메뉴 건너뛰기




Volumn 37, Issue 3-4, 2009, Pages 257-263

Lipophilic pyrazinoic acid amide and ester prodrugs. Stability, activation and activity against M. tuberculosis

Author keywords

Esterases; Pyrazinamide; Pyrazinoic acid; Tuberculosis

Indexed keywords

BUTYLPYRAZINOATE; DODECYLPYRAZINOATE; ESTER DERIVATIVE; HEXADECYLPYRAZINOATE; N DODECYLPYRAZINAMIDE; N HEXADECYLPYRAZINAMIDE; N TETRADECYLPYRAZINAMIDE; PYRAZINOIC ACID; PYRAZINOIC ACID DERIVATIVE; TETRADECYLPYRAZINOATE; UNCLASSIFIED DRUG;

EID: 67349098841     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2009.02.012     Document Type: Article
Times cited : (53)

References (28)
  • 1
    • 0042471938 scopus 로고    scopus 로고
    • Selected lipids activate phagosome actin assembly and maturation resulting in killing of pathogenic mycobacteria
    • Anes E., Kühnel M., Bos E., Moniz-Pereira J., Habermann A., and Griffiths G. Selected lipids activate phagosome actin assembly and maturation resulting in killing of pathogenic mycobacteria. Nat. Cell. Biol. 5 (2003) 793-802
    • (2003) Nat. Cell. Biol. , vol.5 , pp. 793-802
    • Anes, E.1    Kühnel, M.2    Bos, E.3    Moniz-Pereira, J.4    Habermann, A.5    Griffiths, G.6
  • 3
    • 0029780824 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships for the in vitro antimycobacterial activity of pyrazinoic acid esters
    • Bergmann K., Cynamon M., and Welch J. Quantitative structure-activity relationships for the in vitro antimycobacterial activity of pyrazinoic acid esters. J. Med. Chem. 39 (1996) 3394-3400
    • (1996) J. Med. Chem. , vol.39 , pp. 3394-3400
    • Bergmann, K.1    Cynamon, M.2    Welch, J.3
  • 4
    • 0034003580 scopus 로고    scopus 로고
    • pncA mutations as a major mechanism of pyrazinamide resistance in Mycobacterium tuberculosis: spread of a monoresistant strain in Quebec, Canada
    • Cheng S., Thibert L., Sanchez T., Heifets L., and Zhang Y. pncA mutations as a major mechanism of pyrazinamide resistance in Mycobacterium tuberculosis: spread of a monoresistant strain in Quebec, Canada. Antimicrob. Agents Chemother. 44 (2000) 528-532
    • (2000) Antimicrob. Agents Chemother. , vol.44 , pp. 528-532
    • Cheng, S.1    Thibert, L.2    Sanchez, T.3    Heifets, L.4    Zhang, Y.5
  • 6
    • 0001283999 scopus 로고
    • Membrane permeability and transport in Mycobacterium tuberculosis
    • Bloom B.R. (Ed), AFM Press, Washington, DC
    • Connel N.D., and Nikaido H. Membrane permeability and transport in Mycobacterium tuberculosis. In: Bloom B.R. (Ed). Tuberculosis Pathogenesis, Protection and Control (1994), AFM Press, Washington, DC 333-351
    • (1994) Tuberculosis Pathogenesis, Protection and Control , pp. 333-351
    • Connel, N.D.1    Nikaido, H.2
  • 7
    • 0032781772 scopus 로고    scopus 로고
    • Metabolism of primaquine by liver homogenate fractions. Evidence for monoamine oxidase and cytochrome P450 involvement in the oxidative deamination of primaquine to carboxyprimaquine
    • Constantino L., Paixão P., Moreira R., Portela M., Do Rosario V., and Iley J. Metabolism of primaquine by liver homogenate fractions. Evidence for monoamine oxidase and cytochrome P450 involvement in the oxidative deamination of primaquine to carboxyprimaquine. Exp. Toxicol. Pathol. 51 (1999) 299-303
    • (1999) Exp. Toxicol. Pathol. , vol.51 , pp. 299-303
    • Constantino, L.1    Paixão, P.2    Moreira, R.3    Portela, M.4    Do Rosario, V.5    Iley, J.6
  • 9
    • 0026696665 scopus 로고
    • Antimycobacterial activity of a series of pyrazinoic acid esters
    • Cynamon M., Klemens S., Chou T., Gimi R., and Welch J. Antimycobacterial activity of a series of pyrazinoic acid esters. J. Med. Chem. 35 (1992) 1212-1215
    • (1992) J. Med. Chem. , vol.35 , pp. 1212-1215
    • Cynamon, M.1    Klemens, S.2    Chou, T.3    Gimi, R.4    Welch, J.5
  • 10
    • 0028797899 scopus 로고
    • Pulmonary and blood enzyme-kinetics as predictors of pulmonary metabolism of esters
    • Dickinson P., and Taylor G. Pulmonary and blood enzyme-kinetics as predictors of pulmonary metabolism of esters. Int. J. Pharmaceut. 116 (1995) 231-236
    • (1995) Int. J. Pharmaceut. , vol.116 , pp. 231-236
    • Dickinson, P.1    Taylor, G.2
  • 11
    • 51149085652 scopus 로고    scopus 로고
    • Enhancement of the antituberculosis activity of weak acids by inhibitors of energy metabolism but not by anaerobiosis suggests that weak acids act differently from the front-line tuberculosis drug pyrazinamide
    • Gu P., Constantino L., and Zhang Y. Enhancement of the antituberculosis activity of weak acids by inhibitors of energy metabolism but not by anaerobiosis suggests that weak acids act differently from the front-line tuberculosis drug pyrazinamide. J. Med. Microbiol. 57 (2008) 1129-1134
    • (2008) J. Med. Microbiol. , vol.57 , pp. 1129-1134
    • Gu, P.1    Constantino, L.2    Zhang, Y.3
  • 12
    • 0343684856 scopus 로고    scopus 로고
    • Pyrazinamide
    • Yu V.L., Merigan T.C., and Barriere S.L. (Eds), Williams and Wilkins, Baltimore, MD
    • Heifets L.B. Pyrazinamide. In: Yu V.L., Merigan T.C., and Barriere S.L. (Eds). Antimicrobial Therapy and Vaccines (1999), Williams and Wilkins, Baltimore, MD 668-676
    • (1999) Antimicrobial Therapy and Vaccines , pp. 668-676
    • Heifets, L.B.1
  • 15
    • 0014062867 scopus 로고
    • Pyrazinamide susceptibility and amidase activity of tubercle bacilli
    • Konno K., Feldmann F., and McDermott W. Pyrazinamide susceptibility and amidase activity of tubercle bacilli. Am. Rev. Respir. Dis. 95 (1967) 461-469
    • (1967) Am. Rev. Respir. Dis. , vol.95 , pp. 461-469
    • Konno, K.1    Feldmann, F.2    McDermott, W.3
  • 16
    • 27544478172 scopus 로고    scopus 로고
    • Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma
    • Li B., Sedlacek M., Manoharan I., Boopathy R., Duysen E., Masson P., and Lockridge O. Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem. Pharmacol. 70 (2005) 1673-1684
    • (2005) Biochem. Pharmacol. , vol.70 , pp. 1673-1684
    • Li, B.1    Sedlacek, M.2    Manoharan, I.3    Boopathy, R.4    Duysen, E.5    Masson, P.6    Lockridge, O.7
  • 17
    • 67349238888 scopus 로고    scopus 로고
    • Prodrugs of Carboxylic Acids
    • Stella V.J., Borchardt R.T., Hageman M.J., Oliyai R., Maag H., and Tilley J. (Eds), Springer, New York
    • Maag H. Prodrugs of Carboxylic Acids. In: Stella V.J., Borchardt R.T., Hageman M.J., Oliyai R., Maag H., and Tilley J. (Eds). Prodrugs: Challenges and Rewards (2007), Springer, New York 3-30
    • (2007) Prodrugs: Challenges and Rewards , pp. 3-30
    • Maag, H.1
  • 18
    • 84960961533 scopus 로고
    • The fate of Mycobacterium tuberculosis in mouse tissues as determined by the microbial enumeration technique. II. The conversion of tuberculous infection to the latent state by the administration of pyrazinamide and a companion drug
    • McCune R.J., McDermott W., and Tompsett R. The fate of Mycobacterium tuberculosis in mouse tissues as determined by the microbial enumeration technique. II. The conversion of tuberculous infection to the latent state by the administration of pyrazinamide and a companion drug. J. Exp. Med. 104 (1956) 763-802
    • (1956) J. Exp. Med. , vol.104 , pp. 763-802
    • McCune, R.J.1    McDermott, W.2    Tompsett, R.3
  • 19
    • 3042677854 scopus 로고    scopus 로고
    • pncA mutations in pyrazinamide-resistant Mycobacterium tuberculosis isolates in Portugal
    • Portugal I., Barreiro L., Moniz-Pereira J., and Brum L. pncA mutations in pyrazinamide-resistant Mycobacterium tuberculosis isolates in Portugal. Antimicrob. Agents Chemother. 48 (2004) 2736-2738
    • (2004) Antimicrob. Agents Chemother. , vol.48 , pp. 2736-2738
    • Portugal, I.1    Barreiro, L.2    Moniz-Pereira, J.3    Brum, L.4
  • 20
    • 51149102710 scopus 로고    scopus 로고
    • Strober, W., 2001. Trypan blue exclusion test of cell viability. Curr. Protoc. Immunol. Appendix 3, Appendix 3B.
    • Strober, W., 2001. Trypan blue exclusion test of cell viability. Curr. Protoc. Immunol. Appendix 3, Appendix 3B.
  • 23
    • 44449097260 scopus 로고    scopus 로고
    • The proteomic response of Mycobacterium smegmatis to anti-tuberculosis drugs suggests targeted pathways
    • Wang R., and Marcotte E. The proteomic response of Mycobacterium smegmatis to anti-tuberculosis drugs suggests targeted pathways. J. Proteome Res. 7 (2008) 855-865
    • (2008) J. Proteome Res. , vol.7 , pp. 855-865
    • Wang, R.1    Marcotte, E.2
  • 25
    • 17444415369 scopus 로고    scopus 로고
    • The kinetics of phagosome maturation as a function of phagosome/lysosome fusion and acquisition of hydrolytic activity
    • Yates R., Hermetter A., and Russell D. The kinetics of phagosome maturation as a function of phagosome/lysosome fusion and acquisition of hydrolytic activity. Traffic 6 (2005) 413-420
    • (2005) Traffic , vol.6 , pp. 413-420
    • Yates, R.1    Hermetter, A.2    Russell, D.3
  • 26
    • 0037252098 scopus 로고    scopus 로고
    • The curious characteristics of pyrazinamide: a review
    • Zhang Y., and Mitchison D. The curious characteristics of pyrazinamide: a review. Int. J. Tuberc. Lung Dis. 7 (2003) 6-21
    • (2003) Int. J. Tuberc. Lung Dis. , vol.7 , pp. 6-21
    • Zhang, Y.1    Mitchison, D.2
  • 27
    • 0036143960 scopus 로고    scopus 로고
    • Conditions that may affect the results of susceptibility testing of Mycobacterium tuberculosis to pyrazinamide
    • Zhang Y., Permar S., and Sun Z. Conditions that may affect the results of susceptibility testing of Mycobacterium tuberculosis to pyrazinamide. J. Med. Microbiol. 51 (2002) 42-49
    • (2002) J. Med. Microbiol. , vol.51 , pp. 42-49
    • Zhang, Y.1    Permar, S.2    Sun, Z.3
  • 28
    • 0037587282 scopus 로고    scopus 로고
    • Susceptibility of Mycobacterium tuberculosis to weak acids
    • Zhang Y., Zhang H., and Sun Z. Susceptibility of Mycobacterium tuberculosis to weak acids. J. Antimicrob. Chemother. 52 (2003) 56-60
    • (2003) J. Antimicrob. Chemother. , vol.52 , pp. 56-60
    • Zhang, Y.1    Zhang, H.2    Sun, Z.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.