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Review

Inosine 5′-Monophosphate Dehydrogenase Inhibitors as Antimicrobial Agents: Recent Progress and Future Perspectives

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Pages 1415-1429 | Published online: 31 Jul 2015

References

  • Pogue JM , KayeKS, CohenDA, MarchaimD. Appropriate antimicrobial therapy in the era of multidrug-resistant human pathogens. Clin. Microbiol. Infect.21 (4), 302–312 (2015).
  • Goel AK . Anthrax: A disease of biowarfare and public health importance. World J. Clin. Cases3 (1), 20–33 (2015).
  • Spellberg B , BartlettJ, WunderinkR, GilbertDN. Novel approaches are needed to develop tomorrow's antibacterial therapies. Am. J. Respir. Crit. Care Med.191 (2), 135–140 (2015).
  • Fletcher SM , StarkD, HarknessJ, EllisJ. Enteric protozoa in the developed world: a public health perspective. Clin. Microbiol. Rev.25 (3), 420–429 (2012).
  • Umejiego NN , GollapalliD, SharlingLet al. Targeting a prokaryotic protein in a eukaryotic pathogen: identification of lead compounds against cryptosporidiosis. Chem. Biol.15 (1), 70–77 (2008).
  • Baquero F , CoqueTM, CantónR. Counteracting antibiotic resistance: Breaking barriers among antibacterial strategies. Expert Opin. Ther. Targets18 (8), 851–861 (2014).
  • Drinkwater N , McGowanS. From crystal to compound: structure-based antimalarial drug discovery. Biochem. J.461 (3), 349–369 (2014).
  • Mandapati K , GorlaSK, HouseALet al. Repurposing cryptosporidium inosine 5′-monophosphate dehydrogenase inhibitors as potential antibacterial agents. ACS Med. Chem. Lett.5 (8), 846–850 (2014).
  • Hedstorm L . IMP dehydrogenase: structure, mechanism, and inhibition. Chem. Rev.109 (7), 2903–2928 (2009).
  • Gorla SL , McNairNN, YangGet al. Validation of IMP dehydrogenase inhibitors in a mouse model of cryptosporidiosis. Antimicrob. Agents Chemother.58 (3), 1603–1614 (2014).
  • Petrelli R , VitaP, TorquatiIet al. Novel inhibitors of inosine monophosphate dehydrogenase in patent literature of the last decade. Recent Pat. Anticancer Drug Discov.8 (2), 103–125 (2013).
  • Makowska-Grzyska M , KimY, MaltsevaNet al. A novel cofactor-binding mode in bacterial IMP dehydrogenases explains inhibitor selectivity. J. Biol. Chem.290 (9), 5893–5911 (2015).
  • Hedstrom L , LiechtiG, GoldbergJB, GollapalliDR. The antibiotic potential of prokaryotic IMP dehydrogenase inhibitors. Curr. Med. Chem.18 (13), 1909–1918 (2011).
  • Braun-Sand SB , PeetzM. Inosine monophosphate dehydrogenase as a target for antiviral, anticancer, antimicrobial and immunosuppressive therapeutics. Fut. Med. Chem.2 (1), 81–92 (2010).
  • Striepen B , PruijssersAJ, HuangJet al. Gene transfer in the evolution of parasite nucleotide biosynthesis. Proc. Natl Acad. Sci. USA101 (9), 3154–3159 (2004).
  • Chen L , WilsonDJ, XuYet al. Triazole-linked inhibitors of inosine monophosphate dehydrogenase from human and Mycobacterium tuberculosis. J. Med. Chem.53 (12), 4768–4778 (2010).
  • Felczak K , ChenL, WilsonDet al. Cofactor-type inhibitors of inosine monophosphate dehydrogenase via modular approach: targeting the pyrophosphate binding sub-domain. Bioorg. Med. Chem.19 (5), 1594–1605 (2011).
  • Umejiego NN , GollapalliD, SharlingLet al. Targeting a prokaryotic protein in a eukaryotic pathogen: Identification of lead compounds against cryptosporidiosis. Chem. Biol.15 (1), 70–77 (2008).
  • Gorla SK , KavithaM, ZhangMet al. Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5′-monophosphate dehydrogenase. J. Med. Chem.56 (10), 4028–4043 (2013).
  • Sharling L , LiuX, GollapalliDR, MauryaSK, HedstromL, StriepenB. A screening pipeline for antiparasitic agents targeting cryptosporidium inosine monophosphate dehydrogenase. PLoS Negl. Trop. Dis.4 (8), e794 (2010).
  • Maurya SK , GollapalliDR, KirubakaranSet al. Triazole inhibitors of Cryptosporidium parvum inosine 5′-monophosphate dehydrogenase. J. Med. Chem.52 (15), 4623–4630 (2009).
  • Kirubakaran S , GorlaSK, SharlingLet al. Structure-activity relationship study of selective benzimidazole-based inhibitors of Cryptosporidium parvum IMPDH. Bioorg. Med. Chem. Lett.22 (5), 1985–1988 (2012).
  • Johnson CR , GorlaSK, KavithaMet al. Phthalazinone inhibitors of inosine 5′-monophosphate dehydrogenase from Cryptosporidium parvum. Bioorg. Med. Chem. Lett.23 (4), 1004–1007 (2013).
  • Gorla SK , KavithaM, ZhangMet al. Selective and potent urea inhibitors of Cryptosporidium parvum inosine 5′-monophosphate dehydrogenase. J. Med. Chem.55 (17), 7759–7771 (2012).
  • Macpherson IS , KirubakaranS, GorlaSKet al. The structural basis of cryptosporidium-specific IMP dehydrogenase inhibitor selectivity. J. Am. Chem. Soc.132 (4), 1230–1231 (2010).
  • Gollapalli DR , MacphersonIS, LiechtiG, GorlaSK, GoldbergJB, HedstromL. Structural determinants of inhibitor selectivity in prokaryotic IMP dehydrogenases. Chem. Biol.17 (10), 1084–1091 (2010).
  • Makowska-Grzyska M , KimY, WuRet al. Bacillus anthracis inosine 5′-monophosphate dehydrogenase in action: The first bacterial series of structures of phosphate ion-, substrate-, and product-bound complexes. Biochemistry51 (31), 6148–6163 (2012).
  • Nair V , ChiG, ShuQ, JulanderJ, SmeeDF. A heterocyclic molecule with significant activity against dengue virus. Bioorg. Med. Chem. Lett.19 (5), 1425–1427 (2009).
  • Takhampunya R , UbolS, HoungHS, CameronCE, PadmanabhanR. Inhibition of dengue virus replication by mycophenolic acid and ribavirin. J. Gen. Virol.87 (Pt 7), 1947–1952 (2006).
  • Dairaku I , HanY, YanakaN, KatoN. Inhibitory effect of curcumin on IMP dehydrogenase, the target for anticancer and antiviral chemotherapy agents. Biosci. Biotechnol. Biochem.74 (1), 185–187 (2010).
  • Usha V , GurchaSS, LoveringALet al. Identification of novel diphenyl urea inhibitors of Mt-GuaB2 active against Mycobacterium tuberculosis. Microbiology157 (Pt 1), 290–299 (2011).
  • Zhong ZJ , ZhangDJ, PengZGet al. Synthesis and antiviral activity of a novel class of (5-oxazolyl)phenyl amines. Eur. J. Med. Chem.69, 32–43 (2013).
  • Sun Z , KhanJ, Makowska-GrzyskaMet al. Synthesis, in vitro evaluation and cocrystal structure of 4-oxo-[1]benzopyrano[4,3-c]pyrazole Cryptosporidium parvum inosine 5’-monophosphate dehydrogenase (CpIMPDH) inhibitors. J. Med. Chem.57 (24), 10544–10550 (2014).
  • Bentley R . Mycophenolic acid: a one hundred year odyssey from antibiotic to immunosuppressant. Chem. Rev.100 (10), 3801–3826 (2000).
  • Florey HW , GilliverK, JenningsMA. Mycophenolic acid: an antibiotic from Penicillium brevicompactum Dlerckx. Lancet1 (6385), 46–49 (1946).
  • Abraham EP . The effect of mycophenolic acid on the growth of Staphylococcus aureus in heart broth. Biochem. J.39 (5), 398–408 (1945).
  • Quinn CM , BugejaVC, GallagherJA, WhittakerPA. The effect of mycophenolic acid on the cell cycle of Candida albicans. Mycopathologia111 (3), 165–168 (1990).
  • O'Gara MJ , LeeCH, WeinbergGA, NottJM, QueenerSF. IMP dehydrogenase from Pneomocystis carinii as a potential drug target. Antimicrob. Agents Chemother.41 (1), 40–48 (1997).
  • Wilson K , CollartFR, HubermanE, StringerJR, UllmanB. Amplification and molecular cloning of the IMP dehydrogenase gene of Leishmania donovani. J. Biol. Chem.266 (3), 1665–1671 (1991).
  • Wilson K , BerensRL, SifriCD, UllmanB. Amplification of the inosinate dehydrogenase gene in Trypanosoma brucei gambienese due to an increase in chromosome copy number. J. Biol. Chem.269 (46), 28979–28987 (1994).
  • Hupe DJ , AzzolinaBA, BehrensND. IMP dehydrogenase from the intracellular parasitic protozoan Eimeria tenella and its inhibition by mycophenolic acid. J. Biol. Chem.261 (18), 8363–8369 (1986).
  • Khan M , DhanwaniR, PatroIK, RaoPV, ParidaMM. Cellular IMPDH enzyme activity is a potential target for the inhibition of Chikungunya virus replication and virus induced apoptosis in cultured mammalian cells. Antiviral Res.89 (1), 1–8 (2011).
  • Usha V , HobrathJV, GurchaSS, ReynoldsRC, BesraGS. Identification of novel Mt-Guab2 inhibitor series active against M. tuberculosis. PLoS ONE7 (3), e33886 (2012).
  • Yang N , WangJ, LiJ, WangQH, WangY, ChengMS. A three-dimensional pharmacophore model for IMPDH inhibitors. Chem. Biol. Drug Des.78 (1), 175–182 (2011).
  • Dunkern T , PrabhuA, KharkarPSet al. Virtual and experimental high-throughput screening (HTS) in search of novel inosine 5′-monophosphate dehydrogenase II (IMPDH II) inhibitors. J. Comput. Aided Mol. Des.26 (11), 1277–1292 (2012).
  • Dunkern T , ChavanS, BankarDet al. Design, synthesis and biological evaluation of novel inosine 5′-monohosphate dehydrogenase (IMPDH) inhibitors. J. Enzyme Inhib. Med. Chem.29 (3), 408–419 (2014).
  • Alexandra T , RaynaB, Munier-LehmannH. Two classes of bacterial IMPDHs according to their quaternary structures and catalytic properties. PLoS ONE10 (2), e0116578 (2015).
  • Baykov AA , TuominenHK, LahtiR. The CBS domain: a protein module with an emerging prominent role in regulation. ACS Chem. Biol.6 (11), 1156–1163 (2011).
  • Ereño-Orbea J , OyenarteI, Martínez-CruzLA. CBS domains: ligand binding sites and conformational variability. Arch. Biochem. Biophys.540 (1–2), 70–81 (2013).
  • Ignoul S , EggermontJ. CBS domains: structure, function, and pathology in human proteins. Am. J. Physiol. Cell Physiol.289 (6), 1369–1378 (2005).
  • Bateman A . The structure of a domain common to archaebacteria and the homocystinuria disease protein. Trends Biochem. Sci.22 (1), 12–13 (1997).
  • Labesse G , AlexandreT, VaupréLet al. MgATP regulates allostery and fiber formation in IMPDHs. Structure21 (6), 975–985 (2013).

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