Inorganics

Editorial

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3 pages, 197 KiB

Open AccessEditorial

Boron Applications in Prevention, Diagnosis and Therapy for High Global Burden Diseases

by Marvin A. Soriano-Ursúa

Inorganics 2023, 11(9), 358; https://doi.org/10.3390/inorganics11090358 - 30 Aug 2023

Viewed by 1363

Abstract

The role of boron-containing compounds (BCCs) in medicine is growing [...] Full article

(This article belongs to the Special Issue Synthesis and Innovative Biological Activity of Boron-Containing Compounds)

Research

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15 pages, 2306 KiB

Open AccessArticle

Oxidative, Genotoxic and Cytotoxic Damage Potential of Novel Borenium and Borinium Compounds

by Sibel Bayil Oguzkan, Hasan Turkez, Halil Ibrahim Ugras, Arzu Tatar and Adil Mardinoglu

Inorganics 2023, 11(8), 324; https://doi.org/10.3390/inorganics11080324 - 31 Jul 2023

Cited by 1 | Viewed by 1568

Abstract

In this study, the biological properties of novel borenium and borinium compounds in terms of their oxidative, genotoxic, and cytotoxic effects were assessed on cultured human peripheral blood cells, as well as several types of cancer cells. Our results revealed that the borinium [...] Read more.

In this study, the biological properties of novel borenium and borinium compounds in terms of their oxidative, genotoxic, and cytotoxic effects were assessed on cultured human peripheral blood cells, as well as several types of cancer cells. Our results revealed that the borinium compounds yielded the best results in terms of supporting total antioxidant capacity (TAC). In fact, borenium 1, borenium 2, borenium 3, borinium 4, and borinium 5 compounds elevated TAC levels of cultured human blood cells at rates of 42.8%, 101.5%, 69.8%, 33.3%, and 49.2%, respectively. There were no statistically significant differences (p > 0.05) between the negative control and the groups treated with all borinium and borenium concentrations from the micronucleus (MN) and chromosome aberration (CA) assays, demonstrating the non-genotoxic effects. Moreover, borenium 1 (60.7% and 50.7%), borenium 2 (70.4% and 57.2%), borenium 3 (53.1% and 45.2%), borinium 4 (55.1% and 48.1%), and borinium 5 (51.0% and 36.1%) minimized the mitomycin C(MMC)-induced genotoxic damages at different rates as determined using CA and MN assays, respectively. Again, it was found that the borinium compounds exhibited higher cytotoxic activity on cancer cells when compared to borenium compounds. Consequently, in light of our in vitro findings, it was suggested that the novel borinium and borenium compounds could be used safely in pharmacology, cosmetics, and various medical fields due to their antioxidant and non-genotoxic features, as well as their cytotoxicity potential on cancer cells. Full article

(This article belongs to the Special Issue Synthesis and Innovative Biological Activity of Boron-Containing Compounds)

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13 pages, 1153 KiB

Open AccessFeature PaperEditor’s ChoiceArticle

Redox Targets for Phosphine–Boranes

by Yonatan Morocz, Rachel E. Greben and Leonard A. Levin

Inorganics 2023, 11(7), 310; https://doi.org/10.3390/inorganics11070310 - 22 Jul 2023

Cited by 1 | Viewed by 1488

Abstract

Understanding the complex mechanisms underlying redox-mediated biological processes is a fundamental pillar of cellular biology. We describe the identification and quantification of disulfide formation and reduction in response to phosphine–borane complexes. We illustrate the specific cysteine reduction effects of the novel phosphine–borane complex [...] Read more.

Understanding the complex mechanisms underlying redox-mediated biological processes is a fundamental pillar of cellular biology. We describe the identification and quantification of disulfide formation and reduction in response to phosphine–borane complexes. We illustrate the specific cysteine reduction effects of the novel phosphine–borane complex bis(3-propionic acid methyl ester) phenylphosphine–borane complex (PB1) on cultured 661W cells. A total of 1073 unique protein fragments from 628 unique proteins were identified and quantified, of which 13 were found to be statistically significant in comparison to control cells. Among the 13 identified proteins were Notch1, HDAC1, UBA1, USP7, and subunits L4 and L7 of the 60S ribosomal subunit, all of which are involved in redox or cell death-associated pathways. Leveraging the ability of tandem mass tagging mass spectrometry to provide quantitative data in an exploratory manner provides insight into the effect PB1 and other phosphine–borane compounds may have on the cysteine redoxome. Full article

(This article belongs to the Special Issue Synthesis and Innovative Biological Activity of Boron-Containing Compounds)

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14 pages, 3642 KiB

Open AccessArticle

Novel BODIPY Conjugates with Myrtenol: Design, Spectral Characteristics, and Possibilities for Practical Application

by Galina B. Guseva, Elena V. Antina, Mikhail B. Berezin, Liliya E. Nikitina, Ilmir R. Gilfanov, Roman S. Pavelyev, Svetlana A. Lisovskaya, Larisa L. Frolova, Olga V. Ostolopovskaya, Ilfat Z. Rakhmatullin, Vladimir V. Klochkov, Elena Y. Trizna and Airat R. Kayumov

Inorganics 2023, 11(6), 241; https://doi.org/10.3390/inorganics11060241 - 3 Jun 2023

Cited by 4 | Viewed by 1613

Abstract

The synthesis of new fluorescent probes, based on biocompatible luminophors and exhibiting various specificities, is intensively developed worldwide. Many luminophors contain a hydrophobic group that limits their application for cell staining under vital conditions. Herein, we report the synthesis of two BODIPY molecules— [...] Read more.

The synthesis of new fluorescent probes, based on biocompatible luminophors and exhibiting various specificities, is intensively developed worldwide. Many luminophors contain a hydrophobic group that limits their application for cell staining under vital conditions. Herein, we report the synthesis of two BODIPY molecules—BF₂-meso-(4-butan/pentanamido-N-(((1S,5R)-6,6-dimethylbicyclo [3.1.1]hept-2-en-2-yl)methyl)-N,N-dimethylpropan-1-aminium)-3,3′,5,5′-tetramethyl-2,2′-dipyrromethene bromides—designed as 10, 11 with a spacer of either four or three CH₂ groups in length, respectively. These molecules present conjugates of BODIPY luminophors with (+)-myrtenol via a quaternary ammonium group. Both terpene-BODIPY conjugates demonstrated high fluorescence efficiency in various solvents such as OctOH, DMSO and water, and were characterized by their stability at pH 1.65–9.18. The fusion of the myrtenol, a monocyclic terpene, to the BODIPY fluorophore in the meso-substituent facilitated their penetration into the filamentous fungi Fusarium solani, while impairing the binding of the latter with S. aureus, K. pneumoniae and P. aeruginosa. The additional quaternary ammonium group between the myrtenol and fluorophore moieties restored the bacterial cell-staining while it did not affect the staining of fungi. Finally, the BODIPY conjugate 11 was able to stain both Gram-positive and Gram-negative bacteria by its interaction with their cell wall (or the membrane), as well as penetrating into filamentous fungi F. solani and staining their mitochondria. Full article

(This article belongs to the Special Issue Synthesis and Innovative Biological Activity of Boron-Containing Compounds)

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13 pages, 2797 KiB

Open AccessArticle

Reverse Screening of Boronic Acid Derivatives: Analysis of Potential Antiproliferative Effects on a Triple-Negative Breast Cancer Model In Vitro

by Miguel Ortiz-Flores, Marcos González-Pérez, Andrés Portilla, Marvin A. Soriano-Ursúa, Javier Pérez-Durán, Araceli Montoya-Estrada, Guillermo Ceballos and Nayelli Nájera

Inorganics 2023, 11(4), 165; https://doi.org/10.3390/inorganics11040165 - 14 Apr 2023

Cited by 2 | Viewed by 2205

Abstract

It has been demonstrated that different organoboron compounds interact with some well-known molecular targets, including serine proteases, transcription factors, receptors, and other important molecules. Several approaches to finding the possible beneficial effects of boronic compounds include various in silico tools. This work aimed [...] Read more.

It has been demonstrated that different organoboron compounds interact with some well-known molecular targets, including serine proteases, transcription factors, receptors, and other important molecules. Several approaches to finding the possible beneficial effects of boronic compounds include various in silico tools. This work aimed to find the most probable targets for five aromatic boronic acid derivatives. In silico servers, SuperPred, PASS-Targets, and Polypharmacology browser 2 (PPB2) suggested that the analyzed compounds have anticancer properties. Based on these results, the antiproliferative effect was evaluated using an in vitro model of triple-negative breast cancer (4T1 cells in culture). It was demonstrated that phenanthren-9-yl boronic acid and 6-hydroxynaphthalen-2-yl boronic acid have cytotoxic properties at sub-micromolar concentrations. In conclusion, using in silico approaches and in vitro analysis, we found two boronic acid derivatives with potential anticancer activity. Full article

(This article belongs to the Special Issue Synthesis and Innovative Biological Activity of Boron-Containing Compounds)

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14 pages, 9132 KiB

Open AccessArticle

Diester Chlorogenoborate Complex: A New Naturally Occurring Boron-Containing Compound

by Andrei Biţă, Ion Romulus Scorei, Nagendra Rangavajla, Ludovic Everard Bejenaru, Gabriela Rău, Cornelia Bejenaru, Maria Viorica Ciocîlteu, Laura Dincă, Johny Neamţu, Andrei Bunaciu, Otilia Constantina Rogoveanu, Mihai Ioan Pop and George Dan Mogoşanu

Inorganics 2023, 11(3), 112; https://doi.org/10.3390/inorganics11030112 - 9 Mar 2023

Cited by 9 | Viewed by 1947

Abstract

The natural compounds of boron have many applications, primarily as a dietary supplement. The research is based on the discovery that the diester chlorogenoborate complex can be detected and quantified from green coffee beans. The study reports that such a diester molecule can [...] Read more.

The natural compounds of boron have many applications, primarily as a dietary supplement. The research is based on the discovery that the diester chlorogenoborate complex can be detected and quantified from green coffee beans. The study reports that such a diester molecule can also be synthesized in a stable form via the direct reaction of boric acid and chlorogenic acid in a mixture of acetonitrile–water (1:1, v/v) and left to evaporate over a period of 48 h at room temperature, resulting in a spirocyclic form (diester complex). The diester complex, with its molecular structure and digestibility attributes, has potential application as a prebiotic in gut health and oral health, and as a micronutrient essential for microbiota in humans and animals. Full article

(This article belongs to the Special Issue Synthesis and Innovative Biological Activity of Boron-Containing Compounds)

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25 pages, 7439 KiB

Open AccessArticle

Synthesis, In Silico, In Vivo, and Ex Vivo Evaluation of a Boron-Containing Quinolinate Derivative with Presumptive Action on mGluRs

by Mario Emilio Cuevas-Galindo, Brenda Anaid Rubio-Velázquez, Rosa Adriana Jarillo-Luna, Itzia I. Padilla-Martínez, Marvin A. Soriano-Ursúa and José G. Trujillo-Ferrara

Inorganics 2023, 11(3), 94; https://doi.org/10.3390/inorganics11030094 - 26 Feb 2023

Cited by 2 | Viewed by 1684

Abstract

In the brain, canonical excitatory neurotransmission is mediated by L-glutamate and its ionotropic (iGluR) and metabotropic (mGluR) receptors. The wide diversity of these often limits the development of glutamatergic drugs. This is due to the arduousness of achieving selectivity with specific ligands. [...] Read more.

In the brain, canonical excitatory neurotransmission is mediated by L-glutamate and its ionotropic (iGluR) and metabotropic (mGluR) receptors. The wide diversity of these often limits the development of glutamatergic drugs. This is due to the arduousness of achieving selectivity with specific ligands. In the present article, encouraged by reports of bioactive organoboron compounds, a diphenylboroxazolidone derived from quinolinate (BZQuin) was evaluated. BZQuin was synthesized with a yield of 87%. Its LD₅₀ was 174 mg/kg in male CD-1 mice, as estimated by a modified Lorke’s method. BZQuin exerted a reduced ability to cause seizures when compared against its precursor, quinolinate. The latter suggested that it does not directly stimulate the ionotropic NMDA receptors or other ionic channels. The observation that the antiglutamatergic drugs riluzole and memantine displaced the BZQuin effect left the mGluRs as their possible targets. This is in line with results from molecular-docking simulations. During these simulations, BZQuin bound only to orthosteric sites on mGluR1, mGluR2, and mGluR7, with higher affinity than quinolinate. The survival of the neurons of mice previously administered with BZQuin or quinolinate was quantified in four neuroanatomical structures of the brain. The BZQuin effect was more appreciable in brain regions with a high expression of the previously mentioned mGluRs, while both antiglutamatergic drugs exerted a neuroprotective effect against it. Together, these results suggest that BZQuin exerts a positive influence on glutamatergic neurotransmission while selectively interacting with certain mGluRs. Full article

(This article belongs to the Special Issue Synthesis and Innovative Biological Activity of Boron-Containing Compounds)

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11 pages, 1564 KiB

Open AccessFeature PaperEditor’s ChoiceArticle

Synthesis of Novel Multifunctional bora-Ibuprofen Derivatives

by Randika T. Abeysinghe, Alexis C. Ravenscroft, Steven W. Knowlden, Novruz G. Akhmedov, Brian S. Dolinar and Brian V. Popp

Inorganics 2023, 11(2), 70; https://doi.org/10.3390/inorganics11020070 - 2 Feb 2023

Cited by 4 | Viewed by 3294

Abstract

A unique class of β-boron-functionalized non-steroidal anti-inflammatory compound (pinB-NSAID) was previously synthesized via copper-catalyzed 1,2-difunctionalization of the respective vinyl arene with CO₂ and B₂pin₂ reagents. Here, pinacolylboron-functionalized ibuprofen (pinB-ibuprofen) was used as a model substrate to develop the conditions [...] Read more.

A unique class of β-boron-functionalized non-steroidal anti-inflammatory compound (pinB-NSAID) was previously synthesized via copper-catalyzed 1,2-difunctionalization of the respective vinyl arene with CO₂ and B₂pin₂ reagents. Here, pinacolylboron-functionalized ibuprofen (pinB-ibuprofen) was used as a model substrate to develop the conditions for pinacol deprotection and subsequent boron functionalization. Initial pinacol-boronic ester deprotection was achieved by transesterification with diethanolamine (DEA) from the boralactonate organic salt. The resulting DEA boronate adopts a spirocyclic boralactonate structure rather than a diazaborocane–DABO boronate structure. The subsequent acid-mediated hydrolysis of DEA and transesterification/transamination provided a diverse scope of new boron-containing ibuprofen derivatives. Full article

(This article belongs to the Special Issue Synthesis and Innovative Biological Activity of Boron-Containing Compounds)

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Review

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21 pages, 1840 KiB

Open AccessEditor’s ChoiceReview

Effects of Boron-Containing Compounds on Liposoluble Hormone Functions

by Elizabeth Estevez-Fregoso, Ahmet Kilic, Diana Rodríguez-Vera, Luis E. Nicanor-Juárez, C. Elena M. Romero-Rizo, Eunice D. Farfán-García and Marvin A. Soriano-Ursúa

Inorganics 2023, 11(2), 84; https://doi.org/10.3390/inorganics11020084 - 17 Feb 2023

Cited by 12 | Viewed by 6112

Abstract

Boron-containing compounds (BCC), particularly boronic acids and derivatives, are being increasingly tested as diagnostic and therapeutic agents. Some effects of BCC involve phenomena linked to the action of steroid or thyroid hormones; among these, are the effects on muscle mass or basal metabolism. [...] Read more.

Boron-containing compounds (BCC), particularly boronic acids and derivatives, are being increasingly tested as diagnostic and therapeutic agents. Some effects of BCC involve phenomena linked to the action of steroid or thyroid hormones; among these, are the effects on muscle mass or basal metabolism. Additionally, some toxicology reports on mammals, including humans, sound an alert concerning damage to several systems, among which are the negative effects on the induction of male infertility. Systemic and local mechanisms to explain changes in metabolism and impaired fertility were collected and presented. Then, we presented the putative pharmacodynamic and pharmacokinetic mechanisms involved and demonstrated in these events. In addition, it is proposed that there are adducts of some oxygenated BCC with cis-diols in fructose, an essential source of energy for sperm–cell motility, an uncoupling of sex hormone-binding globulin (SHBG) and its ligands, and the modulation of the DNA synthetic rate. These effects share the reactivity of boron-containing compounds on the cis-diols of key molecules. Moreover, data reporting no DNA damage after BCC administration are included. Further studies are required to support the clear role of BCC through these events to disrupt metabolism or fertility in mammals. If such phenomena are confirmed and elucidated, an advance could be useful to design strategies for avoiding BCC toxicity after BCC administration, and possibly for designing metabolism regulators and contraceptive drugs, among other purposes. Boronic derivatives and carboranes have been proposed and studied in this field. Full article

(This article belongs to the Special Issue Synthesis and Innovative Biological Activity of Boron-Containing Compounds)

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