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. 2022 Feb 16:10:830511.
doi: 10.3389/fchem.2022.830511. eCollection 2022.

Tris(2-Pyridylmethylamine)V(O)2 Complexes as Counter Ions of Diprotonated Decavanadate Anion: Potential Antineoplastic Activity

Nidia D Corona-Motolinia  1 , Beatriz Martínez-Valencia  1 , Lisset Noriega  2 , Brenda L Sánchez-Gaytán  1 , Francisco J Melendez  2 , Amalia García-García  3 , Duane Choquesillo-Lazarte  4 , Antonio Rodríguez-Diéguez  3 , María Eugenia Castro  1 , Enrique González-Vergara  1
Affiliations

Tris(2-Pyridylmethylamine)V(O)2 Complexes as Counter Ions of Diprotonated Decavanadate Anion: Potential Antineoplastic Activity

Nidia D Corona-Motolinia et al. Front Chem. .

Abstract

The synthesis and theoretical-experimental characterization of a novel diprotanated decavanadate is presented here due to our search for novel anticancer metallodrugs. Tris(2-pyridylmethyl)amine (TPMA), which is also known to have anticancer activity in osteosarcoma cell lines, was introduced as a possible cationic species that could act as a counterpart for the decavanadate anion. However, the isolated compound contains the previously reported vanadium (V) dioxido-tpma moieties, and the decavanadate anion appears to be diprotonated. The structural characterization of the compound was performed by infrared spectroscopy and single-crystal X-ray diffraction. In addition, DFT calculations were used to analyze the reactive sites involved in the donor-acceptor interactions from the molecular electrostatic potential maps. The level of theory mPW1PW91/6-31G(d)-LANL2DZ and ECP = LANL2DZ for the V atom was used. These insights about the compounds' main interactions were supported by analyzing the noncovalent interactions utilizing the AIM and Hirshfeld surfaces approach. Molecular docking studies with small RNA fragments were used to assess the hypothesis that decavanadate's anticancer activity could be attributed to its interaction with lncRNA molecules. Thus, a combination of three potentially beneficial components could be evaluated in various cancer cell lines.

Keywords: DFT calculations; TPMA; antineoplastic activity; decavanadate; molecular docking; vanadium (V) dioxido compounds.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

FIGURE 1
FIGURE 1
OLEX representation of the asymmetric unit containing half of the diprotonated decavanadate, two slightly different dioxidovanadium(V) tpma moieties (A,B), and two crystallization water molecules.
FIGURE 2
FIGURE 2
Expansion of asymmetric unit using OLEX program shows the tridimensional structure formed by a diprotonated decavanadate unit and four dioxidovanadium(V) complexes, water molecules were removed for clarity.
FIGURE 3
FIGURE 3
OLEX representation of hydrogen bonds connecting both species of V(V).
FIGURE 4
FIGURE 4
Mercury representation of a chain of decavanadate anions connected through water molecule forming rings R3 3 (8) and R4 4 (12).
FIGURE 5
FIGURE 5
Supramolecular structure showing how a single diprotanated decavanadate is surrounded by six moieties of [VO2(tpma)]+.
FIGURE 6
FIGURE 6
Molecular electrostatic potential map of (A) the representation of Compound 1 forming hydrogen bonds connecting both species of V(V), and (B) the asymmetric unit showing to the diprotonated decavanadate unit and four dioxidovanadium(V)-tpma moieties, calculated at the theory level mPW1PW91/6–31G(d)-LANL2DZ using ECP = LANL2DZ for the V atom.
FIGURE 7
FIGURE 7
Molecular graphs of (A) the representation of Compound 1 forming hydrogen bonds connecting both species of V(V), and (B) the asymmetric unit showing to the diprotonated decavanadate unit and four dioxidovanadium(V)-tpma moieties.
FIGURE 8
FIGURE 8
Hirshfeld surfaces (left) and fingerprint plots of noncovalent interactions (right) mapped with dnorm parameter of (A) the representation of Compound 1 forming hydrogen bonds connecting both species of V(V), and (B) the asymmetric unit showing to the diprotonated decavanadate unit and four dioxidovanadium(V)-tpma moieties.
FIGURE 9
FIGURE 9
Docked structures of top molecular pose for: (A) DNA (B) pre-miR-21 (C) l7-miRNA (D) lncRNA with diprotonated decavanadate shown in CPK display style and [VO2(tpma)]+ shown in scaled ball and stick style.
FIGURE 10
FIGURE 10
Interaction of decavanadate with the riboswitch (3DIS) visualized with UCSF Chimera X program, (2021).
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