Molecular Classification of 5-Amino-2-Aroylquinolines and 4-Aroyl-6,7,8-Trimethoxyquinolines as Highly Potent Tubulin Polymerization Inhibitors

2013 ◽  
Vol 3 (2) ◽  
pp. 1-26 ◽  
Author(s):  
Francisco Torrens ◽  
Gloria Castellano
Keyword(s):  
Cancer Cell ◽  
Information Entropy ◽  
Human Cancer ◽  
Selection Criterion ◽  
Chemical Properties ◽  
Cancer Cell Line ◽  
Molecular Classification ◽  
Human Cancer Cell Lines ◽  
Anti Cancer

Algorithms for classification and taxonomy are proposed based on criteria as information entropy and its production. It is classified a series of 5-amino-2-aroylquinolines (AAQs) and 4-aroyl-6,7,8-trimethoxyquinolines (TMQs) combretastatin analogues for anti-cancer activity. 5-Amino-6-methoxy-2-aroylquinoline AAQ showed anti-proliferative activity more potent as compared to combretastatin A-4 (CA4), against various human cancer cell lines and a multidrug resistance (MDR) cancer cell line. On the basis of AAQ/TMQ structure–activity relationship new derivatives are designed. The AAQs/TMQs are classified using nine characteristic chemical properties in molecules. Many classification algorithms are based on information entropy. When applying the procedures to sets of moderate size, an excessive number of results appear compatible with data and suffer a combinatorial explosion. However, after equipartition conjecture, one has a selection criterion between different variants resulting from classification between hierarchical trees. A classification of anti-cancer agents is obtained. The features denote positions R2–8 on the quinoline bicycle.

scholarly journals Synthesis, Characterization and Biological Evaluation of Metal Adamantyl 2-Pyridylhydrazone Complexes

Molecules ◽  
2020 ◽  
Vol 25 (11) ◽  
pp. 2530
Author(s):  
Ihsan A. Shehadi ◽  
Fatima-Azzahra Delmani ◽  
Areej M. Jaber ◽  
Hana Hammad ◽  
Murad A. AlDamen ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Line ◽  
Direct Methods ◽  
Cancer Cell Lines ◽  
Biological Evaluation ◽  
Colorectal Cancer Cell Line ◽  
Breast Cancer Cell Lines ◽  
Human Cancer Cell Lines

Four new complexes derived from adamantly containing hydrazone (APH) ligand with Cu(II) (1), Co(II) (2), Ni(II) (3) and Zn(II) (4), have been synthesized and characterized using different physicochemical methods. The structure of the ligand APH and its copper complex 1 have been established by single-crystal X-ray diffraction direct methods, which reveal that complex 1 has distorted square-pyramidal geometry. Complexes 1–4 are screened against seven human cancer cell lines namely, breast cancer cell lines (MCF7, T47D, MDA-MB-231), prostate cancer cell lines (PC3, DU145) and the colorectal cancer cell line Coco-2, for their antiproliferative activities. Complex 1 has shown a promising anticancer activity compared to the other ones. The structural and spectroscopic analysis of APH and its complexes are confirmed by DFT calculations.

scholarly journals Probing the DNA Reactivity and the Anticancer Properties of a Novel Tubercidin-Pt(II) Complex

Pharmaceutics ◽  
2020 ◽  
Vol 12 (7) ◽  
pp. 627 ◽  
Author(s):  
Stefano D’Errico ◽  
Andrea Patrizia Falanga ◽  
Domenica Capasso ◽  
Sonia Di Gaetano ◽  
Maria Marzano ◽  
...  
Keyword(s):  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Line ◽  
Annexin V ◽  
Cd Spectroscopy ◽  
Neutral Complex ◽  
Molecular Scaffold ◽  
Human Cancer Cell Lines ◽  
Anticancer Properties ◽  
Tumor Agent

Herein, we reported on the synthesis of a novel Pt(II) neutral complex having as ligand the nucleoside tubercidin, a potent anti-tumor agent extracted from the bacterium Streptomyces Tubercidicus. In detail, the chelation of the metal by a diamine linker installed at C6 purine position of tubercidin assured the introduction of a cisplatin-like unit in the molecular scaffold. The behavior of the synthesized complex with a double-strand DNA model was monitored by CD spectroscopy and compared with that of cisplatin and tubercidin. In addition, the cell viability was evaluated against HeLa, A375 and WM266 human cancer cell lines using the MTT test. Lastly, the results of the apoptotic assay (FITC Annexin V) performed on the HeLa cancer cell line are also reported.

The anti-cancer effect of amygdalin on human cancer cell lines

2019 ◽  
Vol 46 (2) ◽  
pp. 2059-2066 ◽  
Author(s):  
Asghar Arshi ◽  
Sayed Mostafa Hosseini ◽  
Fataneh Saleh Khaje Hosseini ◽  
Zahra Yousefnejad Amiri ◽  
Fatemeh Sadat Hosseini ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Lines ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Anti Cancer

Effect of the Method of Preparation on the Composition and Cytotoxic Activity of the Essential Oil of Pituranthos tortuosus

2011 ◽  
Vol 66 (3-4) ◽  
pp. 143-148 ◽  
Author(s):  
Hossam M. Abdallah ◽  
Shahira M. Ezzat
Keyword(s):  
Breast Cancer ◽  
Essential Oil ◽  
Cell Line ◽  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Line ◽  
Cancer Cell Lines ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines

The aerial parts of Pituranthos tortuosus (Desf.) Benth and Hook (Apiaceae), growing wild in Egypt, yielded 0.8%, 0.6%, and 1.5% (v/w) of essential oil when prepared by hydrodistillation (HD), simultaneous hydrodistillation-solvent (n-pentane) extraction (Lickens- Nickerson, DE), and conventional volatile solvent extraction (preparation of the “absolute”, SE), respectively. GC-MS analysis showed that the major components in the HD sample were β-myrcene (18.81%), sabinene (18.49%), trans-iso-elemicin (12.90%), and terpinen- 4-ol (8.09%); those predominent in the DE sample were terpinen-4-ol (29.65%), sabinene (7.38%), γ-terpinene (7.27%), and β-myrcene (5.53%); while the prominent ones in the SE sample were terpinen-4-ol (15.40%), dill apiol (7.90%), and allo-ocimene (4E,6Z) (6.00%). The oil prepared in each case was tested for its cytotoxic activity on three human cancer cell lines, i.e. liver cancer cell line (HEPG2), colon cancer cell line (HCT116), and breast cancer cell line (MCF7). The DE sample showed the most potent activity against the three human cancer cell lines (with IC50 values of 1.67, 1.34, and 3.38 μg/ml against the liver, colon, and breast cancer cell lines, respectively). Terpinen-4-ol, sabinene, γ-terpinene, and β-myrcene were isolated from the DE sample and subjected to a similar evaluation of cytotoxic potency; signifi cant activity was observed

scholarly journals Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of Some Fe(III) Complexes Bearing Unsymmetrical Salen-Type Ligands Derived from 2-Hydroxynaphthaldehyde and Substituted Salicylaldehydes

2021 ◽  
Vol 2021 ◽  
pp. 1-9
Author(s):  
Quang Trung Nguyen ◽  
Phuong Nam Pham Thi ◽  
Nguyen Van Tuyen
Keyword(s):  
Cell Line ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Line ◽  
Tumor Cell Line ◽  
In Vitro Cytotoxicity ◽  
Ionization Mass ◽  
Hek 293 ◽  
Human Cancer Cell Lines

Six Fe(III) complexes bearing unsymmetrical salen-type ligands derived from 2-hydroxynaphthaldehyde and substituted salicylaldehydes were synthesized by coordinating the unsymmetrical salen-type ligands with FeCl3.6H2O. The synthetic complexes were characterized by electrospray ionization mass spectra (ESI-MS), effective magnetic moments (μeff), and infrared (IR) and ultraviolet-visible (UV-Vis) spectra. The spectroscopic data are in good agreement with the suggested molecular formulae of the complexes. Their cyclic voltammetric studies in acetonitrile solutions showed that the Fe(III)/Fe(II) reduction processes are electrochemically irreversible. The in vitro cytotoxicity of the obtained complexes was screened on human cancer cell lines KB (a subline of Hela tumor cell line) and HepG2 (a human liver cancer cell line) and a normal human cell line HEK-293 (Human Embryonic Kidney cell line). The results showed that the synthetic Fe(III) complexes are highly cytotoxic and quite selective. The synthetic complexes bearing unsymmetrical salen-type ligands with different substituted groups in the salicyl ring indicate different cytotoxicity.

scholarly journals Synthesis of Novel Biologically Active Proflavine Ureas Designed on the Basis of Predicted Entropy Changes

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4860
Author(s):  
Ladislav Janovec ◽  
Eva Kovacova ◽  
Martina Semelakova ◽  
Monika Kvakova ◽  
Daniel Kupka ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Line ◽  
Biologically Active ◽  
Standard Entropy ◽  
The Novel ◽  
Urea Derivatives ◽  
Human Cancer Cell Lines ◽  
Pharmacological Model

A novel series of proflavine ureas, derivatives 11a–11i, were synthesized on the basis of molecular modeling design studies. The structure of the novel ureas was obtained from the pharmacological model, the parameters of which were determined from studies of the structure-activity relationship of previously prepared proflavine ureas bearing n-alkyl chains. The lipophilicity (LogP) and the changes in the standard entropy (ΔS°) of the urea models, the input parameters of the pharmacological model, were determined using quantum mechanics and cheminformatics. The anticancer activity of the synthesized derivatives was evaluated against NCI-60 human cancer cell lines. The urea derivatives azepyl 11b, phenyl 11c and phenylethyl 11f displayed the highest levels of anticancer activity, although the results were only a slight improvement over the hexyl urea, derivative 11j, which was reported in a previous publication. Several of the novel urea derivatives displayed GI50 values against the HCT-116 cancer cell line, which suggest the cytostatic effect of the compounds azepyl 11b–0.44 μM, phenyl 11c–0.23 μM, phenylethyl 11f–0.35 μM and hexyl 11j–0.36 μM. In contrast, the novel urea derivatives 11b, 11c and 11f exhibited levels of cytotoxicity three orders of magnitude lower than that of hexyl urea 11j or amsacrine.

Using Chemical Structural Indicators for Periodic Classification of Local Anaesthetics

2011 ◽  
Vol 1 (2) ◽  
pp. 15-35 ◽  
Author(s):  
Francisco Torrens ◽  
Gloria Castellano
Keyword(s):  
Information Entropy ◽  
Selection Criterion ◽  
Chemical Properties ◽  
Principal Component ◽  
Local Anaesthetics ◽  
Combinatorial Explosion ◽  
Hierarchical Trees ◽  
Maximum Similarity ◽  
Structural Indicators

Algorithms for classification and taxonomy based on criteria as information entropy and its production are proposed. Some local anaesthetics, currently in use, are classified using five characteristic chemical properties of different portions of their molecules. Many classification algorithms are based on information entropy. When applying the procedures to sets of moderate size, an excessive number of results appear compatible with data and the number suffers a combinatorial explosion. However, after the equipartition conjecture one has a selection criterion between different variants resulting from classification between hierarchical trees. Information entropy and principal component analyses agree. A table of periodic properties of anaesthetics is obtained. The first three features denote the group while the last two indicate the period in the table. The anaesthetics in the same group and period are suggested to present maximum similarity in properties. Furthermore the ones with only the same group will present important resemblance.

scholarly journals Bonellia albiflora: A Mayan Medicinal Plant That Induces Apoptosis in Cancer Cells

2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
Rosa Moo-Puc ◽  
Juan Chale-Dzul ◽  
Edgar Caamal-Fuentes
Keyword(s):  
Cytotoxic Activity ◽  
Cell Line ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Line ◽  
Bark Extract ◽  
Root Bark ◽  
Active Metabolites ◽  
Cytotoxic Potential ◽  
Human Cancer Cell Lines

Few studies have been carried out on the medical flora of Mexico’s Yucatan Peninsula in search for new therapeutic agents, in particular against cancer. In this paper, we evaluated the cytotoxic potential of the extract ofBonellia albiflora, a plant utilized in the traditional Mayan medicine for treatment of chronic injuries of the mouth. We carried out the methanolic extracts of different parts of the plant by means of extraction with the Soxhlet equipment. We conducted liquid-liquid fractions on each extract with solvents of increasing polarity. All extracts and fractions were evaluated for cytotoxic activity versus four human cancer cell lines and one normal cell line through a tetrazolium dye reduction (MTT) assay in 96-well cell culture plates. The methanolic root-bark extract possessed much greater cytotoxic activity in the human oropharyngeal cancer cell line (KB); its hexanic fraction concentrated the active metabolites and induced apoptosis with the activation of caspases 3 and 8. The results demonstrate the cytotoxic potential of theB. albiflorahexanic fraction and substantiate the importance of the study of the traditional Mayan medicinal plants.

scholarly journals The Chinese Herb Isolate Isorhapontigenin Induces Apoptosis in Human Cancer Cells by Down-regulating Overexpression of Antiapoptotic Protein XIAP

2012 ◽  
Vol 287 (42) ◽  
pp. 35234-35243 ◽  
Author(s):  
Yong Fang ◽  
Yonghui Yu ◽  
Qi Hou ◽  
Xiao Zheng ◽  
Min Zhang ◽  
...  
Keyword(s):  
Cancer Cell ◽  
Molecular Mechanisms ◽  
Human Cancer ◽  
Chinese Herb ◽  
Down Regulation ◽  
Human Cancer Cell Lines ◽  
Xiap Expression ◽  
Apoptosis Protein ◽  
Anti Cancer ◽  
Cancer Activity

Although the Chinese herb Gnetum cleistostachyum has been used as a remedy for cancers for hundred years, the active compounds and molecular mechanisms underlying its anti-cancer activity have not been explored. Recently a new derivative of stilbene compound, isorhapontigenin (ISO), was isolated from this Chinese herb. In the present study, we examined the potential of ISO in anti-cancer activity and the mechanisms involved in human cancer cell lines. We found that ISO exhibited significant inhibitory effects on human bladder cancer cell growth that was accompanied by marked apoptotic induction as well as down-regulation of the X-linked inhibitor of apoptosis protein (XIAP). Further studies have shown that ISO down-regulation of XIAP protein expression was only observed in endogenous XIAP, but not in constitutionally exogenously expressed XIAP in the same cells, excluding the possibility of ISO regulating XIAP expression at the level of protein degradation. We also identified that ISO down-regulated XIAP gene transcription via inhibition of Sp1 transactivation. There was no significant effect of ISO on apoptosis and colony formation of cells transfected with exogenous HA-tagged XIAP. Collectively, current studies, for the first time to the best of our knowledge, identify ISO as a major active compound for the anti-cancer activity of G. cleistostachyum by down-regulation of XIAP expression and induction of apoptosis through specific targeting of a SP1 pathway, and cast new light on the treatment of the cancer patients with XIAP overexpression.

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