Novel amphiphilic pyridinium ionic liquids-supported Schiff bases: ultrasound assisted synthesis, molecular docking and anticancer evaluation

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Abstract

Background

Pyridinium Schiff bases and ionic liquids have attracted increasing interest in medicinal chemistry.

Results

A library of 32 cationic fluorinated pyridinium hydrazone-based amphiphiles tethering fluorinated counteranions was synthesized by alkylation of 4-fluoropyridine hydrazone with various long alkyl iodide exploiting lead quaternization and metathesis strategies. All compounds were assessed for their anticancer inhibition activity towards different cancer cell lines and the results revealed that increasing the length of the hydrophobic chain of the synthesized analogues appears to significantly enhance their anticancer activities. Substantial increase in caspase-3 activity was demonstrated upon treatment with the most potent compounds, namely 8, 28, 29 and 32 suggesting an apoptotic cellular death pathway.

Conclusions

Quantum-polarized ligand docking studies against phosphoinositide 3-kinase α displayed that compounds 2– 6 bind to the kinase site and form H-bond with S774, K802, H917 and D933.

Electronic supplementary material

The online version of this article (10.1186/s13065-018-0489-z) contains supplementary material, which is available to authorized users.

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Most cited references 40

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The Caco-2 cell line as a model of the intestinal barrier: influence of cell and culture-related factors on Caco-2 cell functional characteristics.

Y Sambuy, I. De Angelis, G Ranaldi … (2005)

The human intestinal Caco-2 cell line has been extensively used over the last twenty years as a model of the intestinal barrier. The parental cell line, originally obtained from a human colon adenocarcinoma, undergoes in culture a process of spontaneous differentiation that leads to the formation of a monolayer of cells, expressing several morphological and functional characteristics of the mature enterocyte. Culture-related conditions were shown to influence the expression of these characteristics, in part due to the intrinsic heterogeneity of the parental cell line, leading to selection of sub-populations of cells becoming prominent in the culture. In addition, several clonal cell lines have been isolated from the parental line, exhibiting in general a more homogeneous expression of differentiation traits, while not always expressing all characteristics of the parental line. Culture-related conditions, as well as the different Caco-2 cell lines utilized in different laboratories, often make it extremely difficult to compare results in the literature. This review is aimed at summarizing recent, or previously unreviewed, data from the literature on the effects of culture-related factors and the influence of line sub-types (parental vs. different clonal lines) on the expression of differentiation traits important for the use of Caco-2 cells as a model of the absorptive and defensive properties of the intestinal mucosa. Since the use of Caco-2 cells has grown exponentially in recent years, it is particularly important to highlight these methodological aspects in order to promote the standardization and optimisation of this intestinal model.

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The structure of a human p110alpha/p85alpha complex elucidates the effects of oncogenic PI3Kalpha mutations.

Oleg Schmidt-Kittler, Sandra B. Gabelli, Diana Mandelker … (2007)

PIK3CA, one of the two most frequently mutated oncogenes in human tumors, codes for p110alpha, the catalytic subunit of a phosphatidylinositol 3-kinase, isoform alpha (PI3Kalpha, p110alpha/p85). Here, we report a 3.0 angstrom resolution structure of a complex between p110alpha and a polypeptide containing the p110alpha-binding domains of p85alpha, a protein required for its enzymatic activity. The structure shows that many of the mutations occur at residues lying at the interfaces between p110alpha and p85alpha or between the kinase domain of p110alpha and other domains within the catalytic subunit. Disruptions of these interactions are likely to affect the regulation of kinase activity by p85 or the catalytic activity of the enzyme, respectively. In addition to providing new insights about the structure of PI3Kalpha, these results suggest specific mechanisms for the effect of oncogenic mutations in p110alpha and p85alpha.

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Is Open Access

Biological Activities of Hydrazone Derivatives

Sevim Rollas, S. Küçükgüzel (2007)

There has been considerable interest in the development of novel compounds with anticonvulsant, antidepressant, analgesic, antiinflammatory, antiplatelet, anti- malarial, antimicrobial, antimycobacterial, antitumoral, vasodilator, antiviral and antischistosomiasis activities. Hydrazones possessing an azometine -NHN=C H - proton constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. These observations have been guiding for the development of new hydrazones that possess varied biological activities.

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Author and article information

Contributors

Nadjet Rezki: nadjetrezki@yahoo.fr

Mohamed Reda Aouad: aouadmohamedreda@yahoo.fr

Journal

Journal ID (nlm-ta): Chem Cent J

Journal ID (iso-abbrev): Chem Cent J

Title: Chemistry Central Journal

Publisher: Springer International Publishing (Cham )

ISSN (Electronic): 1752-153X

Publication date (Electronic): 22 November 2018

Publication date PMC-release: 22 November 2018

Publication date Collection: 2018

Volume: 12

Electronic Location Identifier: 118

Affiliations

[1 ]ISNI 0000 0004 1754 9358, GRID grid.412892.4, Department of Chemistry, Faculty of Science, , Taibah University, ; Al-Madinah Al-Munawarah, Medina, 30002 Saudi Arabia

[2 ]Department of Chemistry, Faculty of Sciences, University of Sciences and Technology Mohamed Boudiaf, Laboratoire de Chimie et Electrochimie des Complexes Metalliques (LCECM) USTO-MB, P.O. Box 1505, El M‘nouar, 31000 Oran, Algeria

[3 ]ISNI 0000 0001 2174 4509, GRID grid.9670.8, Department of Pharmaceutical Sciences, Faculty of Pharmacy, , University of Jordan, ; Amman, 11942 Jordan

[4 ]GRID grid.443348.c, Faculty of Pharmacy, , Al-Zaytoonah University, ; Amman, 11733 Jordan

Article

Publisher ID: 489

DOI: 10.1186/s13065-018-0489-z

PMC ID: 6768046

PubMed ID: 30467608

SO-VID: 445572ac-5710-40e8-ab0c-e9f877d967e7

License:

Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License ( http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver ( http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.

History

Date received : 15 March 2018

Date accepted : 13 November 2018

Custom metadata

ScienceOpen disciplines: Chemistry

Keywords: cationic,amphiphilic,pyridinium,hydrazones,ultrasound,anticancer,qpld docking

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ScienceOpen disciplines: Chemistry

Keywords: cationic, amphiphilic, pyridinium, hydrazones, ultrasound, anticancer, qpld docking

Novel amphiphilic pyridinium ionic liquids-supported Schiff bases: ultrasound assisted synthesis, molecular docking and anticancer evaluation

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Most cited references 40

The Caco-2 cell line as a model of the intestinal barrier: influence of cell and culture-related factors on Caco-2 cell functional characteristics.

The structure of a human p110alpha/p85alpha complex elucidates the effects of oncogenic PI3Kalpha mutations.

Biological Activities of Hydrazone Derivatives

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