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Open AccessFeature PaperArticle

Norhierridin B, a New Hierridin B-Based Hydroquinone with Improved Antiproliferative Activity

Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal
CIIMAR/CIMAR, Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Edifício do Terminal de Cruzeiros do Porto de Leixões, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal
LAQV/REQUIMTE, Laboratory of Microbiology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
LAQV/REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal
Department of Biology, Faculty of Sciences, University of Porto, Rua do Campo Alegre, Edifício FC4, 4169-007 Porto, Portugal
Health and Environment Research Centre, School of Health, Polytechnic Institute of Porto, Rua Dr. António Bernardino de Almeida, 400, 4200-072 Porto, Portugal
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2020, 25(7), 1578;
Received: 10 March 2020 / Revised: 26 March 2020 / Accepted: 29 March 2020 / Published: 30 March 2020
(This article belongs to the Special Issue Nature-Inspired Antitumor Agents )
Hierridin B (6), a methylated hydroquinone isolated from the marine picocyanobacterium Cyanobium sp. LEGE 06113, moderately inhibited the growth of colon adenocarcinoma HT-29 cells. Aiming to improve the potential antitumor activity of this natural product, the demethylated analogue, norhierridin B (10), as well as its structurally-related quinone (9), were synthesized and evaluated for their growth inhibitory effect on a panel of human tumor cell lines, including the triple-negative breast cancer (TNBC) cells MDA-MB-231, SKBR3, and MDA-MB-468. Norhierridin B (10) showed a potent growth inhibitory effect on all cancer cell lines. Moreover, the growth inhibitory effect of compound 10 on MDA-MB-231 cells was associated with cell cycle arrest and apoptosis. Norhierridin B (10) interfered with several p53 transcriptional targets, increasing p21, Bax, and MDM2, while decreasing Bcl-2 protein levels, which suggested the potential activation of a p53 pathway. Altogether, these results evidenced a great improvement of the antitumor activity of hydroquinone 10 when compared to 6 and its structurally-related quinone (9). Notably, hydroquinone 10 displayed a prominent growth inhibitory activity against TNBC cells, which are characterized by high therapeutic resistance. View Full-Text
Keywords: antitumor activity; hierridin B; hydroquinones; quinones antitumor activity; hierridin B; hydroquinones; quinones
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MDPI and ACS Style

Brandão, P.; Moreira, J.; Almeida, J.; Nazareth, N.; Sampaio-Dias, I.E.; Vasconcelos, V.; Martins, R.; Leão, P.; Pinto, M.; Saraíva, L.; Cidade, H. Norhierridin B, a New Hierridin B-Based Hydroquinone with Improved Antiproliferative Activity. Molecules 2020, 25, 1578.

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