Modular synthesis of amphiphilic Janus glycodendrimers and their self-assembly into glycodendrimersomes
View Patent ↗The invention concerns compounds of the formula (I) wherein: Y 1 and Y 2 are independently a monosaccharide or disaccharide; X 1 and X 2 are independently —(R 9 —O) m —, —(R 10 ) p —, —O—(R 11 —O) q —, —R 16 —O—R 17 —O— or a covalent bond; Q 1 and Q 2 are independently a nitrogen-containing heterocycle moiety; Z 1 and Z 2 are independently —(O—R 7 )—, —(O—C(═O)—R 8 )a-, —O—C(═O)—R 12 —C(=0)-R 13 —, —O—C(═O)—R 14 —C(═O)—R 15 or a covalent bond; R 7 -R 17 are each independently C 1 -C 6 alkyl; R 1 -R 6 are each independently a linear or branched alkyl group; b, c, d, e, f, and g are 0 or 1, provided b+c+d equals at least 2 and e+f+g equals at least 2; and a, m, p, and q are each an integer from 1-6.
1. A compound of the formula:
wherein:
Y 1 and Y 2 are independently a monosaccharide or disaccharide;
X 1 and X 2 are independently —(R 9 —O) m —, —(R 10 ) p —, —O—(R 11 —O) q —, —R 16 —O—R 17 —O— or a covalent bond;
Q 1 and Q 2 are independently a nitrogen-containing heterocycle moiety;
Z 1 and Z 2 are independently —(O—R 7 )—, —(O—C(═O)—R 8 ) a —, —O—C(═O)—R 12 —C(═O)—R 13 —, —O—C(═O)—R 14 —C(═O)—R 15 or a covalent bond;
R 7 -R 17 are each independently C 1 -C 6 alkyl;
R 1 -R 6 are each independently a linear or branched alkyl group;
b, c, d, e, f, and g are 0 or 1, provided b+c+d equals at least 2 and e+f+g equals at least 2; and
a, m, p, and q are each an integer from 1-6.
2. The compound of claim 1 , wherein R 1 -R 6 are each independently C 4 -C 20 linear or branched alkyl group.
3. The compound of claim 1 , wherein Y 1 and Y 2 are independently D-Mannose, D-Galactose or D-Lactose.
4. The compound of claim 1 , wherein Y 1 and Y 2 are the same.
5. The compound of claim 1 , wherein Q 1 and Q 2 are
where indicates a bond position.
6. The compound of claim 1 , wherein a, m, p, and q are each independently an integer from 1-4.
7. The compound of claim 1 , wherein X 1 , X 2 , Z 1 and Z 2 are covalent bonds.
8. The compound of claim 1 , wherein X 1 and X 2 are covalent bonds.
9. The compound of claim 1 , wherein Z 1 and Z 2 are covalent bonds.
10. A method for producing a compound of formula I
wherein:
Y 1 and Y 2 are independently a monosaccharide or disaccharide;
X 1 and X 2 are independently —(R 9 —O) m —, —(R 10 ) p —, —O—(R 11 —O) q —, —R 16 —O—R 17 —O— or a covalent bond;
Q 1 and Q 2 are independently a nitrogen-containing heterocycle moiety;
Z 1 and Z 2 are independently —(O—R 7 )—, —(O—C(═O)—R 8 ) a —, —O—C(═O)—R 12 —C(═O)—R 13 —, —O—C(═O)—R 14 —C(═O)—R 15 or a covalent bond;
R 7 -R 17 are each independently C 1 -C 6 alkyl;
R 1 -R 6 are each independently a linear or branched alkyl group;
b, c, d, e, f, and g are 0 or 1, provided b+c+d equals at least 2 and e+f+g equals at least 2; and
a, m, p, and q are each an integer from 1-6;
said method comprising contacting compounds of formula Y 1 —X 1 -E and Y 2 —X 2 -E with a compounds of formula IV
wherein A and E are selected from —C≡CH or —N 3 provided that A and E are not the same.
11. The method of claim 10 , wherein X 1 and X 2 are covalent bonds.
12. The method of claim 10 , wherein Z 1 and Z 2 are covalent bonds.
13. The method of claim 10 , wherein X 1 , X 2 , Z 1 and Z 2 are covalent bonds.
14. The method of claim 10 , wherein R 1 -R 6 are each independently C 4 -C 20 linear or branched alkyl group.
15. The method of claim 10 , wherein Y 1 and Y 2 are independently D-Mannose, D-Galactose or D-Lactose.
16. The method of claim 10 , wherein Y 1 and Y 2 are the same.
17. The method of claim 10 , wherein Q 1 and Q 2 are
where indicates a bond position.
18. The method of claim 10 , wherein R 1 -R 6 are the same.
19. A method of producing self-assembled amphiphilic Janus glycodendrimers comprising introducing a compound of claim 1 into an aqueous media.