Discovery of novel anti-tumor curcumin analogues from the optimization of curcumin scaffold

Zhang, Laiyin; Zong, Hui; Lu, Huiping; Gong, Jian-Sheng; Ma, Fengwang

doi:10.1007/s00044-017-1946-2

Cited by 8 publications

(5 citation statements)

References 20 publications

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“…mp = 145 °C. 41 IR (ν max /cm –1 ) 2971.81, 2929.39 (C–H aliphatic/aromatic), 1589.08 (C=O), 1519.66 (C=C), 1353.81 (C ar –N), 1184.10 (C–N aliphatic). 1 H NMR (CDCl 3 , 400 MHz): δ (ppm) 16.43 (br, 1H), 7.60, 6.41 (dd, J = 15.8 Hz, each 2H), 7.44 (d, J = 9.63 Hz, 4H), 6.65 (d, J = 8.4 Hz, 4H), 5.73 (s, 1H), 3.42 (q, J = 6.96 Hz, 8H), 1.23 (t, J = 7.26 Hz, 12H); 13 C NMR (CDCl 3 , 125 MHz): δ (ppm) 183.42 (C=O), 149.28, 140.67, 130.23, 122.36, 118.67, 111.46, 100.84, 44.58 (N( C H 2 CH 3 ) 2 ), 12.73 (N(CH 2 C H 3 ) 2 ).…”

Section: Experimental Sectionmentioning

confidence: 99%

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Curcuminoid-Tailored Interfacial Free Energy of Hydrophobic Fibers for Enhanced Biological Properties

Deus

França

Forero

et al. 2021

ACS Appl. Mater. Interfaces

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The ability of mimicking the extracellular matrix architecture has gained electrospun scaffolds a prominent space into the tissue engineering field. The high surface-to-volume aspect ratio of nanofibers increases their bioactivity while enhancing the bonding strength with the host tissue. Over the years, numerous polyesters, such as poly(lactic acid) (PLA), have been consolidated as excellent matrices for biomedical applications. However, this class of polymers usually has a high hydrophobic character, which limits cell attachment and proliferation, and therefore decreases biological interactions. In this way, functionalization of polyester-based materials is often performed in order to modify their interfacial free energy and achieve more hydrophilic surfaces. Herein, we report the preparation, characterization, and in vitro assessment of electrospun PLA fibers with low contents (0.1 wt %) of different curcuminoids featuring π-conjugated systems, and a central β-diketone unit, including curcumin itself. We evaluated the potential of these materials for photochemical and biomedical purposes. For this, we investigated their optical properties, water contact angle, and surface features while assessing their in vitro behavior using SH-SY5Y cells. Our results demonstrate the successful generation of homogeneous and defect-free fluorescent fibers, which are noncytotoxic, exhibit enhanced hydrophilicity, and as such greater cell adhesion and proliferation toward neuroblastoma cells. The unexpected tailoring of the scaffolds’ interfacial free energy has been associated with the strong interactions between the PLA hydrophobic sites and the nonpolar groups from curcuminoids, which indicate its role for releasing hydrophilic sites from both parts. This investigation reveals a straightforward approach to produce photoluminescent 3D-scaffolds with enhanced biological properties by using a polymer that is essentially hydrophobic combined with the low contents of photoactive and multifunctional curcuminoids

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Section: Experimental Sectionmentioning

confidence: 99%

“…Dark red crystals (yield 40%) from isopropyl alcohol. mp = 145 °C . IR (ν max /cm –1 ) 2971.81, 2929.39 (C–H aliphatic/aromatic), 1589.08 (CO), 1519.66 (CC), 1353.81 (C ar –N), 1184.10 (C–N aliphatic).…”

Section: Experimental Sectionmentioning

confidence: 99%

Curcuminoid-Tailored Interfacial Free Energy of Hydrophobic Fibers for Enhanced Biological Properties

Deus

França

Forero

et al. 2021

ACS Appl. Mater. Interfaces

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“…Curcumin, a major active component of Turmeric, has long been used as a spice, and it possess a wide range of biological activities, including antibacterial and antifungal [ 1 ], antioxidant, anticancer [ 2 , 3 ], antimicrobial [ 4 ], and inflammatory properties [ 5 ]. Curcumin has piqued the interest of many academics since then, and numerous papers have been published on the subject [ 6 , 7 , 8 ]. It was first discovered by Vogel and Pelletier as a powder “yellow coloring matter” from rhizomes of C. longa (Zingiberaceae family) [ 9 ], and characterized and first synthesized by Milobedeska, Lampe et al [ 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Multitask Quantum Study of the Curcumin-Based Complex Physicochemical and Biological Properties

Baira

Ounissi

Merouani

et al. 2022

IJMS

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Density functional theory (DFT), time-dependent density functional theory (TDDFT), quantum theory of atoms in molecules (QTAIM), and extended transition state natural orbitals for chemical valence (ETS-NOCV) have all been used to investigate the physicochemical and biological properties of curcumin and three complexes, i.e., Cur-M (M = Ni, Cu, and Mg). Based on DFT calculations, the enolic form (Cur-Enol) is more stable than the anti-diketone form (Cur-Anti diketone) favored for complexation. This enolic form stability was explained by the presence of three intramolecular hydrogen bonds according to the QTAIM analysis. Furthermore, the ETS-NOCV technique revealed that the enolic form had more significant antioxidant activity compared with the anti-diketone form. The calculations from the COnductor-like Screening MOdel for Realistic Solvents (COSMO-RS) showed that the dimethyl sulfoxide (DMSO) solvent could dissolve all the curcumin tautomers Cur-Enol, Cur-Anti-diketone and Cur-Cu, Cur-Mg, and Cur-Ni complexes in contrast to benzene, acetone, octanol, ethanol, methanol, and water. Furthermore, except for Cur-Mg, which had a relatively low solubility (14 g/L), all complexes were insoluble in water. Cur-Anti-diketone was considerably more soluble than Cur-Enol in the examined solvents.

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“…At the same time, dimethoxy curcumin showed a high metabolic stability compared to curcumin itself [ 88 ]. While another study found that a modification in curcumin’s aromatic ring resulted in the formation of 10 different curcumin analogues with more potent in vitro and in vivo anti-tumor activities than curcumin [ 89 ]. In this study we provide significant evidence that the food additive KBrO 3 induced carcinogenic alteration via induction of ROS and activation of several oncogenic genes, counteracting tumor suppressor genes and favouring cell dedifferentiation.…”

Section: Discussionmentioning

confidence: 99%

Identification of the Multifaceted Chemopreventive Activity of Curcumin Against the Carcinogenic Potential of the Food Additive, KBrO3

Obaidi

Higgins

Bahar

et al. 2018

CPD

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Background: Potassium bromate (KBrO3), a food additive, has been used in many bakery products as an oxidizing agent. It has been shown to induce renal cancer in many in-vitro and in-vivo experimental modelsObjectives: This study evaluated the carcinogenic potential of potassium bromate (KBrO3) and the chemopreventive mechanisms of the anti-oxidant and anti-inflammatory phytochemical, curcumin against KBrO3-induced carcinogenicity.Method: Lactate dehydrogenase (LDH) cytotoxicity assay and morphological characteristics were used to assess curcumin's cytoprotective potential against KBrO3 toxicity. To assess the chemopreventive potential of curcumin against KBrO3-induced oxidative insult, intracellular H2O2 and the nuclear concen-tration of the DNA adduct 8-OHdG were measured. PCR array, qRT-PCR, and western blot analysis were used to identify dysregulated genes by KBrO3 exposure. Furthermore, immunofluorescence was used to evaluate the ciliary loss and the disturbance of cellular tight junction induced by KBrO3.Results: Oxidative stress assays showed that KBrO3 increased the levels of intracellular H2O2 and the DNA adduct 8-OHdG. Combination of curcumin with KBrO3 efficiently reduced the level of H2O2 and 8-OHdG while up-regulating the expression of catalase. PCR array, qRT-PCR, and western blot analysis revealed that KBrO3 dysregulated multiple genes involved in inflammation, proliferation, and apoptosis, namely CTGF, IL-1, and TRAF3. Moreover, qRT-PCR and immunofluorescence studies showed that KBrO3 negatively affected the tight junctional protein (ZO-1) and induced a degeneration of primary ciliary proteins. The negative impact of KBrO3 on cilia was markedly repressed by curcumin.Conclusion: Curcumin could potentially be used as a protective agent against carcinogenicity of KBrO3.

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Discovery of novel anti-tumor curcumin analogues from the optimization of curcumin scaffold

Cited by 8 publications

References 20 publications

Curcuminoid-Tailored Interfacial Free Energy of Hydrophobic Fibers for Enhanced Biological Properties

Curcuminoid-Tailored Interfacial Free Energy of Hydrophobic Fibers for Enhanced Biological Properties

Multitask Quantum Study of the Curcumin-Based Complex Physicochemical and Biological Properties

Identification of the Multifaceted Chemopreventive Activity of Curcumin Against the Carcinogenic Potential of the Food Additive, KBrO3

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