Molecules 2013, 18(9), 10648-10670; doi:10.3390/molecules180910648
Article

Antimycobacterial and Photosynthetic Electron Transport Inhibiting Activity of Ring-Substituted 4-Arylamino-7-Chloroquinolinium Chlorides

1 Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic 2 Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic 3 Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland 4 Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia 5 Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic 6 Department of Veterinary Public Health and Toxicology, Faculty of Veterinary Hygiene and Ecology, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic 7 Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic 8 Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
* Author to whom correspondence should be addressed.
Received: 17 July 2013; in revised form: 19 August 2013 / Accepted: 26 August 2013 / Published: 2 September 2013
(This article belongs to the Section Medicinal Chemistry)
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Abstract: In this study, a series of twenty-five ring-substituted 4-arylamino-7-chloroquinolinium chlorides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts and also primary in vitro screening of the synthesized compounds was performed against mycobacterial species. 4-[(2-Bromophenyl)amino]-7-chloroquinolinium chloride showed high biological activity against M. marinum, M. kansasii, M. smegmatis and 7-chloro-4-[(2-methylphenyl)amino]quinolinium chloride demonstrated noteworthy biological activity against M. smegmatis and M. avium subsp. paratuberculosis. The most effective compounds demonstrated quite low toxicity (LD50 > 20 μmol/L) against the human monocytic leukemia THP-1 cell line within preliminary in vitro cytotoxicity screening. The tested compounds were found to inhibit PET in photosystem II. The PET-inhibiting activity expressed by IC50 value of the most active compound 7-chloro-4-[(3-trifluoromethylphenyl)amino]quinolinium chloride was 27 μmol/L and PET-inhibiting activity of ortho-substituted compounds was significantly lower than this of meta- and para-substituted ones. The structure-activity relationships are discussed for all compounds.
Keywords: 4-arylamino-7-chloroquinolines; photosynthetic electron transport inhibition; spinach chloroplasts; in vitro antimycobacterial activity; in vitro cytotoxicity; structure-activity relationships

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MDPI and ACS Style

Otevrel, J.; Bobal, P.; Zadrazilova, I.; Govender, R.; Pesko, M.; Keltosova, S.; Koleckarova, P.; Marsalek, P.; Imramovsky, A.; Coffey, A.; O'Mahony, J.; Kollar, P.; Cizek, A.; Kralova, K.; Jampilek, J. Antimycobacterial and Photosynthetic Electron Transport Inhibiting Activity of Ring-Substituted 4-Arylamino-7-Chloroquinolinium Chlorides. Molecules 2013, 18, 10648-10670.

AMA Style

Otevrel J, Bobal P, Zadrazilova I, Govender R, Pesko M, Keltosova S, Koleckarova P, Marsalek P, Imramovsky A, Coffey A, O'Mahony J, Kollar P, Cizek A, Kralova K, Jampilek J. Antimycobacterial and Photosynthetic Electron Transport Inhibiting Activity of Ring-Substituted 4-Arylamino-7-Chloroquinolinium Chlorides. Molecules. 2013; 18(9):10648-10670.

Chicago/Turabian Style

Otevrel, Jan; Bobal, Pavel; Zadrazilova, Iveta; Govender, Rodney; Pesko, Matus; Keltosova, Stanislava; Koleckarova, Petra; Marsalek, Petr; Imramovsky, Ales; Coffey, Aidan; O'Mahony, Jim; Kollar, Peter; Cizek, Alois; Kralova, Katarina; Jampilek, Josef. 2013. "Antimycobacterial and Photosynthetic Electron Transport Inhibiting Activity of Ring-Substituted 4-Arylamino-7-Chloroquinolinium Chlorides." Molecules 18, no. 9: 10648-10670.

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