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Factors Affecting Dissolution: Drug pKa, Lipophilicity and GI pH01:21

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Drug absorption within the gastrointestinal (GI) tract is a complex process influenced by several critical factors, including the site pH, the drug's dissociation constant (pKa), and the drug's lipophilicity. The GI tract exhibits a pH gradient, with an acidic environment in the stomach and a more alkaline environment in the small intestine. This pH variation directly affects the ionization state of drugs.
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Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
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Extraction: Effects of pH00:53

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Consider a neutral form of an amine, B, with a partition coefficient, K, in a liquid mixture containing organic and aqueous phases. The pH of the aqueous phase affects the charge on acidic and basic solutes, and the charged form is usually more soluble in the aqueous phase. Suppose the conjugate acid form of the amine is soluble only in the aqueous phase while the base form is soluble in both phases. Then the distribution coefficient, D, can be given as the ratio of amine concentration in the...
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Solvating Effects02:12

Solvating Effects

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An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
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Polyprotic acids of the type H2M constitute two ionizable protons. As a result, on titration with a base, they exhibit two equivalence points in the titration curve. During titration, the species H2M, HM−, and M2− will be present in the solution at different points. The fractions of H2M, HM−, and M2− present at the various instances of the titration are denoted by α0, α1, and α2, respectively.
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Amino acids03:42

Amino acids

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Amino acids are the monomers that comprise proteins. Each amino acid has the same fundamental structure, which consists of a central carbon atom, or the alpha (α) carbon, bonded to an amino group (NH2), a carboxyl group (COOH), and to a hydrogen atom. Every amino acid also has another atom or group of atoms bonded to the central atom known as the R group. There are 20 common amino acids present in proteins, each with a different R group. Variation in the amino acid sequence is responsible for...
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Solubility of Hydrophobic Compounds in Aqueous Solution Using Combinations of Self-assembling Peptide and Amino Acid
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Poly(aspartic acid) with adjustable pH-dependent solubility.

Csaba Németh1, Benjámin Gyarmati1, Timur Abdullin2

  • 1Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary.

Acta Biomaterialia
|December 5, 2016
PubMed
Summary
This summary is machine-generated.

Modified poly(aspartic acid) (PASP) polymers exhibit tunable pH-dependent solubility, making them suitable for enteric coatings. These biocompatible and non-toxic materials demonstrate rapid dissolution in the small intestine for targeted drug delivery.

Keywords:
BiopolymersEnteric coatingsPoly(aspartic acid)Solubility modelspH-dependent solubility

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Biocompatible Polymers

Background:

  • Poly(amino acid) type polymers are explored for pharmaceutical film coatings.
  • Tailoring poly(aspartic acid) (PASP) solubility is key for controlled drug release applications.

Purpose of the Study:

  • Synthesize and characterize PASP derivatives with adjustable pH-dependent solubility.
  • Establish structure-solubility relationships for enteric coating applications.
  • Evaluate the potential of PASP derivatives as enteric coating materials.

Main Methods:

  • Modification of polysuccinimide with alkylamines to create PASP derivatives.
  • Quantitative analysis of pH-dependent solubility using Henderson-Hasselbalch equations.
  • Dissolution rate determination via fluorescence marking and cellular viability assays.

Main Results:

  • PASP derivative solubility is tunable by adjusting side group type and concentration.
  • The extended Henderson-Hasselbalch equation accurately describes pH-dependent solubility.
  • PASP films dissolve rapidly above their pKa and are non-toxic to human cells.

Conclusions:

  • PASP derivatives offer adjustable solubility for enteric coating applications.
  • These polymers are promising biocompatible materials for targeted drug delivery in the gastrointestinal tract.