Three new coordination geometries of homoleptic Zn complexes of curcuminoids and their high antiproliferative potential

Meza-Morales, William; Alvarez-Ricardo, Yair; Obregón‐Mendoza, Marco A.; Arenaza‐Corona, Antonino; Ramírez‐Apán, María Teresa; Toscano, Rubén A.; Poveda-Jaramillo, Juan Carlos; Enríquez, Raúl G.

doi:10.1039/d3ra00167a

Cited by 8 publications

(10 citation statements)

References 46 publications

(82 reference statements)

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“…(iii) Removal of BF 2 with alumina to recover the β-keto-enol function of the curcuminoid (3). The synthetic method was adequate for the synthesis of ligands in good (Dimethoxycurcumin-BF 2 (2), 85%) to excellent (DiMeOC (3), 90%) yields, as reported previously [24,55]. The spectral information of the precursor (2) and ligands (3) were confirmed by infrared (IR), mass spectrometry (MS), and nuclear magnetic resonance (NMR).…”

Section: Resultssupporting

confidence: 57%

“…So, this chemical property has been advantageous in improving its solubility and bioavailability. Different metals of biological interest, such as copper (Cu), iron (Fe), manganese (Mn), zinc (Zn), gallium (Ga), and indium (In), have previously been bonded to curcuminoid-type molecules, forming active metal complexes with antioxidant or cytotoxic activities against breast cancer cell lines (Table 1) [21][22][23][24]. A metal ion related to breast cancer is magnesium (Mg) [25], the second most relevant ion in the human body [26] because it acts as a cofactor for about 300 enzymatic processes involved in maintaining energy metabolism [27], protein synthesis, and DNA replication [28], besides exerting essential antioxidant functions [29].…”

Section: Introductionmentioning

confidence: 99%

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The Antitumoral Effect In Ovo of a New Inclusion Complex from Dimethoxycurcumin with Magnesium and Beta-Cyclodextrin

Obregón-Mendoza,

Meza-Morales,

Rodríguez-Hernández

et al. 2024

IJMS

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Breast cancer is one of the leading causes of death in the female population because of the resistance of cancer cells to many anticancer drugs used. Curcumin has cytotoxic activities against breast cancer cells, although it has limited use due to its poor bioavailability and rapid metabolic elimination. The synthesis of metal complexes of curcumin and curcuminoids is a relevant topic in the search for more active and selective derivatives of these molecular scaffolds. However, solubility and bioavailability are concomitant disadvantages of these types of molecules. To overcome such drawbacks, the preparation of inclusion complexes offers a chemical and pharmacologically safe option for improving the aqueous solubility of organic molecules. Herein, we describe the preparation of the inclusion complex of dimethoxycurcumin magnesium complex (DiMeOC-Mg, (4)) with beta-cyclodextrin (DiMeOC-Mg-BCD, (5)) in the stoichiometric relationship 1:1. This new inclusion complex’s solubility in aqueous media phosphate buffer saline (PBS) was improved by a factor of 6x over the free metal complex (4). Furthermore, 5 affects cell metabolic rate, cell morphology, cell migration, induced apoptosis, and downregulation of the matrix metalloproteinase-2 (MMP-2) and matrix metalloproteinase-9 (MMP-9), interleukin-6 (IL-6), and signal transducer and activator of transcription-3 (STAT3) expression levels on MD Anderson metastasis breast-231 cancer (MDA-MB-231) cell lines. Results of an antitumor assay in an in ovo model showed up to 30% inhibition of tumor growth for breast cancer (MDA-MB-231) when using (5) (0.650 mg/kg dose) and 17.29% inhibition with the free homoleptic metal complex (1.5 mg/kg dose, (4)). While the formulation of inclusion complexes from metal complexes of curcuminoids demonstrates its usefulness in improving the solubility and bioavailability of these metallodrugs, the new compound (5) exhibits excellent potential for use as a therapeutic agent in the battle against breast cancer.

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Section: Resultssupporting

confidence: 57%

Section: Introductionmentioning

confidence: 99%

The Antitumoral Effect In Ovo of a New Inclusion Complex from Dimethoxycurcumin with Magnesium and Beta-Cyclodextrin

Obregón-Mendoza,

Meza-Morales,

Rodríguez-Hernández

et al. 2024

IJMS

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“…The cell viability in the experiments exceeded 95%, as determined with trypan blue. The human tumor cytotoxicity was determined using the protein-binding dye sulforhodamine B (SRB) in a microculture assay to measure cell growth, as described in the protocols established by the NCI and previously [ 69 ]. A dose–response curve was plotted for each complex and the concentration (IC 50 ), resulting in an inhibition of 50% estimated through non-linear regression analysis.…”

Section: Methodsmentioning

confidence: 99%

The Homoleptic Curcumin–Copper Single Crystal (ML2): A Long Awaited Breakthrough in the Field of Curcumin Metal Complexes

Arenaza-Corona,

Obregón-Mendoza,

Meza-Morales

et al. 2023

Molecules

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The first single crystal structure of the homoleptic copper (II) ML2 complex (M=Cu (II), L = curcumin) was obtained and its structure was elucidated by X-ray diffraction showing a square planar geometry, also confirmed by EPR. The supramolecular arrangement is supported by C-H···O interactions and the solvent (MeOH) plays an important role in stabilizing the crystal packing Crystallinity was additionally assessed by XRD patterns. The log P value of the complex (2.3 ± 0.15) was determined showing the improvement in water solubility. The cytotoxic activity of the complex against six cancer cell lines substantially surpasses that of curcumin itself, and it is particularly selective against leukemia (K562) and human glioblastoma (U251) cell lines, with similar antioxidant activity to BHT. This constitutes the first crystal structure of pristine curcumin complexed with a metal ion.

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“…The cell viability in the experiments exceeded 95%, as determined with trypan blue. The human tumor cytotoxicity was determined using the protein-binding dye sulforhodamine B (SRB) in a microculture assay to measure cell growth, as described in the protocols established by the NCI and previously [69]. A doseresponse curve was plotted for each complex and the concentration (IC 50 ), resulting in an inhibition of 50% estimated through non-linear regression analysis.…”

Section: Biological Assaysmentioning

confidence: 99%

The Homoleptic Curcumin-Copper Single Crystal (ML2): A Long Awaited Cherry on the Cake in the Field of Curcumin Metal Complexes

Corona,

Mendoza,

Morales

et al. 2023

Preprint

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The first single crystal structure of the homoleptic copper (II) ML2 complex (M=Cu (II), L=curcumin) was obtained and its structure was elucidated by X-ray diffraction showing a square planar geometry. The supramolecular arrangement is supported by C-H···O interactions and the solvent (MeOH) plays an important role in stabilizing the crystal packing. The cytotoxic activity of the complex against six cancer cell lines substantially surpasses that of curcumin itself, and it is particularly selective against leukemia (K562) and human glioblastoma (U251) cell lines with similar antioxidant activity to BHT. This constitutes the first crystal structure of pristine curcumin complexed with a metal ion.

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Three new coordination geometries of homoleptic Zn complexes of curcuminoids and their high antiproliferative potential

Abstract: We add herein three new geometries of homoleptic type complexes i.e. octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Moreover, the IC50 values for the DiMeOC-Zn complex were 8 or 22 times higher than cisplatin in the U251 and HCT15 cell lines.

Cited by 8 publications

References 46 publications

The Antitumoral Effect In Ovo of a New Inclusion Complex from Dimethoxycurcumin with Magnesium and Beta-Cyclodextrin

The Antitumoral Effect In Ovo of a New Inclusion Complex from Dimethoxycurcumin with Magnesium and Beta-Cyclodextrin

The Homoleptic Curcumin–Copper Single Crystal (ML2): A Long Awaited Breakthrough in the Field of Curcumin Metal Complexes

The Homoleptic Curcumin-Copper Single Crystal (ML2): A Long Awaited Cherry on the Cake in the Field of Curcumin Metal Complexes

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