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- Title
Norhierridin B, a New Hierridin B-Based Hydroquinone with Improved Antiproliferative Activity.
- Authors
Brandão, Pedro; Moreira, Joana; Almeida, Joana; Nazareth, Nair; Sampaio-Dias, Ivo E.; Vasconcelos, Vitor; Martins, Rosário; Leão, Pedro; Pinto, Madalena; Saraíva, Lucília; Cidade, Honorina
- Abstract
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.
- Subjects
HYDROQUINONE; TRIPLE-negative breast cancer; QUINONE; BCL-2 proteins; CELL cycle; CANCER cells; COLON (Anatomy)
- Publication
Molecules, 2020, Vol 25, Issue 7, p1578
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules25071578