Lemon Juice Mediated Reaction under Ultrasound Irradiation: Synthesis of Indolofuroquinoxalines as Potential Anticancer Agents

2019 ◽  
Vol 19 (8) ◽  
pp. 671-678 ◽  
Author(s):  
Gutta Lakshmi Prasanna ◽  
Bodapati Veera Durga Rao ◽  
Alugubelli Gopi Reddy ◽  
Mandava V. Basaveswara Rao ◽  
Manojit Pal
Keyword(s):  
Cell Line ◽  
Cell Lines ◽  
Anticancer Agents ◽  
Hek293 Cell ◽  
Mcf7 Cell ◽  
Ultrasound Irradiation ◽  
Lemon Juice ◽  
Anticancer Properties ◽  
Hek293 Cell Line

Background: A non-hazardous synthetic methodology has been developed for the preparation of compounds based on indolofuroquinoxaline framework. Lemon juice that is known to play the role of a biocatalyst in various organic reactions was used for this purpose. Method: A number of indolofuroquinoxaline derivatives were prepared via the lemon juice mediated condensation of methyl 2-(2-chloro-1H-indol-3-yl)-2-oxoacetate or its N-alkyl derivatives with 1,2- diamines under ultrasound irradiation. All the synthesized compounds were screened via an MTT assay for their potential anticancer properties in vitro using a number of cancer cell lines including MDA-MB 231, and MCF7, K562, Colo-205 and IMR-32 and the non-cancerous HEK293 cell line. Compounds 3a, 3b and 3c showed promising growth inhibition against K562, MDA-MB 231 and MCF7 cell lines but no significant effects on HEK293 cell line suggesting their selectivity towards cancer cells. Results and Conclusion: Moreover, according to their IC50 values, all these compounds appeared to be relatively more potent towards K562 cell line over MDA-MB 231 and MCF7 cell lines indicating their potential against leukemia.

Lemon Juice Mediated Synthesis of 3-Substituted Quinazolin-4(3H)-Ones and their Pharmacological Evaluation

2020 ◽  
Vol 19 (16) ◽  
pp. 2001-2009 ◽  
Author(s):  
Malavattu G. Prasad ◽  
C. Vijaya Lakshmi ◽  
Naresh K. Katari ◽  
Sreekantha B. Jonnalagadda ◽  
Manojit Pal
Keyword(s):  
Cell Line ◽  
Cell Lines ◽  
Hek293 Cell ◽  
Glyoxylic Acid ◽  
Lemon Juice ◽  
Cytotoxic Agents ◽  
Diverse Range ◽  
Hek293 Cell Line ◽  
Three Component Reaction ◽  
Mcf 7

Background: Compounds containing the quinazoline-4(3H)-one framework constitute an important class of fused N-heterocycles that are found in more than 200 naturally occurring alkaloids. These compounds also show a diverse range of pharmacological activities including antitumor properties. This prompted us to explore a series of quinazolin-4-(3H)-one derivatives having no substituent at C-2 as potential cytotoxic agents. Objective: The objective of this study was to synthesize and evaluate 3-substituted quinazolin-4(3H)-one derivatives for their potential cytotoxic properties. Methods: A convenient method has been developed for the rapid synthesis of this class of compounds under a mild and non-hazardous reaction condition in good yields. The methodology involved a three-component reaction employing isatoic anhydride, amines and glyoxylic acid as reactants in the presence of lemon juice in PEG- 400 at room temperature (25-30ºC) under ultrasound irradiation. All the synthesized compounds were screened via an MTT assay for their potential cytotoxic properties in vitro using the cancerous cell lines e.g. A549, A2780, HepG2, K562, MCF-7 and HCT-116 and a non-cancerous HEK293 cell line. Results: Several compounds such as 3a, 3b, 3d, 3e and 3f showed promising growth inhibition against these cancer cell lines but no significant effects on HEK293 cell line. The IC50 values of these compounds were comparable to doxorubicin whereas 3f significantly induced apoptosis in MCF-7 cells that also was comparable to doxorubicin. Conclusion: An ultrasound-assisted MCR facilitated by lemon juice has been developed to synthesize 3- substituted quinazolin-4(3H)-one derivatives that could act as potential anticancer agents.

Ultrasound-assisted Synthesis of 6-substituted indolo[2,3-b]quinolines: their Evaluation as Potential Cytotoxic Agents

2019 ◽  
Vol 19 (7) ◽  
pp. 599-608
Author(s):  
Nagaraju Marepu ◽  
Mahesh Gosi ◽  
Santhoshi Sumana Vedula ◽  
Sunandamma Yeturu ◽  
Manojit Pal
Keyword(s):  
Cell Lines ◽  
Anticancer Agents ◽  
Hek293 Cell ◽  
Mcf7 Cell ◽  
Cytotoxic Agents ◽  
Mcf7 Cells ◽  
Pharmacological Activities ◽  
Bond Forming ◽  
Ultrasound Assisted

<p>Background: The indolo[2,3-b]quinoline framework is often found in various natural products displaying a range of pharmacological activities. This is an attractive template for the design and discovery of potential drugs especially for the identification of new anticancer agents. Methods: The synthesis of 6-substituted indolo[2,3-b]quinolones was undertaken and carried out using a ultrasound assisted method involving two sequential C-N bond forming reactions between 3-(2- bromophenyl)-2-chloroquinoline and amines in a single pot in the presence of Pd(OAc)2 and a ligand (S)-BINAP. All the synthesized compounds were tested in vitro against two cancer cell lines e.g. MCF7 and HepG2 along with non-cancerous HEK293 cell lines. Results: Two of these compounds showed promising and selective growth inhibition of MCF7 cell lines and one induced significant apoptosis in cancer (MCF7) cells. Conclusion: Compounds based on indolo[2,3-b]quinolone framework may be useful for the identification of new cytotoxic agents thereby potential cure for breast cancer.</p>

Lemon Juice as a Biocatalyst Under Ultrasound Irradiation: Synthesis and Pharmacological Evaluation of 2-amino 1,3,4-thiadiazoles

2020 ◽  
Vol 20 (11) ◽  
pp. 1379-1386 ◽  
Author(s):  
Malavattu G. Prasad ◽  
Chapala V. Lakshmi ◽  
Naresh K. Katari ◽  
Manojit Pal
Keyword(s):  
Cell Lines ◽  
Anticancer Agents ◽  
Metastatic Breast ◽  
Ultrasound Irradiation ◽  
Lemon Juice ◽  
Breast Cancer Cell Lines ◽  
Wide Range ◽  
Thiadiazole Derivatives ◽  
Mcf 7

Background: The 2-amino 1,3,4-thiadiazole framework has attracted considerable interest because of its prevalence in compounds possessing a wide range of pharmacological properties including anticancer/antitumor activities. Though a number of methods have been reported for the synthesis of this class of compounds, some of them are not straightforward, inexpensive and environmentally friendly. Objective: To synthesize 2-amino-1,3,4-thiadiazole derivatives that could act as potential anticancer agents. Methods: The use of lemon juice as an inexpensive and readily available biocatalyst was explored in the synthesis of 2-amino 1,3,4-thiadiazole derivatives. Accordingly, a convenient method has been developed for the rapid synthesis of this class of compounds under a mild and non-hazardous reaction condition in good yields. The methodology involved the reaction of various acid hydrazides with TMSNCS in the presence of lemon juice in PEG-400 at room temperature (25-30ºC) under ultrasound irradiation. These compounds were assessed for their cytotoxic properties against two different metastatic breast cancer cell lines e.g., MDAMB-231 and MCF-7 and subsequently against SIRT1. Results: The 2-amino 1,3,4-thiadiazole derivatives 3a, 3i, 3j and 3l showed promising growth inhibition of MDAMB- 231 and MCF-7 cell lines and SIRT1 inhibition in vitro. Indeed, 3i was found to be a potent inhibitor of SIRT1. Conclusion: An ultrasound-assisted method facilitated by lemon juice has been developed to synthesize 2-amino- 1,3,4-thiadiazole derivatives that could act as potential anticancer agents.

scholarly journals Affecting HEK293 Cell Growth and Production Performance by Modifying the Expression of Specific Genes

Cells ◽  
2021 ◽  
Vol 10 (7) ◽  
pp. 1667
Author(s):  
Laura Abaandou ◽  
David Quan ◽  
Joseph Shiloach
Keyword(s):  
Cell Line ◽  
Cell Lines ◽  
Hek293 Cell ◽  
Chinese Hamster ◽  
Production Performance ◽  
Cellular Processes ◽  
Hek293 Cell Line ◽  
Global Engineering ◽  
Genomic Tools ◽  
Serum Free Suspension

The HEK293 cell line has earned its place as a producer of biotherapeutics. In addition to its ease of growth in serum-free suspension culture and its amenability to transfection, this cell line’s most important attribute is its human origin, which makes it suitable to produce biologics intended for human use. At the present time, the growth and production properties of the HEK293 cell line are inferior to those of non-human cell lines, such as the Chinese hamster ovary (CHO) and the murine myeloma NSO cell lines. However, the modification of genes involved in cellular processes, such as cell proliferation, apoptosis, metabolism, glycosylation, secretion, and protein folding, in addition to bioprocess, media, and vector optimization, have greatly improved the performance of this cell line. This review provides a comprehensive summary of important achievements in HEK293 cell line engineering and on the global engineering approaches and functional genomic tools that have been employed to identify relevant genes for targeted engineering.

scholarly journals Synthesis and Experimental Validation of New Designed Heterocyclic Compounds with Antiproliferative Activity versus Breast Cancer Cell Lines MCF-7 and MDA-MB-231

2017 ◽  
Vol 2017 ◽  
pp. 1-10 ◽  
Author(s):  
Vincenza Barresi ◽  
Carmela Bonaccorso ◽  
Domenico A. Cristaldi ◽  
Maria N. Modica ◽  
Nicolò Musso ◽  
...  
Keyword(s):  
Cell Line ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Cancer Cell Line ◽  
Breast Cancer Cell Lines ◽  
Design And Synthesis ◽  
Human Breast Cell ◽  
Mcf 7

Recent drug discovery efforts are highly focused towards identification, design, and synthesis of small molecules as anticancer agents. With this aim, we recently designed and synthesized novel compounds with high efficacy and specificity for the treatment of breast tumors. Based on the obtained results, we constructed a Volsurf+ (VS+) model using a dataset of 59 compounds able to predict the in vitro antitumor activity against MCF-7 cancer cell line for new derivatives. In the present paper, in order to further verify the robustness of this model, we report the results of the projection of more than 150 known molecules and 9 newly synthesized compounds. We predict their activity versus MCF-7 cell line and experimentally verify the in silico results for some promising chosen molecules in two human breast cell lines, MCF-7 and MDA-MB-231.

scholarly journals Cytotoxic Activity of Some Spirooxindole-4H-pyran Derivatives

2019 ◽  
pp. 1-6
Author(s):  
Zeinab Faghih ◽  
Zahra Faghih ◽  
Masoomeh Divar ◽  
Soghra Khabnadideh
Keyword(s):  
Cell Line ◽  
Cell Lines ◽  
Anticancer Agents ◽  
Biological Activities ◽  
Science Research ◽  
Cytotoxic Activities ◽  
Medical Sciences ◽  
Anticancer Properties ◽  
Cancerous Cell ◽  
Mcf 7

Aims: Isatin is a honored scaffold and one of the most favorable class of heterocyclic systems that possesses many interesting biological activities and well-tolerated in humans. Here a series of fifteen spirooxindole-4H-pyran derivatives containing both isatin and pyran moieties (ICa-ICo) will be examine for their anti-cancer activity. Study Design: Cytotoxic evaluation of some spirooxindole-4H-pyran derivatives in two cancerous cell lines.  Place and Duration of Study: Pharmaceutical Science Research Center and Shiraz Institute for Cancer Research, Medical School in Shiraz University of Medical Sciences, Shiraz, Iran, between June 2018 and July 2019. Methodology: MTT assay was used to evaluate the cytotoxic activities of these compounds. The anticancer properties of the tested compounds were determined using A549 and MCF-7 cell lines. Results: Among the tested compounds ICc, ICd and ICf showed the best cytotoxic activities  against both cancerous cell lines. Compounds ICh and ICj showed desirable cytotoxic activities against A549 cell line. Compound ICb showed desirable cytotoxic activities against MCF-7 cell line. Conclusion: We conclude that the isatin-linked pyran analog can serve as a prototype molecule for further development of a new class of anticancer agents.

scholarly journals Design, Synthesis, Molecular Docking, ADME and Biological Evaluation Studies of Some New 1,3,4-oxadiazole Linked Benzimidazoles as Anticancer Agents and Aromatase Inhibitors

2021 ◽  
Author(s):  
ulviye acar çevik ◽  
Ismail Celik ◽  
Ayşen IŞIK ◽  
Yusuf Özkay ◽  
Zafer Asım Kaplancıklı
Keyword(s):  
Molecular Docking ◽  
Cell Line ◽  
Cell Lines ◽  
Anticancer Agents ◽  
Evaluation Studies ◽  
Biological Evaluation ◽  
Binding Modes ◽  
Anticancer Activities ◽  
Mcf 7

Abstract In this study, due to the potential anticancer effects of the benzimidazole ring system, a series of benzimidazole-1,3,4-oxadiazole derivatives were synthesized and characterized by 1H NMR, 13C NMR, and MS spectra analyses. In the in vitro anticancer assay, all the compounds tested anticancer activities using MTT-based assay against five cancer cell lines (MCF-7, A549, HeLa, C6, and HepG2). Among them, compound 5a exhibited the most potent activity with IC50 values of 5,165±0,211 μM and 5,995±0,264 μM against MCF-7 and HepG2 cell lines. Compound 5a was included in the BrdU test to determine the DNA synthesis inhibition effects for both cell types. Furthermore, compound 5c was also found to be more effective than doxorubicin on the HeLa cell line. The selectivity of anticancer activity was evaluated in NIH3T3 (mouse embryo fibroblast cell line) cell line. In vitro, enzymatic inhibition assays of aromatase enzyme were performed for compound 5a acting on the MCF-7 cell line. For compound 5a, in silico molecular docking against aromatase enzyme was performed to determine possible protein-ligand interactions and binding modes.

Synthesis of 2-Substituted 4-Arylidene-5(4H)-oxazolones as Potential Cytotoxic Agents in the Presence of Lemon Juice as a Biocatalyst

2020 ◽  
Vol 22 (9) ◽  
pp. 625-634 ◽  
Author(s):  
Malavattu G. Prasad ◽  
Chapala V. Lakshmi ◽  
Naresh K. Katari ◽  
Krishnan Anand ◽  
Manojit Pal ◽  
...  
Keyword(s):  
Lung Cancer ◽  
Cell Line ◽  
Anticancer Agents ◽  
Human Colon ◽  
Malignant Cell ◽  
Lemon Juice ◽  
Cytotoxic Agents ◽  
Reference Drug ◽  
Initial Objective

Background: The oxazolone class of compounds is known to exert a profound effect on malignant cell proliferation, tumor angiogenesis and /or on the established neoplastic vasculature. Additionally, these compounds are generally known to have a low tendency to interact with DNA which is not common with most of the conventional cytotoxic agents. Thus, this class of compounds is of particular interest for the discovery and development of patient-friendly anticancer agents. Objective: The initial objective of this study was to synthesize and evaluate 2-substituted 4-arylidene- 5(4H)-oxazolones for their potential anticancer properties. Methods: A simple, mild and non-hazardous synthetic methodology has been developed for the preparation of 2-substituted 4-arylidene-5(4H)-oxazolones. The methodology involved lemon juice mediated condensation of N-acyl glycine derivatives including hippuric acid with arylaldehydes in PEG-400 under ultrasound irradiation. All the synthesized compounds were screened via an MTT assay for their potential cytotoxic properties in vitro using the cancerous cell lines e.g. K562 (human chronic myeloid leukemia), Colo-205 (human colon carcinoma), and A549 (human lung carcinoma) and a non-cancerous HEK293 (human embryonic kidney) cell line. Results: Compounds 3a, 3c and 3i showed promising growth inhibition against A549 cell line but no significant effects on HEK293 cell line, indicating their selectivity towards cancer cells. Moreover, their IC50 values suggested that all these compounds were comparable to the reference drug doxorubicin indicating their potential against lung cancer. Conclusion: he 4-arylidene-5(4H)-oxazolone framework presented here could be a new template for the design and discovery of potential anticancer agents especially for lung cancer.

scholarly journals Synthesis, Characterization and In Vitro Evaluation of Novel 5-Ene-thiazolo[3,2-b][1,2,4]triazole-6(5H)-ones as Possible Anticancer Agents

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1162
Author(s):  
Serhii Holota ◽  
Sergiy Komykhov ◽  
Stepan Sysak ◽  
Andrzej Gzella ◽  
Andriy Cherkas ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Cancer Cell Lines ◽  
Hek293 Cells ◽  
In Vitro Evaluation ◽  
Anticancer Properties ◽  
Sar Study

The present paper is devoted to the search for drug-like molecules with anticancer properties using the thiazolo[3,2-b][1,2,4]triazole-6-one scaffold. A series of 24 novel thiazolo-[3,2-b][1,2,4]triazole-6-ones with 5-aryl(heteryl)idene- and 5-aminomethylidene-moieties has been synthesized employing three-component and three-stage synthetic protocols. A mixture of Z/E-isomers was obtained in solution for the synthesized 5-aminomethylidene-thiazolo[3,2-b]-[1,2,4]triazole-6-ones. The compounds have been studied for their antitumor activity in the NCI 60 lines screen. Some compounds present excellent anticancer properties at 10 μM. Derivatives 2h and 2i were the most active against cancer cell lines without causing toxicity to normal somatic (HEK293) cells. A preliminary SAR study had been performed for the synthesized compounds.

Synthesis of 2-substituted Furo[3,2-b]pyridines Under Pd/C-Cu Catalysis Assisted by Ultrasound: Their Evaluation as Potential Cytotoxic Agents

2020 ◽  
Vol 20 (8) ◽  
pp. 932-940 ◽  
Author(s):  
Dandamudi Sri Laxmi ◽  
Suryadevara V. Vardhini ◽  
Venkata R. Guttikonda ◽  
Mandava V.B. Rao ◽  
Manojit Pal
Keyword(s):  
Cell Lines ◽  
Ultrasound Irradiation ◽  
Cytotoxic Agents ◽  
Direct Access ◽  
Pyridine Derivative ◽  
Anticancer Activities ◽  
One Pot ◽  
Anticancer Properties ◽  
Mcf 7

Background: Compounds containing furo[3,2-b]pyridine framework have shown interesting pharmacological properties, including anticancer activities. Though these compounds are generally synthesized via the heteroannulation processes involving acetylenic derivatives, some of them are complex. Objective: The study aimed to explore a series of 2-substituted furo[3,2-b]pyridines for their cytotoxic properties against cancer cell lines in vitro. Methods: We developed a convenient synthesis of 2-substituted furo[3,2-b]pyridines via sequential (i) C-C coupling followed by (ii) C-O bond-forming reactions in a single pot. The reactions were performed under ultrasound irradiation in the presence of Pd/C as an inexpensive, stable and widely used catalyst. A range of 2- substituted furo[3,2-b]pyridines were synthesized via coupling of 3-chloro-2-hydroxy pyridine with terminal alkynes in the presence of 10% Pd/C-CuI-PPh3-Et3N in EtOH. The in vitro evaluation of all these compounds was carried out against MDA-MB-231 and MCF-7 cell lines and subsequently against SIRT1. Results: The furo[3,2-b]pyridine derivative 3b showed encouraging growth inhibition of both MDAMB-231 and MCF-7 cell lines and inhibition of SIRT1. The compound 3b also showed apoptosis-inducing potential when tested against MCF-7 cells. Conclusion: The Pd/C-Cu catalysis under ultrasound accomplished a one-pot and direct access to 2-substituted furo[3,2-b]pyridine derivatives, some of which showed anticancer properties.

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