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1.
Nanotechnology ; 35(30)2024 May 07.
Article in English | MEDLINE | ID: mdl-38636487

ABSTRACT

Despite the discovery of many chemotherapeutic drugs that prevent uncontrolled cell division processes in the last century, many studies are still being carried out to develop drugs with higher anticancer efficacy and lower level of side effects. Herein, we designed, synthesized, and characterized six novel coumarin-triazole hybrids, and evaluated for anticancer activity of the one with the highest potential against the breast cancer cell line, MCF-7 and human cervical cancer cell line, human cervical adenocarcinoma (HeLa). Compound21which was the coumarin derivative including phenyl substituent with the lowest IC50 value displayed the highest cytotoxicity against the studied cancer cell line. Furthermore, the potential use of poly (lactic-co-glycolic acid) nanoparticles (PLGA NPs) prepared by the emulsifying solvent evaporation method as a platform for a drug delivery system was studied on a selected coumarin derivative21. This coumarin derivative-loaded PLGA NPs were produced with an average size of 225.90 ± 2.96 nm, -16.90 ± 0.85 mV zeta potential, and 4.12 ± 0.90% drug loading capacity. The obtained21-loaded PLGA nanoparticles were analyzed spectroscopically and microscopically with FT-IR, UV-vis, and scanning electron microscopy as well as thermogravimetric analysis, Raman, and x-ray diffraction. Thein vitrorelease of21from the nanoparticles exhibited a controlled release profile just over one month following a burst release in the initial six hours and in addition to this a total release ratio of %50 and %85 were obtained at pH 7.4 and 5.5, respectively.21-loaded PLGA nanoparticles displayed remarkably effective anticancer activity than21. The IC50 values were determined as IC50(21-loaded PLGA nanoparticles): 0.42 ± 0.01 mg ml-1and IC50(free21molecule): 5.74 ± 3.82 mg ml-1against MCF-7 cells, and as IC50(21-loaded PLGA nanoparticles): 0.77 ± 0.12 mg ml-1and IC50(free21molecule): 1.32 ± 0.31 mg ml-1against HeLa cells after the incubation period of 24 h. Our findings indicated that triazole-substituted coumarins may be used as an anticancer agent by integrating them into a polymeric drug delivery system providing improved drug loading and effective controlled drug release.


Subject(s)
Antineoplastic Agents , Coumarins , Nanoparticles , Polylactic Acid-Polyglycolic Acid Copolymer , Triazoles , Humans , Coumarins/chemistry , Coumarins/pharmacology , Triazoles/chemistry , Triazoles/pharmacology , Nanoparticles/chemistry , Polylactic Acid-Polyglycolic Acid Copolymer/chemistry , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/administration & dosage , HeLa Cells , MCF-7 Cells , Cell Survival/drug effects , Lactic Acid/chemistry , Drug Carriers/chemistry , Polyglycolic Acid/chemistry , Particle Size , Drug Delivery Systems/methods
2.
Arch Pharm (Weinheim) ; 353(11): e2000137, 2020 Nov.
Article in English | MEDLINE | ID: mdl-32757360

ABSTRACT

The aim of this study was to develop a novel nanosize drug candidate for cancer therapy. For this purpose, (S)-methyl 2-[(7-hydroxy-2-oxo-4-phenyl-2H-chromen-8-yl)methyleneamino]-3-(1H-indol-3-yl)propanoate (ND3) was synthesized by the condensation reaction of 8-formyl-7-hydroxy-4-phenylcoumarin with l-tryptophan methyl ester. Its controlled release formulation was prepared and characterized by different spectroscopic and imaging methods. The cytotoxic effects of ND3 and its controlled release formulation were evaluated against MCF-7 and A549 cancer cell lines, and it was found that both of them have a toxic effect on cancer cells. For drug design and process development, the molecular docking analysis technique helps to clarify the effects of some DNA-targeted anticancer drugs to determine the interaction mechanisms of these drugs on DNA in a shorter time and at a lower cost. By using the molecular docking analysis and DNA binding assays, the interaction between the synthesized compound and DNA was elucidated and non-binding interactions were also determined. To predict the pharmacokinetics, and thereby accelerate drug discovery, the absorption, distribution, metabolism, excretion and toxicity values of the synthesized compound were determined by in silico methods.


Subject(s)
Antineoplastic Agents/pharmacology , Breast Neoplasms/drug therapy , Coumarins/pharmacology , Drug Design , Lung Neoplasms/drug therapy , Nanoparticles , Nanotechnology , A549 Cells , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacokinetics , Breast Neoplasms/pathology , Cell Survival/drug effects , Coumarins/chemical synthesis , Coumarins/pharmacokinetics , Delayed-Action Preparations , Female , Humans , Lung Neoplasms/pathology , MCF-7 Cells , Molecular Docking Simulation
3.
Acta Chim Slov ; 67(4): 1014-1023, 2020 Dec.
Article in English | MEDLINE | ID: mdl-33533456

ABSTRACT

New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0oC in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carboxamido)propanamido)-3-phenylpropanoate (7c) as organocatalyst showed best results under these reaction conditions, and good diastereoselectivities (up to 99%), enantioselectivities (up to 98%) and yields (up to 91%) were observed.

4.
Molecules ; 12(9): 2151-9, 2007 Sep 06.
Article in English | MEDLINE | ID: mdl-17962733

ABSTRACT

The synthesis of new 2,3,5,6-aryl substituted tetrahydro-2H-pyrazolo[3,4-d]- thiazoles 4a-j as potential biologically active compounds by the cyclocondensation of phenyl hydrazine with new 5-arylidene derivatives 2a-j of 2,3-disubstituted-1,3- thiazolidin-4-ones 1a-e is reported.


Subject(s)
Pyrazoles/chemical synthesis , Thiazoles/chemical synthesis , Thiazolidines/chemistry , Pyrazoles/chemistry , Thiazoles/chemistry
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