Antioxidant and Antibacterial Properties of Carbosilane Dendrimers Functionalized with Polyphenolic Moieties.

antibacterial antioxidants carbosilane dendrimers polyphenols

Journal

Pharmaceutics
ISSN: 1999-4923
Titre abrégé: Pharmaceutics
Pays: Switzerland
ID NLM: 101534003

Informations de publication

Date de publication:
24 Jul 2020
Historique:
received: 24 06 2020
revised: 21 07 2020
accepted: 22 07 2020
entrez: 30 7 2020
pubmed: 30 7 2020
medline: 30 7 2020
Statut: epublish

Résumé

A new family of polyphenolic carbosilane dendrimers functionalized with ferulic, caffeic, and gallic acids has been obtained through a straightforward amidation reaction. Their antioxidant activity has been studied by different techniques such as DPPH (2,2'-diphenyl-1-picrylhydrazyl) radical scavenging assay, FRAP assay (ferric reducing antioxidant power), and cyclic voltammetry. The antioxidant analysis showed that polyphenolic dendrimers exhibited higher activities than free polyphenols in all cases. The first-generation dendrimer decorated with gallic acid stood out as the best antioxidant compound, displaying a correlation between the number of hydroxyl groups in the polyphenol structure and the antioxidant activity of the compounds. Moreover, the antibacterial capacity of these new systems has been screened against Gram-positive (+) and Gram-negative (-) bacteria, and we observed that polyphenolic dendrimers functionalized with caffeic and gallic acids were capable of decreasing bacterial growth. In contrast, ferulic carbosilane dendrimers and free polyphenols showed no effect, establishing a correlation between antioxidant activity and antibacterial capacity. Finally, a viability assay in human skin fibroblasts cells (HFF-1) allowed for corroborating the nontoxicity of the polyphenolic dendrimers at their active antibacterial concentration.

Identifiants

pubmed: 32722069
pii: pharmaceutics12080698
doi: 10.3390/pharmaceutics12080698
pmc: PMC7464503
pii:
doi:

Types de publication

Journal Article

Langues

eng

Subventions

Organisme : Ministerio de Ciencia y Tecnología
ID : CTQ2017-86224-
Organisme : Junta de Comunidades de Castilla-La Mancha
ID : SBPLY/17/180501/000358
Organisme : Comunidad de Madrid
ID : IMMUNOTHERCAN-CM B2017/BMD-3733 and NANODENDMED II-CM ref. B2017/BMD-3703
Organisme : Marie Skłodowska-Curie
ID : grant agreement 713714
Organisme : Ministerio de Ciencia y Tecnología
ID : CTQ2017-86441-C2-1-R
Organisme : Comunidad de Madrid
ID : TRANSNANOAVANSENS program (S2018/NMT-4349)
Organisme : Centro de Investigación Biomédica en Red en Bioingeniería, Biomateriales y Nanomedicina
ID : funded by the VI National R&D&i Plan 2008-2011, Iniciativa Ingenio 2010, the Consolider Program, and CIBER Actions and financed by the Instituto de Salud Carlos III with assistance from the European Regional Development Fund.

Commentaires et corrections

Type : ErratumIn

Références

Pharmacology. 2019;103(5-6):315-319
pubmed: 30870859
Chem Phys Lipids. 2012 May;165(4):401-7
pubmed: 22343266
Biochem Biophys Res Commun. 1998 Jun 9;247(1):60-4
pubmed: 9636654
Nutrients. 2018 Dec 21;11(1):
pubmed: 30577684
Bioorg Med Chem Lett. 2009 Nov 15;19(22):6326-30
pubmed: 19822425
Nanoscale. 2019 Jul 28;11(28):13330-13342
pubmed: 31271405
Food Chem Toxicol. 2019 Nov;133:110787
pubmed: 31449895
Front Nutr. 2019 Aug 07;6:121
pubmed: 31448280
Nanomaterials (Basel). 2019 Nov 16;9(11):
pubmed: 31744091
Free Radic Res. 2002 Feb;36(2):177-87
pubmed: 11999386
Free Radic Res. 2019 May;53(5):497-521
pubmed: 31039624
Chemistry. 2007;13(2):483-95
pubmed: 17004291
Anal Biochem. 1996 Jul 15;239(1):70-6
pubmed: 8660627
Cancer Cell Int. 2020 Jan 13;20:18
pubmed: 31956296
J Org Chem. 2007 Nov 9;72(23):8863-9
pubmed: 17929977
Free Radic Biol Med. 1994 Jun;16(6):845-50
pubmed: 8070690
Biomed Res Int. 2013;2013:251754
pubmed: 23956973
Org Lett. 2008 Nov 20;10(22):5171-4
pubmed: 18954060
J Am Chem Soc. 2009 Jan 21;131(2):590-601
pubmed: 19113856
Plant Physiol Biochem. 2019 Nov;144:135-143
pubmed: 31563754
J Biomol Struct Dyn. 2018 Oct;36(13):3487-3495
pubmed: 29019428
Free Radic Biol Med. 2000 Mar 15;28(6):860-70
pubmed: 10802216
Biomolecules. 2019 Sep 27;9(10):
pubmed: 31569790
Int J Mol Sci. 2019 Sep 10;20(18):
pubmed: 31510091
Skin Pharmacol Physiol. 2018;31(6):332-336
pubmed: 30235459
Biochimie. 2015 Apr;111:125-34
pubmed: 25668210
J Agric Food Chem. 2005 May 18;53(10):4290-302
pubmed: 15884874
Nat Chem. 2012 Mar 22;4(4):255-67
pubmed: 22437709

Auteurs

Natalia Sanz Del Olmo (N)

Department of Organic and Inorganic Chemistry, and Research Institute in Chemistry "Andrés M. del Río" (IQAR), 28871 Alcalá de Henares, Spain.
Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Instituto Ramon y Cajal de Investigacion Sanitaria, IRYCIS, Colmenar Viejo Road, Km 9, 100, 28034 Madrid, Spain.

Cornelia E Peña González (CE)

Department of Organic and Inorganic Chemistry, and Research Institute in Chemistry "Andrés M. del Río" (IQAR), 28871 Alcalá de Henares, Spain.
Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Instituto Ramon y Cajal de Investigacion Sanitaria, IRYCIS, Colmenar Viejo Road, Km 9, 100, 28034 Madrid, Spain.

Jose Daniel Rojas (JD)

Department of Analytical Chemistry, Physical Chemistry and Chemical Engineering, University of Alcalá, Institute in Chemistry "Andrés M. del Río" (IQAR), 28871 Alcalá de Henares, Spain.
Faculty of Bioscience and Technology for Food, Agriculture and Environment University of Teramo, 64023 Teramo, Italy.

Rafael Gómez (R)

Department of Organic and Inorganic Chemistry, and Research Institute in Chemistry "Andrés M. del Río" (IQAR), 28871 Alcalá de Henares, Spain.
Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Instituto Ramon y Cajal de Investigacion Sanitaria, IRYCIS, Colmenar Viejo Road, Km 9, 100, 28034 Madrid, Spain.

Paula Ortega (P)

Department of Organic and Inorganic Chemistry, and Research Institute in Chemistry "Andrés M. del Río" (IQAR), 28871 Alcalá de Henares, Spain.
Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Instituto Ramon y Cajal de Investigacion Sanitaria, IRYCIS, Colmenar Viejo Road, Km 9, 100, 28034 Madrid, Spain.

Alberto Escarpa (A)

Department of Analytical Chemistry, Physical Chemistry and Chemical Engineering, University of Alcalá, Institute in Chemistry "Andrés M. del Río" (IQAR), 28871 Alcalá de Henares, Spain.

Francisco Javier de la Mata (FJ)

Department of Organic and Inorganic Chemistry, and Research Institute in Chemistry "Andrés M. del Río" (IQAR), 28871 Alcalá de Henares, Spain.
Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Instituto Ramon y Cajal de Investigacion Sanitaria, IRYCIS, Colmenar Viejo Road, Km 9, 100, 28034 Madrid, Spain.

Classifications MeSH