68
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Novel [1,2,3]triazolo[1,5-a]pyridine Derivatives are Trypanocidal by Sterol Biosynthesis Pathway Alteration

, , , , , , , , , , & show all
Pages 1137-1155 | Received 12 Jun 2018, Accepted 04 Mar 2019, Published online: 08 Jul 2019

References

  • Zingales B , MilesMA, MoraesCBet al. Drug discovery for Chagas disease should consider Trypanosoma cruzi strain diversity. Mem. Inst. Oswaldo Cruz109(6), 828–833 (2014).
  • Rassi A , RassiA, Marin-NetoJA. Chagas disease. Lancet375(9723), 1388–1402 (2010).
  • Ribeiro I , SevcsikAM, AlvesFet al. New, improved treatments for Chagas disease: from the R&D pipeline to the patients. PLoS Negl. Trop. Dis.3(7), e484 (2009).
  • Adam R , Bilbao-RamosP, Lopez-MolinaSet al. Triazolopyridyl ketones as a novel class of antileishmanial agents. DNA binding and BSA interaction. Bioorg. Med. Chem.22(15), 4018–4027 (2014).
  • Lapier M , Zuniga-LopezMC, Aguilera-VenegasBet al. Evaluation of the novel antichagasic activity of [1,2,3]triazolo[1,5-a]pyridine derivatives. Curr. Top. Med. Chem.17(4), 399–411 (2017).
  • Lepesheva GI , WatermanMR. Structural basis for conservation in the CYP51 family. Biochim. Biophys. Acta1814(1), 88–93 (2011).
  • Lepesheva GI , OttRD, HargroveTYet al. Sterol 14alpha-demethylase as a potential target for antitrypanosomal therapy: enzyme inhibition and parasite cell growth. Chem. Biol.14(11), 1283–1293 (2007).
  • Hargrove TY , WawrzakZ, AlexanderPWet al. Complexes of Trypanosoma cruzi sterol 14alpha-demethylase (CYP51) with two pyridine-based drug candidates for Chagas disease: structural basis for pathogen selectivity. J. Biol. Chem.288(44), 31602–31615 (2013).
  • Kessler RL , SoaresMJ, ProbstCM, KriegerMA. Trypanosoma cruzi response to sterol biosynthesis inhibitors: morphophysiological alterations leading to cell death. PLoS One8(1), e55497 (2013).
  • Martinez-Botas J , SuarezY, FerrueloAJ, Gomez-CoronadoD, LasuncionMA. Cholesterol starvation decreases p34(cdc2) kinase activity and arrests the cell cycle at G2. FASEB J.13(11), 1359–1370 (1999).
  • Fernandez C , MartinM, Gomez-CoronadoD, LasuncionMA. Effects of distal cholesterol biosynthesis inhibitors on cell proliferation and cell cycle progression. J. Lipid Res.46(5), 920–929 (2005).
  • Abarca B , BallesterosR, ElmasnaouyM. A facile route to new potential helicating ligands. Tetrahedron54(50), 15287–15292 (1998).
  • Boyer J , GoebelN. Notes- the identification of C12H8N4O, an oxidation product from α-Pyridil monohydrazone. J. Org. Chem.25(2), 304–305 (1960).
  • Bower JD , RamageGR. 907. Heterocyclic systems related to pyrrocoline. Part II. The preparation of polyazaindenes by dehydrogenative cyclisations. J. Chem. Soc. (Resumed)1857, 4506–4510 (1957).
  • Abarca B , BallesterosR, ChadlaouiM. Triazolopyridines. Part 24: New polynitrogenated potential helicating ligands. Tetrahedron60(27), 5785–5792 (2004).
  • Bourguignon SC , MelloCB, SantosDO, GonzalezMS, Souto-PadronT. Biological aspects of the Trypanosoma cruzi (Dm28c clone) intermediate form, between epimastigote and trypomastigote, obtained in modified liver infusion tryptose (LIT) medium. Acta Trop.98(1), 103–109 (2006).
  • Mosmann T . Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods65(1–2), 55–63 (1983).
  • Frisch MJ , TrucksGW, SchlegelHBet al. Gaussian 16 Rev. B.01 (2016).
  • Case DA , BetzRM, CheathamTEIIIet al. AMBER 16 (2016).
  • Chen C-K , LeungSSF, GuilbertC, JacobsonMP, McKerrowJH, PodustLM. Structural characterization of CYP51 from Trypanosoma cruzi and Trypanosoma brucei bound to the antifungal drugs posaconazole and fluconazole. PLoS Negl. Trop. Dis.4(4), e651 (2010).
  • Molecular Operating Environment (MOE), 2015.10. (2015).
  • Maier JA , MartinezC, KasavajhalaK, WickstromL, HauserKE, SimmerlingC. ff14SB: improving the accuracy of protein side chain and backbone parameters from ff99SB. J. Chem. Theory Comput.11(8), 3696–3713 (2015).
  • Aguilera-Venegas B , Olea-AzarC, AranVJet al. Electrochemical, ESR and theoretical insights into the free radical generation by 1,1 ‘-hydrocarbylenebisindazoles and its evaluation as potential bio-active compounds. Int. J. Electrochem. Sci.7(7), 5837–5863 (2012).
  • Aguilera-Venegas B , Olea-AzarC, NorambuenaEet al. ESR, electrochemical, molecular modeling and biological evaluation of 4-substituted and 1,4-disubstituted 7-nitroquinoxalin-2-ones as potential anti-Trypanosoma cruzi agents. Spectrochim Acta A Mol. Biomol. Spectrosc.78(3), 1004–1012 (2011).
  • Morris GM , GoodsellDS, HallidayRSet al. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem.19(14), 1639–1662 (1998).
  • Abarca B , AlkortaI, BallesterosRet al. 3-(2-Pyridyl)-[1,2,3]triazolo[1,5-a]pyridines. An experimental and theoretical (DFT) study of the ring-chain isomerization. Org. Biomol. Chem.3(21), 3905–3910 (2005).
  • Moraes CB , GiardiniMA, KimHet al. Nitroheterocyclic compounds are more efficacious than CYP51 inhibitors against Trypanosoma cruzi: implications for Chagas disease drug discovery and development. Sci. Rep.4, 4703 (2014).
  • Liu XH , SunZH, YangMYet al. Microwave assistant one pot synthesis, crystal structure, antifungal activities and 3D-QSAR of novel 1,2,4-triazolo[4,3-a]pyridines. Chem. Biol. Drug Des.84(3), 342–347 (2014).
  • Liu XH , XuXY, TanCX, WengJQ, XinJH, ChenJ. Synthesis, crystal structure, herbicidal activities and 3D-QSAR study of some novel 1,2,4-triazolo[4,3-a]pyridine derivatives. Pest Manag. Sci.71(2), 292–301 (2015).
  • Lipinski CA , LombardoF, DominyBW, FeeneyPJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev.46(1–3), 3–26 (2001).
  • Meanwell NA . Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety. Chem. Res. Toxicol.24(9), 1420–1456 (2011).
  • McKerrow JH , LipinskiCA. The rule of five should not impede anti-parasitic drug development. Int J Parasitol Drugs Drug Resist7(2), 248–249 (2017).
  • Daina A , MichielinO, ZoeteV. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci. Rep.7, 42717 (2017).
  • Urbina JA . Ergosterol biosynthesis and drug development for Chagas disease. Mem. Inst. Oswaldo Cruz104(Suppl 1), 311–318 (2009).
  • Lepesheva GI , HargroveTY, AndersonSet al. Structural insights into inhibition of sterol 14alpha-demethylase in the human pathogen Trypanosoma cruzi . . J. Biol. Chem. 285(33), 25582–25590 (2010).
  • Hargrove TY , WawrzakZ, AlexanderPWet al. Complexes of Trypanosoma cruzi Sterol 14α-Demethylase (CYP51) with two pyridine-based drug candidates for chagas disease: structural basis for pathogen selectivity. J. Biol. Chem.288(44), 31602–31615 (2013).
  • Chung S , KimSH, SeoY, KimSK, LeeJY. Quantitative analysis of cell proliferation by a dye dilution assay: application to cell lines and cocultures. Cytometry A91(7), 704–712 (2017).
  • Singh P , SaxenaR, SrinivasG, PandeG, ChattopadhyayA. Cholesterol biosynthesis and homeostasis in regulation of the cell cycle. PLoS One8(3), e58833 (2013).
  • Fernandez C , LoboMd Mdel V, Gomez-CoronadoD, LasuncionMA. Cholesterol is essential for mitosis progression and its deficiency induces polyploid cell formation. Exp. Cell Res.300(1), 109–120 (2004).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.