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Original Articles

Pyrimidine-derived disulfides as potential antimicrobial agents: synthesis and evaluation in vitro

, , , , &
Pages 317-325 | Received 03 Feb 2015, Accepted 26 Feb 2015, Published online: 09 Apr 2015

References

  • Then RL. History and future of antimicrobial diaminopyrimidines. J. Chemother. 1993;5:361–368.
  • Lee C-S, Ryu E-J, Oh SH, Paek K-S, Kim MY, Youn H. Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins including against respiratory tract pathogens. Bioorg Med Chem Lett. 2000;10:2123–2127. doi:10.1016/S0960-894X(00)00425-X
  • Lee KS, Lim JH, Kang YK, Yoo KH, Kim DC, Shin KJ, Kim DJ. Synthesis and antibacterial activities of new 1β-methylcarbapenems having aminopyrimidinylthioether moiety. Eur J Med Chem. 2006;41:1347–1351. doi:10.1016/j.ejmech.2006.08.003
  • Semenov VE, Mikhailov AS, Voloshina AD, Kulik NV, Nikitashina AD, Zobov VV, Kharlamov SV, Latypov SK, Reznik VS. Antimicrobial activity of pyrimidinophanes with thiocytosine and uracil moieties. Eur J Med Chem. 2011;46:4715–4724. doi:10.1016/j.ejmech.2011.05.034
  • Zhao Y, Tian Y, Cui Y, Liu W, Ma W, Jiang X. Small molecule-capped gold nanoparticles as potent antibacterial agents that target gram-negative bacteria. J Am Chem Soc. 2010;132:12349–12356. doi:10.1021/ja1028843
  • Palavecino EL. Clinical, epidemiologic, and laboratory aspects of methicillin-resistant Staphylococcus aureus infections. Methods Mol Biol. 2014;1085:1–24. doi:10.1007/978-1-62703-664-1_1
  • Aversa MC, Barattucci A, Bonaccorsi P, Marino-Merlo F, Mastino A, Sciortino MT. Synthesis and biological testing of thioalkane- and thioarene-spaced bis-β-D-glucopyranosides. Bioorg Med Chem. 2009;17:1456–1463. doi: 10.1016/j.bmc.2009.01.010
  • Bonaccorsi P, Marino-Merlo F, Barattucci A, Battaglia G, Papaianni E, Papalia T, Aversa MC, Mastino A. Synthesis and biological evaluation of a new class of glycoconjugated disulfides that exhibit potential anticancer properties. Bioorg Med Chem. 2012;20:3186–3195. doi: 10.1016/j.bmc.2012.03.070
  • Barattucci A, Deni E, Bonaccorsi P, Ceraolo MG, Papalia T, Santoro A, Sciortino MT, Puntoriero F. Oligo(phenylene ethynylene) Glucosides: modulation of cellular uptake capacity preserving light ON. J Org Chem. 2014;79:5113–5120. doi: 10.1021/jo500661u
  • Papalia T, Siracusano G, Colao I, Barattucci A, Aversa MC, Serroni S, Zappalà G, Campagna S, Sciortino MT, Puntoriero F, Bonaccorsi P. Cell internalization of BODIPY-based fluorescent dyes bearing carbohydrate residues. Dyes Pigments. 2014;110:67–71. doi: 10.1016/j.dyepig.2014.05.022
  • Aversa MC, Barattucci A, Bonaccorsi P. Efficient synthesis of unsymmetrical disulfides through sulfenic acids. Eur J Org Chem. 2009;2009(36):6355–6359. doi:10.1002/ejoc.200900986
  • Aversa MC, Barattucci A, Bonaccorsi P. From transient sulfenic acids to disulfide-functionalized tripodal structures. Synlett. 2011;2011(2):254–258. doi:10.1055/s-0030-1259306
  • Bonaccorsi P, Aversa MC, Barattucci A, Papalia T, Torre A, Trischitta F, Faggio C. Sulfenic acid - derived glycoconjugated disulfides and sulfoxides: a biological evaluation on human red blood cells. J Sulfur Chem. 2013;34:684–691. doi: 10.1080/17415993.2013.778259
  • Vacca A, Nativi C, Cacciarini M, Pergoli R, Roelens S. A new tripodal receptor for molecular recognition of monosaccharides. A paradigm for assessing glycoside binding affinities and selectivities by 1H NMR spectroscopy. J Am Chem Soc. 2004;126:16456–16465. doi: 10.1021/ja045813s
  • Barattucci A, Di Gioia ML, Leggio A, Minuti L, Papalia T, Siciliano C, Temperini A, Bonaccorsi P. Stereoselective synthesis of Dithia[3.3]cyclophane S,S′-dioxides with planar and central chirality. Eur J Org Chem. 2014;2099–2104. doi:10.1002/ejoc.201301636
  • Calvaresi EC, Hergenrother PJ. Glucose conjugation for the specific targeting and treatment of cancer. Chem Sci. 2013;4:2319–2333. doi:10.1039/c3sc22205e
  • Hayes W, Osborn HMI, Osborne SD, Rastall RA, Romagnoli B. One-pot synthesis of multivalent arrays of mannose mono- and disaccharides. Tetrahedron. 2003;59:7983–7996. doi: 10.1016/j.tet.2003.08.011
  • Adams H, Anderson JC, Bell R, Jones DN, Peel MR, Tomkinson NCO. The synthesis and Diels-Alder reactions of (E)- and (Z)-1-methoxy-3-(phenylsulfinyl)-1,3-butadienes. J Chem Soc Perkin Trans. 1998;1(23):3967–3974.
  • Clinical and Laboratory Standards Institute. M07-A9. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard. 9th ed. Wayne, PA: CLSI; 2012.
  • NCCLS - National Committee for Clinical Laboratory Standards. Reference Method For Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved standard. 2nd ed. Wayne, PA: NCCLS document M27-A2; 2002.
  • Mineo P, Faggio C, Micali N, Scamporrino E, Villari V. A star polymer based on a polyethylene glycol with a porphyrinic core as a photosensitizing agent for application in photodynamic therapy: tests in vitro on human erythrocytes. R Soc Chem Adv. 2014;4:19389–19395.

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