• Je něco špatně v tomto záznamu ?

Sulfadiazine Salicylaldehyde-Based Schiff Bases: Synthesis, Antimicrobial Activity and Cytotoxicity

M. Krátký, M. Dzurková, J. Janoušek, K. Konečná, F. Trejtnar, J. Stolaříková, J. Vinšová,

. 2017 ; 22 (9) : . [pub] 20170919

Jazyk angličtina Země Švýcarsko

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/bmc19013079

The resistance among microbes has brought an urgent need for new drugs. Thus, we synthesized a series of Schiff bases derived from the sulfa drug sulfadiazine and various salicylaldehydes. The resulting 4-[(2-hydroxybenzylidene)amino]-N-(pyrimidin-2-yl)benzene-sulfonamides were characterized and evaluated against Gram-positive and Gram-negative bacteria, yeasts, moulds, Mycobacterium tuberculosis, nontuberculous mycobacteria (M. kansasii, M. avium) and their cytotoxicity was determined. Among bacteria, the genus Staphylococcus, including methicillin-resistant S. aureus, showed the highest susceptibility, with minimum inhibitory concentration values from 7.81 µM. The growth of Candida sp. and Trichophyton interdigitale was inhibited at concentrations starting from 1.95 µM. 4-[(2,5-Dihydroxybenzylidene)amino]-N-(pyrimidin-2-yl)-benzenesulfonamide was identified as the most selective Schiff base for these strains with no apparent cytotoxicity and a selectivity index higher than 16. With respect to M. tuberculosis and M. kansasii that were inhibited within the range of 8 to 250 µM, unsubstituted 4-[(2-hydroxy-benzylidene)amino]-N-(pyrimidin-2-yl)benzenesulfonamide meets the selectivity requirement. In general, dihalogenation of the salicylic moiety improved the antibacterial and antifungal activity but also increased the cytotoxicity, especially with an increasing atomic mass. Some derivatives offer more advantageous properties than the parent sulfadiazine, thus constituting promising hits for further antimicrobial drug development.

Citace poskytuje Crossref.org

000      
00000naa a2200000 a 4500
001      
bmc19013079
003      
CZ-PrNML
005      
20190405101243.0
007      
ta
008      
190405s2017 sz f 000 0|eng||
009      
AR
024    7_
$a 10.3390/molecules22091573 $2 doi
035    __
$a (PubMed)28925956
040    __
$a ABA008 $b cze $d ABA008 $e AACR2
041    0_
$a eng
044    __
$a sz
100    1_
$a Krátký, Martin $u Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. martin.kratky@faf.cuni.cz.
245    10
$a Sulfadiazine Salicylaldehyde-Based Schiff Bases: Synthesis, Antimicrobial Activity and Cytotoxicity / $c M. Krátký, M. Dzurková, J. Janoušek, K. Konečná, F. Trejtnar, J. Stolaříková, J. Vinšová,
520    9_
$a The resistance among microbes has brought an urgent need for new drugs. Thus, we synthesized a series of Schiff bases derived from the sulfa drug sulfadiazine and various salicylaldehydes. The resulting 4-[(2-hydroxybenzylidene)amino]-N-(pyrimidin-2-yl)benzene-sulfonamides were characterized and evaluated against Gram-positive and Gram-negative bacteria, yeasts, moulds, Mycobacterium tuberculosis, nontuberculous mycobacteria (M. kansasii, M. avium) and their cytotoxicity was determined. Among bacteria, the genus Staphylococcus, including methicillin-resistant S. aureus, showed the highest susceptibility, with minimum inhibitory concentration values from 7.81 µM. The growth of Candida sp. and Trichophyton interdigitale was inhibited at concentrations starting from 1.95 µM. 4-[(2,5-Dihydroxybenzylidene)amino]-N-(pyrimidin-2-yl)-benzenesulfonamide was identified as the most selective Schiff base for these strains with no apparent cytotoxicity and a selectivity index higher than 16. With respect to M. tuberculosis and M. kansasii that were inhibited within the range of 8 to 250 µM, unsubstituted 4-[(2-hydroxy-benzylidene)amino]-N-(pyrimidin-2-yl)benzenesulfonamide meets the selectivity requirement. In general, dihalogenation of the salicylic moiety improved the antibacterial and antifungal activity but also increased the cytotoxicity, especially with an increasing atomic mass. Some derivatives offer more advantageous properties than the parent sulfadiazine, thus constituting promising hits for further antimicrobial drug development.
650    _2
$a aldehydy $x chemická syntéza $x farmakologie $7 D000447
650    _2
$a antibakteriální látky $x chemická syntéza $x chemie $x farmakologie $7 D000900
650    _2
$a antiinfekční látky $x chemická syntéza $x farmakologie $7 D000890
650    _2
$a antifungální látky $x chemická syntéza $x chemie $x farmakologie $7 D000935
650    _2
$a viabilita buněk $x účinky léků $7 D002470
650    _2
$a buňky Hep G2 $7 D056945
650    _2
$a lidé $7 D006801
650    _2
$a mikrobiální testy citlivosti $7 D008826
650    _2
$a pyrimidiny $x chemická syntéza $x farmakologie $7 D011743
650    _2
$a Schiffovy báze $x chemická syntéza $x farmakologie $7 D012545
650    _2
$a vztahy mezi strukturou a aktivitou $7 D013329
650    _2
$a sulfadiazin $x analogy a deriváty $x chemická syntéza $x farmakologie $7 D013411
655    _2
$a časopisecké články $7 D016428
700    1_
$a Dzurková, Magdaléna $u Department of Chemistry, Faculty of Science, J. E. Purkinje University, České mládeže 8, 400 96 Ústí nad Labem, Czech Republic. dzurkova.magda@seznam.cz.
700    1_
$a Janoušek, Jiří $u Department of Pharmacology and Toxicology, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. janousj2@faf.cuni.cz.
700    1_
$a Konečná, Klára $u Department of Biological and Medical Sciences, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. konecna@faf.cuni.cz.
700    1_
$a Trejtnar, František $u Department of Pharmacology and Toxicology, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. trejnarf@faf.cuni.cz.
700    1_
$a Stolaříková, Jiřina $u Laboratory for Mycobacterial Diagnostics and Tuberculosis, Regional Institute of Public Health in Ostrava, Partyzánské námĕstí 7, 702 00 Ostrava, Czech Republic. Jirina.Stolarikova@zu.cz.
700    1_
$a Vinšová, Jarmila $u Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. vinsova@faf.cuni.cz.
773    0_
$w MED00180394 $t Molecules (Basel, Switzerland) $x 1420-3049 $g Roč. 22, č. 9 (2017)
856    41
$u https://pubmed.ncbi.nlm.nih.gov/28925956 $y Pubmed
910    __
$a ABA008 $b sig $c sign $y a $z 0
990    __
$a 20190405 $b ABA008
991    __
$a 20190405101253 $b ABA008
999    __
$a ok $b bmc $g 1392389 $s 1051384
BAS    __
$a 3
BAS    __
$a PreBMC
BMC    __
$a 2017 $b 22 $c 9 $e 20170919 $i 1420-3049 $m Molecules $n Molecules $x MED00180394
LZP    __
$a Pubmed-20190405

Najít záznam

Citační ukazatele

Možnosti archivace