Logo of aacPermissionsJournals.ASM.orgJournalAAC ArticleJournal InfoAuthorsReviewers
Antimicrob Agents Chemother. 1993 Jul; 37(7): 1393–1399.
PMCID: PMC187981

Penetration of lipophilic agents with multiple protonation sites into bacterial cells: tetracyclines and fluoroquinolones as examples.

Full text

Full text is available as a scanned copy of the original print version. Get a printable copy (PDF file) of the complete article (1.3M), or click on a page image below to browse page by page. Links to PubMed are also available for Selected References.

Selected References

These references are in PubMed. This may not be the complete list of references from this article.
  • ALBERT A, REES CW. Avidity of the tetracyclines for the cations of metals. Nature. 1956 Mar 3;177(4505):433–434. [PubMed]
  • Argast M, Beck CF. Tetracycline diffusion through phospholipid bilayers and binding to phospholipids. Antimicrob Agents Chemother. 1984 Aug;26(2):263–265. [PMC free article] [PubMed]
  • Asahina Y, Ishizaki T, Suzue S. Recent advances in structure activity relationships in new quinolones. Prog Drug Res. 1992;38:57–106. [PubMed]
  • Ashby J, Piddock LJ, Wise R. An investigation of the hydrophobicity of the quinolones. J Antimicrob Chemother. 1985 Dec;16(6):805–808. [PubMed]
  • Bean RC, Shepherd WC, Chan H. Permeability of lipid bilayer membranes to organic solutes. J Gen Physiol. 1968 Sep;52(3):495–508. [PMC free article] [PubMed]
  • Bedard J, Wong S, Bryan LE. Accumulation of enoxacin by Escherichia coli and Bacillus subtilis. Antimicrob Agents Chemother. 1987 Sep;31(9):1348–1354. [PMC free article] [PubMed]
  • Celesk RA, Robillard NJ. Factors influencing the accumulation of ciprofloxacin in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 1989 Nov;33(11):1921–1926. [PMC free article] [PubMed]
  • Chapman JS, Georgopapadakou NH. Routes of quinolone permeation in Escherichia coli. Antimicrob Agents Chemother. 1988 Apr;32(4):438–442. [PMC free article] [PubMed]
  • Chopra I, Hawkey PM, Hinton M. Tetracyclines, molecular and clinical aspects. J Antimicrob Chemother. 1992 Mar;29(3):245–277. [PubMed]
  • Cohen SP, Hooper DC, Wolfson JS, Souza KS, McMurry LM, Levy SB. Endogenous active efflux of norfloxacin in susceptible Escherichia coli. Antimicrob Agents Chemother. 1988 Aug;32(8):1187–1191. [PMC free article] [PubMed]
  • Colaizzi JL, Klink PR. pH-Partition behavior of tetracyclines. J Pharm Sci. 1969 Oct;58(10):1184–1189. [PubMed]
  • Diver JM, Piddock LJ, Wise R. The accumulation of five quinolone antibacterial agents by Escherichia coli. J Antimicrob Chemother. 1990 Mar;25(3):319–333. [PubMed]
  • Domagala JM, Hanna LD, Heifetz CL, Hutt MP, Mich TF, Sanchez JP, Solomon M. New structure-activity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay. J Med Chem. 1986 Mar;29(3):394–404. [PubMed]
  • Franzblau SG, White KE. Comparative in vitro activities of 20 fluoroquinolones against Mycobacterium leprae. Antimicrob Agents Chemother. 1990 Feb;34(2):229–231. [PMC free article] [PubMed]
  • Furet YX, Deshusses J, Pechère JC. Transport of pefloxacin across the bacterial cytoplasmic membrane in quinolone-susceptible Staphylococcus aureus. Antimicrob Agents Chemother. 1992 Nov;36(11):2506–2511. [PMC free article] [PubMed]
  • Gelber RH. Activity of minocycline in Mycobacterium leprae-infected mice. J Infect Dis. 1987 Jul;156(1):236–239. [PubMed]
  • Haemers A, Leysen DC, Bollaert W, Zhang MQ, Pattyn SR. Influence of N substitution on antimycobacterial activity of ciprofloxacin. Antimicrob Agents Chemother. 1990 Mar;34(3):496–497. [PMC free article] [PubMed]
  • Hirai K, Aoyama H, Irikura T, Iyobe S, Mitsuhashi S. Differences in susceptibility to quinolones of outer membrane mutants of Salmonella typhimurium and Escherichia coli. Antimicrob Agents Chemother. 1986 Mar;29(3):535–538. [PMC free article] [PubMed]
  • Hirai K, Aoyama H, Suzue S, Irikura T, Iyobe S, Mitsuhashi S. Isolation and characterization of norfloxacin-resistant mutants of Escherichia coli K-12. Antimicrob Agents Chemother. 1986 Aug;30(2):248–253. [PMC free article] [PubMed]
  • Hooper DC, Wolfson JS, Souza KS, Ng EY, McHugh GL, Swartz MN. Mechanisms of quinolone resistance in Escherichia coli: characterization of nfxB and cfxB, two mutant resistance loci decreasing norfloxacin accumulation. Antimicrob Agents Chemother. 1989 Mar;33(3):283–290. [PMC free article] [PubMed]
  • Iravani A, Welty GS, Newton BR, Richard GA. Effects of changes in pH, medium, and inoculum size on the in vitro activity of amifloxacin against urinary isolates of Staphylococcus saprophyticus and Escherichia coli. Antimicrob Agents Chemother. 1985 Apr;27(4):449–451. [PMC free article] [PubMed]
  • Nikaido H, Jarlier V. Permeability of the mycobacterial cell wall. Res Microbiol. 1991 May;142(4):437–443. [PubMed]
  • Kashket ER. Stoichiometry of the H+-ATPase of growing and resting, aerobic Escherichia coli. Biochemistry. 1982 Oct 26;21(22):5534–5538. [PubMed]
  • Klopman G, Macina OT, Levinson ME, Rosenkranz HS. Computer automated structure evaluation of quinolone antibacterial agents. Antimicrob Agents Chemother. 1987 Nov;31(11):1831–1840. [PMC free article] [PubMed]
  • Leive L, Telesetsky S, Coleman WG, Jr, Carr D. Tetracyclines of various hydrophobicities as a probe for permeability of Escherichia coli outer membranes. Antimicrob Agents Chemother. 1984 May;25(5):539–544. [PMC free article] [PubMed]
  • McMurry LM, Cullinane JC, Levy SB. Transport of the lipophilic analog minocycline differs from that of tetracycline in susceptible and resistant Escherichia coli strains. Antimicrob Agents Chemother. 1982 Nov;22(5):791–799. [PMC free article] [PubMed]
  • McMurry L, Petrucci RE, Jr, Levy SB. Active efflux of tetracycline encoded by four genetically different tetracycline resistance determinants in Escherichia coli. Proc Natl Acad Sci U S A. 1980 Jul;77(7):3974–3977. [PMC free article] [PubMed]
  • Moreau N, Lacroix P, Fournel L. Antibiotic uptake by bacteria as measured by partition in polymer aqueous phase systems. Anal Biochem. 1984 Aug 15;141(1):94–100. [PubMed]
  • Mortimer PG, Piddock LJ. A comparison of methods used for measuring the accumulation of quinolones by Enterobacteriaceae, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1991 Nov;28(5):639–653. [PubMed]
  • Nikaido H, Vaara M. Molecular basis of bacterial outer membrane permeability. Microbiol Rev. 1985 Mar;49(1):1–32. [PMC free article] [PubMed]
  • Plésiat P, Nikaido H. Outer membranes of gram-negative bacteria are permeable to steroid probes. Mol Microbiol. 1992 May;6(10):1323–1333. [PubMed]
  • Pugsley AP, Schnaitman CA. Outer membrane proteins of Escherichia coli. VII. Evidence that bacteriophage-directed protein 2 functions as a pore. J Bacteriol. 1978 Mar;133(3):1181–1189. [PMC free article] [PubMed]
  • Smith JT, Ratcliffe NT. Einfluss von pH-Wert und Magnesium auf die antibakterielle Aktivität von Chinolonpräparaten. Infection. 1986;14 (Suppl 1):S31–S35. [PubMed]
  • Smith MC, Chopra I. Energetics of tetracycline transport into Escherichia coli. Antimicrob Agents Chemother. 1984 Apr;25(4):446–449. [PMC free article] [PubMed]
  • Stock JB, Rauch B, Roseman S. Periplasmic space in Salmonella typhimurium and Escherichia coli. J Biol Chem. 1977 Nov 10;252(21):7850–7861. [PubMed]
  • Takács-Novák K, Noszál B, Hermecz I, Keresztúri G, Podányi B, Szász G. Protonation equilibria of quinolone antibacterials. J Pharm Sci. 1990 Nov;79(11):1023–1028. [PubMed]
  • Teoh-Chan CH, Cowlishaw A, Eley A, Slater G, Greenwood D. Laboratory evaluation of enoxacin: comparison with norfloxacin and nalidixic acid. J Antimicrob Chemother. 1985 Jan;15(1):45–52. [PubMed]
  • Timmers K, Sternglanz R. Ionization and divalent cation dissociation constants of nalidixic and oxolinic acids. Bioinorg Chem. 1978 Aug;9(2):145–155. [PubMed]
  • Watanabe M, Inoue M, Mitsuhashi S. In vitro activity of amifloxacin against outer membrane mutants of the family Enterobacteriaceae and frequency of spontaneous resistance. Antimicrob Agents Chemother. 1989 Nov;33(11):1837–1840. [PMC free article] [PubMed]
  • Yamaguchi A, Ohmori H, Kaneko-Ohdera M, Nomura T, Sawai T. Delta pH-dependent accumulation of tetracycline in Escherichia coli. Antimicrob Agents Chemother. 1991 Jan;35(1):53–56. [PMC free article] [PubMed]
  • Yoshida H, Bogaki M, Nakamura S, Ubukata K, Konno M. Nucleotide sequence and characterization of the Staphylococcus aureus norA gene, which confers resistance to quinolones. J Bacteriol. 1990 Dec;172(12):6942–6949. [PMC free article] [PubMed]

Articles from Antimicrobial Agents and Chemotherapy are provided here courtesy of American Society for Microbiology (ASM)


Save items

Related citations in PubMed

See reviews...See all...

Cited by other articles in PMC

See all...


  • Cited in Books
    Cited in Books
    PubMed Central articles cited in books
  • PubMed
    PubMed citations for these articles
  • Substance
    PubChem Substance links

Recent Activity

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

See more...