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Review
. 2020 Dec;10(6):499-516.
doi: 10.1016/j.jpha.2020.03.007. Epub 2020 Mar 21.

Challenges for cysteamine stabilization, quantification, and biological effects improvement

Carla Atallah  1   2 , Catherine Charcosset  2 , Hélène Greige-Gerges  1
Affiliations
Review

Challenges for cysteamine stabilization, quantification, and biological effects improvement

Carla Atallah et al. J Pharm Anal. 2020 Dec.

Abstract

The aminothiol cysteamine, derived from coenzyme A degradation in mammalian cells, presents several biological applications. However, the bitter taste and sickening odor, chemical instability, hygroscopicity, and poor pharmacokinetic profile of cysteamine limit its efficacy. The use of encapsulation systems is a good methodology to overcome these undesirable properties and improve the pharmacokinetic behavior of cysteamine. Besides, the conjugation of cysteamine to the surface of nanoparticles is generally proposed to improve the intra-oral delivery of cyclodextrin-drug inclusion complexes, as well as to enhance the colorimetric detection of compounds by a gold nanoparticle aggregation method. On the other hand, the detection and quantification of cysteamine is a challenging mission due to the lack of a chromophore in its structure and its susceptibility to oxidation before or during the analysis. Derivatization agents are therefore applied for the quantification of this molecule. To our knowledge, the derivatization techniques and the encapsulation systems used for cysteamine delivery were not reviewed previously. Thus, this review aims to compile all the data on these methods as well as to provide an overview of the various biological applications of cysteamine focusing on its skin application.

Keywords: Cysteamine; Detection; Encapsulation; Skin; Stability.

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Conflict of interest statement

The authors declare that there are no conflicts of interest.

Figures

Image 1
Graphical abstract
Fig. 1
Fig. 1
Structure of cys.
Fig. 2
Fig. 2
Oxidation of cys to cystamine.
Fig. 3
Fig. 3
Metabolism of cys [24] (with permission from John Wiley and Sons).
Fig. 4
Fig. 4
Chemical structures of cys forms obtained at different pHs.
Fig. 5
Fig. 5
Synthetic route for DAABD-Cl (7-chloro-N-[2-(dimethylamino)ethyl]-2,1,3-benzoxadiazole-4-sulfonamide).
Fig. 6
Fig. 6
Reaction between bis(p-nitrophenyl) disulfide and mercaptan anion [59].
Fig. 7
Fig. 7
Structure difference between bis(p-nitrophenyl) disulfide and DTNB.
Fig. 8
Fig. 8
Reaction between cys and Ellman’s reagent. DTNB: 5,5′-dithiobis (2-nitrobenzoique acid), TNB: 5’-thio-2-nitrobenzoic acid.
Fig. 9
Fig. 9
Electrocatalytic mechanism for cys determination at the surface of an electrode in the presence of a mediator.
Fig. 10
Fig. 10
Cys pharmacodynamics.
Fig. 11
Fig. 11
Schematic illustration of the mechanism of action of skin whitening agents [111] (with permission from Elsevier).
Fig. 12
Fig. 12
Representation proposed for the interaction between cys and α-CD according to the results of NMR technique (A) interactions of CH2 of cys with H2 and H4 of two different glucopyranose (B) interactions of CH2 of cys with H2 and H4 of a same glucopyranose [13] (with permission from Springer).
Fig. 13
Fig. 13
Synthetic pathway for the generation of thiolated α-CD. cys: cysteamine, CD: cyclodextrins.
Fig. 14
Fig. 14
Colorimetric detection strategy of molecules based on cys modified AuNPs. cys: cysteamine, AuNPs: gold nanoparticles.
Image 2
Image 3
See this image and copyright information in PMC

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