Semi-synthesis of novel thebaine derivatives with low cytotoxicity and their antibacterial and antihemolytic properties
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Semi-synthesis of novel thebaine derivatives with low cytotoxicity and their antibacterial and antihemolytic properties. / Hasanpour, Zahra; Salehi, Peyman; Aliahmadi, Atousa; Hoseinpour, Mahdieh; Behboodi, Hossein; Staerk, Dan; Bararjanian, Morteza.
In: Medicinal Chemistry Research, Vol. 32, 2023, p. 1713–1725.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Semi-synthesis of novel thebaine derivatives with low cytotoxicity and their antibacterial and antihemolytic properties
AU - Hasanpour, Zahra
AU - Salehi, Peyman
AU - Aliahmadi, Atousa
AU - Hoseinpour, Mahdieh
AU - Behboodi, Hossein
AU - Staerk, Dan
AU - Bararjanian, Morteza
N1 - Publisher Copyright: © 2023, The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.
PY - 2023
Y1 - 2023
N2 - In the present study, some new 1,2,3-triazole-tethered analogs of N-northebaine were designed and synthesized. The anti-bacterial properties of novel thebaine derivatives were studied on Staphylococcus aureus (S. aureus) and Escherichia coli (E. coli). Based on the results, compounds 5b, 5j and 5m showed the best activities against S. aureus (minimum inhibitory concentration (MIC) ~ 25 μM) compared to the parent compound (MIC ~ 321 μM). The most active anti-bacterial derivatives (i.e., 5b, 5j and 5m) and thebaine were considered as potent anti-bacterial wound healing agents. In this regard, fibroblast cell cytotoxicity and proliferation as well as anti-hemolytic activities of the mentioned compounds were studied. The cytotoxicity assay by using 3-[4,5-dimethylthiazol-2-yl] 2,5-diphenyltetrazolium bromide (MTT) on human dermal fibroblast cell lines (HDF) revealed that products 5j and 5m didn’t show inhibition of cell line growth after 24 h. Based on the investigation results on blood cell disruption for releasing of hemoglobin, compound 5j didn’t exhibit any hemolysis activity in different doses. Graphical Abstract: [Figure not available: see fulltext.]
AB - In the present study, some new 1,2,3-triazole-tethered analogs of N-northebaine were designed and synthesized. The anti-bacterial properties of novel thebaine derivatives were studied on Staphylococcus aureus (S. aureus) and Escherichia coli (E. coli). Based on the results, compounds 5b, 5j and 5m showed the best activities against S. aureus (minimum inhibitory concentration (MIC) ~ 25 μM) compared to the parent compound (MIC ~ 321 μM). The most active anti-bacterial derivatives (i.e., 5b, 5j and 5m) and thebaine were considered as potent anti-bacterial wound healing agents. In this regard, fibroblast cell cytotoxicity and proliferation as well as anti-hemolytic activities of the mentioned compounds were studied. The cytotoxicity assay by using 3-[4,5-dimethylthiazol-2-yl] 2,5-diphenyltetrazolium bromide (MTT) on human dermal fibroblast cell lines (HDF) revealed that products 5j and 5m didn’t show inhibition of cell line growth after 24 h. Based on the investigation results on blood cell disruption for releasing of hemoglobin, compound 5j didn’t exhibit any hemolysis activity in different doses. Graphical Abstract: [Figure not available: see fulltext.]
KW - 1,2,3-Triazole
KW - Blood hemolysis
KW - Click chemistry
KW - Cytotoxicity
KW - Human fibroblast cell
U2 - 10.1007/s00044-023-03074-2
DO - 10.1007/s00044-023-03074-2
M3 - Journal article
AN - SCOPUS:85161471792
VL - 32
SP - 1713
EP - 1725
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
SN - 1054-2523
ER -
ID: 357511019