Synthesis and antiproliferative activity of aryl- and heteroaryl-hydrazones derived from xanthone carbaldehydes

Varache‐Lembege, Martine; Moreau, Stéphane; Larrouture, Stéphane; Montaudon, Danièle; Robert, Jacques; Nuhrich, A.

doi:10.1016/j.ejmech.2007.09.003

Cited by 56 publications

(32 citation statements)

References 24 publications

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“…133,134 Despite this consideration, assays that utilize MTT or similar cell vitality stain reagents for measuring cellular proliferation and growth continue to be extensively applied for the routine assessment of true chemotherapeutic cytotoxic anti-neoplastic potency. 7,26,30,[135][136][137][138][139] Fourth, cytotoxic anti-neoplastic potency could have been delineated in vivo against human neoplastic xenographs in animal hosts as a model for human neoplasia where the efficacy of a covalent immunochemotherapeutic frequently tends to be higher than in ex vivo tissue culture based models utilizing the same identical cancer cell type. 39,42,140 The enhanced levels of covalent immunochemotherapeutic potency measured in vivo is presumed in part to be dependent upon contributions from endogenous immune responses that include antibody-dependent cell cytotoxicity (ADCC) phenomenon in concert with complemented-mediated cytolysis initiated by the formation of antigen-immunoglobulin complexes on the exterior surface membrane of ''targeted'' neoplastic cells.…”

Section: Cytotoxic Anti-neoplastic Potencymentioning

confidence: 99%

Synthesis of a Covalent Epirubicin-(C₃-amide)-Anti-HER2/neuImmunochemotherapeutic Utilizing a UV-Photoactivated Anthracycline Intermediate

Coyne

Jones²,

Bear³

2012

Cancer Biotherapy and Radiopharmaceuticals

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The C 3 -monoamine on the carbohydrate moiety (daunosamine -NH 2 -3¢) of epirubicin was reacted under anhydrous conditions with succinimidyl 4,4-azipentanoate to create a covalent UV-photoactivated epirubicin-(C 3 -amide) intermediate with primary amine-reactive properties. A synthetic covalent bond between the UV-photoactivated epirubicin-(C 3 -amide) intermediate and the e-amine of lysine residues within the amino acid sequence of anti-HER2/neu monoclonal immunoglobulin was subsequently created by exposure to UV light (354 nm) for 15 minutes. Size-separation by sodium dodecyl sulfate-polyacrylamide gel electrophoresis combined with immunodetection analysis and chemiluminescent autoradiographic imaging revealed a lack of IgG-IgG polymerization or degradative protein fragmentation of the covalent epirubicin-(C 3 -amide)-[anti-HER2/neu] immunochemotherapeutic. Retained binding-avidity of epirubicin-(C 3 -amide)-[anti-HER2/neu] was validated by cell-ELISA utilizing monolayer populations of chemotherapeutic-resistant mammary adenocarcinoma SKBr-3 which highly overexpress membrane-associated HER2/neu complexes. Between epirubicin-equivalent concentrations of 10 -10 to 10 -6 M the covalent epirubicin-(C 3 -amide)-[anti-HER2/neu] immunochemotherapeutic consistently evoked levels of cytotoxic anti-neoplastic potency that were highly analogous to chemotherapeuticequivalent concentrations of epirubicin. Cytotoxic anti-neoplastic potency of epirubicin-(C 3 -amide)-[anti-HER2/ neu] against chemotherapeutic-resistant mammary adenocarcinoma SKBr-3 challenged with epirubicin-(C 3 -amide)-[anti-HER2/neu] at an epirubicin-equivalent concentration of 10 -6 M was 88.5% (e.g., 11.5% residual survival). Between final epirubicin-equivalent concentrations of 10 -8 and 10 -7 M there was a marked threshold increase in the mean cytotoxic anti-neoplastic activity for epirubicin-(C 3 -amide)-[anti-HER2/neu] from 9.9% to 66.9% (90.2% to 33.1% residual survival).

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Section: Cytotoxic Anti-neoplastic Potencymentioning

confidence: 99%

Synthesis of a Covalent Epirubicin-(C₃-amide)-Anti-HER2/neuImmunochemotherapeutic Utilizing a UV-Photoactivated Anthracycline Intermediate

Coyne

Jones²,

Bear³

2012

Cancer Biotherapy and Radiopharmaceuticals

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“…The mixture cooled, stirred with cold water, keeping temperature 0-4°C for 2.5 hours. The resulting solid collected by filtration, washed with water until pH 6 and dried at 60°C (Varache-Lembege et al, 2008). To the intermediate (2 mmol) and alkyl bromide (3 mmol) in acetone (55-60 mL) was added potassium carbonate (2.5 mmol).…”

Section: General Proceduresmentioning

confidence: 99%

Design, synthesis and anti-diabetic activity of some novel xanthone derivatives targeting α-glucosidase

Bairy

Das

Nainwal

et al. 2016

Bangladesh J Pharmacol

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Twenty eight xanthone derivatives were designed and docked into the N-terminal catalytic domain of maltase-glucoamylase (ntMGAM) by considering Miglitol as standard drug. Most of the molecules showed excellent docking scores and docking interaction as compared to the binding cavity of the standard molecule. The five best scoring ligands were synthesized and characterized by a number of analytical and spectroscopic techniques. The molecules were screened for the in vivo antidiabetic activity in streptozotocin (STZ) induced diabetic animal model in Wistar rats. Compound P4 showed the most prominent inhibition among others. The synthesized compounds reported significant (p< 0.01) effect of lowering glucose levels in the blood compared to miglitol as a standard α-glucosidase inhibitor.Video clipInduction of diabetes:

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“…corresponding hydrazide derivatives (17)(18)(19). The physicochemical characteristics of synthesized compounds are presented in Table 1.…”

Section: Kumari Et Almentioning

confidence: 99%

“…The synthesis of the intermediate (2,3) and target compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) was performed according to reactions outlined in Schemes 1 and 2. A methanolic solution of undecylenic acid 1 was refluxed in the presence of sulfuric acid to yield the methyl ester undecylenic acid (2).…”

Section: Spectral Data Analysismentioning

confidence: 99%

“…Further, the previous studies performed by us revealed the significance of different acid derivatives, including undec-10-enoic hydrazide-hydrazone derivatives as antibacterial and antifungal agents [6][7][8][9][10][11]. Studies reported by various research groups also showed that hydrazide-hydrazone derivatives of different acids have wide range of biological activities, viz., antibacterial [12], antifungal [13], antitubercular [14], trypnocidal [15], antimalarial [16], antiviral [8], anti-inflammatory [17], and antitumor [18] activities. Isoniazid (antitubercular) [19], nifuroxazide (antidiarrheal and antitumor) [20], nifurtimox (antiamoebic) [21], furacin (antibiotic) [22], and furazolidone (antibacterial) [23] are hydrazide containing important biologically active drug molecules.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

Kumari

Narang

Nayak

et al. 2017

Asian J Pharm Clin Res

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Objective: In recent years, an increasing frequency and severity of antimicrobial resistance to different antimicrobial agents, demands new remedies for the treatment of infections. Therefore, in this study, a series of undec-10-enehydrazide derivatives were synthesized and screened for in vitro activity against selected pathogenic microbial strains. Methods:The synthesis of the intermediate and target compounds was performed by standard procedure. Synthesized compounds were screened for antimicrobial activity by tube dilution method. Molecular docking study of synthesized derivatives was also performed to find out their interaction with the target site of β-ketoacyl-acyl carrier protein synthase III, (FabH; pdb id:3IL7) by docking technique. Quantitative structure-activity relationship (QSAR) studies were also performed to correlate antimicrobial activity with structural properties of synthesized molecules.Results: Antimicrobial screening results showed that compound 8 having benzylidine moiety with methoxy groups at meta and para position and compound 16 having 3-chloro-2-(3-flourophenyl)-4-oxoazetidine moiety was found to be most potent. QSAR studies revealed the importance of Randic topology parameter (R) in describing the antimicrobial activity of synthesized derivatives. Molecular docking study indicated hydrophobic interaction of deeply inserted aliphatic side chain of the ligand with FabH. The N-atoms of hydrazide moiety interacts with Ala246 and Asn247 through H-bonding. The m-and p-methoxy groups form H-bond with water and side chain of Arg36, respectively. Conclusion:Compound 8 having benzylidine moiety with methoxy groups at meta and para position and compound 16 having 3-chloro-2-(3-flourophenyl)-4-oxoazetidine moiety was found to most potent antibacterial and antifungal compounds, respectively.

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Synthesis and antiproliferative activity of aryl- and heteroaryl-hydrazones derived from xanthone carbaldehydes

Cited by 56 publications

References 24 publications

Synthesis of a Covalent Epirubicin-(C₃-amide)-Anti-HER2/neuImmunochemotherapeutic Utilizing a UV-Photoactivated Anthracycline Intermediate

Synthesis of a Covalent Epirubicin-(C₃-amide)-Anti-HER2/neuImmunochemotherapeutic Utilizing a UV-Photoactivated Anthracycline Intermediate

Design, synthesis and anti-diabetic activity of some novel xanthone derivatives targeting α-glucosidase

Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

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Synthesis and antiproliferative activity of aryl- and heteroaryl-hydrazones derived from xanthone carbaldehydes

Cited by 56 publications

References 24 publications

Synthesis of a Covalent Epirubicin-(C3-amide)-Anti-HER2/neuImmunochemotherapeutic Utilizing a UV-Photoactivated Anthracycline Intermediate

Synthesis of a Covalent Epirubicin-(C3-amide)-Anti-HER2/neuImmunochemotherapeutic Utilizing a UV-Photoactivated Anthracycline Intermediate

Design, synthesis and anti-diabetic activity of some novel xanthone derivatives targeting α-glucosidase

Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

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Product

Resources

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Synthesis of a Covalent Epirubicin-(C₃-amide)-Anti-HER2/neuImmunochemotherapeutic Utilizing a UV-Photoactivated Anthracycline Intermediate

Synthesis of a Covalent Epirubicin-(C₃-amide)-Anti-HER2/neuImmunochemotherapeutic Utilizing a UV-Photoactivated Anthracycline Intermediate