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Article

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Creative Commons Attribution 4.0 License
This work is licensed under a Creative Commons Attribution 4.0 License.

Disciplines

Biology

CIT Disciplines

1.6 BIOLOGICAL SCIENCES

Publication Details

Molecules

Copyright © 2013 Otevrel, T. et al.

This study was supported by the IGA VFU Brno 80/2012/FaF, 91/2013/FaF and 65/2012/FVL, the Slovak Grant Agency VEGA, Grant No. 1/0612/11, by Project APVV-0416-10, by Sanofi-Aventis Pharma Slovakia and by the Irish Department of Agriculture Fisheries and Food (FIRM): Refs 08RDCIT601 & 08RDCIT617.

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.

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