Novel racemic tetrahydrocurcuminoid dihydropyrimidinone analogues as potent acetylcholinesterase inhibitors

Arunkhamkaew, Sarawalee; Athipornchai, Anan; Apiratikul, Nuttapon; Suksamrarn, Apichart; Ajavakom, Vachiraporn

doi:10.1016/j.bmcl.2013.03.069

Cited by 38 publications

(20 citation statements)

References 37 publications

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“…The evaluation of acetylcholinesterase inhibitors for Alzheimer's disease of these analogs showed that they exhibited higher inhibitory activity than the CUR. THBDC-DHPM demonstrated the most potent inhibitory activity with excellent IC 50 value, which is slightly more potent than that of galanthamine 124 . A series of CUR based diarylheptanoid analogs were synthesized using multiple carbon-carbon bond formation on the multifaceted catalytic properties of titanocene complexes and evaluated their anti-glioblastoma and anti-neuroblastoma properties.…”

Section: Biological Activities Of Various Curcuminoid Formulationsmentioning

confidence: 99%

Biological activities of curcuminoids, other biomolecules from turmeric and their derivatives – A review

Amalraj¹,

Pius

Gopi

et al. 2017

Journal of Traditional and Complementary Medicine

708

413

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In recent years, several drugs have been developed deriving from traditional products and current drug research is actively investigating the possible therapeutic roles of many Ayruvedic and Traditional Indian medicinal therapies. Among those being investigated is Turmeric. Its most important active ingredient is curcuminoids. Curcuminoids are phenolic compounds commonly used as a spice, pigment and additive also utilized as a therapeutic agent used in several foods. Comprehensive research over the last century has revealed several important functions of curcuminoids. Various preclinical cell culture and animals studies suggest that curcuminoids have extensive biological activity as an antioxidant, neuroprotective, antitumor, anti-inflammatory, anti-acidogenic, radioprotective and arthritis. Different clinical trials also suggest a potential therapeutic role for curcuminoids in numerous chronic diseases such as colon cancer, lung cancer, breast cancer, inflammatory bowel diseases. The aim of this review is to summarize the chemistry, analog, metal complex, formulations of curcuminoids and their biological activities.

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Section: Biological Activities Of Various Curcuminoid Formulationsmentioning

confidence: 99%

Biological activities of curcuminoids, other biomolecules from turmeric and their derivatives – A review

Amalraj¹,

Pius

Gopi

et al. 2017

Journal of Traditional and Complementary Medicine

708

413

View full text Add to dashboard Cite

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“…Curcumin has been shown to inhibit AChE. THC-induced inhibition of AChE exhibited an IC50 that was about two times better than that of curcumin [76].…”

Section: Neurologic Effectsmentioning

confidence: 99%

Curcumin Differs from Tetrahydrocurcumin for Molecular Targets, Signaling Pathways and Cellular Responses

2014

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Curcumin (diferuloylmethane), a golden pigment from turmeric, has been linked with antioxidant, anti-inflammatory, anticancer, antiviral, antibacterial, and antidiabetic properties. Most of the these activities have been assigned to methoxy, hydroxyl, α,β-unsaturated carbonyl moiety or to diketone groups present in curcumin. One of the major metabolites of curcumin is tetrahydrocurcumin (THC), which lacks α,β-unsaturated carbonyl moiety and is white in color. Whether THC is superior to curcumin on a molecular level is unclear and thus is the focus of this review. Various studies suggest that curcumin is a more potent antioxidant than THC; curcumin (but not THC) can bind and inhibit numerous targets including DNA (cytosine-5)-methyltransferase-1, heme oxygenase-1, Nrf2, β-catenin, cyclooxygenase-2, NF-kappaB, inducible nitric oxide synthase, nitric oxide, amyloid plaques, reactive oxygen species, vascular endothelial growth factor, cyclin D1, glutathione, P300/CBP, 5-lipoxygenase, cytosolic phospholipase A2, prostaglandin E2, inhibitor of NF-kappaB kinase-1, -2, P38MAPK, p-Tau, tumor necrosis factor-α, forkhead box O3a, CRAC; curcumin can inhibit tumor cell growth and suppress cellular entry of viruses such as influenza A virus and hepatitis C virus much more effectively than THC; curcumin affects membrane mobility; and curcumin is also more effective than THC in suppressing phorbol-ester-induced tumor promotion. Other OPEN ACCESSMolecules 2015, 20 186 studies, however, suggest that THC is superior to curcumin for induction of GSH peroxidase, glutathione-S-transferase, NADPH: quinone reductase, and quenching of free radicals. Most studies have indicated that THC exhibits higher antioxidant activity, but curcumin exhibits both pro-oxidant and antioxidant properties.

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“…Arunkhamkaew et al [100] synthesized AB74 analogue bearing a 4-OCH 3 phenyl group and evaluated as an inhibitor of AChE. AB74 was found to be a potent inhibitor of AChE with an excellent IC 50 value of 1.34 ±0.03 µM, which is slightly higher than that of galanthamine (Figure 15).…”

Section: Inhibition Of Achementioning

confidence: 99%

Curcumin in Health and Diseases: Alzheimer’s Disease and Curcumin Analogues, Derivatives, and Hybrids

Chainoglou

Hadjipavlou‐Litina

2020

IJMS

105

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Worldwide, Alzheimer’s disease (AD) is the most common neurodegenerative multifactorial disease influencing the elderly population. Nowadays, several medications, among them curcumin, are used in the treatment of AD. Curcumin, which is the principal component of Curcuma longa, has shown favorable effects forsignificantly preventing or treating AD. During the last decade, the scientific community has focused their research on the optimization of therapeutic properties and on the improvement of pharmacokinetic properties of curcumin. This review summarizes bibliographical data from 2009 to 2019 on curcumin analogues, derivatives, and hybrids, as well as their therapeutic, preventic, and diagnostic applications in AD. Recent advances in the field have revealed that the phenolic hydroxyl group could contribute to the anti-amyloidogenic activity. Phenyl methoxy groups seem to contribute to the suppression of amyloid-β peptide (Aβ42) and to the suppression of amyloid precursor protein (APP) andhydrophobic interactions have also revealed a growing role. Furthermore, flexible moieties, at the linker, are crucial for the inhibition of Aβ aggregation. The inhibitory activity of derivatives is increased with the expansion of the aromatic rings. The promising role of curcumin-based compounds in diagnostic imaging is highlighted. The keto-enol tautomerism seems to be a novel modification for the design of amyloid-binding agents. Molecular docking results, (Q)SAR, as well as in vitro and in vivo tests highlight the structures and chemical moieties that are correlated with specific activity. As a result, the knowledge gained from the existing research should lead to the design and synthesis ofinnovative and multitargetedcurcumin analogues, derivatives, or curcumin hybrids, which would be very useful drug and tools in medicine for both diagnosis and treatment of AD.

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Novel racemic tetrahydrocurcuminoid dihydropyrimidinone analogues as potent acetylcholinesterase inhibitors

Cited by 38 publications

References 37 publications

Biological activities of curcuminoids, other biomolecules from turmeric and their derivatives – A review

Biological activities of curcuminoids, other biomolecules from turmeric and their derivatives – A review

Curcumin Differs from Tetrahydrocurcumin for Molecular Targets, Signaling Pathways and Cellular Responses

Curcumin in Health and Diseases: Alzheimer’s Disease and Curcumin Analogues, Derivatives, and Hybrids

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