Parallel synthesis and biological evolution of quinic acid derivatives as immuno-suppressing agents against T-cell receptors

Huang, Chih Yu; Chen, Li Hsun; Huang, Hsuan Yu; Kao, Feng Sheng; Lee, Yun Ta; Selvaraju, Manikandan; Sun, Chung‐Ming; Chen, Hueih Min

doi:10.1039/c5ra06095h

Cited by 2 publications

(3 citation statements)

References 23 publications

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“…In a further study, a series of cynarin derivatives was evaluated using this method, and results showed that one of the derivatives, Cyn-1324, reached a blocking effect of 31%. 96 In another study, the authors detailed how antagonists prevent receptor activation and evaluated the inhibition strength of vorapaxar (a PAR1 antagonist) to block the native ligand bound to PAR1. 56 They observed that vorapaxar raised the G bu of native ligand binding by ∼2.84 kcal mol −1 and lowered the binding affinity.…”

Section: Drug Discovery and Verification Using Afmmentioning

confidence: 99%

Novel perspective for protein–drug interaction analysis: atomic force microscope

Wang

2023

Analyst

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Section: Drug Discovery and Verification Using Afmmentioning

confidence: 99%

Novel perspective for protein–drug interaction analysis: atomic force microscope

Wang

2023

Analyst

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“…Chlorogenic acid derivatives C4 ( a – h ) were synthesized by following the procedure given in Scheme 1 [53–55]. Evaluation of structure of novel derivatives was confirmed by spectroscopic methods such as IR, 1 H NMR, 13 CNMR and elemental analysis.…”

Section: Resultsmentioning

confidence: 99%

“…The reaction mixture was stirred at room temperature for 1–2 h. Solvent was removed under reduced pressure. The residue HCl was removed by adding EtOEt (20 × 3 mL) under vacuum [53–55]. The residue collected was further dried and product was obtained in good yields.…”

Section: Methodsmentioning

confidence: 99%

In-silico design, synthesis, ADMET studies and biological evaluation of novel derivatives of Chlorogenic acid against Urease protein and H. Pylori bacterium

Kataria¹,

Khatkar

2019

BMC Chemistry

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Background Plants have always played important role in treating human and animal diseases as a therapeutic agent for traditional medicine. Through extensive research throughout the world, potential of natural products have been identified to control the over activity of many enzymes. In - silico screening a library of chlorogenic acid derivatives highlighted some novel compounds which were found effective against urease enzyme and cancer causing H. Pylori bacterium. Selected top ligands possessing minimum binding energy and good docking score were synthesized in wet lab by suitable procedure and evaluated for urease enzyme inhibition and free radical scavenging property. Synthetic scheme includes three step reactions i. e protection of hydroxyl group of quinic acid part of chlorogenic acid with lactonisation process, anilide formation by reaction with substituted anilines followed by extraction with ethyl acetate under vacuum and deprotection of hydroxyl groups by treatment with hydrochloric acid. Results In-vitro results of the series concluded that compounds C4a , C4d and C4b (IC 50 11.01 ± 0.013, 13.8 ± 0.041 and 15.86 ± 0.004 µM respectively in urease inhibition and 5.10 ± 0.018, 5.34 ± 0.007 and 6.01 ± 0.005 µM in antioxidant property against DPPH) were found to be significantly potent with excellent dock score − 10.091, − 10.603, − 9.833 and binding energy − 62.674, − 63.352, 56.267 kg/mol as compared to standard drugs thiourea and acetohydroxamic acid (− 3.459, − 3.049 and − 21.156 kJ/mol and − 17.454 kJ/mol) whereas compounds C4c , C4 ( e , h ) exhibited moderate in vivo activity when compared to standard. Conclusions Selected candidates from the outcome of in vitro urease inhibitory were further examined for anti- H. Pylori activity by well diffusion method against H. pylori bacterium (DSM 4867). Compound C4a showed significant anti- H. Pylori activity with zone of inhibition 10.00 ± 0.00 mm and MIC value 500 μg/mL as compared to standard drug acetohydroxamic acid having zone of inhibition 9.00 ± 0.50 mm and MIC 1000 μg/mL. Molecular docking studies also showed that compounds show strong inhibition by forming strong hydrogen bonding interactions with residues of pocket site in target protein. Hence, the present investigation studies will provide a new vision for the discovery of potent agents against H. Pylori and urease associated diseases.

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Parallel synthesis and biological evolution of quinic acid derivatives as immuno-suppressing agents against T-cell receptors

Abstract: A parallel synthesis of quinic acid derivatives is explored and their biological evolution against T-cells is studied.

Cited by 2 publications

References 23 publications

Novel perspective for protein–drug interaction analysis: atomic force microscope

Novel perspective for protein–drug interaction analysis: atomic force microscope

In-silico design, synthesis, ADMET studies and biological evaluation of novel derivatives of Chlorogenic acid against Urease protein and H. Pylori bacterium

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