Novel 3-((2-chloroquinolin-3-yl)methylene)indolin-2-one derivatives produce anticancer efficacy in ovarian cancer in vitro

Karthikeyan, Chandrabose; Amawi, Haneen; Ashby, Charles R.; Khare, Vishwa M.; Jones, Veronica; Moorthy, N. S. Hari Narayana; Trivedi, Piyush; Tiwari, Amit K.

doi:10.1016/j.heliyon.2019.e01603

Cited by 7 publications

(5 citation statements)

References 26 publications

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“…The flipped anionic PS binds to the Ca 2+ -dependent phospholipid-binding protein, annexin V [ 49 ]. We discovered and reported several potent apoptosis-inducing compounds [ 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 ]. In this study, the result of our morphological studies in MDA-MB-231 cells after incubation with our lead compounds, 4g and 4i, indicated that apoptosis was occurring ( Figure 3 A).…”

Section: Resultsmentioning

confidence: 99%

Novel Chrysin-De-Allyl PAC-1 Hybrid Analogues as Anticancer Compounds: Design, Synthesis, and Biological Evaluation

et al. 2020

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New chrysin-De-allyl-Pac-1 hybrid analogues, tethered with variable heterocyclic systems (4a–4o), were rationally designed and synthesized. The target compounds were screened for in vitro antiproliferative efficacy in the triple-negative breast cancer (TNBC) cell line, MDA-MB-231, and normal human mammary epithelial cells (HMECs). Two compounds, 4g and 4i, had the highest efficacy and selectivity towards MDA-MB-231 cells, and thus, were further evaluated by mechanistic experiments. The results indicated that both compounds 4g and 4i induced apoptosis by (1) inducing cell cycle arrest at the G2 phase in MDA-MB-231 cells, and (2) activating the intrinsic apoptotic pathways in a concentration-dependent manner. Physicochemical characterizations of these compounds suggested that they can be further optimized as potential anticancer compounds for TNBC cells. Overall, our results suggest that 4g and 4i could be suitable leads for developing novel compounds to treat TNBC.

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Section: Resultsmentioning

confidence: 99%

Novel Chrysin-De-Allyl PAC-1 Hybrid Analogues as Anticancer Compounds: Design, Synthesis, and Biological Evaluation

et al. 2020

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“…Metabolites with high ranking seem to be interacting with multiple microbiome species, for example Indolin-2-one is a tryptophan metabolite, likely of gut microbiome origin [ 77 ]. Indolin-2-one compounds have been identified as an effective cancer treatment, with indolin-2-one derivatives showing anticancer effects in vitro against ovarian cancer cells [ 78 , 79 , 80 ]. Louis et al [ 81 ] have also identified higher log blood harmane concentration in colon cancer and other cancers in comparison to those without cancer.…”

Section: Discussionmentioning

confidence: 99%

Integration of the Microbiome, Metabolome and Transcriptomics Data Identified Novel Metabolic Pathway Regulation in Colorectal Cancer

Bisht

Nash

et al. 2021

IJMS

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Integrative multiomics data analysis provides a unique opportunity for the mechanistic understanding of colorectal cancer (CRC) in addition to the identification of potential novel therapeutic targets. In this study, we used public omics data sets to investigate potential associations between microbiome, metabolome, bulk transcriptomics and single cell RNA sequencing datasets. We identified multiple potential interactions, for example 5-aminovalerate interacting with Adlercreutzia; cholesteryl ester interacting with bacterial genera Staphylococcus, Blautia and Roseburia. Using public single cell and bulk RNA sequencing, we identified 17 overlapping genes involved in epithelial cell pathways, with particular significance of the oxidative phosphorylation pathway and the ACAT1 gene that indirectly regulates the esterification of cholesterol. These findings demonstrate that the integration of multiomics data sets from diverse populations can help us in untangling the colorectal cancer pathogenesis as well as postulate the disease pathology mechanisms and therapeutic targets.

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“…Compound 16 was obtained by the reaction of acid hydrazide 3 with 1-(4-aminophenyl)ethan-1-one in propan-2-ol at reflux for 15 h (Supplementary materials, Figures S23 and S24). The 3-methyleneindolin-2-one moiety is a part of naturally occurring compounds and is widely used for the design of biologically active compounds [35,36]. Thus, to incorporate this structural unit into the designed structure, hydrazide 3 was treated with indoline-2,3-dione in refluxing propan-2-ol for 2 h. The product 17 was isolated with a 73% yield (Supplementary materials, Figures S25 and S26).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis of 1-(2-Hydroxyphenyl)- and (3,5-Dichloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives as Promising Scaffolds for the Development of Novel Antimicrobial and Anticancer Agents

Bertašiūtė

Kavaliauskas

Vaickelionienė

et al. 2023

IJMS

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Increasing antimicrobial resistance among Gram-positive pathogens and pathogenic fungi remains one of the major public healthcare threats. Therefore, novel antimicrobial candidates and scaffolds are critically needed to overcome resistance in Gram-positive pathogens and drug-resistant fungal pathogens. In this study, we explored 1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid and its 3,5-dichloro-2-hydroxyphenyl analogue for their in vitro antimicrobial activity against multidrug-resistant pathogens. The compounds showed structure-dependent antimicrobial activity against Gram-positive pathogens (S. aureus, E. faecalis, C. difficile). Compounds 14 and 24b showed promising activity against vancomycin-intermediate S. aureus strains, and favorable cytotoxic profiles in HSAEC-1 cells, making them attractive scaffolds for further development. 5-Fluorobenzimidazole, having a 3,5-dichloro-2-hydroxyphenyl substituent, was found to be four-fold, and hydrazone, with a thien-2-yl fragment, was two-fold stronger than clindamycin against methicillin resistant S. aureus TCH 1516. Moreover, hydrazone, bearing a 5-nitrothien-2-yl moiety, showed promising activity against three tested multidrug-resistant C. auris isolates representing major genetic lineages (MIC 16 µg/mL) and azole-resistant A. fumigatus strains harboring TR34/L98H mutations in the CYP51A gene. The anticancer activity characterization demonstrated that the 5-fluorobenzimidazole derivative with a 3,5-dichloro-2-hydroxyphenyl substituent showed the highest anticancer activity in an A549 human pulmonary cancer cell culture model. Collectively these results demonstrate that 1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives could be further explored for the development of novel candidates targeting Gram-positive pathogens and drug-resistant fungi.

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Novel 3-((2-chloroquinolin-3-yl)methylene)indolin-2-one derivatives produce anticancer efficacy in ovarian cancer in vitro

Cited by 7 publications

References 26 publications

Novel Chrysin-De-Allyl PAC-1 Hybrid Analogues as Anticancer Compounds: Design, Synthesis, and Biological Evaluation

Novel Chrysin-De-Allyl PAC-1 Hybrid Analogues as Anticancer Compounds: Design, Synthesis, and Biological Evaluation

Integration of the Microbiome, Metabolome and Transcriptomics Data Identified Novel Metabolic Pathway Regulation in Colorectal Cancer

Synthesis of 1-(2-Hydroxyphenyl)- and (3,5-Dichloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives as Promising Scaffolds for the Development of Novel Antimicrobial and Anticancer Agents

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