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Volumn 25, Issue 19, 2017, Pages 5133-5141

Synthesis and biological evaluation of Aspergillomarasmine A derivatives as novel NDM-1 inhibitor to overcome antibiotics resistance

Author keywords

Antibiotic resistance; Antibiotics; Aspergillomarasmine A; Metallo lactamases; NDM 1

Indexed keywords

ASPERGILLOMARASMINE A DERIVATIVE; BETA LACTAMASE INHIBITOR; MEROPENEM; METALLO BETA LACTAMASE; NATURAL PRODUCT; NEW DELHI METALLO BETA LACTAMASE; UNCLASSIFIED DRUG; VERONA INTEGRON ENCODED BETA LACTAMASE; ASPARTIC ACID; ASPERGILLOMARASMINE A; BETA LACTAMASE; BETA-LACTAMASE NDM-1;

EID: 85026780365     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2017.07.025     Document Type: Article
Times cited : (46)

References (28)
  • 1
    • 0000378637 scopus 로고
    • On the antibacterial action of cultures of a penicillium, with special reference to their use in the isolation of B. influenzae
    • Fleming, A., On the antibacterial action of cultures of a penicillium, with special reference to their use in the isolation of B. influenzae. Br J Exp Pathol 10 (1929), 226–236.
    • (1929) Br J Exp Pathol , vol.10 , pp. 226-236
    • Fleming, A.1
  • 2
    • 82355169031 scopus 로고    scopus 로고
    • Penicillin: the medicine with the greatest impact on therapeutic outcomes
    • Kardos, N., Demain, A.L., Penicillin: the medicine with the greatest impact on therapeutic outcomes. Appl Microbiol Biotechnol 92 (2011), 677–687.
    • (2011) Appl Microbiol Biotechnol , vol.92 , pp. 677-687
    • Kardos, N.1    Demain, A.L.2
  • 3
    • 84904808187 scopus 로고    scopus 로고
    • Prioritized current unmet needs for antibacterial therapies
    • Spellberg, B., Shlaes, D., Prioritized current unmet needs for antibacterial therapies. Clin Pharmacol Ther 96 (2014), 151–153.
    • (2014) Clin Pharmacol Ther , vol.96 , pp. 151-153
    • Spellberg, B.1    Shlaes, D.2
  • 5
    • 84936863015 scopus 로고    scopus 로고
    • Chemistry, classification, pharmacokinetics, clinical uses and analysis of beta lactam antibiotics: A review
    • Masoud, M.S., Ali, A.E., Nasr, N.M., Chemistry, classification, pharmacokinetics, clinical uses and analysis of beta lactam antibiotics: A review. J Chem Pharm Res 6 (2014), 28–58.
    • (2014) J Chem Pharm Res , vol.6 , pp. 28-58
    • Masoud, M.S.1    Ali, A.E.2    Nasr, N.M.3
  • 6
    • 14844362964 scopus 로고    scopus 로고
    • Bacterial resistance to β-lactam antibiotics: compelling opportunism, compelling opportunity
    • Fisher, J.F., Meroueh, S.O., Mobashery, S., Bacterial resistance to β-lactam antibiotics: compelling opportunism, compelling opportunity. Chem Rev 105 (2005), 395–424.
    • (2005) Chem Rev , vol.105 , pp. 395-424
    • Fisher, J.F.1    Meroueh, S.O.2    Mobashery, S.3
  • 7
    • 80052223781 scopus 로고    scopus 로고
    • Current trends in β-Lactam based β-Lactamases inhibitors
    • Biondi, S., Long, S., Panunzio, M., Qin, W.L., Current trends in β-Lactam based β-Lactamases inhibitors. Curr Med Chem 18 (2011), 4223–4236.
    • (2011) Curr Med Chem , vol.18 , pp. 4223-4236
    • Biondi, S.1    Long, S.2    Panunzio, M.3    Qin, W.L.4
  • 8
    • 74249108028 scopus 로고    scopus 로고
    • Three decades of beta-lactamase inhibitors
    • Drawz, S.M., Bonomo, R.A., Three decades of beta-lactamase inhibitors. Clin Microbiol Rev 23 (2010), 160–201.
    • (2010) Clin Microbiol Rev , vol.23 , pp. 160-201
    • Drawz, S.M.1    Bonomo, R.A.2
  • 9
    • 84655167173 scopus 로고    scopus 로고
    • McGeary. 3-mercapto-1, 2, 4-triazoles and N-acylated thiosemicarbazides as metallo-β-lactamase inhibitors
    • Faridoon, W.M., Hussein, P., Vella, N.U., Islam, D.L., Ollis, G., Schenk, R.P., McGeary. 3-mercapto-1, 2, 4-triazoles and N-acylated thiosemicarbazides as metallo-β-lactamase inhibitors. Bioorg Med Chem Lett 22 (2012), 380–386.
    • (2012) Bioorg Med Chem Lett , vol.22 , pp. 380-386
    • Faridoon, W.M.1    Hussein, P.2    Vella, N.U.3    Islam, D.L.4    Ollis, G.5    Schenk, R.P.6
  • 10
    • 84928492199 scopus 로고    scopus 로고
    • Approved drugs containing thiols as inhibitors of metallo-β-lactamases: strategy to combat multidrug resistant bacteria
    • Klingler, F.M., Wichelhaus, T.A., Frank, D., et al. Approved drugs containing thiols as inhibitors of metallo-β-lactamases: strategy to combat multidrug resistant bacteria. J Med Chem 58 (2015), 3626–3630.
    • (2015) J Med Chem , vol.58 , pp. 3626-3630
    • Klingler, F.M.1    Wichelhaus, T.A.2    Frank, D.3
  • 11
    • 84864417937 scopus 로고    scopus 로고
    • N-heterocyclic dicarboxylic acids: broad-spectrum inhibitors of metallo-β-lactamases with co-antibacterial effect against antibiotic-resistant bacteria
    • Feng, L., Yang, K., Zhou, W.L.S., et al. N-heterocyclic dicarboxylic acids: broad-spectrum inhibitors of metallo-β-lactamases with co-antibacterial effect against antibiotic-resistant bacteria. Bioorg Med Chem Lett 22 (2012), 5185–5189.
    • (2012) Bioorg Med Chem Lett , vol.22 , pp. 5185-5189
    • Feng, L.1    Yang, K.2    Zhou, W.L.S.3
  • 12
    • 84947213893 scopus 로고    scopus 로고
    • Discovery of novel inhibitor scaffolds against the metallo-β-lactamases VIM-2 by Surface Plasmon Resonance (SPR) based fragment screening
    • Christopeit, Tony, Carlsen, Trine Josefine O., Helland, Ronny, Leiros, Hanna-Kirsti S., Discovery of novel inhibitor scaffolds against the metallo-β-lactamases VIM-2 by Surface Plasmon Resonance (SPR) based fragment screening. J Med Chem 58 (2015), 8671–8682.
    • (2015) J Med Chem , vol.58 , pp. 8671-8682
    • Christopeit, T.1    Carlsen, T.J.O.2    Helland, R.3    Leiros, H.-K.S.4
  • 13
    • 84976477345 scopus 로고    scopus 로고
    • Cross-class metallo-β-lactamase inhibition by bisthiazolidines reveals multiple binding modes
    • Hinchliffea, Philip., Gonzálezb, Mariano M., Mojicac, Maria F., et al. Cross-class metallo-β-lactamase inhibition by bisthiazolidines reveals multiple binding modes. Proc Natl Acad Sci USA 113 (2016), E3745–E3754.
    • (2016) Proc Natl Acad Sci USA , vol.113 , pp. E3745-E3754
    • Hinchliffea, P.1    Gonzálezb, M.M.2    Mojicac, M.F.3
  • 14
    • 84886877549 scopus 로고    scopus 로고
    • Β-Lactamase inhibitors: a review of the patent literature (2010–2013)
    • Buynak, J.D., Β-Lactamase inhibitors: a review of the patent literature (2010–2013). Expert Opin Ther Pat 23 (2013), 1469–1481.
    • (2013) Expert Opin Ther Pat , vol.23 , pp. 1469-1481
    • Buynak, J.D.1
  • 16
    • 33845708150 scopus 로고    scopus 로고
    • New antibiotics from bacterial natural products
    • Clardy, J., Fischbach, M.A., Walsh, C.T., New antibiotics from bacterial natural products. Nat Biotechnol 24 (2006), 1541–1550.
    • (2006) Nat Biotechnol , vol.24 , pp. 1541-1550
    • Clardy, J.1    Fischbach, M.A.2    Walsh, C.T.3
  • 17
    • 84922937832 scopus 로고    scopus 로고
    • A new antibiotic kills pathogens without detectable resistance
    • Ling, L.L., Schneider, T., Peoples, A.J., et al. A new antibiotic kills pathogens without detectable resistance. Nature 517 (2015), 455–459.
    • (2015) Nature , vol.517 , pp. 455-459
    • Ling, L.L.1    Schneider, T.2    Peoples, A.J.3
  • 18
    • 84925249755 scopus 로고    scopus 로고
    • 4] vancomycin, and their (4-Chlorobiphenyl) methyl derivatives: synergistic binding pocket and peripheral modifications for the glycopeptide antibiotics
    • Okano, A., Nakayama, A., Wu, K., et al. Total syntheses and initial evaluation of [Ψ[C(=S)NH]Tpg4] vancomycin, [Ψ[C(=NH)NH]Tpg4] vancomycin, [Ψ[CH2NH]Tpg4] vancomycin, and their (4-Chlorobiphenyl) methyl derivatives: synergistic binding pocket and peripheral modifications for the glycopeptide antibiotics. J Am Chem Soc 137 (2015), 3693–3704.
    • (2015) J Am Chem Soc , vol.137 , pp. 3693-3704
    • Okano, A.1    Nakayama, A.2    Wu, K.3
  • 19
    • 17244375099 scopus 로고    scopus 로고
    • A convergent enantioselective route to structurally diverse 6-deoxytetracycline antibiotics
    • Charest, M.G., Lerner, C.D., Brubaker, J.D., Siegel, D.R., Myers, A.G., A convergent enantioselective route to structurally diverse 6-deoxytetracycline antibiotics. Science 308 (2005), 395–398.
    • (2005) Science , vol.308 , pp. 395-398
    • Charest, M.G.1    Lerner, C.D.2    Brubaker, J.D.3    Siegel, D.R.4    Myers, A.G.5
  • 21
    • 0021049908 scopus 로고
    • Novel microbial inhibitors of angiotensin-converting enzyme, aspergillomarasmines A and B
    • Mikami, Y., Suzuki, T., Novel microbial inhibitors of angiotensin-converting enzyme, aspergillomarasmines A and B. Agric Biol Chem 47 (1983), 2693–2695.
    • (1983) Agric Biol Chem , vol.47 , pp. 2693-2695
    • Mikami, Y.1    Suzuki, T.2
  • 22
    • 84903457328 scopus 로고    scopus 로고
    • Aspergillomarasmine A overcomes metallo-β-lactamase antibiotic resistance
    • King, A.M., Reid-Yu, S.A., Wang, W., et al. Aspergillomarasmine A overcomes metallo-β-lactamase antibiotic resistance. Nature 510 (2014), 503–506.
    • (2014) Nature , vol.510 , pp. 503-506
    • King, A.M.1    Reid-Yu, S.A.2    Wang, W.3
  • 23
    • 0000280515 scopus 로고
    • Natsuko Kurokawa. Synthesis of the serine equivalent, (2R) and (2S)-amino-3-butenol derivatives. Synthetic approaches to the metal chelating poly-amino acid, “aspergillomarasmine A”
    • Ohfune, Y., Natsuko Kurokawa. Synthesis of the serine equivalent, (2R) and (2S)-amino-3-butenol derivatives. Synthetic approaches to the metal chelating poly-amino acid, “aspergillomarasmine A”. Tetrahedron Lett 25 (1984), 1071–1074.
    • (1984) Tetrahedron Lett , vol.25 , pp. 1071-1074
    • Ohfune, Y.1
  • 24
    • 84947976362 scopus 로고    scopus 로고
    • Total synthesis and structural reassignment of aspergillomarasmine A
    • Liao, D., Yang, S., Wang, J., et al. Total synthesis and structural reassignment of aspergillomarasmine A. Angew Chem Int Ed 55 (2016), 4291–4295.
    • (2016) Angew Chem Int Ed , vol.55 , pp. 4291-4295
    • Liao, D.1    Yang, S.2    Wang, J.3
  • 25
    • 84957845289 scopus 로고    scopus 로고
    • Total synthesis and activity of the metallo-β-lactamase inhibitor aspergillomarasmine A
    • Koteva, K., King, A.M., Capretta, A., Wright, G.D., Total synthesis and activity of the metallo-β-lactamase inhibitor aspergillomarasmine A. Angew Chem Int Ed 55 (2016), 2210–2212.
    • (2016) Angew Chem Int Ed , vol.55 , pp. 2210-2212
    • Koteva, K.1    King, A.M.2    Capretta, A.3    Wright, G.D.4
  • 26
    • 0034708584 scopus 로고    scopus 로고
    • (1S)-1-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2 hydroxyethylammonium benzoate, a versatile building block for chiral 2-aminoalkanols: concise synthesis and application to Nelfinavir, a potent HIV-protease inhibitor
    • Inaba, T., Yamada, Y., Abe, H., Sagawa, S., Cho, H., (1S)-1-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2 hydroxyethylammonium benzoate, a versatile building block for chiral 2-aminoalkanols: concise synthesis and application to Nelfinavir, a potent HIV-protease inhibitor. J Org Chem 65 (2000), 1623–1628.
    • (2000) J Org Chem , vol.65 , pp. 1623-1628
    • Inaba, T.1    Yamada, Y.2    Abe, H.3    Sagawa, S.4    Cho, H.5
  • 27
    • 84992093037 scopus 로고    scopus 로고
    • Total synthesis of aspergillomarasmine A and related Compounds: a sulfamidate approach enables exploration of structure–activity relationships
    • Albu, S.A., Koteva, K., King, A.M., Al-Karmi, S., Wright, G.D., Capretta, A., Total synthesis of aspergillomarasmine A and related Compounds: a sulfamidate approach enables exploration of structure–activity relationships. Angew Chem Int Ed 55 (2016), 13259–13262.
    • (2016) Angew Chem Int Ed , vol.55 , pp. 13259-13262
    • Albu, S.A.1    Koteva, K.2    King, A.M.3    Al-Karmi, S.4    Wright, G.D.5    Capretta, A.6


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