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(12) Patent Application Publication (10) Pub. No.: US 2010/0203175 A1 ABDUL-MALAK Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2010/0203175 A1 ABDUL-MALAK Et Al US 20100203175A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0203175 A1 ABDUL-MALAK et al. (43) Pub. Date: Aug. 12, 2010 (54) DEGLYCATION OF AGES A63L/352 (2006.01) A63L/404 (2006.01) (75) Inventors: Nabil ABDUL-MALAK, Caluire A63L/05 (2006.01) (FR); Cecile ALTOBELLI, Lyon A63L/35 (2006.01) (FR); Eric PERRIER, Les Cotes A613/60 (2006.01) d'Arey (FR) A63L/403 (2006.01) A63L/35 (2006.01) Correspondence Address: A636/00 (2006.01) BASF Beauty Care Solutions France 46R 8/97 (2006.01) 100 Campus Drive A636/736 (2006.01) Florham Park, NJ 07932 (US) A6IR 8/36 (2006.01) A6IR 8/49 (2006.01) (73) Assignee: BASF BEAUTY CARE A6IR 8/34 (2006.01) SOLUTIONS FRANCE S.A.S., GOIN 33/68 (2006.01) Lyon (FR) A61O 19/00 (2006.01) A6IP 700 (2006.01) (21) Appl. No.: 12/668,061 (52) U.S. Cl. ......... 424/734; 514/570; 514/456; 514/418; 514/731: 514/646; 514/159; 514/411; 514/460; (22) PCT Filed: Jul. 9, 2008 424/725; 424/769; 424/735; 436/86 (86). PCT No.: PCT/EP08/58955 (57) ABSTRACT S371 (c)(1), The invention relates to the use, as an active ingredient, of at least one substance that promotes the deglycation of AGEs for (2), (4) Date: Mar. 10, 2010 preparing a composition, especially for limiting the presence (30) Foreign Application Priority Data of AGEs in a tissue. The invention particularly relates to the use of such a sub Jul. 9, 2007 (FR) ....................................... O756350 stance for preparing a composition intended to prevent and/or combat a reduction in flexibility and/or plasticity and/or elas Publication Classification ticity and/or functionality of a tissue, and/or to prevent and/or (51) Int. Cl. combat the ageing of a tissue, by promoting the deglycation A6 IK 36/67 (2006.01) of AGEs in the tissue, said tissue preferably being the skin, or A6 IK3I/92 (2006.01) the tissue wall of a blood vessel or of an organ. US 2010/0203175 A1 Aug. 12, 2010 DEGLYCATION OFAGES effect of drugs which inhibit glycation, which is expressed by a slowing down of the ageing of certain functions in labora tory animals. In the course of diabetes mellitus an excessive 0001. The invention relates to the use of active principles glycation of the proteins also occurs, which is linked to the for promoting the deglycation of glycated proteins, in other rise in glycaemia. words to promote the reversion of the Maillard reaction. 0013 The solutions proposed in the prior art relate to 0002 The present invention particularly relates to sub active Substances that make it possible to limit the glycation stances that can be used topically or orally to act on the of proteins and also the formation of AGES. glycated proteins in a tissue. Such as for example in the skin, or in the tissue wall of a blood vessel or of an organ, especially OBJECTIVES OF THE INVENTION in a human being. 0014. The main objective of the invention is to solve the PRIOR ART technical problem consisting of the provision of active Sub stances that make it possible to limit the presence of AGEs, by 0003. It is known in the prior art that sugar, especially in reversing the Maillard reaction, especially in a tissue, such as the form of glycans induces glycation of proteins (bonding of for example in the skin, or in the tissue wall of a blood vessel Sugar to the proteins), especially in the skin. This glycationis, or of an organ, and in particular in the skin. however, completely normal when the blood sugar level 0015. One particular objective of the present invention is increases, such as, in particular in diabetic Subjects, during to solve this technical problem within the context of the ageing, or when the food is rich in Sugars. provision of cosmetic, dermatological, or pharmaceutical 0004. It is known in the prior art that non-enzymatic gly compositions that prevent or combat the reduction of the cosylation or glycation is a purely chemical and spontaneous elastic and plastic properties of a tissue. Such as for example reaction that consists in covalently bonding a carbohydrate to in the skin, or in the tissue wall of a blood vessel or of an a peptide chain. organ, and in particular in the skin, especially during ageing 0005 Glycation is a fundamental mechanism of ageing of the tissues or during diabetes. that results from the attachment of free Sugars to amino acids 0016. Another objective of the present invention is to pro or to proteins. vide a method of screening active principles that have the 0006 Glycated proteins are also known as advanced gly aforementioned properties. cation end products or AGES. These compounds, in particu 0017. One particular objective of the present invention is lar, reduce the flexibility, elasticity and functionality of the to solve the technical problem in a reliable and reproducible skin. manner by providing non-toxic active Substances, in particu 0007. The glycation process occurs in three steps: lar for the cosmetics, dermatological, dermopharmaceutical 0008 1—Formation of a Schiffbase resulting from the or pharmaceutical industry, preferably that can be applied attachment of a reducing Sugar (glucose, ribose or fruc topically. tose) or of an aldehyde to the amino acid residues of the 0018. One particular objective of the invention is to pro protein, mainly lysine and the N-terminal amine frac vide Substances that have a low toxicity and that are derma tion. tologically acceptable. 0009 2 Molecular rearrangement, known as Amadori 0019. Another objective of the present invention is to pro rearrangement, resulting from isomerization of the vide active principles, the preparation of which is inexpensive Schiff base. The rate of formation of these Amadori and can be carried out on an industrial scale in a reliable and products is proportional to the Sugar concentration. simple manner. 0010 3 Slow and irreversible accumulation, via rear rangements, hydrogen transfers and formation of very DESCRIPTION OF THE INVENTION reactive intermediates, of glycation end products or Maillard products. This reaction leads to the formation 0020 Glycation is involved in numerous progressive dis of AGEs, better known by the expression Maillard prod eases linked to ageing, such as vascular diseases (for instance ucts. The rate of formation of these compounds is inde atherosclerosis), kidney disease, arthritis, the complications pendent of the Sugar concentration of the medium but of diabetes, cicatrization, etc. It is significant that the diabetic depends on the duration of hyperglycaemia and on the complications due to glycation can occur even at a younger rate of protein turnover. age in diabetic individuals, whose average blood Sugar con 0011. The first two stages (Schiff base and Amadori rear centration is higher than normal. rangement) stabilize at a plateau and can be reversed depend 0021. In diabetes, during which the involvement of free ing on the level of glycaemia. On the other hand, the third radicals is widely documented, the oxidative stress is directly stage progresses regardless of the level of glycaemia. linked to hyperglycaemia. The Sugars that are present in a too 0012 Extracellular matrix proteins, the lifetime of which large amount in the blood then oxidize easily. This oxidation in the body is very long, are affected by glycation. Glycation of the Sugars leads, interalia, to Sugar/protein grafts or gly modifies the properties of these proteins, making them more cation. The increased level of glycated haemoglobin in the resistant to proteolysis and preventing their turnover. Further case of diabetes is the typical example. more, the AGEs induce the formation of molecular bridges 0022. The glycation products, the level of which is pro between the collagen fibres, making them more rigid and less portional to the level of glycaemia, over a long period of time, soluble. Finally, the AGEs might have other actions by bond are partly responsible for tissue ageing, of which the reduc ing themselves to specific receptors present in macrophages, tion of the elastic and plastic properties is one of the causes. endothelial and mesangial cells, by inducing the Secretion of 0023 Thus, the present invention describes the use of an proinflammatory cytokines or growth factors. The impor active Substance that promotes the deglycation of AGES, or tance of the glycation of proteins has been emphasized by the that promotes the reversion of the Maillard reaction with US 2010/0203175 A1 Aug. 12, 2010 respect to AGES, for the preparation of a composition, espe tion of glycated proteins, especially in cutaneous tissue, cially for limiting the presence of AGEs in a tissue. linked to the rise in glycaemia during diabetes mellitus. 0024 Advantageously, this composition is intended, for 0040. The present invention relates to the use of an active example, to combat the reduction in flexibility and/or elastic Substance for preparing a composition to combat the AGES ity and/or plasticity and/or functionality of a tissue. Such as for example in the skin, or in the tissue wall of a blood vessel formed in glomeruli, and especially to reduce the excretion of or of an organ. albumin in a diabetic subject. 0025. The present invention also relates to a composition 0041. The active substance may be concentrated by freeze for combating and/or preventing ageing of the skin, for pre drying, spray-drying, etc. venting and/or combating the reduction in the elastic and 0042 Said active substance is generally used at a concen plastic properties of tissues, and in particular of the skin, via tration between 0.001 and 10%, preferably between 0.01 and deglycation of AGES, or by reversion of the Maillard reaction 5%, and more particularly at 1% for plant extracts, and with respect to AGES, in cutaneous tissue, comprising, as an between 1x107 and 1%, preferably between 1x107 and active Substance, a Substance that promotes the deglycation of 1x10%, more preferably between 1x10 and 1x10%, for AGES.
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