Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
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2016
Authors
Bozinović, NinaSegan, Sandra
Vojnović, Sandra
Pavić, Aleksandar
Solaja, Bogdan A.
Nikodinović-Runić, Jasmina
Opsenica, Igor M.
Article (Published version)
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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:
Zebrafish / Thiepine / Pd-catalyzed S-arylation / Candida sp / antifungalSource:
Chemical Biology & Drug Design, 2016, 88, 6, 795-806Publisher:
- Wiley, Hoboken
Funding / projects:
- Serbian Academy of Sciences and Arts
- The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors (RS-MESTD-Basic Research (BR or ON)-172008)
- Microbial diversity study and characterization of beneficial environmental microorganisms (RS-MESTD-Basic Research (BR or ON)-173048)
DOI: 10.1111/cbdd.12809
ISSN: 1747-0277
PubMed: 27316378
WoS: 000387362800002
Scopus: 2-s2.0-84978886752
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Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Bozinović, Nina AU - Segan, Sandra AU - Vojnović, Sandra AU - Pavić, Aleksandar AU - Solaja, Bogdan A. AU - Nikodinović-Runić, Jasmina AU - Opsenica, Igor M. PY - 2016 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/919 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 EP - 806 IS - 6 SP - 795 VL - 88 DO - 10.1111/cbdd.12809 ER -
@article{ author = "Bozinović, Nina and Segan, Sandra and Vojnović, Sandra and Pavić, Aleksandar and Solaja, Bogdan A. and Nikodinović-Runić, Jasmina and Opsenica, Igor M.", 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", pages = "806-795", number = "6", volume = "88", doi = "10.1111/cbdd.12809" }
Bozinović, N., Segan, S., Vojnović, S., Pavić, A., Solaja, B. A., Nikodinović-Runić, J.,& Opsenica, I. M.. (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
Bozinović N, Segan S, Vojnović S, Pavić A, Solaja BA, Nikodinović-Runić J, Opsenica IM. 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 .
Bozinović, Nina, Segan, Sandra, Vojnović, Sandra, Pavić, Aleksandar, Solaja, Bogdan A., Nikodinović-Runić, Jasmina, Opsenica, Igor M., "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 . .