Informacja

Drogi użytkowniku, aplikacja do prawidłowego działania wymaga obsługi JavaScript. Proszę włącz obsługę JavaScript w Twojej przeglądarce.

Tytuł pozycji:

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

Tytuł:
Tumoricidal Potential of Novel Amino-1,10-phenanthroline Derived Imine Ligands: Chemical Preparation, Structure, and Biological Investigations.
Autorzy:
Prasad KS; Department of Sciences, Amrita School of Arts and Sciences, Amrita Vishwa Vidyapeetham, Mysuru 5700 26, Karnataka, India.
Pillai RR; Central Polytechnic College, Vattiyoorkavu, Trivandrum 695013, Kerala, India.; Department of Physics, T.K.M. College of Arts and Science, Karicode, Kollam 691 005, Kerala, India.
Shivamallu C; Division of Biotechnology and Bioinformatics, School of Life Sciences, JSS Academy of Higher Education & Research, Mysuru 570 015, Karnataka, India.
Prasad SK; Division of Biotechnology and Bioinformatics, School of Life Sciences, JSS Academy of Higher Education & Research, Mysuru 570 015, Karnataka, India.
Jain AS; Department of Physics, T.K.M. College of Arts and Science, Karicode, Kollam 691 005, Kerala, India.
Pradeep S; Division of Biotechnology and Bioinformatics, School of Life Sciences, JSS Academy of Higher Education & Research, Mysuru 570 015, Karnataka, India.
Armaković S; Department of Physics, Faculty of Sciences, University of Novi Sad, Trg D. Obradovića 4, Novi Sad 21000, Serbia.
Armaković SJ; Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg D. Obradovića 3, Novi Sad 21000, Serbia.
Srinivasa C; Department of Biotechnology, Davangere University, Shivagangotri, Davangere 577 007, Karnataka, India.
Kallimani S; Department of PG Studies & Research in Food Technology, Davangere University, Shivagangotri, Davangere 577 007, Karnataka, India.
Amachawadi RG; Department of Clinical Sciences, College of Veterinary Medicine, Kansas State University, Manhattan, KS 66506, USA.
Ankegowda VM; Department of Chemistry, Bangalore Institute of Technology, K.R. Road, V V Puram, Bangalore 560 004, Karnataka, India.
Marraiki N; Department of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
Elgorban AM; Department of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.; Centre of Excellence in Biotechnology Research, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
Syed A; Department of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
Źródło:
Molecules (Basel, Switzerland) [Molecules] 2020 Jun 22; Vol. 25 (12). Date of Electronic Publication: 2020 Jun 22.
Typ publikacji:
Journal Article
Język:
English
Imprint Name(s):
Original Publication: Basel, Switzerland : MDPI, c1995-
MeSH Terms:
Cell Proliferation/*drug effects
Imines/*pharmacology
Neoplasms/*drug therapy
Phenanthrolines/*pharmacology
Cell Line, Tumor ; Humans ; Imines/chemical synthesis ; Imines/chemistry ; Ligands ; Molecular Docking Simulation ; Neoplasms/pathology ; Phenanthrolines/chemical synthesis ; Phenanthrolines/chemistry ; Water/chemistry
References:
Pharm Res. 2015 Jan;32(1):300-10. (PMID: 25115828)
J Med Chem. 2003 Jan 2;46(1):12-5. (PMID: 12502355)
Spectrochim Acta A Mol Biomol Spectrosc. 2015 Apr 15;141:316-26. (PMID: 25670089)
Eur J Med Chem. 2011 Jun;46(6):1992-6. (PMID: 21474217)
Asian Pac J Cancer Prev. ;18(8):2243-2247. (PMID: 28843263)
Bioinorg Chem Appl. 2013;2013:437134. (PMID: 23424390)
Cancers (Basel). 2019 Apr 04;11(4):. (PMID: 30987271)
Biomed Res Int. 2015;2015:397563. (PMID: 26491668)
J Pharm Sci. 2014 Jul;103(7):1949-1955. (PMID: 24823496)
Org Biomol Chem. 2011 Jan 21;9(2):480-90. (PMID: 21072412)
Spectrochim Acta A Mol Biomol Spectrosc. 2015;149:731-43. (PMID: 25988819)
Angew Chem Int Ed Engl. 2003 Jun 30;42(25):2876-9. (PMID: 12833346)
Chem Rev. 2015 Feb 11;115(3):1597-621. (PMID: 25543900)
ChemMedChem. 2008 Sep;3(9):1427-34. (PMID: 18537202)
J Pharm Anal. 2020 Apr;10(2):187-193. (PMID: 32373390)
J Immunol Methods. 1986 May 22;89(2):271-7. (PMID: 3486233)
Grant Information:
451-03-68‬/‪2020-14‬/ 200125 Ministarstvo Prosvete, Nauke i Tehnološkog Razvoja; RG-1441-313 Deanship of Scientific Research, King Saud University
Contributed Indexing:
Keywords: MD simulations; Phenanthrolin-5-yl; computational analysis; selective cytotoxicity
Substance Nomenclature:
0 (Imines)
0 (Ligands)
0 (Phenanthrolines)
059QF0KO0R (Water)
Entry Date(s):
Date Created: 20200626 Date Completed: 20210217 Latest Revision: 20210217
Update Code:
20240105
PubMed Central ID:
PMC7356530
DOI:
10.3390/molecules25122865
PMID:
32580359
Czasopismo naukowe
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 IC 50 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 IC 50 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.
Zaloguj się, aby uzyskać dostęp do pełnego tekstu.

Ta witryna wykorzystuje pliki cookies do przechowywania informacji na Twoim komputerze. Pliki cookies stosujemy w celu świadczenia usług na najwyższym poziomie, w tym w sposób dostosowany do indywidualnych potrzeb. Korzystanie z witryny bez zmiany ustawień dotyczących cookies oznacza, że będą one zamieszczane w Twoim komputerze. W każdym momencie możesz dokonać zmiany ustawień dotyczących cookies