A New Terminal Cyano Group-containing Benzodiazepine Alkaloid from the Mangrove Endophytic Fungus <i>Penicillium</i> sp

Benzodiazepines that consist of one α- and one β-amino acid residues linked together in a seven-membered heterocyclic ring could be treated as small, rigid, cyclic dipeptides capable of exhibiting a wide range of biological activities. During our research on novel analogues of anthramycin, a tricyclic antibiotic benzodiazepine, we developed the synthesis of two benzodiazepine dimers, obtained through the cyclization of appropriate linear tripeptides. The synthesized compounds were tested on a panel of seven cancer and normal cell lines. The developed molecules exhibited promising cytotoxic activity against the lung cancer cell lines A549 and NCI-H1299 and the epidermoid carcinoma cell line A-431. Moreover, they showed significant selectivity compared to the reference cell lines (BJ—human normal skin fibroblasts and MRC-5—human normal lung cell line). When tested on two isogenic cell lines, HCT116 and HCT116p53-/- (colon cancer), contrary to cisplatin being used as a positive control, the obtained compounds showed a cytotoxic effect independent of the p53 protein status. For the above reasons, the obtained compounds can be considered a new group of promising anticancer agents, useful in the fight against p53-dependent drug resistance in cancers. They can also be treated as convenient, leading structures suitable for further optimization and searching for more active and selective molecules.

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Dimeric Benzodiazepines as Peptide Mimetics to Overcome p53-Dependent Drug Resistance of Tumors

Speina

Wilczek

Mieczkowski

2023

Biomolecules

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Secondary Metabolites and Bioactivities of Penicillium sp. Sourced from Mangrove from 2007 to 2020

Zeng¹,

Huang²,

Wang³

et al. 2021

Chinese Journal of Organic Chemistry

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Mangrove plants grow in tropical and subtropical intertidal zones with acid, salt and oxygen deficit. The particularity of the growth environment provides a special host environment for mangrove fungi. The unique genetic background and metabolic pathway of mangrove-derived fungi make their secondary metabolites have novel structures and diverse biological activities. The genus of Penicillium is widely distributed, which is a large group of mangrove-derived fungi. It can produce metabolites with various structural types and novel structures such as alkaloids, peptides, terpenes, polyketones and other metabolites. Most of them have anti-tumor, anti-inflammatory, anti-bacterial, enzyme inhibitors and other bioactivities. The advances of the 276 natural products produced from mangrove-derived Penicillium in recent 14 years (from 2007 to 2020) are reviewed, in order to provide reference for the development of new natural drugs of mangrove Penicillium sp. fungi.

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A New Terminal Cyano Group-containing Benzodiazepine Alkaloid from the Mangrove Endophytic Fungus Penicillium sp

Cited by 2 publications

References 23 publications

Dimeric Benzodiazepines as Peptide Mimetics to Overcome p53-Dependent Drug Resistance of Tumors

Dimeric Benzodiazepines as Peptide Mimetics to Overcome p53-Dependent Drug Resistance of Tumors

Secondary Metabolites and Bioactivities of Penicillium sp. Sourced from Mangrove from 2007 to 2020

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