Antibacterial profiling of abietane-type diterpenoids

Autor: Mikko Vahermo, Fatih Demirci, Vânia M. Moreira, Sara Krogerus, Andreas Helfenstein, Jari Yli-Kauhaluoma, Dorota A. Nawrot, Gökalp İşcan, Päivi Tammela
Přispěvatelé: Faculty of Pharmacy, Bioactivity Screening Group, Division of Pharmaceutical Biosciences, Division of Pharmaceutical Chemistry and Technology, Jari Yli-Kauhaluoma / Principal Investigator, Pharmaceutical Design and Discovery group, Drug Research Program, Anadolu Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Demirci, Fatih, İşcan, Gökalp
Rok vydání: 2017
Předmět:
0301 basic medicine
Antifungal Agents
BALB 3T3 Cells
Abietic acid
Cytotoxicity
116 Chemical sciences
Clinical Biochemistry
Antibiotics
Pharmaceutical Science
medicine.disease_cause
01 natural sciences
Biochemistry
TRYPANOSOMA-CRUZI
Mice
chemistry.chemical_compound
Staphylococcus epidermidis
Streptococcus mitis
Drug Discovery
Abietane
biology
Bacterial Infections
Antimicrobial
Dehydroabietic acid
Anti-Bacterial Agents
3. Good health
317 Pharmacy
Staphylococcus aureus
GROWTH
Molecular Medicine
Methicillin-Resistant Staphylococcus aureus
medicine.drug_class
DEHYDROABIETIC ACID-DERIVATIVES
PINUS-ELLIOTTII
Microbial Sensitivity Tests
Microbiology
03 medical and health sciences
CYTOTOXIC ACTIVITIES
medicine
Animals
Humans
Amino acid derivative
Molecular Biology
ANTIMICROBIAL ACTIVITY
Bacteria
010405 organic chemistry
Organic Chemistry
Fungi
biology.organism_classification
0104 chemical sciences
030104 developmental biology
Mycoses
chemistry
Abietanes
1182 Biochemistry
cell and molecular biology
Zdroj: Bioorganic & Medicinal Chemistry. 25:132-137
ISSN: 0968-0896
0003-9705
DOI: 10.1016/j.bmc.2016.10.019
Popis: WOS: 000397052800016
PubMed ID: 27793449
Abietic and dehydroabietic acid are interesting diterpenes with a highly diverse repertoire of associated bioactivities. They have, among others, shown antibacterial and antifungal activity, potentially valuable in the struggle against the increasing antimicrobial resistance and imminent antibiotic shortage. In this paper, we describe the synthesis of a set of 9 abietic and dehydroabietic acid derivatives containing amino acid side chains and their in vitro antimicrobial profiling against a panel of human pathogenic microbial strains. Furthermore, their in vitro cytotoxicity against mammalian cells was evaluated. The experimental results showed that the most promising compound was 10 [methyl N-(abiet-8,11, 13-trien-18-yl)-D-serinate], with an MIC90 of 60 mu g/mL against Staphylococcus aureus ATCC 25923, and 8 mu g/mL against methicillin-resistant S. aureus, Staphylococcus epidermidis and Streptococcus mitis. The IC50 value for compound 10 against Balb/c 3T3 cells was 45 mu g/mL
European Union Programme FP7 WoodWisdom-Net+ under Academy of Finland [256515]; TUBITAK [110O951]; Academy of Finland [277001, 284477, 264020, 265481]; Magnus Ehrnrooth Foundation [ME2012n44]
This work was supported by the European Union Seventh Framework Programme FP7 WoodWisdom-Net+ under Academy of Finland grant agreement no. 256515 (GREASE) and TUBITAK 110O951. A.H. and P.T. (Grant nos. 277001 and 284477) and J.Y. K. (Grants nos. 264020 and 265481) were also supported by the Academy of Finland. V.M.M. thanks the Magnus Ehrnrooth Foundation (project ME2012n44) for financial support.
Databáze: OpenAIRE
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