/j.ica.2017.03.033]
[27]
Hoeschele, J.D.; Kasparkova, J.; Kostrhunova, H.; Novakova, O.; Pracharova, J.; Pineau, P.; Brabec, V. Synthesis, antiproliferative activity in cancer cells and DNA interaction studies of [Pt(cis-1,3-diaminocycloalkane)Cl2] analogs. J. Biol. Inorg. Chem., 2020, 25(6), 913-924.
[http://dx.doi.org/10.1007/s00775-020-01809-9] [PMID: 32851480]
[28]
Zhao, X.; Zhang, Y.; Hou, X.; Shi, J.; Shen, S.; Huo, S. Synthesis, characterization, and cytotoxicity of Pt (IV) complexes containing 1, 10-phenanthroline and 2, 2′-bipyridine and diaminocyclohexane ligands. Transit. Met. Chem., 2017, 42(3), 219-228.
[http://dx.doi.org/10.1007/s11243-017-0125-0]
[29]
Xu, G.; Zhao, J.; Gou, S.; Pang, J. Antitumor platinum (II) complexes of N-cyclobutyl-1R, 2R-diaminocyclohexane with dicarboxylates as leaving groups. Bioorg. Med. Chem. Lett., 2015, 25(2), 221-224.
[http://dx.doi.org/10.1016/j.bmcl.2014.11.069] [PMID: 25499430]
[30]
Zhang, H.; Gou, S.; Zhao, J.; Chen, F.; Xu, G.; Liu, X. Cytotoxicity profile of novel sterically hindered platinum(II) complexes with (1R,2R)-N(1),N(2)-dibutyl-1,2-diaminocyclohexane. Eur. J. Med. Chem., 2015, 96, 187-195.
[http://dx.doi.org/10.1016/j.ejmech.2015.04.019] [PMID: 25874342]
[31]
Wang, Z.; Yu, H.; Gou, S.; Chen, F.; Fang, L. Design, synthesis, and biological features of platinum (II) complexes with rigid steric hindrance. Inorg. Chem., 2016, 55(9), 4519-4528.
[http://dx.doi.org/10.1021/acs.inorgchem.6b00361] [PMID: 27074104]
[32]
Choi, S.; Filotto, C.; Bisanzo, M.; Delaney, S.; Lagasee, D.; Whitworth, J.L.; Jusko, A.; Li, C.; Wood, N.A.; Willingham, J. Reduction and anticancer activity of platinum (IV) complexes. Inorg. Chem., 1998, 37(10), 2500-2504.
[http://dx.doi.org/10.1021/ic971047x]
[33]
Kratochwil, N.A.; Parkinson, J.A.; Bednarski, P.J.; Sadler, P.J. Nucleotide platination induced by visible light. Angew. Chem. Int. Ed. Engl., 1999, 38(10), 1460-1463.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19990517)38:10<1460:AID-ANIE1460>3.0.CO;2-Z] [PMID: 29711587]
[34]
Braddock, P.D.; Connors, T.A.; Jones, M.; Khokhar, A.R.; Melzack, D.H.; Tobe, M.L. Structure and activity relationships of platinum complexes with anti-tumour activity. Chem. Biol. Interact., 1975, 11(3), 145-161.
[http://dx.doi.org/10.1016/0009-2797(75)90095-2] [PMID: 1157188]
[35]
Bramwell, V.H.; Crowther, D.; O’Malley, S.; Swindell, R.; Johnson, R.; Cooper, E.H.; Thatcher, N.; Howell, A. Activity of JM9 in advanced ovarian cancer: a phase I-II trial. Cancer Treat. Rep., 1985, 69(4), 409-416.
[PMID: 3995511]
[36]
McKeage, M.J.; Raynaud, F.; Ward, J.; Berry, C.; O’Dell, D.; Kelland, L.R.; Murrer, B.; Santabárabara, P.; Harrap, K.R.; Judson, I.R. Phase I and pharmacokinetic study of an oral platinum complex given daily for 5 days in patients with cancer. J. Clin. Oncol., 1997, 15(7), 2691-2700.
[http://dx.doi.org/10.1200/JCO.1997.15.7.2691] [PMID: 9215842]
[37]
Pendyala, L.; Arakali, A.V.; Sansone, P.; Cowens, J.W.; Creaven, P.J. DNA binding of iproplatin and its divalent metabolite cis-dichloro-bis-isopropylamine platinum (II). Cancer Chemother. Pharmacol., 1990, 27(3), 248-250.
[http://dx.doi.org/10.1007/BF00685722] [PMID: 2265462]
[38]
Qin, X.; Xu, G.; Chen, F.; Fang, L.; Gou, S. Novel platinum(IV) complexes conjugated with a wogonin derivative as multi-targeted anticancer agents. Bioorg. Med. Chem., 2017, 25(8), 2507-2517.
[http://dx.doi.org/10.1016/j.bmc.2017.03.007] [PMID: 28314511]
[39]
Wheate, N.J.; Collins, J.G.J.C. Multi-nuclear platinum complexes as anti-cancer drugs. Coord. Chem. Rev., 2003, 241(1-2), 133-145.
[http://dx.doi.org/10.1016/S0010-8545(03)00050-X]
[40]
Roberts, J.D.; Peroutka, J.; Farrell, N. Cellular pharmacology of polynuclear platinum anti-cancer agents. J. Inorg. Biochem., 1999, 77(1-2), 51-57.
[http://dx.doi.org/10.1016/S0162-0134(99)00147-6] [PMID: 10626354]
[41]
Wu, P.K.; Kharatishvili, M.; Qu, Y.; Farrell, N. A circular dichroism study of ethidium bromide binding to Z-DNA induced by dinuclear platinum complexes. J. Inorg. Biochem., 1996, 63(1), 9-18.
[http://dx.doi.org/10.1016/0162-0134 (95)00163-8] [PMID: 8699175]
[42]
Rauter, H.; Di Domenico, R.; Menta, E.; Oliva, A.; Qu, Y.; Farrell, N.J.I.C. Selective platination of biologically relevant polyamines. Linear coordinating spermidine and spermine as amplifying linkers in dinuclear platinum complexes. Inorg. Chem., 1997, 36(18), 3919-3927.
[http://dx.doi.org/10.1021/ic9701827]
[43]
Bierbach, U.; Hambley, T.W.; Farrell, N. Modification of platinum (II) antitumor complexes with sulfur ligands. 1. Synthesis, structure, and spectroscopic properties of cationic complexes of the types [PtCl (diamine) (L)] NO3 and [{PtCl (diamine)} 2 (LL)](NO3) 2 (L= monofunctional thiourea derivative; LL= bifunctional thiourea derivative). Inorg. Chem., 1998, 37(4), 708-716.
[http://dx.doi.org/10.1021/ic970420y]
[44]
Yun, Q.; Farrell, N.; Kasparkova, J.; Brabec, V. DNA binding of properties of trinuclear platinum complex. J. Inorg. Biochem., 1997, 67(1-4), 174-174.
[http://dx.doi.org/10.1016/S0162-0134(97)80052-9]
[45]
Perego, P.; Caserini, C.; Gatti, L.; Carenini, N.; Romanelli, S.; Supino, R.; Colangelo, D.; Viano, I.; Leone, R.; Spinelli, S.; Pezzoni, G.; Manzotti, C.; Farrell, N.; Zunino, F. A novel trinuclear platinum complex overcomes cisplatin resistance in an osteosarcoma cell system. Mol. Pharmacol., 1999, 55(3), 528-534.
[PMID: 10051537]
[46]
Jansen, J.; van der Zwan, J.; Reedijk, J.; den Dulk, H.; Brouwer, J.A. Tetranuclear platinum compound designed to overcome cisplatin resistance. Eur. J. Inorg. Chem., 1999, 1999(9), 1429-1433.
[http://dx.doi.org/10.1002/(SICI)1099-0682(199909)1999:9<1429:AID-EJIC1429>3.0.CO;2-8]
[47]
Noji, M.; Kizu, R.; Takeda, Y.; Akiyama, N.; Yoshizaki, I.; Eriguchi, M.; Kidani, Y. Preparation of antitumor oxaliplatin/cisplatin docking dinuclear platinum complex. Biomed. Pharmacother., 2005, 59(5), 224-229.
[http://dx.doi.org/10.1016/j.biopha.2004.06.006] [PMID: 15919175]
[48]
Kalayda, G.V.; Komeda, S.; Ikeda, K.; Sato, T.; Chikuma, M.; Reedijk, J. Synthesis, Structure, and Biological Activity of New Azine-Bridged Dinuclear Platinum (II) Complexes− a New Class of Anticancer Compounds. Eur. J. Inorg. Chem., 2003, 2003(24), 4347-4355.
[http://dx.doi.org/10.1002/ejic.200300315]
[49]
Alexander, C.; Prajith, N.U.; Priyanka, P.V.; Nithyakumar, A.; Arockia Samy, N. Dinuclear platinum(II) complexes of imidazophenanthroline-based bridging ligands as potential anticancer agents: synthesis, characterization, and in vitro cytotoxicity studies. J. Biol. Inorg. Chem., 2019, 24(3), 405-418.
[http://dx.doi.org/10.1007/s00775-019-01656-3] [PMID: 30945024]
[50]
Qin, Q-P.; Wang, Z-F.; Wang, S-L.; Luo, D-M.; Zou, B-Q.; Yao, P-F.; Tan, M-X.; Liang, H. In vitro and in vivo antitumor activities of three novel binuclear platinum (II) complexes with 4′-substituted-2,2′:6′,2″-terpyridine ligands. Eur. J. Med. Chem., 2019, 170, 195-202.
[http://dx.doi.org/10.1016/j.ejmech.2019.03.014] [PMID: 30897397]
[51]
Zunino, F.; Savi, G.; Pasini, A. Synthesis and antitumor activity of a platinum (II)-doxorubicin complex. Cancer Chemother. Pharmacol., 1986, 18(2), 180-182.
[http://dx.doi.org/10.1007/BF00262293] [PMID: 3791563]
[52]
Bowler, B.E.; Ahmed, K.J.; Sundquist, W.I.; Hollis, L.S.; Whang, E.E.; Lippard, S.J. Synthesis, characterization, and DNA-binding properties of (1, 2-diaminoethane) platinum (II) complexes linked to the DNA intercalator acridine orange by trimethylene and hexamethylene chains. J. Am. Chem. Soc., 1989, 111(4), 1299-1306.
[http://dx.doi.org/10.1021/ja00186a022]
[53]
Palmer, B.D.; Lee, H.H.; Johnson, P.; Baguley, B.C.; Wickham, G.; Wakelin, L.P.; McFadyen, W.D.; Denny, W.A. DNA-directed alkylating agents. 2. Synthesis and biological activity of platinum complexes linked to 9-anilinoacridine. J. Med. Chem., 1990, 33(11), 3008-3014.
[http://dx.doi.org/10.1021/jm00173a015] [PMID: 2231598]
[54]
Ho, Y-P.; To, K.K.; Au-Yeung, S.C.; 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(13), 2065-2068.
[http://dx.doi.org/10.1021/jm000476t] [PMID: 11405643]
[55]
Dahlman-Wright, K.; Cavailles, V.; Fuqua, S.A.; Jordan, V.C.; Katzenellenbogen, J.A.; Korach, K.S.; Maggi, A.; Muramatsu, M.; Parker, M.G.; Gustafsson, J-Å. International union of pharmacology. LXIV. Estrogen receptors. Pharmacol. Rev., 2006, 58(4), 773-781.
[http://dx.doi.org/10.1124/pr.58.4.8] [PMID: 17132854]
[56]
Hartman, J.; Lindberg, K.; Morani, A.; Inzunza, J.; Ström, A.; Gustafsson, J-Å. Estrogen receptor β inhibits angiogenesis and growth of T47D breast cancer xenografts. Cancer Res., 2006, 66(23), 11207-11213.
[http://dx.doi.org/10.1158/0008-5472.CAN-06-0017] [PMID: 17145865]
[57]
Hannon, M.J.; Green, P.S.; Fisher, D.M.; Derrick, P.J.; Beck, J.L.; Watt, S.J.; Ralph, S.F.; Sheil, M.M.; Barker, P.R.; Alcock, N.W.; Price, R.J.; Sanders, K.J.; Pither, R.; Davis, J.; Rodger, A. An estrogen-platinum terpyridine conjugate: DNA and protein binding and cellular delivery. Chemistry, 2006, 12(31), 8000-8013.
[http://dx.doi.org/10.1002/chem.200501012] [PMID: 16881027]
[58]
Kim, E.; Rye, P.T.; Essigmann, J.M.; Croy, R.G. A bifunctional platinum (II) antitumor agent that forms DNA adducts with affinity for the estrogen receptor. J. Inorg. Biochem., 2009, 103(2), 256-261.
[http://dx.doi.org/10.1016/j.jinorgbio.2008.10.013] [PMID: 19054566]
[59]
Descôteaux, C.; Leblanc, V.; Bélanger, G.; Parent, S.; Asselin, E.; Bérubé, G. Improved synthesis of unique estradiol-linked platinum(II) complexes showing potent cytocidal activity and affinity for the estrogen receptor alpha and beta. Steroids, 2008, 73(11), 1077-1089.
[http://dx.doi.org/10.1016/j.steroids.2008.04.009] [PMID: 18572212]
[60]
Provencher-Mandeville, J.; Descôteaux, C.; Mandal, S.K.; Leblanc, V.; Asselin, E.; Bérubé, G. Synthesis of 17β-estradiol-platinum(II) hybrid molecules showing cytotoxic activity on breast cancer cell lines. Bioorg. Med. Chem. Lett., 2008, 18(7), 2282-2287.
[http://dx.doi.org/10.1016/j.bmcl.2008.03.005] [PMID: 18356047]
[61]
Gust, R.; Beck, W.; Jaouen, G.; Schönenberger, H. Optimization of cisplatin for the treatment of hormone-dependent tumoral diseases: Part 2: Use of non-steroidal ligands. Coord. Chem. Rev., 2009, 253(21-22), 2760-2779.
[http://dx.doi.org/10.1016/j.ccr.2009.02.029]
[62]
Gupta, A.; Mandal, S.K.; Leblanc, V.; Descôteaux, C.; Asselin, E.; Bérubé, G. Synthesis and cytotoxic activity of benzopyran-based platinum(II) complexes. Bioorg. Med. Chem. Lett., 2008, 18(14), 3982-3987.
[http://dx.doi.org/10.1016/j.bmcl.2008.06.013] [PMID: 18571403]
[63]
Schobert, R.; Bernhardt, G.; Biersack, B.; Bollwein, S.; Fallahi, M.; Grotemeier, A.; Hammond, G.L. Steroid conjugates of dichloro(6-aminomethylnicotinate)platinum(II): effects on DNA, sex hormone binding globulin, the estrogen receptor, and various breast cancer cell lines. ChemMedChem, 2007, 2(3), 333-342.
[http://dx.doi.org/10.1002/cmdc.200600173] [PMID: 17266159]
[64]
Kvasnica, M.; Rarova, L.; Oklestkova, J.; Budesinsky, M.; Kohout, L. Synthesis and cytotoxic activities of estrone and estradiol cis-dichloroplatinum(II) complexes. Bioorg. Med. Chem., 2012, 20(24), 6969-6978.
[http://dx.doi.org/10.1016/j.bmc.2012.10.013] [PMID: 23142322]
[65]
Kitteringham, E.; Andriollo, E.; Gandin, V.; Montagner, D.; Griffith, D. M. J. I. C. A. Synthesis, characterisation and in vitro antitumour potential of novel Pt (II) estrogen linked complexes. 2019, 495, 495.
[66]
Berger, I.; Nazarov, A.A.; Hartinger, C.G.; Groessl, M.; Valiahdi, S.M.; Jakupec, M.A.; Keppler, B.K.J.C.C.E.D.D. A glucose derivative as natural alternative to the cyclohexane-1,2-diamine ligand in the anticancer drug oxaliplatin? ChemMedChem, 2007, 2(4), 505-514.
[http://dx.doi.org/10.1002/cmdc.200600279] [PMID: 17340670]
[67]
Sun, R.W-Y.; Ma, D-L.; Wong, E.L-M.; Che, C-M. Some uses of transition metal complexes as anti-cancer and anti-HIV agents. Dalton Trans., 2007, (43), 4884-4892.
[PMID: 17992273]
[68]
Prashar, D.; Shi, Y.; Bandyopadhyay, D.; Dabrowiak, J.C.; Luk, Y-Y. Adamantane-platinum conjugate hosted in β-cyclodextrin: enhancing transport and cytotoxicity by noncovalent modification. Bioorg. Med. Chem. Lett., 2011, 21(24), 7421-7425.
[http://dx.doi.org/10.1016/j.bmcl.2011.10.006] [PMID: 22050886]
[69]
Horvath, G.; Premkumar, T.; Boztas, A.; Lee, E.; Jon, S.; Geckeler, K.E. Supramolecular nanoencapsulation as a tool: solubilization of the anticancer drug trans-dichloro(dipyridine)platinum(II) by complexation with β-cyclodextrin. Mol. Pharm., 2008, 5(2), 358-363.
[http://dx.doi.org/10.1021/mp700144t] [PMID: 18281942]
[70]
Annunziata, A.; Cucciolito, M.E.; Esposito, R.; Imbimbo, P.; Petruk, G.; Ferraro, G.; Pinto, V.; Tuzi, A.; Monti, D.M.; Merlino, A.; Ruffo, F. A highly efficient and selective antitumor agent based on a glucoconjugated carbene platinum(ii) complex. Dalton Trans., 2019, 48(22), 7794-7800.
[http://dx.doi.org/10.1039/C9DT01614G] [PMID: 31069352]
[71]
Ma, J.; Wang, Q.; Yang, X.; Hao, W.; Huang, Z.; Zhang, J.; Wang, X.; Wang, P.G. Glycosylated platinum(iv) prodrugs demonstrated significant therapeutic efficacy in cancer cells and minimized side-effects. Dalton Trans., 2016, 45(29), 11830-11838.
[http://dx.doi.org/10.1039/C6DT02207C] [PMID: 27373800]
[72]
Xue, Z.; Lin, M.; Zhu, J.; Zhang, J.; Li, Y.; Guo, Z. Platinum(II) compounds bearing bone-targeting group: synthesis, crystal structure and antitumor activity. Chem. Commun. (Camb.), 2010, 46(8), 1212-1214.
[http://dx.doi.org/10.1039/b922222g] [PMID: 20449253]
[73]
Alvarez-Valdes, A.; Matesanz, A. I.; Perles, J.; Fernandes, C.; Correia, J. D.; Mendes, F.; Quiroga, A. G. J. J. o. i. b. Novel structures of platinum complexes bearing N-bisphosphonates and study of their biological properties., 2019, 191, 112-118.
[http://dx.doi.org/10.1016/j.jinorgbio.2018.11.010]
[74]
Sun, Y.; Zhao, J.; Ji, Z. J. C. biodiversity, Bifunctional platinum (II) complexes with bisphosphonates substituted diamine derivatives: synthesis and in vitro cytotoxicity. 2017, 14(12), e1700348.
[75]
Margiotta, N.; Ostuni, R.; Ranaldo, R.; Denora, N.; Laquintana, V.; Trapani, G.; Liso, G.; Natile, G. Synthesis and characterization of a platinum(II) complex tethered to a ligand of the peripheral benzodiazepine receptor. J. Med. Chem., 2007, 50(5), 1019-1027.
[http://dx.doi.org/10.1021/jm0612160] [PMID: 17286392]
[76]
Margiotta, N.; Denora, N.; Ostuni, R.; Laquintana, V.; Anderson, A.; Johnson, S.W.; Trapani, G.; Natile, G. Platinum(II) complexes with bioactive carrier ligands having high affinity for the translocator protein. J. Med. Chem., 2010, 53(14), 5144-5154.
[http://dx.doi.org/10.1021/jm100429r] [PMID: 20568783]
[77]
Jeon, W.S.; Moon, K.; Park, S.H.; Chun, H.; Ko, Y.H.; Lee, J.Y.; Lee, E.S.; Samal, S.; Selvapalam, N.; Rekharsky, M.V.; Sindelar, V.; Sobransingh, D.; Inoue, Y.; Kaifer, A.E.; Kim, K. Complexation of ferrocene derivatives by the cucurbit[7]uril host: a comparative study of the cucurbituril and cyclodextrin host families. J. Am. Chem. Soc., 2005, 127(37), 12984-12989.
[http://dx.doi.org/10.1021/ja052912c] [PMID: 16159293]
[78]
Wagner, B.D.; Arnold, A.E.; Gallant, S.T.; Grinton, C.R.; Locke, J.K.; Mills, N.D.; Snow, C.A.; Uhlig, T.B.; Vessey, C.N. The polarity sensitivity factor of some fluorescent probe molecules used for studying supramolecular systems and other heterogeneous environments. Can. J. Chem., 2018, 96(7), 629-635.
[http://dx.doi.org/10.1139/cjc-2017-0727]
[79]
Wheate, N.J.; Buck, D.P.; Day, A.I.; Collins, J.G. Cucurbit[n]uril binding of platinum anticancer complexes. Dalton Trans., 2006, (3), 451-458.
[http://dx.doi.org/10.1039/B513197A] [PMID: 16395444]
[80]
Sharma, R.; Malhotra, M.; Gaba, T.; Sharma, K. A.; R Bhardwaj, T. Discovery, Design, synthesis and in-vitro cytotoxicity of novel platinum (II) complexes with phthalate as the leaving group. Lett. Drug Des. Discov., 2013, 10(9), 872-878.
[http://dx.doi.org/10.2174/15701808113109990018]
[81]
Sharma, R.; Rawal, R.K.; Gaba, T.; Singla, N.; Malhotra, M.; Matharoo, S.; Bhardwaj, T.R. Design, synthesis and ex vivo evaluation of colon-specific azo based prodrugs of anticancer agents. Bioorg. Med. Chem. Lett., 2013, 23(19), 5332-5338.
[http://dx.doi.org/10.1016/j.bmcl.2013.07.059] [PMID: 23968824]
[82]
Hu, W.; Zhao, J.; Hua, W.; Gou, S. J. M. study on platinum (IV) species containing an estrogen receptor modulator to reverse tamoxifen resistance of breast cancer. 2018, 10(2), 346-359.

Rights & Permissions Print Cite
Article Metrics
109
1
© 2024 Bentham Science Publishers | Privacy Policy