Review of Pseudopeptidic Compounds for Biocompatible Gels

Apr 1, 2012 | Contact Author | By: Santiago V. Luis, PhD; M. Isabel Burguete, PhD; Vicente Martí-Centelles; and Jenifer Rubio, PhD Department of Inorganic and Organic Chemistry, University Jaume I, Castellón, Spain
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Title: Review of Pseudopeptidic Compounds for Biocompatible Gels
pseudopeptidesx gelsx organogelatorsx biocompatibilityx
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Keywords: pseudopeptides | gels | organogelators | biocompatibility

Abstract: Simple pseudopeptides derived from natural amino acids can be designed and prepared as efficient gelators for a variety of solvents, and with a high potential for biocompatibility. The appropriate selection of structural components, reviewed herein, shows how to produce gels with tailored properties, including high thermal stability.

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SV Luis, MI Burguete, V Martí-Centelles and J Rubio, Review of pseudopeptidic compounds for biocompatible gels, Cosm & Toil 127(4) 282-290 (Apr 2012)

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Gels are formed when a compound present in a solution self-assembles to form a highly cross-linked fibrillar network in which the solvent molecules remain entrapped. The resulting material has properties that are intermediate between those of liquids and solids. Usually, gels are classified according to the nature of the solvent involved. Thus, hydrogels refer to gels formed in the presence of water, while organogels are those in which organic solvents are involved.

Many different types of compounds have been developed and used either as hydrogelators or as organogelators; according to the foods industry, natural and nonnatural polymers originally were tested for the formation of gels. Nevertheless, the use of low molecular weight gelators has gained increasing importance in recent years. Since low molecular weight compounds possess a well-defined structure, their properties including self-assembling behavior can be more easily studied, which allows for the more efficient design and fine-tuning of gelating agents. As a consequence, a large number of technological applications have recently been reported for gels formed either in water or organic solvents through the use of low molecular weight molecules.

In particular, gel formulations are used as penetration enhancers for drug and cosmetic actives release. This is due to the fact that incorporating the active component in a gel matrix can control its release rate, increasing the application time and consequently, the corresponding activity. The appropriate selection of structural components, reviewed herein, shows how to produce gels with tailored properties, including high thermal stability.

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This is an excerpt of an article from GCI Magazine. The full version can be found here.

 

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Table 1. Selected examples

Table 1. Selected examples

Selected examples for the gelation behavior of bis-urea pseudopeptidic compounds in different organic solvents

Figure 1. Examples of first generation amino acid-derived organogelators

Figure 1. Examples of first generation amino acid-derived organogelators

Long chain alkylamides of N-carbobenzyloxy amino acids such as compounds a) and b), shown here, were reported to act as organogelators for a variety of organic solvents.

Figure 2. Examples of organogelating compounds with C2 or C3 symmetry

Figure 2. Examples of organogelating compounds with C<sub>2</sub> or C<sub>3</sub> symmetry

Simple pseudopeptidic compounds based on the general structure f), here, have a large potential for diversity and their synthesis is relatively simple and can be achieved in high yields.

Figure 3. Examples of organogelating compounds

Figure 3. Examples of organogelating compounds

The role of preorganization provided by macrocyclic structures was clearly highlighted when simple compounds such as n), shown here, were studied.

Figure 4. Gels with high transparency can be formed from pseudopeptidic structures

Figure 4. Gels with high transparency can be formed from pseudopeptidic structures

The gels obtained from low concentrations of gelating agent in particular are also very transparent and stable; the sample shown here was prepared by the authors from a pseudopeptidic structure.

Figure 5. Examples of organogelating compounds

Figure 5. Examples of organogelating compounds

Organogelating compounds with cosmetic and pharmaceutical applications

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