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EDTA: Auxiliary Complexing Reagents01:26

EDTA: Auxiliary Complexing Reagents

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EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...
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Bioavailability Enhancement: Drug Stability Enhancement and GI Retention01:05

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Improving a drug's stability in the gastrointestinal (GI) tract is paramount for enhancing its bioavailability and therapeutic effectiveness. Various strategies are employed to protect the drug from the harsh gastric milieu and to ensure its release and absorption at the desired site within the GI tract.Polymer coatings are one such method used to shield drugs from the stomach's acidic environment. By preventing premature drug release, these coatings improve the bioavailability of unstable...
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EDTA: Chemistry and Properties01:22

EDTA: Chemistry and Properties

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Polydentate ligands are most widely used in complexometric titrations because they form more stable complexes with the metal ions than mono- or bidentate ligands due to the chelate effect. Examples of polydentate ligands are ethylenediaminetetraacetic acid (EDTA), crown ethers, and cryptands. The most important feature of optimal polydentate ligands is the ability to form 1:1 complexes in a single-step process. Amino carboxylic acid derivatives are frequently used as complexing agents. EDTA is...
4.1K
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

1.7K
In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
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EDTA: Conditional Formation Constant01:09

EDTA: Conditional Formation Constant

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Each EDTA molecule has six binding sites: four carboxyl groups and two amino groups. The fully protonated form of EDTA is represented as H6Y2+. However, it can exist in different forms, H5Y+, H4Y, H3Y−, H2Y2−, and HY3−, depending on the pH of the solution. In very basic solutions with pH > 10.17, the fully deprotonated form, Y4−, is the predominant species that readily complexes with metal ions in a 1:1 ratio.
For the equilibrium reaction of the metal with the...
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Masking and Demasking Agents01:19

Masking and Demasking Agents

4.0K
EDTA titrations may necessitate masking and demasking agents to temporarily protect a particular metal ion in a mixture from the EDTA reaction. These agents facilitate the sequential analysis of the metal ions by forming stable complexes with some—but not all—metal ions during certain steps.
There are many masking agents, such as cyanide, fluoride, triethanolamine, thiourea, and 2,3-bis(sulfanyl)propan-1-ol (formerly 2,3-dimercapto-1-propanol), with the masking agent chosen based on...
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Triethanolamine stabilization of methotrexate-β-cyclodextrin interactions in ternary complexes.

Jahamunna A A Barbosa1, Ariana Zoppi2, Mario A Quevedo3

  • 1Graduate Program on Pharmaceutical Sciences, Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Av. General Gustavo Cordeiro de Farias, Petrópolis, 59072-570 Natal, Brazil. jamunauepb@gmail.com.

International Journal of Molecular Sciences
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Methotrexate (MTX) solubility significantly increased thirty-fold with beta-cyclodextrin (β-CD) and triethanolamine (TEA). This ternary complex enhances drug stability and dissolution for improved drug delivery systems.

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Area of Science:

  • Pharmaceutical Sciences
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Methotrexate (MTX) is a crucial chemotherapeutic agent with limited solubility.
  • Beta-cyclodextrin (β-CD) is a known host molecule for drug complexation.
  • Triethanolamine (TEA) can potentially modify cyclodextrin complexation.

Purpose of the Study:

  • To investigate the ternary complexation mechanism of MTX with β-CD in the presence of TEA.
  • To elucidate the role of TEA in stabilizing the MTX:β-CD complex.
  • To evaluate the impact of this ternary complex on MTX solubility, stability, and dissolution.

Main Methods:

  • Solubility diagram studies.
  • 2D ROESY NMR spectroscopy.
  • Molecular modeling.
  • FTIR, DSC, TG/DTG, CHN analysis, and XRD studies.
  • In vitro drug dissolution studies.

Main Results:

  • A synergistic thirty-fold increase in MTX solubility was observed.
  • Molecular modeling and ROESY confirmed MTX aromatic ring inclusion into β-CD cavity.
  • TEA was found to intensify MTX-β-CD interaction and stabilize the ternary complex via electrostatic interactions.
  • Solid-state analyses confirmed the maintenance of MTX-β-CD interactions and enhanced drug stability in the ternary complex.
  • In vitro dissolution studies demonstrated significantly improved MTX release from the ternary complex.

Conclusions:

  • The MTX:β-CD:TEA ternary complexation significantly enhances MTX solubility and stability.
  • TEA plays a critical role in stabilizing the complex through electrostatic interactions.
  • This ternary system represents a promising new material for advanced drug delivery applications.