Abstract
In this chapter it is presented an overview regarding some examples presented in the literature regarding photochemical applications of metal complexes as DNA cleavage and microbiocidal agents. In photodynamic therapy (PDT) oxygen is required, which is photochemically converted in singlet oxygen or hydroxyl species that promotes DNA cleavage, microbial killing, and other kinds of cell damage. In these field, many strategies have been applied to improve the photophysical properties and potential as DNA intercalators of metal complexes (mainly Ru and Cu), including the utilization of an organic molecule with extended aromatic rings which presents potential ability to increase the 3MLCT lifetimes, in the case of Ru complexes.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Sadler, P.J.: Photoactivatable metal complexes: from theory to applications in biotechnology and medicine. Preface. Philos. Trans. Roy. Soc. A Math. Phys. Eng. Sci. 371, 20130125 (2013)
Sadler, P.J., Guo, Z.J.: Metal complexes in medicine: design and mechanism of action. Pure Appl. Chem. 70, 863–871 (1998)
Glasson, C.R.K., Lindoy, L.F., Meehan, G.V.: Coord. Chem. Rev. 252, 940–963 (2008)
Santini, C., Pellei, M., Gandin, V., Porchia, M., Tisato, F., Marzano, C.: Advances in copper complexes as anticancer agents. Chem. Rev. 114, 815–862 (2014)
Imran, M., Ayub, W., Butler, I.S., Zia-ur-Rehman: Photoactivated platinum-based anticancer drugs. Coord. Chem. Rev. 376, 405–429 (2018)
Balzani, V., Bergamini, G., Ceroni, P.: From the photochemistry of coordination compounds to light-powered nanoscale devices and machines. Coord. Chem. Rev. 252, 2456–2469 (2008)
Mari, C., Pierroz, V., Ferrari, S., Gasser, G.: Combination of Ru(ii) complexes and light: new frontiers in cancer therapy. Chem. Sci. 6, 2660–2686 (2015)
Knoll, J.D., Albani, B.A., Turro, C.: Excited state investigation of a new Ru(II) complex for dual reactivity with low energy light. Chem. Commun. 51, 8777–8780 (2015)
Juris, A., Balzani, V., Barigelletti, F., Campagna, S., Belser, P., Vonzelewsky, A.: Ru(II) polypyridine complexes - photophysics, photochemistry, electrochemistry, and chemi-luminescence. Coord. Chem. Rev. 84, 85–277 (1988)
Abreu, F.D.D., Diógenes, I.C.N., Lopes, L.G.F., Sousa, E.H., de Carvalho, I.M.M.: Ruthenium(II) bipyridine complexes with pendant anthracenyl and naphthyl moieties: a strategy for a ROS generator with DNA binding selectivity. Inorg. Chim. Acta. 439, 92–99 (2016)
de Carvalho, I.M.M., Moreira, I.D., Gehlen, M.H.: Synthesis, characterization, and photophysical studies of new bichromophoric ruthenium(II) complexes. Inorg. Chem. 42, 1525–1531 (2003)
Sun, Y., Joyce, L.E., Dickson, N.M., Turro, C.: Efficient DNA photocleavage by [Ru(bpy)2(dppn)]2+ with visible light. Chem. Commun. 46, 2426–2428 (2010)
Chen, X., Gao, F., Zhou, Z.X., Yang, W.Y., Guo, L.T., Ji, L.N.: Effect of ancillary ligands on the topoisomerases II and transcription inhibition activity of polypyridyl ruthenium(II) complexes. J. Inorg. Biochem. 104, 576–582 (2010)
Zhang, Y., Zhou, Q., Zheng, Y., Li, K., Jiang, G., Hou, Y., Zhang, B., Wang, X.: DNA photocleavage by non-innocent ligand-based Ru(II) complexes. Inorg. Chem. 55, 4296–4300 (2016)
Dobrucki, J.W.: Interaction of oxygen-sensitive luminescent probes Ru(phen)32+ and Ru(bipy)32+ with animal and plant cells in vitro: mechanism of phototoxicity and conditions for non-invasive oxygen measurements. J. Photochem. Photobiol. B Biol. 65, 136–144 (2001)
Harriman, A., Hissler, M., Khatyr, A., Ziessel, R.: A ruthenium(II) tris(2,2′-bipyridine) derivative possessing a triplet lifetime of 42 μs. Chem. Commun., 735–736 (1999)
Hissler, M., Harriman, A., Khatyr, A., Ziessel, R.: Intramolecular triplet energy transfer in pyrene-metal polypyridine dyads: a strategy for extending the triplet lifetime of the metal complex. Chem Eur J. 5, 3366–3381 (1999)
Kozlov, D.V., Tyson, D.S., Goze, C., Ziessel, R., Castellano, F.N.: Room temperature phosphorescence from ruthenium(II) complexes bearing conjugated pyrenylethynylene subunits. Inorg. Chem. 43, 6083–6092 (2004)
Goze, C., Kozlov, D.V., Tyson, D.S., Ziessel, R., Castellano, F.N.: Synthesis and photophysics of ruthenium(II) complexes with multiple pyrenylethynylene subunits. New J. Chem. 27, 1679–1683 (2003)
Friedman, A.E., Chambron, J.C., Sauvage, J.P., Turro, N.J., Barton, J.K.: Molecular light switch for DNA - Ru(Bpy)2(Dppz)2+. J. Am. Chem. Soc. 112, 4960–4962 (1990)
Knoll, J.D., Turro, C.: Control and utilization of ruthenium and rhodium metal complex excited states for photoactivated cancer therapy. Coord. Chem. Rev. 282, 110–126 (2015)
Hartshorn, R.M., Barton, J.K.: Novel dipyridophenazine complexes of ruthenium(ii) - exploring luminescent reporters of DNA. J. Am. Chem. Soc. 114, 5919–5925 (1992)
Brennaman, M.K., Meyer, T.J., Papanikolas, J.M.: [Ru(pbpy)2dppz]2+ light-switch mechanism in protic solvents as studied through temperature-dependent lifetime measurements. J. Phys. Chem. A. 108, 9938–9944 (2004)
Li, G.Y., Sun, L.L., Ji, L.N., Chao, H.: Ruthenium(II) complexes with dppz: from molecular photoswitch to biological applications. Dalton Trans. 45, 13261–13276 (2016)
Burya, S.J., Luttermana, D.A., Turro, C.: Absence of quenching by [Fe(CN)6]4- is not proof of DNA intercalation. Chem. Commun. 47, 1848–1850 (2011)
Burya, D.L.S.J., Turro, C.: Absence of quenching by [Fe(CN)6]4- is not proof of DNA intercalation. Chem. Commun. 47, 1848–1850 (2011)
Abreu, F.D., Paulo, T.D., Gehlen, M.H., Ando, R.A., Lopes, L.G.F., Gondim, A.C.S., Vasconcelos, M.A., Teixeira, E.H., Sousa, E.H.S., de Carvalho, I.M.M.: Aryl-substituted ruthenium(II) complexes: a strategy for enhanced photocleavage and efficient DNA binding. Inorg. Chem. 56, 9084–9096 (2017)
Schoonover, J.R., Dattelbaum, D.M., Malko, A., Klimov, V.I., Meyer, T.J., Styers-Barnett, D.J., Gannon, E.Z., Granger, J.C., Aldridge, W.S., Papanikolas, J.M.: Ultrafast energy transfer between the (MLCT)-M-3 state of [RuII(dmb)2(bpy-an)]2+ and the covalently appended anthracene. J. Phys. Chem. A. 109, 2472–2475 (2005)
Fong, J., Kasimova, K., Arenas, Y., Kaspler, P., Lazic, S., Mandel, A., Lilge, L.: A novel class of ruthenium-based photosensitizers effectively kills in vitro cancer cells and in vivo tumors. Photochem. Photobiol. Sci. 14, 2014–2023 (2015)
Monro, S., Colón, K.L., Yin, H., Roque, J., Konda, P., Gujar, S., Thummel, R.P., Lilge, L., Cameron, C.G., McFarland, S.A.: Transition metal complexes and photodynamic therapy from a tumor-centered approach: challenges, opportunities, and highlights from the development of TLD1433. Chem. Rev. 119(2), 797–828 (2019)
Li, A., Turro, C., Kodanko, J.J.: Ru(II) polypyridyl complexes derived from tetradentate ancillary ligands for effective photocaging. Acc. Chem. Res. 51, 1415–1421 (2018)
Knoll, J.D., Albani, B.A., Turro, C.: New Ru(II) complexes for dual photoreactivity: ligand exchange and O-1(2) generation. Acc. Chem. Res. 48, 2280–2287 (2015)
Greenough, S.E., Roberts, G.M., Smith, N.A., Horbury, M.D., McKinlay, R.G., Zurek, J.M., Paterson, M.J., Sadler, P.J., Stavros, V.G.: Ultrafast photo-induced ligand solvolysis of cis-[Ru(bipyridine)(2)(nicotinamide)(2)](2+): experimental and theoretical insight into its photoactivation mechanism. Phys. Chem. Chem. Phys. 16, 19141–19155 (2014)
Nunes, E.D., Villela, A.D., Basso, L.A., Teixeira, E.H., Andrade, A.L., Vasconcelos, M.A., Nascimento Neto, L.G., Gondim, A.C.S., Diógenes, I.C.N., Romo, A.I.B., Nascimento, O.R., Zampieri, D., Paulo, T.F., Carvalho, I.M.M., Lopes, L.G.F., Sousa, E.H.S.: Light-induced disruption of an acyl hydrazone link as a novel strategy for drug release and activation: isoniazid as a proof-of-concept case. Inorg. Chem. Front. 7, 859–870 (2020)
Silva, C.D.S., Paz, I.A., Abreu, F.D., de Sousa, A.P., Verissimo, C.P., Nascimento, N.R.F., Paulo, T.F., Zampieri, D., Eberlin, M.N., Gondim, A.C.S., Andrade, L.C., Carvalho, I.M.M., Sousa, E.H.S., Lopes, L.G.F.: Thiocarbonyl-bound metallonitrosyl complexes with visible-light induced DNA cleavage and promising vasodilation activity. J. Inorg. Biochem. 182, 83–91 (2018)
Festa, R.A., Thiele, D.J.: Copper: an essential metal in biology. Curr. Biol. 21, R877–R883 (2011)
Solomon, E.I., Heppner, D.E., Johnston, E.M., Ginsbach, J.W., Cirera, J., Qayyum, M., Kieber-Emmons, M.T., Kjaergaard, C.H., Hadt, R.G., Tian, L.: Copper active sites in biology. Chem. Rev. 114, 3659–3853 (2014)
Chen, A.Y., Adamek, R.N., Dick, B.L., Credille, C.V., Morrison, C.N., Cohen, S.M.: Targeting metalloenzymes for therapeutic intervention. Chem. Rev. 119(2), 1323–1455 (2019)
McGivern, T.J.P., Afsharpour, S., Marmion, C.J.: Copper complexes as artificial DNA metallonucleases: from Sigman’s reagent to next generation anti-cancer agent? Inorg. Chim. Acta. 472, 12–39 (2018)
Sigman, D.S., Graham, D.R., D’Aurora, V., Stern, A.M.: Oxygen-dependent cleavage of DNA by the 1,10-phenanthroline . cuprous complex. Inhibition of Escherichia coli DNA polymerase I. J. Biol. Chem. 254, 12269–12272 (1979)
Joshi, R.R., Likhite, S.M., Krishna Kumar, R., Ganesh, K.N.: DNA cleavage by Cu(II)-desferal: identification of C1′-hydroxylation as the initial event for DNA damage. Biochim. Biophys. Acta Gen. Subj. 1199, 285–292 (1994)
Strekas, T.C., Baker, A.D., Harripersad-morgan, O., Morgan, R.J.: Characterization of copper(I) and copper(II) complexes of a bis-diimine coordinated to ruthenium(II) and their interaction with calf thymus DNA. J. Coord. Chem. 34, 77–85 (1995)
Zareie, M.H., Erdem, G., Oner, C., Oner, R., Ogus, A., Piskin, E.: Investigation of ascorbate-Cu (II) induced cleavage of DNA by scanning tunneling microscopy. Int. J. Biol. Macromol. 19, 69–73 (1996)
Itoh, T., Hisada, H., Sumiya, T., Hosono, M., Usui, Y., Fujii, Y.: Hydrolytic cleavage of DNA by a novel copper(ii) complex with cis,cis-1,3,5-triaminocyclohexane. Chem. Commun., 677–678 (1997)
Routier, S., Bernier, J.-L., Catteau, J.-P., Bailly, C.: Recognition and cleavage of DNA by a distamycin-salen·copper conjugate. Bioorg. Med. Chem. Lett. 7, 1729–1732 (1997)
Pitié, M., Sudres, B., Meunier, B.: Dramatic increase of the DNA cleavage activity of Cu(Clip-phen) by fixing the bridging linker on the C3 position of the phenanthroline units. Chem. Commun., 2597–2598 (1998)
Mahadevan, S., Palaniandavar, M.: Spectral and electrochemical behavior of copper(II)−phenanthrolines bound to calf thymus DNA. [(5,6-dimethyl-OP)2Cu]2+ (5,6-dimethyl-OP = 5,6-dimethyl-1,10-phenanthroline) induces a conformational transition from B to Z DNA. Inorg. Chem. 37, 3927–3934 (1998)
Lamour, E., Routier, S., Bernier, J.-L., Catteau, J.-P., Bailly, C., Vezin, H.: Oxidation of CuII to CuIII, free radical production, and DNA cleavage by hydroxy-salen−copper complexes. Isomeric effects studied by ESR and electrochemistry. J Am Chem Soc. 121, 1862–1869 (1999)
Eppley, H.J., Lato, S.M., Zaleski, J.M., Ellington, A.D.: Transition metal Kinamycin model as a DNA photocleaver for hypoxic environments: bis(9-diazo-4,5-diazafluorene)copper(II) nitrate†. Chem. Commun., 2405–2406 (1999)
Kou, J., Dou, D., Yang, L.: Porphyrin photosensitizers in photodynamic therapy and its applications. Oncotarget. 8, 81591–81603 (2017)
Heinemann, F., Karges, J., Gasser, G.: Critical overview of the use of Ru(II) polypyridyl complexes as photosensitizers in one-photon and two-photon photodynamic therapy. Acc. Chem. Res. 50, 2727–2736 (2017)
Nicewicz, D.A., Nguyen, T.M.: Recent applications of organic dyes as photoredox catalysts in organic synthesis. ACS Catal. 4, 355–360 (2014)
Bortolotto, T., Silva-Caldeira, P.P., Pich, C.T., Pereira-Maia, E.C., Terenzi, H.: Tunable DNA cleavage activity promoted by copper(ii) ternary complexes with N-donor heterocyclic ligands. Chem. Commun. 52, 7130–7133 (2016)
Chen, G.J., Qiao, X., Qiao, P.Q., Xu, G.J., Xu, J.Y., Tian, J.L., Gu, W., Liu, X., Yan, S.P.: Synthesis, DNA binding, photo-induced DNA cleavage, cytotoxicity and apoptosis studies of copper(II) complexes. J. Inorg. Biochem. 105, 119–126 (2011)
Roy, S., Saha, S., Majumdar, R., Dighe, R.R., Chakravarty, A.R.: Photo-activated cytotoxicity of a pyrenyl-terpyridine copper(II) complex in HeLa cells. Polyhedron. 29, 3251–3256 (2010)
Roy, S., Saha, S., Majumdar, R., Dighe, R.R., Chakravarty, A.R.: DNA photocleavage and anticancer activity of terpyridine copper(II) complexes having phenanthroline bases. Polyhedron. 29, 2787–2794 (2010)
Garcia-Gimenez, J.L., Hernandez-Gil, J., Martinez-Ruiz, A., Castineiras, A., Liu-Gonzalez, M., Pallardo, F.V., Borras, J., Alzuet Pina, G.: DNA binding, nuclease activity, DNA photocleavage and cytotoxic properties of Cu(II) complexes of N-substituted sulfonamides. J. Inorg. Biochem. 121, 167–178 (2013)
Patra, A.K., Dhar, S., Nethaji, M., Chakravarty, A.R.: Visible light-induced nuclease activity of a ternary mono-phenanthroline copper(II) complex containing L-methionine as a photosensitizer. Chem. Commun. 13, 1562–1563 (2003)
Patra, A.K., Dhar, S., Nethaji, M., Chakravarty, A.R.: Metal-assisted red light-induced DNA cleavage by ternary L-methionine copper(II) complexes of planar heterocyclic bases. Dalton Trans. 5, 896–902 (2005)
Patra, A.K., Nethaji, M., Chakravarty, A.R.: Red-light photosensitized cleavage of DNA by (l-lysine)(phenanthroline base)copper(II) complexes. Dalton Trans. 16, 2798–2804 (2005)
Patra, A.K., Nethaji, M., Chakravarty, A.R.: Synthesis, crystal structure, DNA binding and photo-induced DNA cleavage activity of (S-methyl-L-cysteine)copper(II) complexes of heterocyclic bases. J. Inorg. Biochem. 101, 233–244 (2007)
Patra, A.K., Bhowmick, T., Ramakumar, S., Nethaji, M., Chakravarty, A.R.: DNA cleavage in red light promoted by copper(II) complexes of alpha-amino acids and photoactive phenanthroline bases. Dalton Trans. 48, 6966–6976 (2008)
Goswami, T.K., Chakravarthi, B.V., Roy, M., Karande, A.A., Chakravarty, A.R.: Ferrocene-conjugated L-tryptophan copper(II) complexes of phenanthroline bases showing DNA photocleavage activity and cytotoxicity. Inorg. Chem. 50, 8452–8464 (2011)
Goswami, T.K., Gadadhar, S., Karande, A.A., Chakravarty, A.R.: Photocytotoxic ferrocene-appended (L-tyrosine)copper(II) complexes of phenanthroline bases. Polyhedron. 52, 1287–1298 (2013)
Maity, B., Roy, M., Banik, B., Majumdar, R., Dighe, R.R., Chakravarty, A.R.: Ferrocene-promoted photoactivated DNA cleavage and anticancer activity of terpyridyl copper(II) phenanthroline complexes. Organometallics. 29, 3632–3641 (2010)
Abu-Dief, A.M., Mohamed, I.M.A.: A review on versatile applications of transition metal complexes incorporating Schiff bases. Beni. Suef. Univ. J. Basic. Appl. Sci. 4, 119–133 (2015)
Hameed, A., Al-Rashida, M., Uroos, M., Abid Ali, S., Khan, K.M.: Schiff bases in medicinal chemistry: a patent review (2010-2015). Expert Opinion on Therapeutic Patent. 27, 63–79 (2017)
Zoubi, W.A.: Biological activities of Schiff bases and their complexes: a review of recent works. Int. J. Org. Chem. 03(03), 24 (2013)
Dhar, S., Senapati, D., Das, P.K., Chattopadhyay, P., Nethaji, M., Chakravarty, A.R.: Ternary copper complexes for photocleavage of DNA by red light: direct evidence for sulfur-to-copper charge transfer and d-d band involvement. J. Am. Chem. Soc. 125, 12118–12124 (2003)
Lahiri, D., Majumdar, R., Mallick, D., Goswami, T.K., Dighe, R.R., Chakravarty, A.R.: Remarkable photocytotoxicity in hypoxic HeLa cells by a dipyridophenazine copper(II) Schiff base thiolate. J. Inorg. Biochem. 105, 1086–1094 (2011)
Saswati, A., Chakraborty, S., Dash, P., Panda, A.K., Acharyya, R., Biswas, A., Mukhopadhyay, S., Bhutia, S.K., Crochet, A., Patil, Y.P., Nethaji, M., Dinda, R.: Synthesis, X-ray structure and in vitro cytotoxicity studies of Cu(I/II) complexes of thiosemicarbazone: special emphasis on their interactions with DNA. Dalton Trans. 44, 6140–6157 (2015)
Rogolino, D., Gatti, A., Carcelli, M., Pelosi, G., Bisceglie, F., Restivo, F.M., Degola, F., Buschini, A., Montalbano, S., Feretti, D., Zani, C.: Thiosemicarbazone scaffold for the design of antifungal and antiaflatoxigenic agents: evaluation of ligands and related copper complexes. Sci. Rep. 7, 11214 (2017)
Serda, M., Kalinowski, D.S., Rasko, N., Potuckova, E., Mrozek-Wilczkiewicz, A., Musiol, R., Malecki, J.G., Sajewicz, M., Ratuszna, A., Muchowicz, A., Golab, J., Simunek, T., Richardson, D.R., Polanski, J.: Exploring the anti-cancer activity of novel thiosemicarbazones generated through the combination of retro-fragments: dissection of critical structure-activity relationships. PLoS One. 9, e110291 (2014)
Mbah, J.A., Ayimele, G.A., Eyonganyoh, E.N., Nfor, E.N.: Synthesis, molecular structure and antibacterial activity of benzylmethyl-4-methyl-3-thiosemicarbazone. Int. J. Organic Chem. 07, 83–90 (2017)
Saha, S., Majumdar, R., Roy, M., Dighe, R.R., Chakravarty, A.R.: An iron complex of dipyridophenazine as a potent photocytotoxic agent in visible light. Inorg. Chem. 48, 2652–2663 (2009)
Maity, B., Chakravarthi, B.V.S.K., Roy, M., Karande, A.A., Chakravarty, A.R.: DNA photocleavage and cytotoxic properties of ferrocene conjugates. Eur. J. Inorg. Chem. 2011, 1379–1386 (2011)
Ameerunisha Begum, M.S., Saha, S., Nethaji, M., Chakravarty, A.R.: Iron(III) Schiff base complexes of arginine and lysine as netropsin mimics showing AT-selective DNA binding and photonuclease activity. J. Inorg. Biochem. 104, 477–484 (2010)
Sun, Y., Joyce, L.E., Dickson, N.M., Turro, C.: DNA photocleavage by an osmium(II) complex in the PDT window. Chem. Commun. 46, 6759–6761 (2010)
Chen, G.J., Qiao, X., Gao, C.Y., Xu, G.J., Wang, Z.L., Tian, J.L., Xu, J.Y., Gu, W., Liu, X., Yan, S.P.: Synthesis, DNA binding, photo-induced DNA cleavage and cell cytotoxicity studies of a family of light rare earth complexes. J. Inorg. Biochem. 109, 90–96 (2012)
Chen, G.J., Wang, Z.G., Qiao, X., Xu, J.Y., Tian, J.L., Yan, S.P.: Synthesis, DNA binding, photo-induced DNA cleavage, cytotoxicity studies of a family of heavy rare earth complexes. J. Inorg. Biochem. 127, 39–45 (2013)
Jori, G., Camerin, M., Soncin, M., Guidolin, L., Coppellotti, O.: Antimicrobial photodynamic therapy: basic principles. In: Hamblin, M.R., Jori, G. (eds.) Photodynamic Inactivation of Microbial Pathogens: Medical and Environmental Applications Comprehensive Series in Photochemistry and Photobiology, vol. 11. Royal Society Publishing Cambridge, UK, (2011)
Lerch, M.M., Hansen, M.J., van Dam, G.M., Szymanski, W., Feringa, B.L.: Emerging targets in photopharmacology. Angewandt Chemie International Edition. 55, 10978–10999 (2016)
Denis, T.G.S., Dai, T.H., Izikson, L., Astrakas, C., Anderson, R.R., Hamblin, M.R., Tegos, G.P.: All you need is light antimicrobial photoinactivation as an evolving and emerging discovery strategy against infectious disease. Virulence. 2, 509–520 (2011)
Crespy, D., Landfester, K., Schubert, U.S., Schiller, A.: Potential photoactivated metallopharmaceuticals: from active molecules to supported drugs. Chem. Commun. 46, 6651–6662 (2010)
Wang, Y.C., Wang, Y., Wang, Y.G., Murray, C.K., Hamblin, M.R., Hooper, D.C., Dai, T.H.: Antimicrobial blue light inactivation of pathogenic microbes: state of the art. Drug Resist. Updat. 33–35, 1–22 (2017)
Raab, O.: Über die Wirkung fl uoreszcierender Stoff e aus Infusorien. Z. Biol. 39, 524 (1900)
Bown, S.G.: Photodynamic therapy for photochemists. Philos. Trans. Roy. Soc. A Math. Phys. Eng. Sci. 371, 20120371 (2013)
Wainwright, M.: Photoantimicrobials - a PACT against resistance and infection. Drugs Future. 29, 85–93 (2004)
Wilson, M., Burns, T., Pratten, J., Pearson, G.J.: Bacteria in supragingival plaque samples can be killed by low-power laser-light in the presence of a photosensitizer. J. Appl. Bacteriol. 78, 569–574 (1995)
Merchat, M., Bertolini, G., Giacomini, P., Villanueva, A., Jori, G.: Meso-substituted cationic porphyrins as efficient photosensitizers of gram-positive and gram-negative bacteria. J. Photochem. Photobiol. B. 32, 153–157 (1996)
Minnock, A., Vernon, D.I., Schofield, J., Griffiths, J., Parish, J.H., Brown, S.B.: Photoinactivation of bacteria. Use of a cationic water-soluble zinc phthalocyanine to photoinactivate both gram-negative and gram-positive bacteria. J. Photochem. Photobiol. B. 32, 159–164 (1996)
Huang, H.Y., Banerjee, S., Sadler, P.J.: Recent advances in the design of targeted iridium(III) photosensitizers for photodynamic therapy. Chembiochem. 19, 1574–1589 (2018)
Monro, S., Colon, K.L., Yin, H., Roque 3rd, J., Konda, P., Gujar, S., Thummel, R.P., Lilge, L., Cameron, C.G., McFarland, S.A.: Transition metal complexes and photodynamic therapy from a tumor-centered approach: challenges, opportunities, and highlights from the development of TLD1433. Chem. Rev. 119(2), 797–828 (2019)
Regiel-Futyra, A., Dabrowski, J.M., Mazuryk, O., Spiewak, K., Kyziol, A., Pucelik, B., Brindell, M., Stochel, G.: Bioinorganic antimicrobial strategies in the resistance era. Coord. Chem. Rev. 351, 76–117 (2017)
Kharkwal, G.B., Sharma, S.K., Huang, Y.Y., Dai, T.H., Hamblin, M.R.: Photodynamic therapy for infections: clinical applications. Lasers Surg. Med. 43, 755–767 (2011)
Skwor, T.A., Klemm, S., Zhang, H.Y., Schardt, B., Blaszczyk, S., Bork, M.A.: Photodynamic inactivation of methicillin-resistant staphylococcus aureus and Escherichia coli: a metalloporphyrin comparison. J. Photochem. Photobiol. B. 165, 51–57 (2016)
Lei, W.H., Zhou, Q.X., Jiang, G.Y., Zhang, B.W., Wang, X.S.: Photodynamic inactivation of Escherichia coli by Ru(II) complexes. Photochem. Photobiol. Sci. 10, 887–890 (2011)
Huang, H.Y., Zhang, P.Y., Qiu, K.Q., Huang, J.J., Chen, Y., Ji, L.N.A., Chao, H.: Mitochondrial dynamics tracking with two-photon phosphorescent terpyridyl iridium(III) complexes. Sci. Rep. 6, 20887 (2016)
Feuvrie, C., Maury, O., Le Bozec, H., Ledoux, I., Morrall, J.P., Dalton, G.T., Samoc, M., Humphrey, M.G.: Nonlinear optical and two-photon absorption properties of octupolar tris(bipyridyl)metal complexes. J. Phys. Chem. A. 111, 8980–8985 (2007)
Zhang, P.Y., Chiu, C.K.C., Huang, H.Y., Lam, Y.P.Y., Habtemariam, A., Malcomson, T., Paterson, M.J., Clarkson, G.J., O’Connor, P.B., Chao, H., Sadler, P.J.: Organoiridium photosensitizers induce specific oxidative attack on proteins within cancer cells. Angewandte Chemie-International Edition. 56, 14898–14902 (2017)
Wang, Y.C., Zhou, Q.X., Wang, Y., Ren, J., Zhao, H.Y., Wu, S.M., Yang, J.Y., Zhen, J., Luo, Y.P., Wang, X.S., Gu, Y.: In vitro photodynamic inactivation effects of Ru(II) complexes on clinical methicillin-resistant Staphylococcus aureus planktonic and biofilm cultures. Photochem. Photobiol. 91, 124–133 (2015)
Frei, A., Rubbiani, R., Tubafard, S., Blacque, O., Anstaett, P., Felgentrager, A., Maisch, T., Spiccia, L., Gasser, G.: Synthesis, characterization, and biological evaluation of new Ru(II) polypyridyl photosensitizers for photodynamic therapy. J. Med. Chem. 57, 7280–7292 (2014)
Abreu, F.D., Diogenes, I.C.N., Lopes, L.G.D., Sousa, E.H.S., de Carvalho, I.M.M.: Ruthenium(II) bipyridine complexes with pendant anthracenyl and naphthyl moieties: a strategy for a ROS generator with DNA binding selectivity. Inorg. Chim. Acta. 439, 92–99 (2016)
Zhao, Y., Farrer, N.J., Li, H.L., Butler, J.S., McQuitty, R.J., Habtemariam, A., Wang, F.Y., Sadler, P.J.: De novo generation of singlet oxygen and ammine ligands by photoactivation of a platinum anticancer complex. Angewandte Chemie-International Edition. 52, 13633–13637 (2013)
Smith, N.A., Sadler, P.J.: Photoactivatable metal complexes: from theory to applications in biotechnology and medicine. Philos. Trans. Roy. Soc. A Math. Phys. Eng. Sci. 371, 20120519 (2013)
Ford, P.C.: Metal complex strategies for photo-uncaging the small molecule bioregulators nitric oxide and carbon monoxide. Coord. Chem. Rev. 376, 548–564 (2018)
Karaoun, N., Renfrew, A.K.: A luminescent ruthenium(II) complex for light-triggered drug release and live cell imaging. Chem. Commun. 51, 14038–14041 (2015)
Smith, N.A., Zhang, P.Y., Greenough, S.E., Horbury, M.D., Clarkson, G.J., McFeely, D., Habtemariam, A., Salassa, L., Stavros, V.G., Dowson, C.G., Sadler, P.J.: Combatting AMR: photoactivatable ruthenium(II)-isoniazid complex exhibits rapid selective antimycobacterial activity. Chem. Sci. 8, 395–404 (2017)
Garner, R.N., Pierce, C.G., Reed, C.R., Brennessel, W.W.: Photoinitiated treatment of mycobacterium using Ru(II) isoniazid complexes. Inorg. Chim. Acta. 461, 261–266 (2017)
Chang, J.E., Oak, C.H., Sung, N., Jheon, S.: The potential application of photodynamic therapy in drug-resistant tuberculosis. J. Photochem. Photobiol. B. 150, 60–65 (2015)
Sung, N., Back, S., Jung, J., Kim, K.H., Kim, J.K., Lee, J.H., Ra, Y., Yang, H.C., Lim, C., Cho, S., Kim, K., Jheon, S.: Inactivation of multidrug resistant (MDR)-and extensively drug resistant (XDR)-Mycobacterium tuberculosis by photodynamic therapy. Photodiagn. Photodyn. Ther. 10, 694–702 (2013)
Wareham, L.K., Poole, R.K., Tinajero-Trejo, M.: CO-releasing metal carbonyl compounds as antimicrobial agents in the post-antibiotic era. J. Biol. Chem. 290, 18999–19007 (2015)
Schairer, D.O., Chouake, J.S., Nosanchuk, J.D., Friedman, A.J.: The potential of nitric oxide releasing therapies as antimicrobial agents. Virulence. 3, 271–279 (2012)
de Sousa, A.P., Ellena, J., Gondim, A.C.S., Lopes, L.G.F., Sousa, E.H.S., de Vasconcelos, M.A., Teixeira, E.H., Ford, P.C., Holanda, A.K.M.: Antimicrobial activity of cis-[Ru(bpy)(2)(L)(L ′)](n+) complexes, where L=4-(4-chlorobenzoyl)pyridine or 4-(benzoyl)pyridine and L′ = Cl- or CO. Polyhedron. 144, 88–94 (2018)
de Sousa, A.P., Fernandes, A.F., Paz, I.A., Nascimento, N.R.F., Ellena, J., Sousa, E.H.S., Lopes, L.G.F., Holanda, A.K.M.: A potential visible-light NO releaser: synthesis, reactivity and vasodilator properties. J. Braz. Chem. Soc. 28, 2117–2129 (2017)
de Sousa, A.P., Carvalho, E.M., Ellena, J., Sousa, E.H.S., de Sousaa, J.R., Lopes, L.G.F., Ford, P.C., Holanda, A.K.M.: Photochemical studies of cis-[Ru(bpy)(2)(4-bzpy)(CO)] (PF6)(2) and cis-[Ru (bpy)(2)(4-bzpy)(Cl)](PF6): blue light-induced nucleobase binding. J. Inorg. Biochem. 173, 144–151 (2017)
Carvalho, J.M.D., Batista, A.H.D., Nogueira, N.A.P., Holanda, A.K.M., de Sousa, J.R., Zampieri, D., Bezerra, M.J.B., Barreto, F.S., de Moraes, M.O., Batista, A.A., Gondim, A.C.S., Paulo, T.D.F., Lopes, L.G.D., Sousa, E.H.S.: A biphosphinic ruthenium complex with potent anti-bacterial and anti-cancer activity. New J. Chem. 41, 13085–13095 (2017)
Candido, M.C.L., Oliveira, A.M., Silva, F.O.N., Holanda, A.K.M., Pereira, W.G., Sousa, E.H.S., Carneiro, Z.A., Silva, R.S., Lopes, L.G.F.: Photochemical and electrochemical study of the release of nitric oxide from [Ru(bpy)(2)L(NO)](PF6)(n) complexes (L = imidazole, 1-methylimidazole, sulfite and thiourea), toward the development of therapeutic photodynamic agents. J. Braz. Chem. Soc. 26, 1824–1830 (2015)
Rana, N., Jesse, H.E., Tinajero-Trejo, M., Butler, J.A., Tarlit, J.D., zur Muhlen, M.L.U., Nagel, C., Schatzschneider, U., Poole, R.K.: A manganese photosensitive tricarbonyl molecule [Mn(CO)(3)(tpa-kappa N-3)]Br enhances antibiotic efficacy in a multi-drug-resistant Escherichia coli. Microbiology-Sgm. 163, 1477–1489 (2017)
Nobre, L.S., Seixas, J.D., Romao, C.C., Saraiva, L.M.: Antimicrobial action of carbon monoxide-releasing compounds. Antimicrob. Agents Chemother. 51, 4303–4307 (2007)
Nobre, L.S., Jeremias, H., Romao, C.C., Saraiva, L.M.: Examining the antimicrobial activity and toxicity to animal cells of different types of CO-releasing molecules. Dalton Trans. 45, 1455–1466 (2016)
Arora, D.P., Hossain, S., Xu, Y.M., Boon, E.M.: Nitric oxide regulation of bacterial biofilms. Biochemistry. 54, 3717–3728 (2015)
Robinson, J.L., Adolfsen, K.J., Brynildsen, M.P.: Deciphering nitric oxide stress in bacteria with quantitative modeling. Curr. Opin. Microbiol. 19, 16–24 (2014)
Heilman, B.J., Gonzalez, M.A., Mascharak, P.K.: Photoactive metal nitrosyl and carbonyl complexes derived from designed auxiliary ligands: an emerging class of photochemotherapeutics. Prog. Inorg. Chem. 58(58), 185–224 (2014)
Silva, J.J.N., Guedes, P.M.M., Zottis, A., Balliano, T.L., Silva, F.O.N., Lopes, L.G.F., Ellena, J., Oliva, G., Andricopulo, A.D., Franco, D.W., Silva, J.S.: Novel ruthenium complexes as potential drugs for Chagas’s disease: enzyme inhibition and in vitro/in vivo trypanocidal activity. Br. J. Pharmacol. 160, 260–269 (2010)
Miranda, M.M., Panis, C., Cataneo, A.H.D., da Silva, S.S., Kawakami, N.Y., Lopes, L.G.D., Morey, A.T., Yamauchi, L.M., Andrade, C.G.T.D., Cecchini, R., da Silva, J.J.N., Sforcin, J.M., Conchon-Costa, I., Pavanelli, W.R.: Nitric oxide and Brazilian propolis combined accelerates tissue repair by modulating cell migration, cytokine production and collagen deposition in experimental leishmaniasis. PLoS One. 10, e0125101 (2015)
Pavanelli, W.R., da Silva, J.J.N., Panis, C., Cunha, T.M., Costa, I.C., de Menezes, M.C.N.D., Oliveira, F.J.D., Lopes, L.G.D., Cecchini, R., Cunha, F.D., Watanabe, M.A.E., Itano, E.N.: Experimental chemotherapy in paracoccidioidomycosis using ruthenium NO donor. Mycopathologia. 172, 95–107 (2011)
Heilman, B.J., John, J.S., Oliver, S.R.J., Mascharak, P.K.: Light-triggered eradication of acinetobacter baumannii by means of NO delivery from a porous material with an entrapped metal nitrosyl. J. Am. Chem. Soc. 134, 11573–11582 (2012)
Halpenny, G.M., Gandhi, K.R., Mascharak, P.K.: Eradication of pathogenic bacteria by remote delivery of NO via light triggering of nitrosyl-containing materials. ACS Med. Chem. Lett. 1, 180–183 (2010)
Heinrich, T.A., Tedesco, A.C., Fukuto, J.M., da Silva, R.S.: Production of reactive oxygen and nitrogen species by light irradiation of a nitrosyl phthalocyanine ruthenium complex as a strategy for cancer treatment. Dalton Trans. 43, 4021–4025 (2014)
Dolansky, J., Henke, P., Mala, Z., Zarska, L., Kubat, P., Mosinger, J.: Antibacterial nitric oxide- and singlet oxygen-releasing polystyrene nanoparticles responsive to light and temperature triggers. Nanoscale. 10, 2639–2648 (2018)
Rohrabaugh, T.N., Collins, K.A., Xue, C., White, J.K., Kodanko, J.J., Turro, C.: New Ru(ii) complex for dual photochemotherapy: release of cathepsin K inhibitor and (1)O2 production. Dalton Trans. 47, 11851–11858 (2018)
Acknowledgments
E. H. S. Sousa (CNPq researcher fellowship # 308383/2018-4, Universal 403866/2016-2), L. G. F. Lopes (CNPq researcher fellowship #303355/2018-2, FUNCAP/PRONEX PR2 0101-00030.01.00/15, CAPES (23038.008968/2012-87 and 23038.000936/2018-46)) and CAPES/PRINT (8887.311905/2018-00) are thankful for financial support.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2022 Springer Nature Switzerland AG
About this chapter
Cite this chapter
de Carvalho, I.M.M., Gouveia, F.S., Sousa, E.H.S., Lopes, L.G.F. (2022). Metal Complexes as DNA Cleavage and Antimicrobial Agents. In: Bahnemann, D., Patrocinio, A.O.T. (eds) Springer Handbook of Inorganic Photochemistry. Springer Handbooks. Springer, Cham. https://doi.org/10.1007/978-3-030-63713-2_36
Download citation
DOI: https://doi.org/10.1007/978-3-030-63713-2_36
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-63712-5
Online ISBN: 978-3-030-63713-2
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)