Abstract
Inorganic chemistry plays an essential role in human life. As depicted in Fig. 1.1, there are 24 known essential elements, but the possible biological roles of some other elements (e.g., Cr, B) in life science remain to be understood. For those bioactive metal ions, their biological properties can be significantly affected by their coordinating ligands. Similarly, the biological activities of metallodrugs are affected both by the metal ion and by the coordinating ligand(s). Coordination of appropriate ligand(s) to metal ions can adjust the reduction potentials and/or ligand exchange reactions with biomolecules, thereby regulating the important biological processes.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Farrer NJ, Sadler PJ (2011) Medicinal inorganic chemistry: state of the art, new trends, and a vision of the future. In: Alessio E (ed) Bioinorg Med Chem. Wiley-VCH, Germany, pp 1–37
Ronconi L, Sadler PJ (2007) Using coordination chemistry to design new medicines. Coord Chem Rev 251(13–14):1633–1648
Lo-Coco F, Avvisati G, Vignetti M, Thiede C, Orlando SM, Iacobelli S, Ferrara F, Fazi P, Cicconi L, Di Bona E, Specchia G, Sica S, Divona M, Levis A, Fiedler W, Cerqui E, Breccia M, Fioritoni G, Salih HR, Cazzola M, Melillo L, Carella AM, Brandts CH, Morra E, von Lilienfeld-Toal M, Hertenstein B, Wattad M, Lübbert M, Hänel M, Schmitz N, Link H, Kropp MG, Rambaldi A, La Nasa G, Luppi M, Ciceri F, Finizio O, Venditti A, Fabbiano F, Döhner K, Sauer M, Ganser A, Amadori S, Mandelli F, Döhner H, Ehninger G, Schlenk RF, Platzbecker U (2013) Retinoic acid and arsenic trioxide for acute promyelocytic leukemia. N Engl J Med 369(2):111–121
Au W-Y, Kumana CR, Kou M, Mak R, Chan GCF, Lam C-W, Kwong Y-L (2003) Oral arsenic trioxide in the treatment of relapsed acute promyelocytic leukemia 102(1). doi:10.1182/blood-2003-01-0298
Barry NPE, Sadler PJ (2012) Dicarba-closo-dodecarborane-containing half-sandwich complexes of ruthenium, osmium, rhodium and iridium: biological relevance and synthetic strategies. Chem Soc Rev 41(8):3264–3279
Abeysinghe PM, Harding MM (2007) Antitumour Bis(cyclopentadienyl) metal complexes: titanocene and molybdocene dichloride and derivatives. Dalton Trans 32:3474–3482
Che C-M, Sun RW-Y, Yu W-Y, Ko C-B, Zhu N, Sun H (2003) Gold(III) porphyrins as a new class of anticancer drugs: cytotoxicity, DNA binding and induction of apoptosis in human cervix epitheloid cancer cells. Chem Commun 14:1718–1719
Berners-Price SJ, Mirabelli CK, Johnson RK, Mattern MR, McCabe FL, Faucette LF, Sung C-M, Mong S-M, Sadler PJ, Crooke ST (1986) In vivo antitumor activity and in vitro cytotoxic properties of Bis[1,2-bis(diphenylphosphino)ethane]gold(I) chloride. Cancer Res 46(11):5486–5493
Ni W-X, Man W-L, Cheung MT-W, Sun RW-Y, Shu Y-L, Lam Y-W, Che C-M, Lau T-C (2011) Osmium(VI) complexes as a new class of potential anti-cancer agents. Chem Commun 47(7):2140–2142
Alama A, Viale M, Cilli M, Bruzzo C, Novelli F, Tasso B, Sparatore F (2009) In vitro cytotoxic activity of Tri-n-Butyltin(IV)lupinylsulfide hydrogen fumarate (IST-FS 35) and Preliminary antitumor activity in vivo. Invest New Drugs 27(2):124–130
Bandoli G, Dolmella A, Tisato F, Porchia M, Refosco F (2009) Mononuclear six-coordinated Ga(III) complexes: a comprehensive survey. Coord Chem Rev 253(1–2):56–77
Tisato F, Marzano C, Porchia M, Pellei M, Santini C (2010) Copper in diseases and treatments, and copper-based anticancer strategies. Med Res Rev 30(4):708–749
Magda D, Lecane P, Wang Z, Hu W, Thiemann P, Ma X, Dranchak PK, Wang X, Lynch V, Wei W, Csokai V, Hacia JG, Sessler JL (2008) Synthesis and anticancer properties of water-soluble zinc ionophores. Cancer Res 68(13):5318–5325
Li H, Lai CS, Wu J, Ho PC, de Vos D, Tiekink ERT (2007) Cytotoxicity, Qualitative Structure-Activity Relationship (QSAR), and anti-tumor activity of bismuth dithiocarbamate complexes. J Inorg Biochem 101(5):809–816
Yamase T (2005) Anti-tumor, -Viral, and -Bacterial activities of polyoxometalates for realizing an inorganic drug. J Mater Chem 15(45):4773–4782
Rosenberg B, Van Camp L, Krigas T (1965) Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode. Nature 205(4972):698–699
Rosenberg B, Vancamp L, Trosko JE, Mansour VH (1969) Platinum compounds: a new class of potent antitumour agents. Nature 222(5191):385–386
Kelland L (2007) The resurgence of platinum-based cancer chemotherapy. Nat Rev Cancer 7(8):573–584
Wheate NJ, Walker S, Craig GE, Oun R (2010) The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton Trans 39(35):8113–8127
Oberoi HS, Nukolova NV, Kabanov AV, Bronich TK (2013) Nanocarriers for delivery of platinum anticancer drugs. Adv Drug Deliv Rev 65(13–14):1667–1685
Fichtinger-Schepman AMJ, van Oosterom AT, Lohman PHM, Berends F (1987) cis-diamminedichloroplatinum(II)-induced DNA adducts in peripheral leukocytes from seven cancer patients: quantitative immunochemical detection of the adduct induction and removal after a single dose of cis-diamminedichloroplatinum(II). Cancer Res 47(11):3000–3004
Baik M-H, Friesner RA, Lippard SJ (2003) Theoretical study of cisplatin binding to purine bases: why does cisplatin prefer guanine over adenine? J Am Chem Soc 125(46):14082–14092
Legendre F, Bas V, Kozelka J, Chottard J-C (2000) A complete kinetic study of GG versus AG Platination suggests that the doubly aquated derivatives of cisplatin are the actual DNA binding species. Chem Eur J 6(11):2002–2010
Kozelka J, Legendre F, Reeder F, Chottard J-C (1999) Kinetic aspects of interactions between DNA and platinum complexes. Coord Chem Rev 190–192:61–82
Legendre F, Kozelka J, Chottard J-C (1998) GG versus AG Platination: a kinetic study on hairpin-stabilized duplex oligonucleotides. Inorg Chem 37(16):3964–3967
Reedijk J (2003) New clues for platinum antitumor chemistry: kinetically controlled metal binding to DNA. Proc Natl Acad Sci 100(7):3611–3616
Reedijk J (1999) Why does cisplatin reach guanine-N7 with Competing S-donor Ligands available in the cell? Chem Rev 99(9):2499–2510
Mandic A, Hansson J, Linder S, Shoshan MC (2003) Cisplatin induces endoplasmic reticulum stress and nucleus-independent apoptotic signaling. J Biol Chem 278(11):9100–9106
Lacour S, Hammann A, Grazide S, Lagadic-Gossmann D, Athias A, Sergent O, Laurent G, Gambert P, Solary E, Dimanche-Boitrel M-T (2004) Cisplatin-induced CD95 redistribution into membrane lipid rafts of HT29 human colon cancer cells. Cancer Res 64(10):3593–3598
Aris SM, Farrell NP (2009) Towards antitumor active trans-platinum compounds. Eur J Inorg Chem 10:1293–1302
Chen S, Xu D, Jiang H, Xi Z, Zhu P, Liu Y (2012) Trans-Platinum/Thiazole complex interferes with Sp1 Zinc-Finger Protein. Angew Chem Int Ed 51(49):12258–12262
Laguna A (2008) Modern supramolecular gold chemistry: gold-metal interactions and applications. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Fricker SP (2010) Cysteine proteases as targets for metal-based drugs. Metallomics 2(6):366–377
de Almeida A, Soveral G, Casini A (2014) Gold compounds as aquaporin inhibitors: new opportunities for therapy and imaging. Med Chem Comm 5:1444–1453
Bindoli A, Rigobello MP, Scutari G, Gabbiani C, Casini A, Messori L (2009) Thioredoxin reductase: a target for gold compounds acting as potential anticancer drugs. Coord Chem Rev 253(11–12):1692–1707
Urig S, Fritz-Wolf K, Réau R, Herold-Mende C, Tóth K, Davioud-Charvet E, Becker K (2006) Undressing of phosphine gold(I) complexes as irreversible inhibitors of human disulfide reductases. Angew Chem Int Ed 45(12):1881–1886
Angelucci F, Sayed AA, Williams DL, Boumis G, Brunori M, Dimastrogiovanni D, Miele AE, Pauly F, Bellelli A (2009) Inhibition of schistosoma mansoni thioredoxin-glutathione reductase by auranofin: structural and kinetic aspects. J Biol Chem 284(42):28977–28985
Ilari A, Baiocco P, Messori L, Fiorillo A, Boffi A, Gramiccia M, Di Muccio T, Colotti G (2012) A cold-containing drug against parasitic polyamine metabolism: the X-Ray structure of trypanothione reductase from leishmania infantum in complex with auranofin reveals a dual mechanism of enzyme inhibition. Amino Acids 42(2–3):803–811
Cheng Q, Sandalova T, Lindqvist Y, Arnér ESJ (2009) Crystal structure and catalysis of the selenoprotein thioredoxin reductase 1. J Biol Chem 284(6):3998–4008
Karver MR, Krishnamurthy D, Kulkarni RA, Bottini N, Barrios AM (2009) Identifying potent, selective protein tyrosine phosphatase inhibitors from a library of Au(I) complexes. J Med Chem 52(21):6912–6918
Jeon K-I, Jeong J-Y, Jue D-M (2000) Thiol-reactive metal compounds inhibit NF-κB activation by blocking IκB kinase. J Immunol 164(11):5981–5989
Zhang J-J, Ng K-M, Lok C-N, Sun RW-Y, Che C-M (2013) Deubiquitinases as potential anti-cancer targets for gold(III) complexes. Chem Commun 49(45):5153–5155
Martins AP, Ciancetta A, de Almeida A, Marrone A, Re N, Soveral G, Casini A (2013) Aquaporin Inhibition by gold(III) compounds: new insights. Chem Med Chem 8(7):1086–1092
Martins AP, Marrone A, Ciancetta A, Cobo AG, Echevarrya M, Moura TF, Re N, Casini A, Soveral G (2012) Targeting aquaporin function: potent inhibition of aquaglyceroporin-3 by a gold-based compound. PLoS ONE 7(5):e37435
Zou J, Taylor P, Dornan J, Robinson SP, Walkinshaw MD, Sadler PJ (2000) First crystal structure of a medicinally relevant gold protein complex: unexpected binding of [Au(PEt3)]+ to histidine. Angew Chem Int Ed 39(16):2931–2934
Messori L, Scaletti F, Massai L, Cinellu MA, Russo Krauss I, di Martino G, Vergara A, Paduano L, Merlino A (2014) Interactions of gold-based drugs with proteins: crystal structure of the adduct formed between ribonuclease A and a cytotoxic gold(III) compound. Metallomics 6:233–236
Messori L, Scaletti F, Massai L, Cinellu MA, Gabbiani C, Vergara A, Merlino A (2013) The mode of action of anticancer gold-based drugs: a structural perspective. Chem Commun 49(86):10100–10102
Berners-Price SJ, Filipovska A (2011) Gold compounds as therapeutic agents for human diseases. Metallomics 3(9):863–873
Pillarsetty N, Katti KK, Hoffman TJ, Volkert WA, Katti KV, Kamei H, Koide T (2003) In vitro and in vivo antitumor properties of tetrakis((trishydroxymethyl) phosphine)gold(I) chloride. J Med Chem 46:1130–1132
Tian S, Siu F-M, Kui SCF, Lok C-N, Che C-M (2011) Anticancer gold(I)-phosphine complexes as potent autophagy-inducing agents. Chem Commun 47(33):9318–9320
Simon TM, Kunishima DH, Vibert GJ, Lorber A (1981) Screening trial with the coordinated gold compound auranofin using mouse lymphocytic leukemia P388. Cancer Res 41(1):94–97
Christopher P, Leamon JAR, Vlahov Iontcho R, Kleindl Paul J, Vetzel Marilynn, Westrick Elaine (1985) Evaluation of the in vivo antitumor activity and in vitro cytotoxic properties of auranofin, a coordinated gold compound, in murine tumor models. Cancer Res 45:32–39
Sadler PJ, Sue RE (1994) The chemistry of gold drugs. Met-Based Drugs 1(2–3):107–144
Shaw CF III (1999) Gold-Based Therapeutic Agents. Chem Rev 99(9):2589–2600
Kamei H, Koide T, Kojima T, Hashimoto Y, Hasegawa M (1998) Effect of gold on survival of tumor-bearing mice. Cancer Biother Radiopharm 13(5):403–406
Stallings-Mann M, Jamieson L, Regala RP, Weems C, Murray NR, Fields AP (2006) A novel small-molecule inhibitor of protein kinase ciota blocks transformed growth of non-small-cell lung cancer cells. Cancer Res 66(3):1767–1774
Baker MV, Barnard PJ, Berners-Price SJ, Brayshaw SK, Hickey JL, Skelton BW, White AH (2006) Cationic, linear Au(I) N-heterocyclic carbene complexes: synthesis. Struct Anti-Mitochondrial Act Dalton Trans 30:3708–3715
Hickey JL, Ruhayel RA, Barnard PJ, Baker MV, Berners-Price SJ, Filipovska A (2008) Mitochondria-targeted chemotherapeutics: the rational design of gold(I) N-heterocyclic carbene complexes that are selectively toxic to cancer cells and target protein selenols in preference to thiols. J Am Chem Soc 130(38):12570–12571
Rubbiani R, Kitanovic I, Alborzinia H, Can S, Kitanovic A, Onambele LA, Stefanopoulou M, Geldmacher Y, Sheldrick WS, Wolber G, Prokop A, Wölfl S, Ott I (2010) Benzimidazol-2-ylidene gold(I) complexes are thioredoxin reductase inhibitors with multiple antitumor properties. J Med Chem 53(24):8608–8618
Rubbiani R, Can S, Kitanovic I, Alborzinia H, Stefanopoulou M, Kokoschka M, Mönchgesang S, Sheldrick WS, Wölfl S, Ott I (2011) comparative in vitro evaluation of N-heterocyclic carbene gold(I) complexes of the benzimidazolylidene type. J Med Chem 54(24):8646–8657
Meyer A, Bagowski CP, Kokoschka M, Stefanopoulou M, Alborzinia H, Can S, Vlecken DH, Sheldrick WS, Wölfl S, Ott I (2012) On the biological properties of alkynyl phosphine gold(I) complexes. Angew Chem Int Ed 51(39):8895–8899
Ott I, Qian X, Xu Y, Vlecken DHW, Marques IJ, Kubutat D, Will J, Sheldrick WS, Jesse P, Prokop A, Bagowski CP (2009) A gold(I) phosphine complex containing naphthalimide ligand functions as a TrxR inhibiting antiproliferative agent and angiogenesis inhibitor. J Med Chem 52(3):763–770
Chui CH, Wong RS-M, Gambari R, Cheng GY-M, Yuen MC-W, Chan K-W, Tong S-W, Lau F-Y, Lai PB-S, Lam K-H, Ho C-L, Kan C-W, Leung KS-Y, Wong W-Y (2009) Antitumor activity of diethynylfluorene derivatives of gold(I). Bioorg Med Chem 17(23):7872–7877
Yan K, Lok C-N, Bierla K, Che C-M (2010) Gold(I) complex of N, N′-disubstituted cyclic thiourea with in vitro and in vivo anticancer properties-potent tight-binding inhibition of thioredoxin reductase. Chem Commun 46:7691–7693
Sun RW-Y, Li CK-L, Ma D-L, Yan JJ, Lok C-N, Leung C-H, Zhu N, Che C-M (2010) Stable anticancer gold(III)-porphyrin complexes: effects of porphyrin structure. Chem Eur J 16(10):3097–3113
Lum CT, Liu X, Sun RW-Y, Li X-P, Peng Y, He M-L, Kung HF, Che C-M, Lin MCM (2010) Gold(III) porphyrin 1a inhibited nasopharyngeal carcinoma metastasis in vivo and inhibited cell migration and invasion in vitro. Cancer Lett 294(2):159–166
Lum CT, Yang ZF, Li HY, Wai-Yin Sun R, Fan ST, Poon RTP, Lin MCM, Che C-M, Kung HF (2006) Gold(III) compound is a novel chemocytotoxic agent for hepatocellular carcinoma. Int J Cancer 118(6):1527–1538
Tu SP, Sun RW-Y, Lin MCM, Cui JT, Zou B, Gu Q, Kung HF, Che C-M, Wong BCY (2009) Gold (III) porphyrin complexes induce apoptosis and cell cycle arrest and inhibit tumor growth in colon cancer. Cancer 115(19):4459–4469
Li W, Xie Y, Sun RWY, Liu Q, Young J, Yu WY, Che CM, Tam PK, Ren Y (2009) Inhibition of Akt sensitises neuroblastoma cells to gold(III) porphyrin 1a, a novel antitumour drug induced apoptosis and growth inhibition. Br J Cancer 101(2):342–349
Lum CT, Huo L, Sun RW-Y, Li M, Kung HF, Che C-M, Lin MCM (2011) Gold(III) porphyrin 1a prolongs the survival of melanoma-bearing mice and inhibits angiogenesis. Acta Oncol 50(5):719–726
Lum CT, Wong A, Lin MC, Che C-M, Sun RW-Y (2013) Gold(III) porphyrin complex as an anti-cancer candidate to inhibit growth of cancer-stem cells. Chem Commun 49:4364–4366
Sun RW-Y, Lok C-N, Fong TT-H, Li CK-L, Yang ZF, Zou T, Siu AF-M, Che C-M (2013) A dinuclear cyclometalated gold(III)-phosphine complex targeting thioredoxin reductase inhibits hepatocellular carcinoma in vivo. Chem Sci 4:1979–1988
Yan JJ, Chow AL-F, Leung C-H, Sun RW-Y, Ma D-L, Che C-M (2010) Cyclometalated gold(III) complexes with N-heterocyclic carbene ligands as topoisomerase I poisons. Chem Commun 46(22):3893–3895
Buckley RG, Elsome AM, Fricker SP, Henderson GR, Theobald BRC, Parish RV, Howe BP, Kelland LR (1996) Antitumor properties of some 2-[(Dimethylamino)methyl]phenylgold(III) complexes. J Med Chem 39(26):5208–5214
Parish RV, Howe BP, Wright JP, Mack J, Pritchard RG, Buckley RG, Elsome AM, Fricker SP (1996) Chemical and biological studies of dichloro(2-((dimethylamino)methyl)phenyl)gold(III). Inorg Chem 35(6):1659–1666
Zhu Y, Cameron BR, Mosi R, Anastassov V, Cox J, Qin L, Santucci Z, Metz M, Skerlj RT, Fricker SP (2011) Inhibition of the cathepsin cysteine proteases B and K by square-planar cycloaurated gold(III) compounds and investigation of their anti-cancer activity. J Inorg Biochem 105(5):754–762
Messori L, Marcon G, Cinellu MA, Coronnello M, Mini E, Gabbiani C, Orioli P (2004) Solution chemistry and cytotoxic properties of novel organogold(III) compounds. Biorg Med Chem 12(23):6039–6043
Gabbiani C, Mastrobuoni G, Sorrentino F, Dani B, Rigobello MP, Bindoli A, Cinellu MA, Pieraccini G, Messori L, Casini A (2011) Thioredoxin reductase, an emerging target for anticancer metallodrugs: enzyme inhibition by cytotoxic gold(III) compounds studied with combined mass spectrometry and biochemical assays. Med Chem Comm 2(1):50–54
Shaik N, Martínez A, Augustin I, Giovinazzo H, Varela-Ramírez A, Sanaú M, Aguilera RJ, Ma Contel (2009) synthesis of apoptosis-inducing iminophosphorane organogold(III) complexes and study of their interactions with biomolecular targets. Inorg Chem 48(4):1577–1587
Vela L, Contel M, Palomera L, Azaceta G, Marzo I (2011) Iminophosphorane–Organogold(III) complexes induce cell death through mitochondrial ROS production. J Inorg Biochem 105(10):1306–1313
Zhang J-J, Sun RW-Y, Che C-M (2012) A dual cytotoxic and anti-angiogenic water-soluble gold(III) complex induces endoplasmic reticulum damage in hela cells. Chem Commun 48(28):3388–3390
Messori L, Abbate F, Marcon G, Orioli P, Fontani M, Mini E, Mazzei T, Carotti S, O′Connell T, Zanello P (2000) Gold(III) complexes as potential antitumor agents: solution chemistry and cytotoxic properties of some selected gold(III) compounds. J Med Chem 43(19):3541–3548
Nobili S, Mini E, Landini I, Gabbiani C, Casini A, Messori L (2010) Gold compounds as anticancer agents: chemistry, cellular pharmacology, and preclinical studies. Med Res Rev 30(3):550–580
Gabbiani C, Scaletti F, Massai L, Michelucci E, Cinellu MA, Messori L (2012) Medicinal gold compounds form tight adducts with the copper chaperone Atox-1: biological and pharmacological implications. Chem Commun 48:11623–11625
Milacic V, Chen D, Ronconi L, Landis-Piwowar KR, Fregona D, Dou QP (2006) A novel anticancer gold(III) dithiocarbamate compound inhibits the activity of a purified 20S Proteasome and 26S proteasome in human breast cancer cell cultures and xenografts. Cancer Res 66(21):10478–10486
Saggioro D, Rigobello MP, Paloschi L, Folda A, Moggach SA, Parsons S, Ronconi L, Fregona D, Bindoli A (2007) Gold(III)-dithiocarbamato complexes induce cancer cell death triggered by thioredoxin redox system inhibition and activation of ERK pathway. Chem Biol 14(10):1128–1139
Ronconi L, Aldinucci D, Dou QP, Fregona D (2010) Latest insights into the anticancer activity of gold(III)-dithiocarbamato complexes. Anti-Cancer Agents Med Chem 10:283–292
Dhar S, Liu Z, Thomale J, Dai H, Lippard SJ (2008) targeted single-wall carbon nanotube-mediated Pt(IV) prodrug delivery using folate as a homing device. J Am Chem Soc 130(34):11467–11476
Muller P, Schroder B, Parkinson JA, Kratochwil NA, Coxall RA, Parkin A, Parsons S, Sadler PJ (2003) Nucleotide cross-linking induced by photoreactions of platinum(IV)-azide complexes. Angew Chem Int Ed 42(3):335–339
Farrer NJ, Woods JA, Salassa L, Zhao Y, Robinson KS, Clarkson G, Mackay FS, Sadler PJ (2010) A potent trans-diimine platinum anticancer complex photoactivated by visible light. Angew Chem Int Ed 49(47):8905–8908
Zhao Y, Farrer NJ, Li H, Butler JS, McQuitty RJ, Habtemariam A, Wang F, Sadler PJ (2013) De novo generation of singlet oxygen and ammine ligands by photoactivation of a platinum anticancer complex. Angew Chem Int Ed 52(51):13633–13637
Min Y, Li J, Liu F, Yeow EK, Xing B (2013) Near-infrared light-mediated photoactivation of a platinum antitumor prodrug and simultaneous cellular apoptosis imaging by upconversion-luminescent nanoparticles. Angew Chem Int Ed 53(4):1012–1016
Dai Y, Xiao H, Liu J, Yuan Q, Pa Ma, Yang D, Li C, Cheng Z, Hou Z, Yang P, Lin J (2013) In vivo multimodality imaging and cancer therapy by near-infrared light-triggered trans-platinum pro-drug-conjugated upconverison nanoparticles. J Am Chem Soc 135(50):18920–18929
Pathak RK, Marrache S, Choi JH, Berding TB, Dhar S (2014) The prodrug platin-A: simultaneous release of cisplatin and aspirin. Angew Chem Int Ed 53(7):1963–1967
Chin CF, Yap SQ, Li J, Pastorin G, Ang WH (2014) Ratiometric delivery of cisplatin and doxorubicin using tumour-targeting carbon-nanotubes entrapping platinum(IV) prodrugs. Chem Sci 5:2265–2270
Jennette KW, Lippard SJ, Vassiliades GA, Bauer WR (1974) Metallointercalation reagents. 2-hydroxyethanethiolato(2,2′,2″-terpyridine)-platinum(II) monocation binds strongly to DNA by intercalation. Proc Natl Acad Sci USA 71(10):3839–3843
Wang AHJ, Nathans J, van der Marel G, van Boom JH, Rich A (1978) Molecular Structure of a double helical DNA fragment intercalator complex between deoxy CpG and a terpyridine platinum compound. Nature 276(5687):471–474
Cummings SD (2009) Platinum complexes of terpyridine: interaction and reactivity with biomolecules. Coord Chem Rev 253(9–10):1495–1516
Liu H-Q, Peng S-M, Che C-M (1995) Interaction of a luminescent platinum(II) Complex of Substituted 2,2′-bipyridine with DNA. spectroscopic and photophysical studies. J Chem Soc Chem Commun 5:509–510
Liu H-Q, Cheung T-C, Che C-M (1996) Cyclometallated platinum(II) complexes as luminescent switches for calf-thymus DNA. Chem Commun 1039–1040
Che C-M, Yang M, Wong K-H, Chan H-L, Lam W (1999) Platinum(II) complexes of dipyridophenazine as metallointercalators for DNA and potent cytotoxic agents against carcinoma cell lines. Chem Eur J 5(11):3350–3356
Ma D-L, Che C-M (2003) A bifunctional platinum(ii) complex capable of intercalation and hydrogen-bonding interactions with DNA: binding studies and cytotoxicity. Chem Eur J 9(24):6133–6144
Chan H-L, Ma D-L, Yang M, Che C-M (2003) Bis-intercalative dinuclear platinum(II) 6-phenyl-2,2′-bipyridine complexes exhibit enhanced DNA affinity but similar cytotoxicity compared to the mononuclear unit. J Biol Inorg Chem 8(7):761–769
Ma D-L, Shum TY-T, Zhang F, Che C-M, Yang M (2005) Water soluble luminescent platinum terpyridine complexes with glycosylated acetylide and arylacetylide ligands: photoluminescent properties and cytotoxicities. Chem Commun 37:4675–4677
Wang P, Leung C-H, Ma D-L, Sun RW-Y, Yan S-C, Chen Q-S, Che C-M (2011) Specific blocking of CREB/DNA binding by cyclometalated platinum(II) complexes. Angew Chem Int Ed 50(11):2554–2558
Suryadi J, Bierbach U (2012) DNA metalating-intercalating hybrid agents for the treatment of chemoresistant cancers. Chem Eur J 18(41):12926–12934
Ding S, Qiao X, Suryadi J, Marrs GS, Kucera GL, Bierbach U (2013) Using fluorescent post-labeling to probe the subcellular localization of DNA-targeted platinum anticancer agents. Angew Chem Int Ed 52(12):3350–3354
Wheate NJ, Brodie CR, Collins JG, Kemp S, Aldrich-Wright JR (2007) DNA intercalators in cancer therapy: organic and inorganic drugs and their spectroscopic tools of analysis. Mini-Rev Med Chem 7(6):627–648
Garbutcheon-Singh KB, Leverett P, Myers S, Aldrich-Wright JR (2013) Cytotoxic platinum(II) intercalators that incorporate 1R, 2R-diaminocyclopentane. Dalton Trans 42(4):918–926
Whan RM, Messerle BA, Hambley TW (2009) Binding of [Pt(1C3)(dien)]2+ to the Duplex DNA Oligonucleotide 5′-d(TGGCCA)-3′: the effect of an appended positive charge on the orientation and location of anthraquinone intercalation. Dalton Trans 6:932–939
Duskova K, Sierra S, Fernández M-J, Gude L, Lorente A (2012) Synthesis and DNA interaction of ethylenediamine platinum(II) complexes linked to DNA intercalants. Bioorg Med Chem 20(24):7112–7118
Ma D-L, Che C-M, Yan S-C (2009) Platinum(II) complexes with dipyridophenazine ligands as human telomerase inhibitors and luminescent probes for G-quadruplex DNA. J Am Chem Soc 131(5):1835–1846
Wu P, Ma D-L, Leung C-H, Yan S-C, Zhu N, Abagyan R, Che C-M (2009) Stabilization of G-Quadruplex DNA with platinum(II) Schiff base complexes: luminescent probe and down-regulation of c-myc oncogene expression. Chem Eur J 15(47):13008–13021
Wang P, Leung C-H, Ma D-L, Yan S-C, Che C-M (2010) Structure-based design of platinum(II) complexes as c-myc oncogene down-regulators and luminescent probes for G-Quadruplex DNA. Chem Eur J 16(23):6900–6911
Castor KJ, Liu Z, Fakhoury J, Hancock MA, Mittermaier A, Moitessier N, Sleiman HF (2013) A platinum(II) Phenylphenanthroimidazole with an extended side-chain exhibits slow dissociation from a c-Kit G-Quadruplex Motif. Chem Eur J 19(52):17836–17845
Wang P, Leung C-H, Ma D-L, Lu W, Che C-M (2010) Organoplatinum(II) complexes with nucleobase motifs as inhibitors of human topoisomerase II catalytic activity. Chem Asian J 5(10):2271–2280
Liu J, Leung C-H, Chow AL-F, Sun RW-Y, Yan S-C, Che C-M (2011) Cyclometalated platinum(II) complexes as topoisomerase IIα poisons. Chem Commun 47(2):719–721
Sun RW-Y, Chow AL-F, Li X-H, Yan JJ, Chui SS-Y, Che C-M (2011) Luminescent cyclometalated platinum(II) complexes containing N-heterocyclic carbene ligands with potent in vitro and in vivo anti-cancer properties accumulate in cytoplasmic structures of cancer cells. Chem Sci 2:728–736
Frezza M, Dou QP, Xiao Y, Samouei H, Rashidi M, Samari F, Hemmateenejad B (2011) In vitro and in vivo antitumor activities and DNA binding mode of five coordinated cyclometalated organoplatinum(II) complexes containing biphosphine ligands. J Med Chem 54(18):6166–6176
Visbal R, Gimeno MC (2014) N-heterocyclic carbene metal complexes: photoluminescence and applications. Chem Soc Rev 43:3551–3574
Díez-González S, Marion N, Nolan SP (2009) N-heterocyclic carbenes in late transition metal catalysis. Chem Rev 109(8):3612–3676
Hindi KM, Panzner MJ, Tessier CA, Cannon CL, Youngs WJ (2009) The medicinal applications of imidazolium carbene–metal complexes. Chem Rev 109(8):3859–3884
Poater A, Cosenza B, Correa A, Giudice S, Ragone F, Scarano V, Cavallo L (2009) SambVca: a web application for the calculation of the buried volume of N-heterocyclic carbene ligands. Eur J Inorg Chem 13:1759–1766
Ortiz AM, Gómez-Sal P, Flores JC, de Jesús E (2014) Learning about steric effects in NHC complexes from a 1D silver coordination polymer with Fréchet Dendrons. Organometallics 33(2):600–603
Benhamou L, Chardon E, Lavigne G, SP Bellemin-Laponnaz, César V (2011) Synthetic routes to N-Heterocyclic carbene precursors. Chem Rev 111(4):2705–2733
Furstner A, Alcarazo M, Cesar V, Lehmann CW (2006) Convenient, scalable and flexible method for the preparation of imidazolium salts with previously inaccessible substitution patterns. Chem Commun 20:2176–2178
Queval P, Jahier C, Rouen M, Artur I, Legeay J-C, Falivene L, Toupet L, Crévisy C, Cavallo L, Baslé O, Mauduit M (2013) Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes. Angew Chem Int Ed 52(52):14103–14107
Kalinowski J, Fattori V, Cocchi M, Williams JAG (2011) Light-emitting devices based on organometallic platinum complexes as emitters. Coord Chem Rev 255(21–22):2401–2425
Chen X, Zhou Y, Peng X, Yoon J (2010) Fluorescent and colorimetric probes for detection of thiols. Chem Soc Rev 39(6):2120–2135
Chow C-F, Chiu BKW, Lam MHW, Wong W-Y (2003) A trinuclear heterobimetallic Ru(II)/Pt(II) complex as a chemodosimeter selective for sulfhydryl-containing amino acids and peptides. J Am Chem Soc 125:7802–7803
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2016 Springer Science+Business Media Singapore
About this chapter
Cite this chapter
Zou, T. (2016). Introduction. In: Anti-Cancer N-Heterocyclic Carbene Complexes of Gold(III), Gold(I) and Platinum(II). Springer Theses. Springer, Singapore. https://doi.org/10.1007/978-981-10-0657-9_1
Download citation
DOI: https://doi.org/10.1007/978-981-10-0657-9_1
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-10-0656-2
Online ISBN: 978-981-10-0657-9
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)