Design, Synthesis, and Evaluation of Novel Boronic-Chalcone Derivatives as Antitumor Agents

Kumar, Srinivas K.; Hager, Erin R.; Pettit, Catherine; Gurulingappa, Hallur; Davidson, Nancy E.; Khan, Saeed R.

doi:10.1021/jm030213+

Cited by 300 publications

(197 citation statements)

References 29 publications

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“…Because typical chalcones are known to have antitumoral properties, 20 we examined the effects of chalcones with or without the p-toluenesulfonylamido group on TM4SF5-mediated multilayer growth. Interestingly, the compounds lacking the p-toluenesulfonylamido group failed to restore monolayer growth, indicating its significance (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…TSAHC is a chalcone functionalized with a p-toluenesulfonylamido group, which is critical for its anti-TM4SF5 effects. Typical chalcones lacking the 4Ј-(p-toluenesulfonylamido) group have antitumoral activities, 20 however, these compounds did not antagonize TM4SF5. Removal of the 4Ј-(p-toluenesulfonylamido) group abolished the inhibitory effect on TM4SF5-mediated multilayer growth and tumor formation in nude mice.…”

Section: Discussionmentioning

confidence: 99%

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Blockade of four-transmembrane L6 family member 5 (TM4SF5)-mediated tumorigenicity in hepatocytes by a synthetic chalcone derivative #

et al. 2009

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We previously reported that the four-transmembrane L6 family member 5 (TM4SF5) was highly expressed in hepatocarcinoma, induced morphological elongation and epithelialmesenchymal transition, and caused abnormal cell growth in multilayers in vitro and tumor formation in vivo. In this study, we identified a synthetic compound, 4 -(p-toluenesulfonylamido)-4-hydroxychalcone (TSAHC) that antagonized both the TM4SF5-mediated multilayer growth and TM4SF5-enhanced migration/invasion. TSAHC treatment induced multilayer-growing cells to grow in monolayers, recovering contact inhibition without accompanying apoptosis, and inhibited chemotactic migration and invasion. E pithelial monolayer integrity is maintained by integrin-mediated cell adhesion between the cell and the extracellular matrix (ECM) and by E-cadherin-mediated contact between adjacent cells. 1 Epithelial-mesenchymal transition (EMT) through loss of cellcell contacts disrupts monolayer integrity and alters cell-ECM interactions. 2 Tumor cells disseminated from primary tumors via loss of cell adhesion and contact can migrate to and invade distal tissues. 3 We recently reported that TM4SF5-mediated EMT results in a loss of contact inhibition and multilayer growth. 4 Therefore, altered cell adhesion and contact may lead to both a loss of contact inhibition and a dissemination of metastatic cells from the primary tumor. 5 Integrin-mediated cell adhesion reorganizes actin filaments 6 through activation of diverse intracellular signaling molecules, including focal adhesion kinase (FAK), Rho guanosine triphosphatases (RhoA, Rac1, and CDC42), and others, 7 which are critical for cellular morphology and migration. 8 TM4SF proteins (i.e., tetraspanins or tetraspans) are a group of membrane proteins with four transmembrane

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Blockade of four-transmembrane L6 family member 5 (TM4SF5)-mediated tumorigenicity in hepatocytes by a synthetic chalcone derivative #

et al. 2009

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“…ibly disrupts Mdm2-p53 protein complexes (27,31), and measured its effect on p53 ubiquitination in mock-and IAV-infected cells. The ladders of polyubiquitinated p53 were detected in mock-infected cells in the presence of MG132 (Fig.…”

Section: Accumulation and Activation Of P53 Protein In Iav-infected Cmentioning

confidence: 99%

Stabilization of p53 in Influenza A Virus-infected Cells Is Associated with Compromised MDM2-mediated Ubiquitination of p53

Wang

Deng

Yan

et al. 2012

Journal of Biological Chemistry

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“…The presence of a reactive, unsaturated keto function in chalcones is found to be responsible for their antimicrobial activity, which may be altered depending on the type and position of substituent on the rings. In the present communication we report the reaction of 3-acetylpyridine with different aromatic aldehydes (2 a-g ) to form chalcones [1][2][3][4][5][6][7][8][9][10][11][12][13] (3 a-g ) in the presence of alkali. The resulting chalcones after purification and characterization by physical and spectral methods have been successfully converted into substituted pyrimidines [14][15][16][17][18][19] (4 a-g ) by reaction with guanidine hydrochloride.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Some Novel Chalcones of 3-Acetyl Pyridine and their Pyrimidine Derivatives

Jyothi¹,

Prasad²,

Venkatesh³

et al. 2012

Chem Sci Trans

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Chalcones afford a facile route of access to many of the heterocyclic systems containing oxygen and nitrogen. An attempt is therefore made to synthesize chalcones from 3-acetylpyridine by reaction with either aromatic or heteroaromatic aldehyde using Claisen-Schmidt condensation. The resulting chalcones after purification and characterization by physical and spectral methods have been successfully converted into substituted pyrimidines by reaction with guanidine hydrochloride. All these compounds were characterized by means of their IR, 1 H NMR, 13 C NMR and mass spectral data. These compounds were evaluated for antimicrobial activities by cup plate method.

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Design, Synthesis, and Evaluation of Novel Boronic-Chalcone Derivatives as Antitumor Agents

Abstract: A series of boronic-chalcone derivatives were synthesized and tested for antitumor activity against human breast cancer cell lines. The results show the boronic-chalcones are more toxic to breast cancer cells compared to normal breast cells than other known chalcones.

Cited by 300 publications

References 29 publications

Blockade of four-transmembrane L6 family member 5 (TM4SF5)-mediated tumorigenicity in hepatocytes by a synthetic chalcone derivative #

Blockade of four-transmembrane L6 family member 5 (TM4SF5)-mediated tumorigenicity in hepatocytes by a synthetic chalcone derivative #

Stabilization of p53 in Influenza A Virus-infected Cells Is Associated with Compromised MDM2-mediated Ubiquitination of p53

Synthesis and Antimicrobial Activity of Some Novel Chalcones of 3-Acetyl Pyridine and their Pyrimidine Derivatives

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