Therapeutic efficacy of liposomes containing 4-(5-pentadecyl-1,3,4-oxadiazol-2-yl)pyridine in a murine model of progressive pulmonary tuberculosis

WHO, 2014 Becerril-Montes, 2012, A population-based study of first and second-line drug-resistant tuberculosis in a high-burden area of the Mexico/United States border, Mem. Inst. Oswaldo Cruz, 108, 160, 10.1590/0074-0276108022013006 Banerjee, 2008, Extensively drug-resistant tuberculosis in California, 1993–2006, Clin. Infect. Dis., 47, 450, 10.1086/590009 Pasipanodya, 2013, A meta-analysis of self-administered vs directly observed therapy effect on microbiologic failure, relapse, and acquired drug resistance in tuberculosis patients, Clin. Infect. Dis., 57, 21, 10.1093/cid/cit167 Sagwa, 2013, Adverse events during treatment of drug-resistant tuberculosis: a comparison between patients with or without human immunodeficiency virus co-infection, Expert. Opin. Drug Saf., 36, 1087 Van der Walt, 2013, Serious treatment related adverse drug reactions amongst anti-retroviral naïve MDR-TB patients. (Abstract), PLoS One, 8, e58817, 10.1371/journal.pone.0058817 Grosset, 2012, New drugs for the treatment of tuberculosis: hope and reality, Int. J. Tuberc. Lung Dis., 16, 1005, 10.5588/ijtld.12.0277 Salomon, 2012, Natural products as leads for tuberculosis drug development, Curr. Top. Med. Chem., 12, 735, 10.2174/156802612799984526 Liu, 2012, Exploring anti-TB leads from natural products library originated from marine microbes and medicinal plants, A Van Leeuw. J. Microbiol., 102, 447, 10.1007/s10482-012-9777-0 Zumla, 2013, Advances in the development of new tuberculosis drugs and treatment regimens, Nat. Rev. Drug Discov., 12, 388, 10.1038/nrd4001 Engohang-Ndong, 2012, Antimycobacterial drugs currently in Phase II clinical trials and preclinical phase for tuberculosis treatment, Expert. Opin. Invest. Drugs, 21, 1789, 10.1517/13543784.2012.724397 Villemagne, 2012, Tuberculosis: the drug development pipeline at a glance, Eur. J. Med. Chem., 51, 1, 10.1016/j.ejmech.2012.02.033 STOP TB Partnership, Working Group on New TB Drugs, Available at: http://www.newtbdrugs.org/pipeline.php (last accessed 05.12.14.). WHO, 2013 Mukhopadhyay, 2012, Pathogenesis in tuberculosis: transcriptomic approaches to unraveling virulence mechanisms and finding new drug targets, FEMS Microbiol. Rev., 36, 463, 10.1111/j.1574-6976.2011.00302.x Janssen, 2012, Exploring prospects of novel drugs for tuberculosis, Drug Des Dev Ther., 6, 217 Silva, 2010, New strategies in fighting TB: targeting Mycobacterium tuberculosis-secreted phosphatases MptpA & MptpB, Future Med. Chem., 2, 1325, 10.4155/fmc.10.214 Kumar, 2010, Discovery of anti-TB agents that target the cell-division protein FtsZ, Future Med. Chem., 2, 1305, 10.4155/fmc.10.220 Rodrigues, 2011, Inhibition of drug efflux in mycobacteria with phenothiazines and other putative efflux inhibitors, Recent Pat. Antiinfect Drug Discov., 6, 118, 10.2174/157489111796064579 Kumar, 2014, Synthesis of novel 1,2,3-triazole derivatives of isoniazid and their in vitro and in vivo antimycobacterial activity evaluation, Eur. J. Med. Chem., 81, 301, 10.1016/j.ejmech.2014.05.005 Mamolo, 2005, Antimycobacterial activity of new 3-substituted 5-(pyridine-4-yl)-3H-1,3,4-oxadiazol-2-one and 2-thione derivatives. Preliminary molecular modeling investigations, Bioorg. Med. Chem., 13, 3797, 10.1016/j.bmc.2005.03.013 de Oliveira, 2012, Synthetic approaches and pharmacological activity of 1,3,4-oxadiazoles: a review of the literature from 2000-2012, Molecules, 17, 10192, 10.3390/molecules170910192 Khalilullah, 2012, 1,3,4-oxadiazole: a biologically active scaffold, Mini Rev. Med. Chem., 12, 789, 10.2174/138955712801264800 Kun, 2011, Synthesis of variously coupled conjugates of D-glucose, 1,3,4-oxadiazole, and 1,2,3-triazole for inhibition of glycogen phosphorylase, Carbohydr. Res., 346, 1427, 10.1016/j.carres.2011.03.004 Bankar, 2009, Vasorelaxant effect in rat aortic rings through calcium channel blockage: a preliminary in vitro assessment of a 1,3,4-oxadiazole derivative, Chem. Biol. Interact., 181, 377, 10.1016/j.cbi.2009.07.014 Akhter, 2011, Synthesis and biological evaluation of 2,5-disubstituted 1,3,4-oxadiazole derivatives with both COX and LOX inhibitory activity, J. Enzyme Inhib. Med. Chem., 26, 767, 10.3109/14756366.2010.550890 Jayashankar, 2009, Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis (heterocycle) derivatives as anti-inflammatory and analgesic agents, Eur. J. Med. Chem., 44, 3898, 10.1016/j.ejmech.2009.04.006 Zarghi, 2005, Design and synthesis of new 2-substituted-5-(2-benzylthiophenyl)-1,3,4- oxadiazoles as benzodiazepine receptor agonists, Bioorg. Med. Chem. Lett., 15, 3126, 10.1016/j.bmcl.2005.04.018 Tu, 2013, Synthesis and antiproliferative assay of 1,3,4-oxadiazole and 1,2,4-triazole derivatives in cancer cells, Drug Discov. Ther., 7, 58 Jha, 2010, Design, synthesis and biological evaluation of 1,3,4-oxadiazole derivatives, Eur. J. Med. Chem., 45, 4963, 10.1016/j.ejmech.2010.08.003 Sangshetti, 2011, Synthesis of some novel 3-(1-(1-substitutedpiperidin-4-yl)-1H-1,2,3-triazol-4-yl)-5-substituted phenyl-1,2,4-oxadiazoles as antifungal agents, Eur. J. Med. Chem., 46, 1040, 10.1016/j.ejmech.2011.01.015 Li, 2011, 1,3,4-oxadiazole: a privileged structure in antiviral agents, Mini Rev. Med. Chem., 11, 1130, 10.2174/138955711797655407 Navarrete-Vázquez, 2007, Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines, Bioorg. Med. Chem., 15, 5502, 10.1016/j.bmc.2007.05.053 Biava, 2008, 1,5-Diphenylpyrrole derivatives as antimycobacterial agents. Probing the influence on antimycobacterial activity of lipophilic substituents at the phenyl rings, J. Med. Chem., 51, 3644, 10.1021/jm701560p Biava, 2009, 1,5-Diaryl-2-ethyl pyrrole derivatives as antimycobacterial agents: design, synthesis, and microbiological evaluation, Eur. J. Med. Chem., 44, 4734, 10.1016/j.ejmech.2009.06.005 Khoshneviszadeh, 2009, Synthesis and biological evaluation of some new 1,4-dihydropyridines containing different ester substitute and diethyl carbamoyl group as anti-tubercular agents, Bioorg. Med. Chem., 17, 1579, 10.1016/j.bmc.2008.12.070 Onajole, 2009, Pentacyclo-undecane derived cyclic tetra-amines: synthesis and evaluation as potent anti-tuberculosis agents, Eur. J. Med. Chem., 44, 4297, 10.1016/j.ejmech.2009.07.015 Wong-Baeza, 2012, Molecular organization of the non-bilayer phospholipid arrangements that induce an autoimmune disease resembling human lupus in mice, Mol. Membr. Biol., 29, 52, 10.3109/09687688.2012.667577 Molina-Salinas, 2006, Bactericidal activity of organic extracts from Flourensia cernua DC against strains of Mycobacterium tuberculosis, Arch. Med. Res., 37, 45, 10.1016/j.arcmed.2005.04.010 Jarnagin, 1980, The use of fluorescein diacetate and ethidium bromide as a stain for evaluating viability of mycobacteria, Stain Technol., 55, 253, 10.3109/10520298009067249 Singh, 1954, Bactericidal activity of streptomycin and isoniazid against tubercle bacilli, BMJ Br. Med. J., 1, 130, 10.1136/bmj.1.4854.130 Timmins, 2006, Mechanisms of action of isoniazid, Mol. Microbiol., 62, 1220, 10.1111/j.1365-2958.2006.05467.x Janin, 2007, Antituberculosis drugs: ten years of research, Bioorg. Med. Chem., 15, 2479, 10.1016/j.bmc.2007.01.030 Wilder-Smith, 1966, Some recently synthesised tuberculostatic 4-substituted oxadiazolones and oxadiazol-thiones. VI, Arzneim. Forsch., 16, 1034 Warner, 2006, Tuberculosis chemotherapy: the influence of bacillary stress and damage response pathways on drug efficacy, Clin. Microbiol. Rev., 19, 558, 10.1128/CMR.00060-05 Hernández Pando, 2006, A combination of transforming growth factor-β antagonists and an inhibitor of cyclooxygenase inhibitors is an effective treatment for murine pulmonary tuberculosis, Clin. Exp. Immunol., 144, 264, 10.1111/j.1365-2249.2006.03049.x Hernández Pando, 2005, 16-α-Bromoepiandrosterone restores T helper cell type 1 activity and accelerates chemotherapy-induced bacterial clearance in a model of progressive pulmonary tuberculosis, J. Infect. Dis., 191, 299, 10.1086/426453 Briones, 2008, Delivery systems to increase the selectivity of antibiotics in phagocytic cells, J. Control Release, 125, 210, 10.1016/j.jconrel.2007.10.027 Dube, 2012, Tuberculosis: from molecular pathogenesis to effective drug carrier design, Drug Discov. Today, 17, 760, 10.1016/j.drudis.2012.03.012