• Je něco špatně v tomto záznamu ?

Towards Anticancer and Antibacterial Agents: Design and Synthesis of 1,2,3-Triazol-quinobenzothiazine Derivatives

E. Kisiel-Nawrot, D. Pindjakova, M. Latocha, A. Bak, V. Kozik, K. Suwinska, A. Cizek, J. Jampilek, A. Zięba

. 2023 ; 24 (17) : . [pub] 20230826

Jazyk angličtina Země Švýcarsko

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/bmc23016498

In this paper, we describe a new method for synthesizing hybrid combinations of 1,2,3-triazoles with a tetracyclic quinobenzothiazinium system. The developed approach allowed for the production of a series of new azaphenothiazine derivatives with the 1,2,3-triazole system in different positions of the benzene ring. In practice, the methodology consists of the reaction of triazole aniline derivatives with thioquinanthrenediinium bis-chloride. The structure of the products was determined by 1H-NMR, 13C-NMR spectroscopy, and HR-MS spectrometry, respectively. Moreover, the spatial structure of the molecule and the arrangement of molecules in the crystal (unit cell) were determined by X-ray crystallography. The anticancer activity profiles of the synthesized compounds were tested in vitro against human cancer cells of the A549, SNB-19, and T47D lines and the normal NHDF cell line. Additional tests of antibacterial activity against methicillin-sensitive and methicillin-resistant staphylococci, vancomycin-sensitive and vancomycin-resistant enterococci, and two mycobacterial strains were also performed. In fact, the dependence of anticancer and antibacterial activity on the substituent type and its position in the quinobenzothiazinium system was observed. Furthermore, the distance-guided property evaluation was performed using principal component analysis (PCA) and hierarchical clustering analysis (HCA) on the pool of the calculated descriptors. Finally, the theoretically approximated partition coefficients (clogP) were (inter-)correlated with each other and cross-compared with the empirically specified logPTLC parameters.

Citace poskytuje Crossref.org

000      
00000naa a2200000 a 4500
001      
bmc23016498
003      
CZ-PrNML
005      
20231026105752.0
007      
ta
008      
231013s2023 sz f 000 0|eng||
009      
AR
024    7_
$a 10.3390/ijms241713250 $2 doi
035    __
$a (PubMed)37686059
040    __
$a ABA008 $b cze $d ABA008 $e AACR2
041    0_
$a eng
044    __
$a sz
100    1_
$a Kisiel-Nawrot, Ewa $u Department of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Jagiellońska 4, 41-200 Sosnowiec, Poland
245    10
$a Towards Anticancer and Antibacterial Agents: Design and Synthesis of 1,2,3-Triazol-quinobenzothiazine Derivatives / $c E. Kisiel-Nawrot, D. Pindjakova, M. Latocha, A. Bak, V. Kozik, K. Suwinska, A. Cizek, J. Jampilek, A. Zięba
520    9_
$a In this paper, we describe a new method for synthesizing hybrid combinations of 1,2,3-triazoles with a tetracyclic quinobenzothiazinium system. The developed approach allowed for the production of a series of new azaphenothiazine derivatives with the 1,2,3-triazole system in different positions of the benzene ring. In practice, the methodology consists of the reaction of triazole aniline derivatives with thioquinanthrenediinium bis-chloride. The structure of the products was determined by 1H-NMR, 13C-NMR spectroscopy, and HR-MS spectrometry, respectively. Moreover, the spatial structure of the molecule and the arrangement of molecules in the crystal (unit cell) were determined by X-ray crystallography. The anticancer activity profiles of the synthesized compounds were tested in vitro against human cancer cells of the A549, SNB-19, and T47D lines and the normal NHDF cell line. Additional tests of antibacterial activity against methicillin-sensitive and methicillin-resistant staphylococci, vancomycin-sensitive and vancomycin-resistant enterococci, and two mycobacterial strains were also performed. In fact, the dependence of anticancer and antibacterial activity on the substituent type and its position in the quinobenzothiazinium system was observed. Furthermore, the distance-guided property evaluation was performed using principal component analysis (PCA) and hierarchical clustering analysis (HCA) on the pool of the calculated descriptors. Finally, the theoretically approximated partition coefficients (clogP) were (inter-)correlated with each other and cross-compared with the empirically specified logPTLC parameters.
650    _2
$a lidé $7 D006801
650    12
$a antibakteriální látky $x farmakologie $7 D000900
650    12
$a vankomycin $7 D014640
650    _2
$a buněčné linie $7 D002460
650    _2
$a chloridy $7 D002712
650    _2
$a shluková analýza $7 D016000
655    _2
$a časopisecké články $7 D016428
700    1_
$a Pindjakova, Dominika $u Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 842 15 Bratislava, Slovakia
700    1_
$a Latocha, Malgorzata $u Department of Cell Biology, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Jedności 9, 41-200 Sosnowiec, Poland
700    1_
$a Bak, Andrzej $u Institute of Chemistry, University of Silesia, Szkolna 9, 40-006 Katowice, Poland $1 https://orcid.org/0000000298421289
700    1_
$a Kozik, Violetta $u Institute of Chemistry, University of Silesia, Szkolna 9, 40-006 Katowice, Poland
700    1_
$a Suwinska, Kinga $u Faculty of Mathematics and Natural Sciences, Cardinal Stefan Wyszyński University, K. Woycickiego 1/3, 01-938 Warszawa, Poland
700    1_
$a Cizek, Alois $u Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary Sciences Brno, Palackeho tr. 1946/1, 612 42 Brno, Czech Republic $1 https://orcid.org/0000000157064601
700    1_
$a Jampilek, Josef $u Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 842 15 Bratislava, Slovakia $u Institute of Neuroimmunology, Slovak Academy of Sciences, Dubravska Cesta 9, 845 10 Bratislava, Slovakia $1 https://orcid.org/0000000320039052 $7 xx0027075
700    1_
$a Zięba, Andrzej $u Department of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Jagiellońska 4, 41-200 Sosnowiec, Poland $1 https://orcid.org/0000000278413097
773    0_
$w MED00176142 $t International journal of molecular sciences $x 1422-0067 $g Roč. 24, č. 17 (2023)
856    41
$u https://pubmed.ncbi.nlm.nih.gov/37686059 $y Pubmed
910    __
$a ABA008 $b sig $c sign $y - $z 0
990    __
$a 20231013 $b ABA008
991    __
$a 20231026105747 $b ABA008
999    __
$a ok $b bmc $g 2000172 $s 1202860
BAS    __
$a 3
BAS    __
$a PreBMC-MEDLINE
BMC    __
$a 2023 $b 24 $c 17 $e 20230826 $i 1422-0067 $m International journal of molecular sciences $n Int J Mol Sci $x MED00176142
LZP    __
$a Pubmed-20231013

Najít záznam

Citační ukazatele

Možnosti archivace