Abstract
Cellular thiol level is associated with cellular redox balances that are linked up with various diseases such as cancers and AIDS [1–6]. Due to the high binding affinity toward thiols, soft metal ions and their complexes are usually utilized in the design of metal-based thiol probes as well as new anticancer drug leads which could specifically target thiol-/selenol-containing proteins/enzymes [7–11]. Au(I) is one kind of soft metal ions having high binding affinity toward-SH groups and can be generated by the reduction of Au(III) with thiols. Most reported Au(III) complexes are known to be readily reduced to Au(I) and/or Au(0) by cellular thiols (e.g., glutathione, GSH) [7, 12–14]. In view of the fact that Au(III) is 4-coordinated, whereas Au(I) is usually 2-coordinated, reduction of Au(III) to Au(I) is accompanied by the release of coordinated ligand(s).
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References
Herzenberg LA, De Rosa SC, Dubs JG, Roederer M, Anderson MT, Ela SW, Deresinski SC, Herzenberg LA (1997) Glutathione deficiency is associated with impaired survival in hiv disease. Proc Natl Acad Sci USA 94(5):1967–1972
Rahman I, MacNee W (2000) Regulation of redox glutathione levels and gene transcription in lung inflammation: therapeutic approaches. Free Radical Biol Med 28(9):1405–1420
Escobedo J, Rusin O, Wang W, Alptürk O, Kim KK, Xu X, Strongin R (2006) Detection of biological thiols. In: Geddes C, Lakowicz J (eds) Reviews in fluorescence 2006, vol 2006. Springer, US, pp 139–162. doi:10.1007/0-387-33016-X_6
Zhang M, Yu M, Li F, Zhu M, Li M, Gao Y, Li L, Liu Z, Zhang J, Zhang D, Yi T, Huang C (2007) A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging. J Am Chem Soc 129(34):10322–10323
Bindoli A, Rigobello MP, Scutari G, Gabbiani C, Casini A, Messori L (2009) Thioredoxin reductase: a aarget for gold compounds acting as potential anticancer drugs. Coord Chem Rev 253(11–12):1692–1707
Zhao Q, Huang C, Li F (2011) Phosphorescent heavy-metal complexes for bioimaging. Chem Soc Rev 40(5):2508–2524
Sadler PJ, Sue RE (1994) The chemistry of gold drugs. Met-Based Drugs 1(2–3):107–144
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(26):7802–7803
Shao N, Jin JY, Cheung SM, Yang RH, Chan WH, Mo T (2006) A spiropyran-based ensemble for visual recognition and quantification of cysteine and homocysteine at physiological levels. Angew Chem Int Ed 45(30):4944–4948
Yang Y-K, Shim S, Tae J (2010) Rhodamine-sugar based turn-on fluorescent probe for the detection of cysteine and homocysteine in water. Chem Commun 46(41):7766–7768
Chen X, Zhou Y, Peng X, Yoon J (2010) Fluorescent and colorimetric probes for detection of thiols. Chem Soc Rev 39(6):2120–2135
Shaw CF III (1999) Gold-Based Therapeutic Agents. Chem Rev 99(9):2589–2600
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
Berners-Price SJ, Filipovska A (2011) Gold compounds as therapeutic agents for human diseases. Metallomics 3(9):863–873
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
Pizarro AM, Habtemariam A, Sadler PJ (2010) Activation mechanisms for organometallic anticancer complexes. Top Organomet Chem 32 (Medicinal Organometallic Chemistry):21–56
Che C-M, Siu F-M (2010) Metal Complexes in Medicine with a Focus on Enzyme Inhibition. Curr Opin Chem Biol 14(2):255–261
Che C-M, Sun RW-Y (2011) Therapeutic applications of gold complexes: lipophilic Gold(III) cations and Gold(I) complexes for anti-cancer treatment. Chem Commun 47(34):9554–9560
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
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
Meggers E (2009) Targeting proteins with metal complexes. Chem Commun 9:1001–1010
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
Rubbiani R, Kitanovic I, Alborzinia H, Can S, Kitanovic A, Onambele LA, Stefanopoulou M, Geldmacher Y, Sheldrick WS, Wolber G, Prokop A, Wӧlfl 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
Ray S, Mohan R, Singh JK, Samantaray MK, Shaikh MM, Panda D, Ghosh P (2007) Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver N-heterocyclic carbene complexes. J Am Chem Soc 129(48):15042–15053
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
Teyssot M-L, Jarrousse A-S, Manin M, Chevry A, Roche S, Norre F, Beaudoin C, Morel L, Boyer D, Mahiou R, Gautier A (2009) Metal-NHC complexes: a survey of anti-cancer properties. Dalton Trans 35:6894–6902
Lemke J, Pinto A, Niehoff P, Vasylyeva V, Metzler-Nolte N (2009) Synthesis, structural characterisation and anti-proliferative activity of NHC gold amino acid and peptide conjugates. Dalton Trans 35:7063–7070
Weaver J, Gaillard S, Toye C, Macpherson S, Nolan SP, Riches A (2011) Cytotoxicity of Gold(I) N-heterocyclic carbene complexes assessed by using human tumor cell lines. Chem Eur J 17(24):6620–6624
Wang C-H, Shih W-C, Chang HC, Kuo Y-Y, Hung W-C, Ong T-G, Li W-S (2011) Preparation and characterization of amino-linked heterocyclic carbene palladium, gold, and silver complexes and their use as anticancer agents that act by triggering apoptotic cell death. J Med Chem 54(14):5245–5249
Sivaram H, Tan J, Huynh HV (2012) Syntheses, characterizations, and a preliminary comparative cytotoxicity study of Gold(I) and Gold(III) complexes bearing benzimidazole—and pyrazole-derived N-heterocyclic carbenes. Organometallics 31:5875–5883
Schuh E, Pflüger C, Citta A, Folda A, Rigobello MP, Bindoli A, Casini A, Mohr F (2012) Gold(I) carbene complexes causing thioredoxin 1 and thioredoxin 2 oxidation as potential anticancer agents. J Med Chem 55(11):5518–5528
Li G, Huang J, Zhang M, Zhou Y, Zhang D, Wu Z, Wang S, Weng X, Zhou X, Yang G (2008) Bis(benzimidazole)pyridine derivative as a new class of G-quadruplex inducing and stabilizing ligand. Chem Commun 38:4564–4566
Boča M, Jameson RF, Linert W (2011) Fascinating variability in the chemistry and properties of 2,6-bis-(benzimidazol-2-yl)-pyridine and 2,6-bis-(benzthiazol-2-yl)-pyridine and their complexes. Coord Chem Rev 255(1–2):290–317
Serratrice M, Edafe F, Mendes F, Scopelliti R, Zakeeruddin SM, Grätzel M, Santos I, Cinellu MA, Casini A (2012) Cytotoxic gold compounds: synthesis, biological characterization and investigation of their inhibition properties of the zinc finger protein PARP-1. Dalton Trans 41(11):3287–3293
Hashiguchi BG, Young KJH, Yousufuddin M, Goddard WA III, Periana RA (2010) Acceleration of nucleophilic CH activation by strongly basic solvents. J Am Chem Soc 132(36):12542–12545
Lin IJB, Vasam CS (2007) Preparation and application of N-heterocyclic carbene complexes of Ag(I). Coord Chem Rev 251(5–6):642–670
Baker MV, Barnard PJ, Berners-Price SJ, Brayshaw SK, Hickey JL, Skelton BW, White AH (2005) Synthesis and structural characterization of linear Au(I) N-heterocyclic carbene complexes: new analogues of the Au(I) phosphine drug auranofin. J Organomet Chem 690(24–25):5625–5635
Lee CK, Vasam CS, Huang TW, Wang HMJ, Yang RY, Lee CS, Lin IJB (2006) Silver(I) N-heterocyclic carbenes with long N-Alkyl chains. Organometallics 25(15):3768–3775
Sheldrick GM (2008) A short history of SHELX. Acta Cryst A64(1):112–122
Schneider CA, Rasband WS, Eliceiri KW (2012) NIH Image to ImageJ: 25 Years of image analysis. Nat Methods 9(7):671–675
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
Zou T, Lum CT, Chui SS-Y, Che C-M (2013) Gold(III) complexes containing N-heterocyclic carbene ligands: thiol “switch-on” fluorescent probes and anti-cancer agents. Angew Chem Int Ed 52(10):2930–2933
Au VK-M, Wong KM-C, Zhu N, Yam VW-W (2009) Luminescent cyclometalated N-heterocyclic carbene-containing Organogold(III) complexes: synthesis, characterization, electrochemistry, and photophysical studies. J Am Chem Soc 131(25):9076–9085
Gaillard S, Slawin AMZ, Bonura AT, Stevens ED, Nolan SP (2010) Synthetic and structural studies of [AuCl3(NHC)] complexes. Organometallics 29(2):394–402
de Frémont P, Singh R, Stevens ED, Petersen JL, Nolan SP (2007) Synthesis, characterization and reactivity of N-heterocyclic carbene Gold(III) complexes. Organometallics 26(6):1376–1385
Jothibasu R, Huynh HV, Koh LL (2008) Au(I) and Au(III) complexes of a sterically bulky benzimidazole-derived N-heterocyclic carbene. J Organomet Chem 693(3):374–380
Petzold H, Sadler PJ (2008) Oxidation induced by the antioxidant glutathione (GSH). Chem Commun 37:4413–4415
Ji S, Guo H, Yuan X, Li X, Ding H, Gao P, Zhao C, Wu W, Wu W, Zhao J (2010) A highly selective OFF-ON red-emitting phosphorescent thiol probe with large stokes shift and long luminescent lifetime. Org Lett 12(12):2876–2879
Wang H, Wang W-S, Zhang H-S (2001) Spectrofluorimetic determination of cysteine based on the fluorescence inhibition of Cd(II)–8-hydroxyquinoline-5-sulphonic acid complex by cysteine. Talanta 53(5):1015–1019
Sugio S, Kashima A, Mochizuki S, Noda M, Kobayashi K (1999) Crystal structure of human serum albumin at 2.5 a resolution. Protein Eng 12(6):439–446
Bhattacharya AA, Grüne T, Curry S (2000) Crystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin. J Mol Biol 303(5):721–732
Dhar S, Gu FX, Langer R, Farokhzad OC, Lippard SJ (2008) Targeted delivery of cisplatin to prostate cancer cells by aptamer functionalized Pt(IV) prodrug-PLGA-PEG nanoparticles. Proc Natl Acad Sci USA 105(45):17356–17361
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Zou, T. (2016). Gold(III) Complexes Containing N-Heterocyclic Carbene Ligand Serve as Dual Fluorescent Thiol “Switch-On” Probe and Anticancer Agent. 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_3
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DOI: https://doi.org/10.1007/978-981-10-0657-9_3
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