Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Nov 19:33:106545.
doi: 10.1016/j.dib.2020.106545. eCollection 2020 Dec.

Data for the cytotoxicity, self-assembling properties and synthesis of 4-pyridinium-1,4-dihydropyridines

Klavs Pajuste  1 , Martins Rucins  1 , Ilona Domracheva  1 , Arkadij Sobolev  1 , Nadiia Pikun  1 , Mara Plotniece  2 , Gunars Duburs  1 , Karlis Pajuste  1 , Aiva Plotniece  1
Affiliations

Data for the cytotoxicity, self-assembling properties and synthesis of 4-pyridinium-1,4-dihydropyridines

Klavs Pajuste et al. Data Brief. .

Abstract

In this data file the synthetic procedures for preparation of the original 4-pyridinium-1,4-dihydropyridines (4-Py-1,4-DHP) and their parent compounds - dialkyl 2,6-dimethyl-4-(3-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylates were described. In total, 5 unpublished compounds were obtained and characterised. All the structures of original compounds were confirmed by Nuclear Magnetic Resonance (NMR, including 1H NMR and 13C NMR) and low resolution mass spectra (MS) data. Additionally, the cytotoxic properties of four 4-Py-1,4-DHPs were evaluated on 3 cell lines - normal NIH3T3 (mouse embryonic fibroblast), cancerous HT-1080 (human lung fibrosarcoma) and MH-22A (mouse hepatoma) and self-assembling properties were studied and characterisation of formed nanoparticles were performed using dynamic light scattering technique. In this article provided data are directly related to the previously published research articles - "Novel cationic amphiphilic 1,4-dihydropyridine derivatives for DNA delivery" [1] where compound 5 was tested as gene delivery agent without full physico-chemical characterisation and "Synthesis and studies of calcium channel blocking and antioxidant activities of novel 4-pyridinium and/or N-propargyl substituted 1,4-dihydropyridine derivatives" [2] where synthesis and physico-chemical characterisation as well as calcium channel blocking and antioxidant activities were described for compound 6. Synthesis of other compounds - parent 1,4-DHPs 1 and 2, and 4-Py-1,4-DHPs 3-5, their characterisation, estimation of cytotoxicity and self-assembling properties for all 4-Py-1,4-DHPs 3-6 are reported herein for the first time. Information provided in this data file can be used in medicinal chemistry by other scientists to estimate structure-activity relationships for the analysis and construction of various cationic 1,4-dihydropyridine derivatives and related heterocycles.

Keywords: 1,4-dihydropyridine; Cytotoxicity; Nanoparticles; Pyridinium; Quaternisation; Self-assembling; Structure-activity relationships.

PubMed Disclaimer

Conflict of interest statement

The authors declare that they have no known competing financial interests or personal relationships which have, or could be perceived to have, influenced the work reported in this article.

Figures

Fig. 1
Fig. 1
Synthesis of 4-pyridyl-1,4-DHPs 1,2 and 4-N-pyridinium-1,4-DHPs 3–5.
See this image and copyright information in PMC

References

    1. Hyvonen Z., Plotniece A., Reine I., Chekavichus B., Duburs G., Urtti A. Novel cationic amphiphilic 1,4-dihydropyridine derivatives for DNA delivery. Biochim. Biophys. Acta. 2000;1509(1–2):451–466. - PubMed
    1. Rucins M., Kaldre D., Pajuste K., Fernandes M.A.S., Vicente J.A.F., Klimaviciusa L., Jaschenko E., Kanepe-Lapsa I., Shestakova I., Plotniece M., Gosteva M., Sobolev A., Jansone B., Muceniece R., Klusa V., Plotniece A. Synthesis and studies of calcium channel blocking and antioxidant activities of novel 4-pyridinium and/or N-propargyl substituted 1,4-dihydropyridine derivatives. C. R. Chim. 2014;17(1):69–80. doi: 10.1016/j.crci.2013.07.003. - DOI
    1. Fox H.H., Lewis J.I., Wenner W. Derivatives of 1,3-Dimethyl-2-Azafluorene (1,3-Dimethyl-9-Indeno[2,1-c]Pyridine) J. Org. Chem. 1951;16(8):1259–1270. doi: 10.1021/jo50002a012. - DOI
    1. da Costa Cabrera D., Santa-Helena E., Leal H.P., de Moura R.R., Nery L.E.M., Gonçalves C.A.N., Russowsky D., Montes D'Oca M.G. Synthesis and antioxidant activity of new lipophilic dihydropyridines. Bioorg. Chem. 2019;84:1–16. doi: 10.1016/j.bioorg.2018.11.009. - DOI - PubMed
    1. Meekel A.A.P., Wagenaar A., Šmisterová J., Kroeze J.E., Haadsma P., Bosgraaf B., Stuart M.C.A., Brisson A., Ruiters M.H.J., Hoekstra D., Engberts J.B.F.N. Synthesis of pyridinium amphiphiles used for transfection and some characteristics of Amphiphile/DNA complex formation. Eur. J. Org. Chem. 2000;2000(4):665–673. 10.1002/(sici)1099-0690(200002)2000:4<665::aid−ejoc665>3.0.co;2-a.

LinkOut - more resources