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Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives

Authorized Users Only
2016
Authors
Bozinovic, Nina
Šegan, Sandra
Vojnovic, Sandra
Pavić, Aleksandar
Šolaja, Bogdan
Nikodinović-Runić, Jasmina
Opsenica, Igor
Article (Published version)
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Abstract
A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the... antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.

Keywords:
antifungal / Candida sp / Pd-catalyzed S-arylation / Thiepine / Zebrafish
Source:
Chemical Biology & Drug Design, 2016, 88, 6, 795-806
Publisher:
  • Wiley, Hoboken
Funding / projects:
  • The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors (RS-172008)
  • Microbial diversity study and characterization of beneficial environmental microorganisms (RS-173048)
  • Serbian Academy of Sciences and Arts
Note:
  • The peer-reviewed version: http://cer.ihtm.bg.ac.rs/handle/123456789/3192

DOI: 10.1111/cbdd.12809

ISSN: 1747-0277

PubMed: 27316378

WoS: 000387362800002

Scopus: 2-s2.0-84978886752
[ Google Scholar ]
9
7
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1887
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Bozinovic, Nina
AU  - Šegan, Sandra
AU  - Vojnovic, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1887
AB  - A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.
PB  - Wiley, Hoboken
T2  - Chemical Biology & Drug Design
T1  - Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
VL  - 88
IS  - 6
SP  - 795
EP  - 806
DO  - 10.1111/cbdd.12809
ER  - 
@article{
author = "Bozinovic, Nina and Šegan, Sandra and Vojnovic, Sandra and Pavić, Aleksandar and Šolaja, Bogdan and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
abstract = "A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology & Drug Design",
title = "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives",
volume = "88",
number = "6",
pages = "795-806",
doi = "10.1111/cbdd.12809"
}
Bozinovic, N., Šegan, S., Vojnovic, S., Pavić, A., Šolaja, B., Nikodinović-Runić, J.,& Opsenica, I.. (2016). Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design
Wiley, Hoboken., 88(6), 795-806.
https://doi.org/10.1111/cbdd.12809
Bozinovic N, Šegan S, Vojnovic S, Pavić A, Šolaja B, Nikodinović-Runić J, Opsenica I. Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design. 2016;88(6):795-806.
doi:10.1111/cbdd.12809 .
Bozinovic, Nina, Šegan, Sandra, Vojnovic, Sandra, Pavić, Aleksandar, Šolaja, Bogdan, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives" in Chemical Biology & Drug Design, 88, no. 6 (2016):795-806,
https://doi.org/10.1111/cbdd.12809 . .

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