Design,synthesis and anti-Alzheimer properties of dimethylaminomethyl-substituted curcumin derivatives |
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| Affiliation: | 1. Pharmaceutical Research Center and Jiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China;2. State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China;1. School of Pharmacy, Anhui Medical University, Hefei 230032, PR China;2. Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, PR China;3. State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China;1. Department of Chemistry, California State University, Fresno, 2555 E. San Ramon Avenue, M/S SB70, Fresno, CA 93740, USA;2. Department of Chemistry, Xavier University of Louisiana, 1 Drexel Drive, New Orleans, LA 70125, USA;3. RCMI Cancer Research Program, Xavier University of Louisiana, 1 Drexel Drive, New Orleans, LA 70125, USA;1. Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt;2. Department of Pharmacology, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt;3. Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt |
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| Abstract: | Eight dimethylaminomethyl-substituted curcumin derivatives were designed and synthesized. The antioxidant test revealed that the synthesized compounds had higher free radical scavenging activity towards both 2,2-diphenyl-1-picrylhydrazyl free radicals (DPPH) (IC50 1.5–29.9 μM) and galvinoxyl radicals (IC50 4.9–41.1 μM) than the lead compound curcumin. Besides, compound 3a could effectively inhibit the Aβ self-aggregation in vitro. Investigated in phosphate-buffered solutions (pH = 7.4) in the presence or absence of 0.1% FBS 3a showed a good stability while curcumin did not. Furthermore, 3a showed a good lipophilicity (log P = 3.48), suggesting a potential ability to penetrate the blood–brain-barrier. The aqueous solubility of the hydrochloride salt of 3a (16.7 mg/mL) has also been significantly improved as compared with curcumin (<0.1 mg/mL). |
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| Keywords: | Curcumin derivatives Antioxidant Aβ aggregation inhibition Stability Anti-Alzheimer |
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