Self-assembly of novel molecular complexes of 1,10-phenanthroline and 5-amino-1,10-phenanthroline and evaluation of their in vitro antitumour activity

Kaloyanov, Nikolay; Alexandrova, Radostina; Wesselinova, Diana; Mayer‐Figge, Heike; Sheldrick, William S.; Dimitrov, Georgi

doi:10.1016/j.ejmech.2011.02.018

Cited by 8 publications

(14 citation statements)

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“…In a recent investigation conducted by Zasheva et al (2019), it was concluded that the molecular complexes comprising of phenanthroline moiety were potent anti-breast and anti-prostate cancer candidates [ 12 ]. Similar observation was made by Kaloyanov et al (2011) where the novel molecular complexes containing 5-amino-1,10-phenanthroline exhibiting cytotoxicic potential against the human laryngeal carcinoma (Hep2), human liver cancer (HepG2) and Human glioblastoma multiforme brain tumor (8-MG-BA) cell lines without inhibiting the in vitro human embryonic stem Lep3 cell growth [ 13 ]. All of which established the selective cytotoxicity of the novel amino-1,10-phenanthroline derived imine ligands, PIB and PTM, as observed in the current study.…”

Section: Resultssupporting

confidence: 75%

“…The condensation reaction of 1,10-phenanthrolin-5-amine with 5-bromo-2-hydroxybenzaldehyde and thiophene-3-carbaldehyde yielded PIB and PTM ligands, respectively, as depicted in the Scheme 1. The structural details were elucidated by 1 H, 13 C NMR and mass spectral analysis. In the proton NMR spectra of PIB and PTM ( Figures S1 and S4), the multiplet signals corresponding to the aromatic protons appeared in the region 8.03-6.58 ppm in PIB and 7.84-6.08 ppm in PTM, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…A singlet observed at 8.94 ppm in PIB and at 8.99 ppm in PTM corresponds to imino proton (CH=N). The corresponding 13 C NMR spectra are provided in Figure S2 and S5, which showed imine carbon atom signal at 167.75 and 167.51 ppm in PIB and PTM ligands, respectively. In addition, the aromatic carbon atoms were observed between 126 and 139 ppm.…”

Section: Resultsmentioning

confidence: 99%

“…However, the above observed IC 50 values of PIB as well as PTM when compared against that of the standard drug for cancer, Cisplatin, are high. Cisplatin has a reported IC 50 values of 3.2 μM in MCF-7 [ 13 ], 10.07 μM in HeLa [ 14 ], 4.2 μM in HCT-116 [ 15 ], 3.3 μM in PC-3 [ 16 ] cell lines. However, the associations of cisplatin treatment with nausea, nephro-, cardio-, hepato- and neuro-toxicities are well known [ 17 ].…”

Section: Resultsmentioning

confidence: 99%

“…Supplementary Materials: The following are available online at http://www.mdpi.com/1420-3049/25/12/2865/s1: 1 H, 13 C-NMR and mass spectra of the synthesized compounds.…”

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confidence: 99%

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Tumoricidal Potential of Novel Amino-1,10-phenanthroline Derived Imine Ligands: Chemical Preparation, Structure, and Biological Investigations

Prasad

Pillai²,

Shivamallu

et al. 2020

Molecules

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Herein we report the synthesis and structural elucidation of two novel imine-based ligands, 2-(1,10-phenanthrolin-5-yl)imino)methyl)-5-bromophenol (PIB) and N-(1,10-phenanthrolin-5-yl)-1-(thiophen-3-yl)methanimine (PTM) ligands. An in vitro cytotoxicity assay of the synthesized molecules was carried out against breast, cervical, colorectal, and prostate cancer cell lines as well as immortalized human keratinocytes. The observations indicated that both the molecules possesses dose-dependent selective cytotoxicity of cancer cells with no detrimental effect on the normal cell lines. Furthermore, the detailed computational analysis of newly synthetized ligands (PIB and PTM) has been conducted in order to identify their most important parts from the perspective of local reactivity. The IC50 values of PIB treatment on MCF-7, HeLa, HCT-116 and PC-3 were 15.10, 16.25, 17.88, 17.55 and 23.86 micromoles, respectively. Meanwhile, the IC50 values of PTM on MCF-7, HeLa, HCT-116, PC-3 and HaCat were observed to be 14.82, 15.03, 17.88, 17.28 and 21.22 micromoles, respectively. For computational analysis, we have employed the combination of Density Functional Theory (DFT) calculations and MD simulations. DFT calculations provided us with information about structure and reactivity descriptors based on the electron distribution. Surfaces of molecular electrostatic potential (MEP) and averaged local ionization energy (ALIE) indicated the sites within studied molecules that are most reactive. These results indicated the importance of nitrogen atoms and OH group. Additionally, the values of bond dissociation for hydrogen abstraction showed that both molecules, especially the PTM, are stable toward the influence of autoxidation mechanism. On the other side, MD simulations gave us an insight how ligands interact with water molecules. Namely, the radial distribution functions (RDF) indicated that the hydrogen atom of the OH group in the case of the PIB has the most pronounced interactions with water.

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Section: Resultssupporting

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Supplementary Materials: The following are available online at http://www.mdpi.com/1420-3049/25/12/2865/s1: 1 H, 13 C-NMR and mass spectra of the synthesized compounds.…”

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confidence: 99%

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