Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones
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Basić, J.Kalinić, Marko

Ivković, Branka

Erić, Slavica
Milenković, Marina

Vladimirov, S.
Vujić, Zorica

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Twelve 2'-hydroxy chalcones were synthesized and their in vitro antibacterial activity was tested using eight standard strains of bacteria: S. aureus (ATCC 25923), S. epidermidis (ATCC 12228), B. subtilis (ATCC 6633), M. luteus (ATCC 10240), M. flavus (ATCC 9341), E. faecalis (ATCC 29212), K. pneumoniae (NCIMB 9111) and P. aeruginosa (ATCC 27853). All 2'-hydroxy chalcones have shown moderate to good antimicrobial activity, determined by microdilution method. QSAR analysis was performed for all the cases, R-2 = 0.918 - 0.997. The results of our QSAR analysis indicate that an alternative and complementary mechanism of action is a major determinant of 2'-hydroxy chalcone antibacterial efficiency. These chalcone derivatives posses the ability to act as bidendate chelating agents whereby the ketone moiety forms a coordinate bond and the 2'-hydroxy group forms a covalent bond with a corresponding metal ion. Chelate formation can disrupt the function of bacterial metalloproteins wich may affe...ct the further growth of bacterial cells.
Keywords:
Synthesis / Chalcones / QSAR / antybacterial activitySource:
Digest Journal of Nanomaterials and Biostructures, 2014, 9, 4, 1537-1546Publisher:
- Inst Materials Physics, Bucharest
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PharmacyTY - JOUR AU - Basić, J. AU - Kalinić, Marko AU - Ivković, Branka AU - Erić, Slavica AU - Milenković, Marina AU - Vladimirov, S. AU - Vujić, Zorica PY - 2014 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2114 AB - Twelve 2'-hydroxy chalcones were synthesized and their in vitro antibacterial activity was tested using eight standard strains of bacteria: S. aureus (ATCC 25923), S. epidermidis (ATCC 12228), B. subtilis (ATCC 6633), M. luteus (ATCC 10240), M. flavus (ATCC 9341), E. faecalis (ATCC 29212), K. pneumoniae (NCIMB 9111) and P. aeruginosa (ATCC 27853). All 2'-hydroxy chalcones have shown moderate to good antimicrobial activity, determined by microdilution method. QSAR analysis was performed for all the cases, R-2 = 0.918 - 0.997. The results of our QSAR analysis indicate that an alternative and complementary mechanism of action is a major determinant of 2'-hydroxy chalcone antibacterial efficiency. These chalcone derivatives posses the ability to act as bidendate chelating agents whereby the ketone moiety forms a coordinate bond and the 2'-hydroxy group forms a covalent bond with a corresponding metal ion. Chelate formation can disrupt the function of bacterial metalloproteins wich may affect the further growth of bacterial cells. PB - Inst Materials Physics, Bucharest T2 - Digest Journal of Nanomaterials and Biostructures T1 - Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones VL - 9 IS - 4 SP - 1537 EP - 1546 UR - https://hdl.handle.net/21.15107/rcub_farfar_2114 ER -
@article{ author = "Basić, J. and Kalinić, Marko and Ivković, Branka and Erić, Slavica and Milenković, Marina and Vladimirov, S. and Vujić, Zorica", year = "2014", abstract = "Twelve 2'-hydroxy chalcones were synthesized and their in vitro antibacterial activity was tested using eight standard strains of bacteria: S. aureus (ATCC 25923), S. epidermidis (ATCC 12228), B. subtilis (ATCC 6633), M. luteus (ATCC 10240), M. flavus (ATCC 9341), E. faecalis (ATCC 29212), K. pneumoniae (NCIMB 9111) and P. aeruginosa (ATCC 27853). All 2'-hydroxy chalcones have shown moderate to good antimicrobial activity, determined by microdilution method. QSAR analysis was performed for all the cases, R-2 = 0.918 - 0.997. The results of our QSAR analysis indicate that an alternative and complementary mechanism of action is a major determinant of 2'-hydroxy chalcone antibacterial efficiency. These chalcone derivatives posses the ability to act as bidendate chelating agents whereby the ketone moiety forms a coordinate bond and the 2'-hydroxy group forms a covalent bond with a corresponding metal ion. Chelate formation can disrupt the function of bacterial metalloproteins wich may affect the further growth of bacterial cells.", publisher = "Inst Materials Physics, Bucharest", journal = "Digest Journal of Nanomaterials and Biostructures", title = "Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones", volume = "9", number = "4", pages = "1537-1546", url = "https://hdl.handle.net/21.15107/rcub_farfar_2114" }
Basić, J., Kalinić, M., Ivković, B., Erić, S., Milenković, M., Vladimirov, S.,& Vujić, Z.. (2014). Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones. in Digest Journal of Nanomaterials and Biostructures Inst Materials Physics, Bucharest., 9(4), 1537-1546. https://hdl.handle.net/21.15107/rcub_farfar_2114
Basić J, Kalinić M, Ivković B, Erić S, Milenković M, Vladimirov S, Vujić Z. Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones. in Digest Journal of Nanomaterials and Biostructures. 2014;9(4):1537-1546. https://hdl.handle.net/21.15107/rcub_farfar_2114 .
Basić, J., Kalinić, Marko, Ivković, Branka, Erić, Slavica, Milenković, Marina, Vladimirov, S., Vujić, Zorica, "Synthesis, QSAR analysis and mechanism of antybacterial activity of simple 2 '-hydroxy chalcones" in Digest Journal of Nanomaterials and Biostructures, 9, no. 4 (2014):1537-1546, https://hdl.handle.net/21.15107/rcub_farfar_2114 .