Novel Re(I) tricarbonyl coordination compounds based on 2-pyridyl-1,2,3-triazole derivatives bearing a 4-amino-substituted benzenesulfonamide arm: synthesis, crystal structure, computational studies and inhibitory activity against carbonic anhydrase I, II, and IX isoforms†

References

• Chen Y, Liu W, Jin JS. Rhenium(I) tricarbonyl complexes with bispyridine ligands attached to sulfur-rich core: syntheses, structures and properties. J Organomet Chem 2009;694:763–70.
   Web of Science ®Google Scholar
• Chabolla SA, Machan CW, Yin J, et al. Bio-inspired CO2 reduction by a rhenium tricarbonyl bipyridine-based catalyst appended to amino acids and peptidic platforms: incorporating proton relays and hydrogen-bonding functional groups. Faraday Discuss 2017;198:279–300.
   PubMed Web of Science ®Google Scholar
• (a) Chu WK, Ko CC, Chan KC, et al. A Simple design for strongly emissive sky-blue phosphorescent neutral rhenium complexes: synthesis, photophysics, and electroluminescent devices. Chem Mater 2014;26:2544–50.
   Web of Science ®Google Scholar
  (b) Velmurugan G, Ramamoorthi BK, Venuvanalingam P. Are Re(I) phenanthroline complexes suitable candidates for OLEDs? Answers from DFT and TD-DFT investigations. Phys Chem Chem Phys 2014;16:21157–71.
   PubMed Web of Science ®Google Scholar
  (c) Li X, Zhang D, Lu G, et al. Synthesis and characterization of novel rhenium (I) complexes with large Stokes shift for applications in organic electroluminescent devices. J Photochem Photobiol A Chem 2012;241:1–7.
   Web of Science ®Google Scholar
• (a) Patrocinio AOT, Iha NYM. Photoswitches and luminescent rigidity sensors based on fac-[Re(CO)3(Me4phen)(L)]+. Inorg Chem 2008;47:10851–7.
   PubMed Web of Science ®Google Scholar
  (b) Sun SS, Lees AJ. Transition metal based supramolecular systems: synthesis, photophysics, photochemistry and their potential applications as luminescent anion chemosensors. Coord Chem Rev 2002;230:171–92.
   Web of Science ®Google Scholar
  (c) Bullock S, Hallett AJ, Harding LP, et al. Luminescent rhenium fac-tricarbonyl-containing complexes of androgenic oxo-steroids. Dalton Trans 2012;41:14690–6.
   PubMed Web of Science ®Google Scholar
• (a) Pierri AE, Pallaoro A, Wu G, et al. A luminescent and biocompatible photoCORM. J Am Chem Soc 2012;134:18197–200.
   PubMed Web of Science ®Google Scholar
  (b) Carrington SJ, Chakraborty I, Bernard JML, et al. A theranostic two-tone luminescent photocorm derived from Re(I) and (2-pyridyl)-benzothiazole: trackable CO delivery to malignant cells. Inorg Chem 2016;55:7852–8.
   PubMed Web of Science ®Google Scholar
  (c) Prieto L, Rossier J, Derszniak K, et al. Modified biovectors for the tuneable activation of anti-platelet carbon monoxide release. Chem Commun 2017;53:6840–3.
   PubMed Web of Science ®Google Scholar
  (d) Kianfar E, Schafer C, Lornejad-Schafer MR, et al. New photo-CORMs: deeply-coloured biocompatible rhenium complexes for the controlled release of carbon monoxide. Inorg Chim Acta 2015;435:174–7.
   Web of Science ®Google Scholar
• (a) Müller C, Schubiger PA, Schibli R. Isostructural folate conjugates radiolabeled with the matched pair 99mTc/188Re: a potential strategy for diagnosis and therapy of folate receptor-positive tumors. Nucl Med Biol 2007;34:595–601.
   PubMed Web of Science ®Google Scholar
  (b) Kluba CA, Mindt TL. Click-to-Chelate: development of technetium and rhenium-tricarbonyl labeled radiopharmaceuticals. Molecules 2013;18:3206–26.
   PubMed Web of Science ®Google Scholar
  (c) Brink A, Helliwell JR. New leads for fragment-based design of rhenium/technetium radiopharmaceutical agents. IUCrJ 2017;4:283–90.
   PubMed Web of Science ®Google Scholar
  (d)Eychenne R, Guizani S, Wang J-H, et al. Rhenium complexes based on an N2O tridentate click scaffold: from synthesis, structural and theoretical characterization to a radiolabelling study. Eur J Inorg Chem 2017; 2017:69–81.
   Web of Science ®Google Scholar
• Schibli R, Schubiger PA. Current use and future potential of organometallic radiopharmaceuticals. Eur J Nucl Med 2002;29:1529–42.
   Google Scholar
• (a) Wright PJ, Muzzioli S, Werrett MV, et al. Synthesis, photophysical and electrochemical investigation of dinuclear tetrazolato-bridged rhenium complexes. Organometallics 2012;31:7566–78.
   Web of Science ®Google Scholar
  (b) Werrett MV, Huff GS, Muzzioli S, et al. Methylated Re(I) tetrazolato complexes: photophysical properties and light emitting devices. Dalton Trans 2015;44:8379–93.
   PubMed Web of Science ®Google Scholar
• (a) Coleman A, Brennan C, Vos JG, et al. Photophysical properties and applications of Re(I) and Re(I)–Ru(II) carbonyl polypyridyl complexes. Coord Chem Rev 2008;252:2585–95.
   Web of Science ®Google Scholar
  (b) Lo KKW, Louie MW, Zhang KY. Design of luminescent iridium(III) and rhenium(I) polypyridine complexes as in vitro and in vivo ion, molecular and biological probes. Coord Chem Rev 2010;254:2603–22.
   Web of Science ®Google Scholar
• (a) Boulay A, Seridi A, Zedde C, et al. Tricarbonyl Re(I) complexes from functionalised pyridine–triazole derivatives: from mononuclear to unexpected dimeric complexes. Eur J Inorg Chem 2010;2010:5058–62.
   Web of Science ®Google Scholar
  (b) Wolff M, Munoz L, François A, et al. Tricarbonylrhenium complexes from 2-pyridyl-1,2,3-triazole ligands bearing a 4-substituted phenyl arm: a combined experimental and theoretical study. Dalton Trans 2013;42:7019–31.
   PubMed Web of Science ®Google Scholar
  (c) François A, Auzanneau C, Le Morvan V, et al. A functionalized heterobimetallic 99mTc/Re complex as a potential dual-modality imaging probe: synthesis, photophysical properties, cytotoxicity and cellular imaging investigations. Dalton Trans 2014;43:439–50.
   PubMed Web of Science ®Google Scholar
  (d) Clède S, Lambert F, Sandt C, et al. A rhenium tris-carbonyl derivative as a single core multimodal probe for imaging (SCoMPI) combining infrared and luminescent properties. Chem Commun 2012;48:7729–31.
   PubMed Web of Science ®Google Scholar
  (e) Bertrand HC, Clède S, Guillot R, et al. Luminescence modulations of rhenium tricarbonyl complexes induced by structural variations. Inorg Chem 2014;53:6204–23.
   PubMed Web of Science ®Google Scholar
  (f) Ching HYV, Wang X, He M, et al. Rhenium complexes based on 2-pyridyl-1,2,3-triazole ligands: a new class of CO2 reduction catalysts. Inorg Chem 2017;56:2966–76.
   PubMed Web of Science ®Google Scholar
  (g) Kim TY, Elliott ABS, Shaffer KJ, et al. Rhenium(I) complexes of readily functionalized bidentate pyridyl-1,2,3-triazole “click” ligands: a systematic synthetic, spectroscopic and computational study. Polyhedron 2013;52:1391–8.
   Web of Science ®Google Scholar
  (h) Lo WKC, Huff GS, Cubanski JR, et al. Comparison of inverse and regular 2-pyridyl-1,2,3-triazole “click” complexes: structures, stability, electrochemical, and photophysical properties. Inorg Chem 2015;54:1572–87.
   PubMed Web of Science ®Google Scholar
• Obata M, Kitamura A, Mori A, et al. Syntheses, structural characterization and photophysical properties of 4-(2-pyridyl)-1,2,3-triazole rhenium(I) complexes. Dalton Trans 2008;3292–300.
   PubMed Web of Science ®Google Scholar
• (a) Seridi A, Wolff M, Boulay A, et al. Rhenium(I) and technetium(I) complexes of a novel pyridyltriazole-based ligand containing an arylpiperazine pharmacophore: synthesis, crystal structures, computational studies and radiochemistry. Inorg Chem Commun 2011;14:238–42.
   Web of Science ®Google Scholar
  (b) Kilpin KJ, Gavey EL, McAdam CJ, et al. Palladium(II) Complexes of readily functionalized bidentate 2-pyridyl-1,2,3-triazole “click” ligands: a synthetic, structural, spectroscopic, and computational study. Inorg Chem 2011;50:6334–46.
   PubMed Web of Science ®Google Scholar
• (a) Güzel-Akdemir Ö, Akdemir A, Karal N, et al. Discovery of novel isatin-based sulfonamides with potent and selective inhibition of the tumor-associated carbonic anhydrase isoforms IX and XII. Org Biomol Chem 2015;13:6493–9.
   PubMed Web of Science ®Google Scholar
  (b) Carta F, Ferraroni M, Scozzafava A, et al. Fluorescent sulfonamide carbonic anhydrase inhibitors incorporating 1,2,3-triazole moieties: kinetic and X-ray crystallographic studies. Bioorg Med Chem 2016;24:104–12.
   PubMed Web of Science ®Google Scholar
  (c) Pala N, Micheletto L, Sechi M, et al. Carbonic anhydrase inhibition with benzenesulfonamides and tetrafluorobenzenesulfonamides obtained via click chemistry. ACS Med Chem Lett 2014;5:927–30.
   PubMed Web of Science ®Google Scholar
  (d) Alterio V, Di Fiore A, D’Ambrosio K, et al. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev 2012;112:4421–68.
   PubMed Web of Science ®Google Scholar
  (e) Winum JY, Supuran CT. Recent advances in the discovery of zinc-binding motifs for the development of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2015;30:321–4.
   PubMed Web of Science ®Google Scholar
• (a) Akurathi V, Dubois L, Lieuwes NG, et al. Synthesis and biological evaluation of a 99mTc-labelled sulfonamide conjugate for in vivo visualization of carbonic anhydrase IX expression in tumor hypoxia. Nucl Med Biol 2010;37:557–64.
   PubMed Web of Science ®Google Scholar
  (b) Lu G, Hillier SM, Maresca KP, et al. Synthesis and SAR of novel Re/99mTc-labeled benzenesulfonamide carbonic anhydrase IX inhibitors for molecular imaging of tumor hypoxia. J Med Chem 2013;56:510–20.
   PubMed Web of Science ®Google Scholar
  (c) Can D, Spingler B, Schmutz P, et al. (Cp-R)M(CO)3 (M = Re or 99mTc) Arylsulfonamide, arylsulfamide, and arylsulfamate conjugates for selective targeting of human carbonic anhydrase IX. Angew Chem Int Ed 2012;51:3354–7.
   PubMed Web of Science ®Google Scholar
  (d) Nakai M, Pan J, Lin KS, et al. Evaluation of 99mTc-sulfonamide and sulfocoumarin derivatives for imaging carbonic anhydrase IX expression. Inorg Biochem 2018;185:63–70.
   PubMed Web of Science ®Google Scholar
  (e) Huentupil Y, Peña L, Novoa N, et al. New sulfonamides containing organometallicacylhydrazones: synthesis, characterisation and biological evaluation as inhibitors of human carbonic anhydrases. J Enzyme Inhib Med Chem 2019;34:451–8.
   PubMed Web of Science ®Google Scholar
• Chambers JM, Hill PA, Aaron JA, et al. Cryptophane Xenon-129 nuclear magnetic resonance biosensors targeting human carbonic anhydrase. J Am Chem Soc 2009;131:563–9.
   PubMed Web of Science ®Google Scholar
• Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem 2015;71:3–8.
   PubMed Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, revision A.1. Wallingford CT: Gaussian, Inc.; 2009.
   Google Scholar
• Dennington IIR, Keith T, Milliam J, GaussView version 4.1.2. Shawnee Mission, KS: Semichem Inc.; 2007.
   Google Scholar
• (a) Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988;37:785–9.
   PubMed Web of Science ®Google Scholar
  (b) Becke AD. Density‐functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993;98:5648–52.
   Web of Science ®Google Scholar
• Hay PJ, Wadt WR. Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals. J Chem Phys 1985;82:299–310.
   Web of Science ®Google Scholar
• Glendening ED, Badenhoop JK, Reed AE, et al. NBO 6.0. Theoretical chemistry institute. Madison: University of Wisconsin; 2013.
   Google Scholar
• (a) Casida ME, Jamorski C, Casida KC, et al. Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: characterization and correction of the time-dependent local density approximation ionization threshold. J Chem Phys 1998;108:4439.
   Web of Science ®Google Scholar
  (b) Stratmann RE, Scuseria GE, Frisch MJ. An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules. J Chem Phys 1998;109:8218.
   Web of Science ®Google Scholar
  (c) Bauernschmitt R, Ahlrichs R. Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem Phys Lett 1996;256:454–64.
   Web of Science ®Google Scholar
• (a) Cancès E, Mennucci B, Tomasi J. A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys 1997;107:3032.
   Web of Science ®Google Scholar
  (b) Cossi M, Barone V, Mennucci B, et al. Ab initio study of ionic solutions by a polarizable continuum dielectric model. Chem Phys Lett 1998;286:253–60.
   Web of Science ®Google Scholar
  (c) Mennucci B, Tomasi J. Continuum solvation models: a new approach to the problem of solute’s charge distribution and cavity boundaries. J Chem Phys 1997;106:5151.
   Web of Science ®Google Scholar
  (d) Cossi M, Scalmani G, Rega N, et al. New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution. J Chem Phys 2002;117:43.
   Web of Science ®Google Scholar
• Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–73.
   PubMed Web of Science ®Google Scholar
• Sharma A, Tiwari M, Supuran CT. Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX. J Enzyme Inhib Med Chem 2014;29:292–6.
   PubMed Web of Science ®Google Scholar
• Durdagi S, Scozzafava G, Vullo D, et al. Inhibition of mammalian carbonic anhydrases I-XIV with grayanotoxin III: solution and in silico studies. J Enzyme Inhib Med Chem 2014;29:469–75.
   PubMed Web of Science ®Google Scholar
• Alterio V, Hilvo M, Di Fiore A, et al. Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX. Proc Natl Acad Sci USA 2009;106:16233–8.
   PubMed Web of Science ®Google Scholar
• La Regina G, Coluccia A, Famiglini V, et al. Discovery of 1,1'-biphenyl-4-sulfonamides as a new class of potent and selective carbonic anhydrase XIV inhibitors. J Med Chem 2015;58:8564–72.
   PubMed Web of Science ®Google Scholar
• Suntrup L, Klenk S, Klein J, et al. Gauging donor/acceptor properties and redox stability of chelating click-derived triazoles and triazolylidenes: a case study with rhenium(I) complexes. Inorg Chem 2017;56:5771–83.
   PubMed Web of Science ®Google Scholar
• (a) Schweinfurth D, Pattacini R, Strobel S, et al. New 1,2,3-triazole ligands through click reactions and their palladium and platinum complexes. Dalton Trans 2009;9291–7.
   PubMed Web of Science ®Google Scholar
  (b) Crowley JD, Bandeen PH, Hanton LR. A one pot multi-component CuAAC “click” approach to bidentate and tridentate pyridyl-1,2,3-triazole ligands: synthesis, X-ray structures and copper(II) and silver(I) complexes. Polyhedron 2010;29:70–83.
   Web of Science ®Google Scholar
  (c) Crowley JD, Bandeen PH. A multicomponent CuAAC “click” approach to a library of hybrid polydentate 2-pyridyl-1,2,3-triazole ligands: new building blocks for the generation of metallosupramolecular architectures. Dalton Trans 2010;39:612–23.
   Web of Science ®Google Scholar
• Kilpin KJ, Crowley JD. Palladium(II) and platinum(II) complexes of bidentate 2-pyridyl-1,2,3-triazole “click” ligands: synthesis, properties and X-ray structures. Polyhedron 2010;29:3111–17.
   Web of Science ®Google Scholar
• Scattergood PA, Sinopoli A, Elliott PIP. Photophysics and photochemistry of 1,2,3-triazole-based complexes. Coord Chem Rev 2017;350:136–54.
   Web of Science ®Google Scholar