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Design and synthesis of amphiphilic 2-hydroxybenzylphosphonium salts with antimicrobial and antitumor dual action
Affiliation:1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov Str. 8, Kazan 420088, Russian Federation;2. Kazan Federal University, Kremlevskaya str. 18, Kazan 420008, Russian Federation;1. The New Zealand Institute for Plant & Food Research Limited, Private Bag 4704, Christchurch Mail Centre, Christchurch, 8140, New Zealand;2. School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand;3. School of Biological Sciences, University of Auckland, Auckland, 1010, New Zealand;4. The New Zealand Institute for Plant & Food Research Limited, 412 No. 1 Road, RD2, Te Puke, 3182, New Zealand;1. Department of Chemistry, College of Sciences, University of Sharjah, Sharjah, PO Box 27272, United Arab Emirates;2. National Centre for Advanced Tribology at Southampton, Department of Mechanical Engineering, University of Southampton, Highfield, Southampton, SO17 1BJ, United Kingdom;3. Electrochemical Engineering Laboratory and Materials Engineering Research Group, Engineering Sciences, University of Southampton, Highfield, Southampton, SO17 1BJ, United Kingdom;1. Kazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, Russia;2. A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov str. 8, Kazan 420088, Russia;1. Department of Biomedical Engineering, Jinan University, Guangzhou 510632, PR China;2. Office of Scientific Research and Development, Sun Yat-Sen University, Guangzhou 510275, PR China
Abstract:Here we report the synthesis and biological evaluation of a series of new 2-hydroxybenzylphosphonium salts (QPS) with antimicrobial and antitumor dual action. The most active compounds exhibit antimicrobial activity at a micromolar level against Gram-positive bacteria Sa (ATCC 209p and clinical isolates), Bc (1–2 μM) and fungi Tm and Ca, and induced no notable hemolysis at MIC. The change in nature of substituents of the same length led to a drastic change of biological activity. Self-assembly behavior of the octadecyl and oleyl derivatives was studied. QPS demonstrated self-assembly within the micromolar range with the formation of nanosized aggregates capable of the solubilizing hydrophobic probe. The synthesized phosphonium salts were tested for cytotoxicity. The most potent salt was active against on M−Hela cell line with IC50 on the level of doxorubicin and good selectivity. According to the cytofluorimetry analysis, the salts induced mitochondria-dependent apoptosis.
Keywords:Phosphonium salts  Grignard reagents  Antimicrobial activity  Cytotoxicity  Phosphine oxides  Cyclization  Critical micelle concentration  Cytofluorimetry
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