Synthesis and Antimicrobial Activity of P-Tria- zinylphosphonium Salts

Beata Kolesińska 1Zbigniew J. Kamiński 1Wiesław Kaca 2Michał Arabski 2Iwona Konieczna 2

1. Technical University of Łódź, Institute of Organic Chemistry (PŁ), Żeromskiego 116, Łódź 90-924, Poland
2. Department of Microbiology, Institue of Biology, Jan Kochanowski University, Świętokrzyska, Kielce 25-406, Poland

Abstract

Antibiotics are one of our most important weapons in fighting bacterial infections and have greatly benefited the health-related quality of human life since their introduction. However, many commonly used antibiotics have become less and less effective against certain illnesses due to emergence of drug-resistant bacteria. To prevent resistance it is essential to continue search for the new agents, expecting minor resistance of pathogens against them.

Long chain quaternary ammonium compounds exert antibacterial activity against both Gram-positive and Gram-negative bacteria, as well as against other pathogenic species of fungi and protozoa [1]. Quaternary ammonium salts belong to group of hard antibacterial agents [2] that are biologically active and non-metabolizable in vivo (soft drugs [3] are defined as drugs, which are characterized by predictable and controllable in vivo destruction to form non-toxic products after they have achieved their therapeutic role). Thus, although the soft analogs have been shown to possess antibacterial activity in vitro, it is likely that their in vivo activity will be hampered by their chemical instability.

It has been found that quaternary phosphonium salts also showed hard antibacterial activity [4] but scarce motivation to research in this area was caused by difficulties in synthesis of phosphonium salts and limited availability of trialkylphosphines used as starting materials.

In this communication we present results of synthesis and preliminary studies on biological activity of new phosphonium salts obtained in reaction between Bu3P and PPh3 and
2-chloro-4,6-disubstituded-1,3,5-triazines.

Acknowledgements: The study was supported by the Ministry of Science and High Education under the Research Project: N N204 228734.

[1] Petrocci, A.N. Surface-Active Agents: Quaternary Ammonium compounds. In Disinfection, Sterilization and Preservation.; Block, S. S., Ed.; Lea & Febiger Pub.: Philadelphia, 1983; pp 309-329.

[2] (a)Thorsteinsson, T.; Loftsson, T.; Masson, M., Curr. Med.Chem., 2003, 10, 1129-1136; (b) Thorsteinsson, T.; Másson, M.; Kristinsson, K.G.; Hjálmarsdóttir, M.A.; Hilmarsson, H.; Loftsson, T., J. Med. Chem. 2003, 46, 4173-4181.

[3] Bodor, N.; Kaminski, J.J.; Selk, S. J. Med. Chem. 1980, 23, 469-474.

[4] Kanazawa, A.; Ikeda, T.; Endo, T., Antimicrob. Agents Chemotherap, 1994, 38, 945-952.

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Presentation: Poster at VII Multidyscyplinarna Konferencja Nauki o Leku, by Beata Kolesińska
See On-line Journal of VII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2010-03-19 14:52
Revised:   2010-04-13 20:27
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