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|Title:||Insights into the anticancer activity of chiral alkylidene-β-lactams and alkylidene-γ-lactams: Synthesis and biological investigation||Authors:||Alves, Américo J. S.
Alves, Nuno G.
Gomes, Clara S. B.
Gonçalves, Ana Cristina
Ribeiro, Ana Bela Sarmento
Botelho, M. Filomena
Pinho e Melo, Teresa M. V. D.
|Keywords:||Alkylidene-β-lactam; Alkylidene-γ-lactam; Anticancer agents; Esophageal cancer; Fibrosarcoma; Lung cancer; Melanoma; Penicillanates||Issue Date:||1-Jun-2022||Publisher:||Elsevier||Project:||info:eu-repo/grantAgreement/FCT/UIDB/00313/2020
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID/NEU/04539/2019/PT
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB/04539/2020/PT
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP/04539/2020/PT
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB/50006/2020/PT/Associated Laboratory for Green Chemistry - Clean Technologies and Processes
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP/50006/2020/PT/Associated Laboratory for Green Chemistry - Clean Technologies and Processes
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB/04378/2020/PT/Applied Molecular Biosciences Unit
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP/04378/2020/PT/Applied Molecular Biosciences Unit
info:eu-repo/grantAgreement/FCT/3599-PPCDT/RECI/BBB-BEP/0124/2012/PT/Modern Structural Biology: Resources for the advancement of in-house X-ray Crystallography
info:eu-repo/grantAgreement/FCT/OE/SFRH/BD/128910/2017/PT/Novel spiro-lactams as new antimicrobial agents
|Serial title, monograph or event:||Bioorganic & Medicinal Chemistry||Volume:||63||Abstract:||Chiral alkylidene-β-lactams and alkylidene-γ-lactams were synthesized and screened for their in vitro activity against four human cancer cell lines (melanoma, esophageal, lung and fibrosarcoma carcinoma). Alkylidene-β-lactams were synthesized via Wittig reaction of diverse phosphorus ylides with benzhydryl 6-oxopenicillanate, derived from 6-aminopenicillanic acid. Moreover, novel chiral alkylidene-γ-lactams were synthesized through a multistep strategy starting from a chiral substrate (d-penicillamine). The in vitro assays allowed the identification of four compounds with IC50 values < 10 μM for A375 cell line, and three compounds with IC50 values < 10 μM for OE19 cell line. The effect of the most promising compounds on cell death mechanism, reactive oxygen species generation as well as the evaluation of their ability to act as MMP-9 inhibitors were studied. The reported results unveil the potential of alkylidene-β-lactams as anticancer agents.||URI:||https://hdl.handle.net/10316/107426||ISSN:||09680896||DOI:||10.1016/j.bmc.2022.116738||Rights:||embargoedAccess|
|Appears in Collections:||FMUC Medicina - Artigos em Revistas Internacionais|
I&D CIBB - Artigos em Revistas Internacionais
I&D ICBR - Artigos em Revistas Internacionais
I&D CQC - Artigos em Revistas Internacionais
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