Mixed Antimony(V) Complexes with Different Sugars to Modulate the Oral Bioavailability of Pentavalent  Antimonial Drugs

Ferreira, Weverson Alves; Islam, Arshad; Andrade, Aretha P.S.; Frézard, Frédéric; Demicheli, Cynthia

doi:10.3390/molecules19055478

Cited by 12 publications

(3 citation statements)

References 18 publications

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“…Recently, antimony complexes have been investigated for different applications: antimony(V) complexes were tested for their cytotoxic activity [ 16 ], for their antibacterial activities and cytotoxicity against macrophages [ 17 ]. Different sugars were combined with antimony(V) complexes to modulate the oral bioavailability of antimony containing drugs [ 18 ]. The biological potential of antimony(III) dithiocarbamate complexes has been recently reflected in a review article [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

New Complexes of Antimony(III) with Tridentate O,E,O-Ligands (E = O, S, Se, Te, NH, NMe) Derived from N-Methyldiethanolamine

Böhme

Herbig

2023

Molecules

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We synthesized a series of new antimony(III) compounds by reaction of Sb(OEt)3 with organic ligands of the type E(CH2-CH2-OH)2, with E = NH, NMe, O, S, Se, and Te. The synthesized compounds have the general composition [E(CH2-CH2-O)2]Sb(OEt). For comparison, the compound (O-CH2-CH2-S)Sb(OEt) was prepared. All compounds are characterized using NMR, IR, and Raman spectroscopy. The molecular structures of the products reveal the formation of chelate complexes, wherein the ligand molecules coordinate as tridentate O,E,O-ligands to the antimony atom. Dimer formation in the solid state allows the antimony atoms to reach pentacoordination. Quantum chemical calculations including topological analysis of electron density reveal that there are polar shared bonds between antimony and the oxygen atoms bound to antimony. The interactions between the donor atom E and the Sb atom and the interactions in the dimers can be characterized as Van der Waals interactions. The reactivity of [MeN(CH2-CH2-O)2]Sb(OEt) was investigated as an example. For this purpose, the compound reacted with a range of organic compounds such as carboxylic acids and carboxylic anhydrides and small molecules like CO2 and NH3. This study establishes a new and easy accessible class of antimony(III) compounds, provides new insights into the chemistry of antimony compounds and opens up new opportunities for further research in this field.

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Section: Introductionmentioning

confidence: 99%

New Complexes of Antimony(III) with Tridentate O,E,O-Ligands (E = O, S, Se, Te, NH, NMe) Derived from N-Methyldiethanolamine

Böhme

Herbig

2023

Molecules

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“…This solution was stirred for 3 h at 55 °C, pH 7 adjusted by aqueous NaOH. At the end of this time after cooling down the solution, a precipitate was produced by adding 75 mL of acetone which was then filtered off and dried to give 9a-e , and 10-14 as the desired complexes ( 14 15 ).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and antileishmanial activity of antimony (V) complexes of hydroxypyranone and hydroxypyridinone ligands

et al. 2018

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A novel series of antimony (V) complexes with the hydroxypyranone and hydroxypyridinone ligands were synthesized and characterized by 1HNMR, FT-IR and electron spin ionization mass spectroscopic (ESI-MS) techniques. The synthesis process involved protection of hydroxyl group followed by the reaction of the intermediate with primary amines and finally deprotection. All compounds were evaluated for in vitro activities against the amastigote and promastigote forms of Leishmania major. Most of the synthesized compounds exhibited good antileishmanial activity against both forms of L. major. IC50 values of the most active compounds; 9d, 9d and 9e, after 24, 48 and 72 h against amastigote model were 15, 12.5 and 5.5 μg/mL, respectively. 9e, 11 and 9e inhibited the promastigote form of parasite after 24, 48 and 72 h with IC50 values of 10, 2 and 1 μg/mL, respectively.

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“…It is no surprise that the most widely used drugs against leishmaniasis are antimony-derived sugar-based molecules: sodium stibogluconate and meglumine antimoniate (El Fadili et al, 2008;Frézard, Demicheli, & Ribeiro, 2009). Inspired by these facts, efforts have been made to employ this "Trojan horse" strategy in antileishmanial metallodrug-based chemotherapy (Ferreira et al, 2010(Ferreira et al, , 2014. Thus, these four less toxic d-gluconate-derived gold(I) complexes represent potential antileishmanial agents that deserve attention in further drug development studies, including sugar-mediated drug delivery strategies.…”

Section: Synthesis Of Gold(i) Complexesmentioning

confidence: 99%

Anticancer and antileishmanial in vitro activity of gold(I) complexes with 1,3,4‐oxadiazole‐2(3H)‐thione ligands derived from δ‐D‐gluconolactone

et al. 2020

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Gold(I) complexes with saccharide-based ligands have been extensively studied in recent years, as they have shown significant in vitro cytotoxic activity against many cisplatin-resistant tumor cell lines (Rigobello et al., 2008). Unlike cisplatin, which targets DNA to exert its cytotoxic effect, gold(I) complexes interrupt intracellular protein signaling mechanisms (particularly thioredoxin reductase), leading to cell apoptosis (da Silva Maia, Deflon, & Abram, 2014). The structure of ligands used to synthesize gold(I) complexes has great influence on their biological activity (Yeo et al., 2013). An important factor is the lipophilicity of the ligand, which directly impacts the ability of the complex to penetrate through cell membranes. The insertion of a tertiary phosphine group in some gold(I) complexes (as in auranofin) has consistently resulted in increased biological activity, when compared to their analogous non-phosphorated compounds (Ott et al., 2009).

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Mixed Antimony(V) Complexes with Different Sugars to Modulate the Oral Bioavailability of Pentavalent Antimonial Drugs

Cited by 12 publications

References 18 publications

New Complexes of Antimony(III) with Tridentate O,E,O-Ligands (E = O, S, Se, Te, NH, NMe) Derived from N-Methyldiethanolamine

New Complexes of Antimony(III) with Tridentate O,E,O-Ligands (E = O, S, Se, Te, NH, NMe) Derived from N-Methyldiethanolamine

Synthesis and antileishmanial activity of antimony (V) complexes of hydroxypyranone and hydroxypyridinone ligands

Anticancer and antileishmanial in vitro activity of gold(I) complexes with 1,3,4‐oxadiazole‐2(3H)‐thione ligands derived from δ‐D‐gluconolactone

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