Literature DB >> 31260187

Antifungal, anticancer, and docking studies of colchiceine complexes with monovalent metal cation salts.

Joanna Kurek1, Patrycja Kwaśniewska-Sip2, Krzysztof Myszkowski3, Grzegorz Cofta4, Piotr Barczyński1, Marek Murias3, Rafał Kurczab5, Paweł Śliwa6, Piotr Przybylski1.   

Abstract

Complexes of colchiceine with monovalent cation perchlorates and iodides have been obtained and characterized by spectroscopic methods. DFT and spectroscopic studies reveal that the dihedral angle ω1-1a-12-12a , crucial for colchicine biological mechanism of action, that is, binding to tubulins depends on the diameter of the complexed metal cation. Biological tests indicated no antifungal properties of colchicine (it was active only toward A.pullulans), in contrast to its derivative-(colchiceine). Complexation of colchiceine with metal cations improved significantly the antifungal potency, even below MIC <1 μg/ml. The colchiceine complexes were more potent than colchiceine, and some of them were even more potent than the fungicidal standard IPBC. The highest potency of colchiceine complexes was noted against A. pullulans (MIC = 0.5 μg/ml). In contrast to the findings concerning antifungal potency, the anticancer studies showed complexes of colchicine more active (~IC50  = 2 nM) than those of colchiceine (~IC50  = 6 μM). MDA-MB-231 breast cancer cell lines and human lung fibroblasts CCD39Lu were also tested.
© 2019 John Wiley & Sons A/S.

Entities:  

Keywords:  colchiceine; complexes with metal iodides and perchlorates; cytotoxic activity; fungistatic activity; tropolone alkaloids

Year:  2019        PMID: 31260187     DOI: 10.1111/cbdd.13583

Source DB:  PubMed          Journal:  Chem Biol Drug Des        ISSN: 1747-0277            Impact factor:   2.817


  2 in total

1.  Design, synthesis and antifungal activity of (E)-3-acyl-5-(methoxyimino)-1,5-dihydrobenzo[e][1,2]oxazepin-4(3H)-one analogues.

Authors:  Dongyan Yang; Haixia Wang; Zhijin Fan; Zhengming Li; Shuang Zhou; Zesheng Hao; You Lv; Tatiana A Kalinina; Tatiana V Glukhareva
Journal:  Mol Divers       Date:  2020-01-21       Impact factor: 2.943

2.  Regioselective approach to colchiceine tropolone ring functionalization at C(9) and C(10) yielding new anticancer hybrid derivatives containing heterocyclic structural motifs.

Authors:  Krystian Pyta; Natalia Skrzypczak; Piotr Ruszkowski; Franz Bartl; Piotr Przybylski
Journal:  J Enzyme Inhib Med Chem       Date:  2022-12       Impact factor: 5.051

  2 in total

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