Labeling of hyaluronic acids with a Re-tricarbonyl tag and percutaneous penetration studied by multimodal imaging

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Labeling of hyaluronic acids with a Re-tricarbonyl tag and percutaneous penetration studied by multimodal imaging, Bioconjugate Chem., 2018

 

Hyaluronic acid (HA) is a polymer of disaccharides made of D-glucuronic acid and D-Nacetylglucosamine moieties, linked by alternating .-1,4 and .-1,3-glycosidic bonds, with molecular weights (MW) up to 107 Da. HA is found in tissues and body fluids of almost all living organisms. This highly hydrophilic molecule binds a thousand times its volume of water, and is commonly used as a medicine, for instance injected into joints to treat arthritis or in dermis to fill facial wrinkles.4 Low MW HAs are only used to maintain hydration of epidermis after topical application whereas high MW HAs are also used as filing agent after cutaneous injection.

 

 

In conclusion, we were able to efficiently label HAs of different MW with a Re(CO)3 SCoMPI at different rates using a Ugi reaction. Their penetration into human skin biopsies was monitored using IR and fluorescence microscopies. The label percentage was an important parameter to ensure detection without modifying to a too large extent the physico-chemical properties of the biopolymer: if too low, the compound (6, 10 kDa, 3-4%) was not seen, but when too high (8, 10 kDa, 40% and 9, 400-1000 kDa, 20%), solubility was impaired and hence penetration as well. After a 7-hour exposure, 7 (10 kDa, 20%) was localized at some spots in the SC (Figure S9), whereas 10 (400-1000 kDa, 5%) was not detected (not shown). After a 24-hour exposure, 7 was homogeneously distributed in the SC and slightly in the VE (Figure 2), but was not detected in the deeper layers of the skin whereas 10 was only located at some spots in the SC (Figure S9). The present data showed that the penetration of a cosmetic relevant compound in the skin can be efficiently probed using a SCoMPI. As expected, the penetration is highly dependent on the size of HAs, with no modification of the skin structure.

 

 

Résumé: 

Bioconjugate Chem., 2018

 

Hyaluronic acids were labeled with a Re-tricarbonyl used as Single Core Multimodal Probe for Imaging and their penetration into human skin biopsies was studied using IR microscopy and fluorescence imaging. The penetration was shown to be dependent on the molecular weight of the molecule and limited to the upper layer of the skin.

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Labeling of hyaluronic acids with a Re-tricarbonyl tag and percutaneous penetration studied by multimodal imaging

 

Lucas Henry, Nicolas Delsuc, Cécile Laugel, François Lambert, Christophe Sandt, Sarah Hostachy, Anne-Sophie Bernard, Hélène Charlotte Bertrand, Laurence Grimaud, Arlette Baillet-Guffroy, and Clotilde Policar

 

Bioconjugate Chem., 2018

 

DOI: 10.1021/acs.bioconjchem.7b00825