메뉴 건너뛰기




Volumn 40, Issue 16, 1997, Pages 2609-2625

Design and synthesis of novel imidazole-substituted dipeptide amides as potent and selective inhibitos of Candida albicans myristoylCoA:protein N- myristoyltransferase and identification of related tripeptide inhibitors with mechanism-based antifungal activity

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; IMIDAZOLE DERIVATIVE; PEPTIDE;

EID: 15144355281     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970094w     Document Type: Article
Times cited : (70)

References (30)
  • 2
    • 0031019429 scopus 로고    scopus 로고
    • Understanding covalent modifications of proteins by lipids: Where cell biology and biophysics mingle
    • Bhatnagar, R. S.; Gordon, J. I. Understanding covalent modifications of proteins by lipids: Where cell biology and biophysics mingle. Trends Cell Biol. 1997, 7, 14-20.
    • (1997) Trends Cell Biol. , vol.7 , pp. 14-20
    • Bhatnagar, R.S.1    Gordon, J.I.2
  • 3
    • 0029058605 scopus 로고
    • The myristoyl-electrostatic switch: A modulator of reversible protein-membrane interactions
    • McLaughlin, S.; Aderem, A. The myristoyl-electrostatic switch: a modulator of reversible protein-membrane interactions. Trends Biochem. Sci. 1995, 20, 272-276.
    • (1995) Trends Biochem. Sci. , vol.20 , pp. 272-276
    • McLaughlin, S.1    Aderem, A.2
  • 4
    • 0024590280 scopus 로고
    • Disruption of the yeast N-myristoyl transferase gene causes recessive lethality
    • Duronio, R. J.; Towler, D. A.; Heuckeroth, R. O.; Gordon, J. I. Disruption of the yeast N-myristoyl transferase gene causes recessive lethality. Science 1989, 243, 796-800.
    • (1989) Science , vol.243 , pp. 796-800
    • Duronio, R.J.1    Towler, D.A.2    Heuckeroth, R.O.3    Gordon, J.I.4
  • 5
    • 0026544934 scopus 로고
    • Mutations of human myristoylCoA:protein N-myristoyltransferase cause temperature-sensitive myristic acid auxotrophy in Saccharomyces cerevisiae
    • Duronio, R. J.; Reed, S. I.; Gordon, J. I. Mutations of human myristoylCoA:protein N-myristoyltransferase cause temperature-sensitive myristic acid auxotrophy in Saccharomyces cerevisiae. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 4129-4133.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 4129-4133
    • Duronio, R.J.1    Reed, S.I.2    Gordon, J.I.3
  • 6
    • 0028000667 scopus 로고
    • Comparison of myristoylCoA:protein N-myristoyltransferases from three pathogenic fungi - Cryptococcus neoformans, Histoplasma capsulatum, and Candida albicans
    • Lodge, J. K.; Johnson, R. L.; Weinberg, R. A.; Gordon, J. I. Comparison of myristoylCoA:protein N-myristoyltransferases from three pathogenic fungi - Cryptococcus neoformans, Histoplasma capsulatum, and Candida albicans. J. Biol. Chem. 1994, 269, 2996-3009.
    • (1994) J. Biol. Chem. , vol.269 , pp. 2996-3009
    • Lodge, J.K.1    Johnson, R.L.2    Weinberg, R.A.3    Gordon, J.I.4
  • 7
    • 0026767886 scopus 로고
    • The Candida albicans myristoylCoA:Protein N-myristoyl-transferase gene: Isolation and expression in S. cerevisiae and E. coli
    • Wiegand, R. C.; Minnerly, J. C.; Pauley, A. M.; Carron, C. P.; Carr, C. Z.; Langner, C.; Duronio, R. J.; Gordon, J. I. The Candida albicans myristoylCoA:Protein N-myristoyl-transferase gene: isolation and expression in S. cerevisiae and E. coli. J. Biol. Chem. 1992, 267, 8591-8598.
    • (1992) J. Biol. Chem. , vol.267 , pp. 8591-8598
    • Wiegand, R.C.1    Minnerly, J.C.2    Pauley, A.M.3    Carron, C.P.4    Carr, C.Z.5    Langner, C.6    Duronio, R.J.7    Gordon, J.I.8
  • 8
    • 0025834950 scopus 로고
    • Kinetic and Structural Evidence for a Sequential Ordered Bi Bi Mechanism of Catalysis by Saccharomyces cerevisiae myristoylCoA: Protein N-myristoyltransferase
    • Rudnick, D. A.; McWherter, C. A.; Rocque, W. J.; Lennon, P. J.; Getman, D. P.; Gordon, J. I. Kinetic and Structural Evidence for a Sequential Ordered Bi Bi Mechanism of Catalysis by Saccharomyces cerevisiae myristoylCoA: protein N-myristoyltransferase. J. Biol. Chem. 1991, 266, 9732-9971.
    • (1991) J. Biol. Chem. , vol.266 , pp. 9732-9971
    • Rudnick, D.A.1    McWherter, C.A.2    Rocque, W.J.3    Lennon, P.J.4    Getman, D.P.5    Gordon, J.I.6
  • 9
    • 0028053746 scopus 로고
    • Targeted gene replacement demonstrates that myristoyl-CoA:protein N-myristoyltransferase is essential for the viability of Cryptococcus neoformans
    • Lodge, J. K.; Jackson-Machelski, E.; Toffaletti, D. L.; Perfect, J. R.; Gordon, J. I. Targeted gene replacement demonstrates that myristoyl-CoA:protein N-myristoyltransferase is essential for the viability of Cryptococcus neoformans. Proc. Natl. Acad Sci. U.S.A. 1994, 91, 12008-12012.
    • (1994) Proc. Natl. Acad Sci. U.S.A. , vol.91 , pp. 12008-12012
    • Lodge, J.K.1    Jackson-Machelski, E.2    Toffaletti, D.L.3    Perfect, J.R.4    Gordon, J.I.5
  • 10
    • 0029070249 scopus 로고
    • Genetic studies reveal that myristoylCoA:protein N-myristoyltransferase is an essential enzyme in Candida albicans
    • Weinberg, R. A.; McWherter, C. A.; Freeman, S. K.; Wood, D. C.; Gordon, J. I.; Lee, S. C. Genetic studies reveal that myristoylCoA:protein N-myristoyltransferase is an essential enzyme in Candida albicans. Mol. Microbiol. 1995, 16 (2), 241-250.
    • (1995) Mol. Microbiol. , vol.16 , Issue.2 , pp. 241-250
    • Weinberg, R.A.1    McWherter, C.A.2    Freeman, S.K.3    Wood, D.C.4    Gordon, J.I.5    Lee, S.C.6
  • 11
    • 0028289602 scopus 로고
    • Human Mycoses: Drugs and Targets for Emerging Pathogens
    • Georgopapadakou, N. H.; Walsh, T. J. Human Mycoses: Drugs and Targets for Emerging Pathogens. Science 1994, 264, 371-373.
    • (1994) Science , vol.264 , pp. 371-373
    • Georgopapadakou, N.H.1    Walsh, T.J.2
  • 13
    • 0030594977 scopus 로고    scopus 로고
    • A chiral recognition element with an unusual size constraint affects the potency and selectivity for peptidomometic inhibitors of Candida albicans myristoylCoA:protein N-myristoyltransferase
    • Devadas, B.; Freeman, S. K.; McWherter, C. A.; Kuneman, D. W.; Vinjamoori, D. V.; Sikorski, J. A. A chiral recognition element with an unusual size constraint affects the potency and selectivity for peptidomometic inhibitors of Candida albicans myristoylCoA:protein N-myristoyltransferase. Bioorg. Med. Chem. Lett. 1996, 6 (16), 1977-1982.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , Issue.16 , pp. 1977-1982
    • Devadas, B.1    Freeman, S.K.2    McWherter, C.A.3    Kuneman, D.W.4    Vinjamoori, D.V.5    Sikorski, J.A.6
  • 14
    • 0027529190 scopus 로고
    • A comparison of the acyl chain specificities of human myristoyl-CoA synthetase and human myristoyl-CoA:protein N-myristoyltransferase
    • Kishore, N. S.; Wood, D. C.; Mehta, P. P.; Wade, A. C.; Lu, T., Gokel, G. W.; Gordon, J. I. A comparison of the acyl chain specificities of human myristoyl-CoA synthetase and human myristoyl-CoA:protein N-myristoyltransferase. J. Biol. Chem. 1993, 268, 4889-4902.
    • (1993) J. Biol. Chem. , vol.268 , pp. 4889-4902
    • Kishore, N.S.1    Wood, D.C.2    Mehta, P.P.3    Wade, A.C.4    Lu, T.5    Gokel, G.W.6    Gordon, J.I.7
  • 15
    • 0027276545 scopus 로고
    • A comparative analysis of the kinetic mechanism and peptide substrate specificity of human and Saccharomyces cerevisiae myristoyl-CoAiprotein N-myristoyltransferase
    • Rocque, W. J.; McWherter, C. A.; Wood, D. C.; Gordon, J. I. A comparative analysis of the kinetic mechanism and peptide substrate specificity of human and Saccharomyces cerevisiae myristoyl-CoAiprotein N-myristoyltransferase. J. Biol. Chem. 1993, 268, 9964-9971.
    • (1993) J. Biol. Chem. , vol.268 , pp. 9964-9971
    • Rocque, W.J.1    McWherter, C.A.2    Wood, D.C.3    Gordon, J.I.4
  • 16
    • 0027459010 scopus 로고
    • Use of photoactivatable peptide substrates of Saccharomyces cerevisiae myristoyl-CoA: Protein N-myristoyl-transferase (Nmt1p) to characterize a myristoyl-CoA-Nmt1p-peptide ternary complex and to provide evidence for an ordered reaction mechanism
    • Rudnick, D. A.; Rocque, W. J.; McWherter, C. A.; Toth, M. V.; Jackson-Machelski, E.; Gordon, J. I. Use of photoactivatable peptide substrates of Saccharomyces cerevisiae myristoyl-CoA: protein N-myristoyl-transferase (Nmt1p) to characterize a myristoyl-CoA-Nmt1p-peptide ternary complex and to provide evidence for an ordered reaction mechanism. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1097-1091.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 1097-11091
    • Rudnick, D.A.1    Rocque, W.J.2    McWherter, C.A.3    Toth, M.V.4    Jackson-Machelski, E.5    Gordon, J.I.6
  • 17
    • 0030923009 scopus 로고    scopus 로고
    • Scanning alanine mutagenesis and de-peptidization of a Candida albicans myristoyl-CoA:protein N-myristoyltransferase octapeptide substrate reveals three elements critical for molecular recognition
    • McWherter, C. A.; Rocque, W. J.; Zupec, M. E.; Freeman, S. K.; Brown, D. L.; Devadas, B.; Getman, D. P.; Sikorski, J. A.; Gordon, J. I. Scanning alanine mutagenesis and de-peptidization of a Candida albicans myristoyl-CoA:protein N-myristoyltransferase octapeptide substrate reveals three elements critical for molecular recognition. J. Biol. Chem. 1997, 272, 11874-11880.
    • (1997) J. Biol. Chem. , vol.272 , pp. 11874-11880
    • McWherter, C.A.1    Rocque, W.J.2    Zupec, M.E.3    Freeman, S.K.4    Brown, D.L.5    Devadas, B.6    Getman, D.P.7    Sikorski, J.A.8    Gordon, J.I.9
  • 18
    • 0025221221 scopus 로고
    • ADP ribosylation factor is an essential protein in Saccharomyces cerevisiae and is encoded by two genes
    • Stearns, T.; Kahn, R. A.; Botstein, D.; Hayt, M. A. ADP ribosylation factor is an essential protein in Saccharomyces cerevisiae and is encoded by two genes. Mol. Cell. Biol. 1990, 10, 6690-6699.
    • (1990) Mol. Cell. Biol. , vol.10 , pp. 6690-6699
    • Stearns, T.1    Kahn, R.A.2    Botstein, D.3    Hayt, M.A.4
  • 19
    • 0018085004 scopus 로고
    • Selective inhibition of prostaglandin endoperoxide thromboxane isomerase by 1-carboxyalkylimidazoles
    • (a) Yoshimoto, T.; Yamamoto, S.; Hayaishi, O. Selective inhibition of prostaglandin endoperoxide thromboxane isomerase by 1-carboxyalkylimidazoles. Prostaglandins 1978, 16 (4), 529-540.
    • (1978) Prostaglandins , vol.16 , Issue.4 , pp. 529-540
    • Yoshimoto, T.1    Yamamoto, S.2    Hayaishi, O.3
  • 21
    • 9644285669 scopus 로고
    • A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenens, and bromopyridines
    • Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenens, and bromopyridines. Tetrahedron Lett. 1975, 4467-4470.
    • (1975) Tetrahedron Lett. , pp. 4467-4470
    • Sonogashira, K.1    Tohda, Y.2    Hagihara, N.3
  • 22
    • 0018069223 scopus 로고
    • Facile Synthesis of 2-Substituted Imidazoles
    • Kirk, K. L. Facile Synthesis of 2-Substituted Imidazoles. J. Org. Chem. 1978, 43 (22), 4381-4382.
    • (1978) J. Org. Chem. , vol.43 , Issue.22 , pp. 4381-4382
    • Kirk, K.L.1
  • 23
    • 0001926444 scopus 로고
    • Solid-Phase Synthesis
    • vol. 2, Gross, E., Meienhofer, J., Eds.; Academic Press: New York
    • Barany, G.; Merrifield, R. B. Solid-Phase Synthesis. In The Peptides, vol. 2, Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1979; Vol. 2, pp 1-284.
    • (1979) The Peptides , vol.2 , pp. 1-284
    • Barany, G.1    Merrifield, R.B.2
  • 24
    • 0028227322 scopus 로고
    • Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography
    • Armstrong, D. W.; Tang, Y.; Chen S.; Zhou, Y.; Bagwill, C.; Chen, J. Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography. Anal. Chem. 1994, 66, 1473-1484.
    • (1994) Anal. Chem. , vol.66 , pp. 1473-1484
    • Armstrong, D.W.1    Tang, Y.2    Chen, S.3    Zhou, Y.4    Bagwill, C.5    Chen, J.6
  • 25
    • 0002700089 scopus 로고
    • Methods for studying myristoylCoA:protein N -myristoyltransferase
    • Hooper, N. M., Turner, A. J., Eds.; IRL Press: Oxford
    • Rudnick, D. A.; Durino, R. J.; Gordon, J. I. Methods for studying myristoylCoA:protein N -myristoyltransferase. In Lipid Modifications of Proteins: A Practical Approach; Hooper, N. M., Turner, A. J., Eds.; IRL Press: Oxford, 1992; pp 37-61.
    • (1992) Lipid Modifications of Proteins: A Practical Approach , pp. 37-61
    • Rudnick, D.A.1    Durino, R.J.2    Gordon, J.I.3
  • 27
    • 15144352323 scopus 로고    scopus 로고
    • Conformationally constrained p-(ω-aminoalkyl)-Phenacetyl-L-Seryl-L-Lysyl-Dipeptide amides as Potent peptidomimetic Inhibitors of Candida albicans and Human MyristoylCoA:Protein N-Myristoyltransferase
    • Nagarajan, S.; Devadas, B.; Zupec, M. E.; Freeman, S. K.; Brown, D. L.; Lu, H.-F.; McWherter, C. A.; Getman, D. P.; Gordon, J. I.; Sikorski, J. A. Conformationally constrained p-(ω-aminoalkyl)-Phenacetyl-L-Seryl-L-Lysyl-Dipeptide amides as Potent peptidomimetic Inhibitors of Candida albicans and Human MyristoylCoA:Protein N-Myristoyltransferase. J. Med. Chem. 1997, 40, 1422-1438.
    • (1997) J. Med. Chem. , vol.40 , pp. 1422-1438
    • Nagarajan, S.1    Devadas, B.2    Zupec, M.E.3    Freeman, S.K.4    Brown, D.L.5    Lu, H.-F.6    McWherter, C.A.7    Getman, D.P.8    Gordon, J.I.9    Sikorski, J.A.10
  • 30
    • 0010673821 scopus 로고
    • Bergmann, E. D., Pullman, B., Eds.; D. Reidel Publishing Co.: Boston, MA
    • Ganellin, C. R. In Molecular and Quantum Pharmacology, Bergmann, E. D., Pullman, B., Eds.; D. Reidel Publishing Co.: Boston, MA, 1975; p 43.
    • (1975) Molecular and Quantum Pharmacology , pp. 43
    • Ganellin, C.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.