Nano-assemblies of conjugates of retinoids and amino acids

1 . A nano-assembly comprising conjugates of the following formula (1)

wherein X is selected from the group consisting of

and/or comprising conjugates of the following formula (4)

2 . The nano-assembly according to claim 1 , wherein the nano-assembly comprises conjugates of formula (1).

3 . The nano-assembly according to claim 1 , wherein the nano-assembly further comprises conjugates of the following formula (5)

conjugates of the following formula (6)

conjugates of the following formula (2)

conjugates of the following formula (3)

and/or combinations of two or more thereof, and wherein R 1 and R 2 are independently selected from the group consisting of —H, —CH 3 , —CH 2 CH 3 , and —CH 2 CH 2 —(O—CH 2 CH 2 ) m —R 3 , wherein m is in a range of from 1 to 20, and wherein R 3 is selected from the group consisting of —H, —OH, —NH 2 , —SH, —COOH, and —OCH 3 .

4 . The nano-assembly according to claim 1 , wherein the nano-assembly further comprises at least one additional retinoid compound, at least one additional vitamin E compound, at least one additional vitamin D compound, and/or at least one additional vitamin K compound bound to the nano-assembly by non-covalent interactions.

5 . The nano-assembly according to claim 4 , wherein the additional retinoid compound is all-trans retinoic acid.

6 . The nano-assembly according to claim 1 , wherein X is selected from the group consisting of

7 . The nano-assembly according to claim 1 , comprising a first conjugate having formula (1), and further comprising a second conjugate having formula (1) wherein X of formula (1) is different from X of the second conjugate.

8 . The nano-assembly according to claim 1 , comprising conjugates of formula (1) wherein X is

and further comprising conjugates of formula (1) wherein X is

9 . The nano-assembly according to claim 1 , wherein a molar proportion of the conjugates of formula (1) is at least 50 mol% as compared to a total molar amount of conjugates constituting the nano-assembly.

10 . A method of producing the nano-assembly of claim 1 , the method comprising

incubating a mixture of a retinoid compound and an amino acid in a mixture of a polar solvent A and a polar solvent B for a time of from 1 hour to 48 hours, and

removing solvent B;

wherein solvent A has a higher polarity index as compared to solvent B.

11 . The method according to claim 10 , wherein a molar ratio of the retinoid compound and the amino acid in the mixture is in a range of from 1:50 to 1:1.

12 . The method according to claim 10 , wherein the retinoid compound is all trans retinal.

13 . The method according to claim 10 , wherein the polarity index of solvent A is at least 8.0.

14 . The method of according to claim 10 , further comprising addition of at least one additional retinoid compound to the mixture of the retinoid compound and the amino acid.

15 . A method of treating dermatological diseases or conditions and/or pulmonary diseases or conditions, comprising administering a therapeutically effective amount of the nano-assembly according to claim 1 to a patient in need thereof.

16 . A pharmaceutical composition comprising the nano-assembly according to claim 1 , and a pharmaceutically acceptable carrier.

17 . A method for managing or reducing stretch marks on skin (striae), smooth wrinkles, and fine lines comprising administering an effective amount of the nano-assembly according to claim 1 to a person in need thereof.

18 . A method for treating androgenetic alopecia comprising administering an effective amount of the nano-assembly according to claim 1 to a person in need thereof.