Flavonoid Glycosides with a Triazole Moiety for Marine Antifouling Applications: Synthesis and Biological Activity Evaluation.


Journal

Marine drugs
ISSN: 1660-3397
Titre abrégé: Mar Drugs
Pays: Switzerland
ID NLM: 101213729

Informations de publication

Date de publication:
24 Dec 2020
Historique:
received: 05 12 2020
revised: 19 12 2020
accepted: 21 12 2020
entrez: 30 12 2020
pubmed: 31 12 2020
medline: 18 5 2021
Statut: epublish

Résumé

Over the last decades, antifouling coatings containing biocidal compounds as active ingredients were used to prevent biofouling, and eco-friendly alternatives are needed. Previous research from our group showed that polymethoxylated chalcones and glycosylated flavones obtained by synthesis displayed antifouling activity with low toxicity. In this work, ten new polymethoxylated flavones and chalcones were synthesized for the first time, including eight with a triazole moiety. Eight known flavones and chalcones were also synthesized and tested in order to construct a quantitative structure-activity relationship (QSAR) model for these compounds. Three different antifouling profiles were found: three compounds (

Identifiants

pubmed: 33374188
pii: md19010005
doi: 10.3390/md19010005
pmc: PMC7823860
pii:
doi:

Substances chimiques

Flavonoids 0
Glycosides 0
Triazoles 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Subventions

Organisme : Fundação para a Ciência e a Tecnologia
ID : PTDC/BTA-BTA/31422/2017
Organisme : Fundação para a Ciência e a Tecnologia
ID : PTDC/SAU-PUB/28736/2017
Organisme : Fundação para a Ciência e a Tecnologia
ID : PTDC/AAG-TEC/0739/2014
Organisme : North Portugal Regional Operational Programme (Norte 2020)
ID : NORTE-01-0145-FEDER-000040

Références

Mar Drugs. 2017 Aug 28;15(9):
pubmed: 28846624
Sci Total Environ. 2018 Dec 1;643:98-106
pubmed: 29936172
J Environ Monit. 2005 Apr;7(4):288-94
pubmed: 15798794
Int J Mol Sci. 2009 Apr 29;10(5):1978-98
pubmed: 19564933
Bioorg Med Chem Lett. 2015 Jun 15;25(12):2540-4
pubmed: 25959813
Expert Opin Drug Discov. 2012 Jun;7(6):489-501
pubmed: 22607210
J Nat Prod. 2014 Feb 28;77(2):364-9
pubmed: 24547899
Planta Med. 1982 May;45(5):31-4
pubmed: 17396775
J Org Chem. 2005 Apr 1;70(7):2855-8
pubmed: 15787587
J Org Chem. 2002 May 3;67(9):3057-64
pubmed: 11975567
Mar Drugs. 2014 Dec 17;12(12):6113-24
pubmed: 25522319
ScientificWorldJournal. 2013 Jun 06;2013:649485
pubmed: 23844408
Biotechnol Adv. 2015 May-Aug;33(3-4):343-57
pubmed: 25749324
J R Soc Interface. 2006 Feb 22;3(6):37-43
pubmed: 16849215
Aquat Toxicol. 2014 Dec;157:47-56
pubmed: 25456219
Environ Sci Technol. 2017 Feb 7;51(3):1840-1847
pubmed: 28026967
PLoS One. 2015 Apr 21;10(4):e0123652
pubmed: 25897858
Biofouling. 2009;25(4):297-311
pubmed: 19191083
J Pharm Pharmacol. 2001 May;53(5):653-68
pubmed: 11370705
Sci Rep. 2017 Feb 13;7:42424
pubmed: 28205590
Biofouling. 2010;26(2):223-34
pubmed: 19960389
Nat Prod Res. 2019 Nov;33(22):3260-3272
pubmed: 29726719
Drug Des Devel Ther. 2015 Mar 12;9:1585-99
pubmed: 25792812
Drug Discov Today. 2003 Dec 15;8(24):1128-37
pubmed: 14678739
Biofouling. 2013;29(4):381-400
pubmed: 23574197
J Chem Inf Model. 2015 Jul 27;55(7):1316-22
pubmed: 26099013
Mar Pollut Bull. 2003 Nov;46(11):1491-4
pubmed: 14607547
PLoS One. 2016 Feb 10;11(2):e0149131
pubmed: 26863533
Biofouling. 2016 Sep;32(8):871-81
pubmed: 27450150
Comb Chem High Throughput Screen. 2006 Mar;9(3):213-28
pubmed: 16533155
Angew Chem Int Ed Engl. 2002 Jul 15;41(14):2596-9
pubmed: 12203546
PLoS One. 2016 Dec 13;11(12):e0168172
pubmed: 27959916
Chemosphere. 2019 Dec;237:124475
pubmed: 31549636
Environ Toxicol Pharmacol. 2018 Jan;57:115-130
pubmed: 29258017
Biochem Pharmacol. 1961 Jul;7:88-95
pubmed: 13726518
ChemMedChem. 2020 May 6;15(9):749-755
pubmed: 32162478
Mar Drugs. 2017 Aug 28;15(9):
pubmed: 28846626
Chemosphere. 2013 Jan;90(3):1140-8
pubmed: 23069205
Med Res Rev. 2008 Mar;28(2):278-308
pubmed: 17763363
Toxins (Basel). 2015 Jul 24;7(8):2739-56
pubmed: 26213967
Int J Cosmet Sci. 2008 Oct;30(5):353-60
pubmed: 18822041
J Comput Aided Mol Des. 2003 Feb-Apr;17(2-4):241-53
pubmed: 13677490
Sci Total Environ. 2007 Nov 15;387(1-3):166-74
pubmed: 17765949
Chem Asian J. 2011 Oct 4;6(10):2696-718
pubmed: 21954075
Bioorg Med Chem. 2012 Jan 1;20(1):25-33
pubmed: 22177409

Auteurs

Daniela Pereira (D)

Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal.
CIIMAR-Centro Interdisciplinar de Investigação Marinha e Ambiental, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal.

Catarina Gonçalves (C)

CIIMAR-Centro Interdisciplinar de Investigação Marinha e Ambiental, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal.

Beatriz T Martins (BT)

Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal.

Andreia Palmeira (A)

Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal.
CIIMAR-Centro Interdisciplinar de Investigação Marinha e Ambiental, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal.

Vitor Vasconcelos (V)

CIIMAR-Centro Interdisciplinar de Investigação Marinha e Ambiental, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal.
Departamento de Biologia, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre S/N, 4169-007 Porto, Portugal.

Madalena Pinto (M)

Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal.
CIIMAR-Centro Interdisciplinar de Investigação Marinha e Ambiental, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal.

Joana R Almeida (JR)

CIIMAR-Centro Interdisciplinar de Investigação Marinha e Ambiental, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal.

Marta Correia-da-Silva (M)

Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal.
CIIMAR-Centro Interdisciplinar de Investigação Marinha e Ambiental, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal.

Honorina Cidade (H)

Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal.
CIIMAR-Centro Interdisciplinar de Investigação Marinha e Ambiental, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal.

Articles similaires

Robotic Surgical Procedures Animals Humans Telemedicine Models, Animal

Odour generalisation and detection dog training.

Lyn Caldicott, Thomas W Pike, Helen E Zulch et al.
1.00
Animals Odorants Dogs Generalization, Psychological Smell
Animals TOR Serine-Threonine Kinases Colorectal Neoplasms Colitis Mice
Animals Tail Swine Behavior, Animal Animal Husbandry

Classifications MeSH