-
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,
Jazyk angličtina Země Švýcarsko
Typ dokumentu časopisecké články
Free Medical Journals od 1997
PubMed Central od 2001
Europe PubMed Central od 2001
ProQuest Central od 1997-01-01
Open Access Digital Library od 1997-01-01
Medline Complete (EBSCOhost) od 2009-03-01
Health & Medicine (ProQuest) od 1997-01-01
Odkazy
PubMed
28925956
DOI
10.3390/molecules22091573
Knihovny.cz E-zdroje
- MeSH
- aldehydy chemická syntéza farmakologie MeSH
- antibakteriální látky chemická syntéza chemie farmakologie MeSH
- antifungální látky chemická syntéza chemie farmakologie MeSH
- antiinfekční látky chemická syntéza farmakologie MeSH
- buňky Hep G2 MeSH
- lidé MeSH
- mikrobiální testy citlivosti MeSH
- pyrimidiny chemická syntéza farmakologie MeSH
- Schiffovy báze chemická syntéza farmakologie MeSH
- sulfadiazin analogy a deriváty chemická syntéza farmakologie MeSH
- viabilita buněk účinky léků MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
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.
- 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