Influence of conversion of penicillin G into a basic derivative on its accumulation and subcellular localization in cultured macrophages

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Published inAntimicrobial Agents and Chemotherapy Vol. 31; no. 3; pp. 410 - 416
Main Authors RENARD, C, VANDERHAEGHE, H. J, CLAES, P. J, ZENEBERGH, A, TULKENS, P. M
Format Journal Article
LanguageEnglish
Published Washington, DC American Society for Microbiology 01.03.1987
Subjects
Animals
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Carbon Radioisotopes
Cells, Cultured
Chemical Phenomena
Chemistry
Macrophages
Macrophages - metabolism
Macrophages - ultrastructure
Medical sciences
Mice
Penicillin G
Penicillin G - analogs & derivatives
Penicillin G - metabolism
Pharmacology. Drug treatments
Research Article
Structure-Activity Relationship
Cell culture
Antibiotic
Lactam
Prodrug
In vitro
Accumulation
Uptake
Activity metabolism relation
Macrophage
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AbstractList beta-Lactam antibiotics do not accumulate in phagocytes, probably because of their acidic character. We therefore synthesized a basic derivative of penicillin G, namely, 14C-labeled N-(3-dimethylamino-propyl)benzylpenicillinamide (ABP), and studied its uptake and subcellular localization in J774 macrophages compared with that of 14C-labeled penicillin G. Whereas the intracellular concentration (Ci) of penicillin G remained lower than its extracellular concentration (Ce), ABP reached a Ci/Ce ratio of 4 to 5. Moreover, approximately 50% of intracellular ABP was found associated with lysosomes after isopycnic centrifugation of cell homogenates in isoosmotic Percoll or hyperosmotic sucrose gradients. The behavior of ABP was thus partly consistent with the model of de Duve et al. (C. de Duve, T. de Barsy, B. Poole, A. Trovet, P. Tulkens, and A. Van Hoof, Biochem. Pharmacol. 23:2495-2531, 1974), in which they described the intralysosomal accumulation of weak organic bases in lysosomes. Although ABP is microbiologically inactive, our results show that beta-lactam antibiotics can be driven into cells by appropriate modification. Further efforts therefore may be warranted in the design of active compounds or prodrugs that may prove useful in the chemotherapy of intracellular infections.
beta -Lactam antibiotics do not accumulate in phagocytes, probably because of their acidic character. The authors therefore synthesized a basic derivative of penicillin G, namely, super(14)C-labeled N-(3-dimethylaminopropyl)benzylpenicillinamide (ABP), and studied its uptake and subcellular localization in J774 macrophages compared with that of super(14)C-labeled penicillin G. Whereas the intracellular concentration (C sub(i)) of penicillin G remained lower than its extracellular concentration (C sub(e)), ABP reached a C sub(i)/C sub(e) ratio of 4 to 5.
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Author P M Tulkens
C Renard
P J Claes
H J Vanderhaeghe
A Zenebergh
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Issue 3
Keywords Cell culture
Antibiotic
Lactam
Prodrug
In vitro
Accumulation
Uptake
Activity metabolism relation
Macrophage
Language English
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PublicationTitle Antimicrobial Agents and Chemotherapy
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beta-Lactam antibiotics do not accumulate in phagocytes, probably because of their acidic character. We therefore synthesized a basic derivative of penicillin...
beta -Lactam antibiotics do not accumulate in phagocytes, probably because of their acidic character. The authors therefore synthesized a basic derivative of...
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SubjectTerms Animals
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Carbon Radioisotopes
Cells, Cultured
Chemical Phenomena
Chemistry
Macrophages
Macrophages - metabolism
Macrophages - ultrastructure
Medical sciences
Mice
Penicillin G
Penicillin G - analogs & derivatives
Penicillin G - metabolism
Pharmacology. Drug treatments
Research Article
Structure-Activity Relationship
Title Influence of conversion of penicillin G into a basic derivative on its accumulation and subcellular localization in cultured macrophages
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Volume 31
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