Anticancer Efficacy of Antibacterial Quinobenzothiazines
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F23%3A73622850" target="_blank" >RIV/61989592:15310/23:73622850 - isvavai.cz</a>
Result on the web
<a href="https://www.mdpi.com/2076-3417/13/5/2886" target="_blank" >https://www.mdpi.com/2076-3417/13/5/2886</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/app13052886" target="_blank" >10.3390/app13052886</a>
Alternative languages
Result language
angličtina
Original language name
Anticancer Efficacy of Antibacterial Quinobenzothiazines
Original language description
The antitumor potency of a series of designed and prepared antibacterial quinobenzothiazines was evaluated against different types of human cancer cell lines, such as glioblastoma SNB-19, lung adenocarcinoma A549 and breast cancer T47D, and the activities of the compounds were compared to cisplatin and doxorubicin. 9-Propoxy-5-methyl-12H-quino[3,4-b][1,4]benzo- thiazinium chloride (4a), 9-allyloxy-5-methyl-12H-quino[3,4-b][1,4]benzothiazinium chloride (4d) and 11-benzyloxy-5-methyl-12H-quino[3,4-b][1,4]benzothiazinium chloride (4l) were the most active compounds; their IC50 values against all three cell lines ranged from 5.3 to 9.3 µM. The effective derivatives showed no cytotoxic effect up to 100 µM on normal human dermal fibroblasts (NHDFs). To explore the structure–activity relationship, the effect of the type/nature and position of the substituents on the tetracyclic quinobenzothiazine system on the anticancer activity was investigated. Additionally, the receptor-dependent approach was used to specify the mutual ligand–enzyme (bio)compositions that might be potentially valid for the antitumor characteristics of new quinobenzothiazine derivatives. In particular, the molecular docking procedure was applied for the most potent agents against the human breast cancer line T47D in order to obtain comprehensive knowledge about the aromatase–inhibitor binding mode. The docking study revealed that some regularities in the spatial atomic distribution and nonbonding interactions (e.g., hydrophobic patterns) can be observed for the most active molecules. The surface of the electron-rich aromatic rings of 4d and 4l molecules could also contribute to π–π stacking interactions with protoporphyrin IX (HEM) as well as to the formation of π–cation interactions with the adjacent iron cofactor.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Applied Sciences-Basel
ISSN
2076-3417
e-ISSN
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Volume of the periodical
13
Issue of the periodical within the volume
5
Country of publishing house
CH - SWITZERLAND
Number of pages
9
Pages from-to
"2886-1"-"2886-9"
UT code for WoS article
000948038400001
EID of the result in the Scopus database
2-s2.0-85150197899