Molecular transporters based on sugar and its analogues and processes for the preparation thereof
View Patent ↗The inventive molecular transporter compound shows significantly high permeability through a biological membrane such as a plasma membrane, nuclear membrane and blood-brain barrier, and accordingly, can be effectively used in delivering various biologically active molecules.
1. A sugar alcohol of formula (1):
wherein,
R 1 and R 2 are each independently H, alkyl, arylalkyl, cycloalkyl, heteroalkyl, —(CH 2 ) m NHR′, —(CH2) l CO 2 R″, —COR′″, —SO 2 R″″ or a physiologically active molecule; R′, R″, R′″ and R″″ being each independently H, alkyl, arylalkyl, cycloalkyl, heteroalkyl or a physiologically active molecule; m being an integer in the range of 2 to 5; and l being an integer in the range of 1 to 5;
R 3 is
n being an integer in the range of 1 to 12.
2. The sugar alcohol of claim 1 , which is an alditol having the skeleton of sorbitol, mannitol, galactitol, or a salt thereof.
3. A sugar alcohol of formula (4):
wherein,
R is
n being an integer in the range of 1 to 12.
4. The sugar alcohol of claim 3 , which is an alditol having the skeleton of sorbitol, mannitol, galactitol, or a salt thereof.
5. A composition for delivering a biologically active molecule across a biological membrane into a cell, wherein the biologically active molecule is selected from the group consisting of a peptide, a nucleic acid, a therapeutic molecule, and a diagnostic agent, comprising the compound of formula (1) or formula (4):
wherein, R 1 , R 2 and R 3 are the same as defined in claim 1 , or
wherein, R 1 is the same as defined in claim 3 ,
and the biologically active agent.
6. The composition of claim 5 , wherein the biologically active molecule is an organic compound having a molecular weight ranging from 100 to 1500 g/mol.
7. The composition of claim 5 , wherein the biologically active molecule is a peptide and a nucleic acid.
8. The composition of claim 5 , wherein the compound of formula 1 forms a conjugate with the biologically active molecule through a covalent bond.
9. The composition of claim 5 , wherein the compound of formula 1 forms an ionic complex with the biologically active molecule through ionic bonds.
10. A method for delivering a biologically active molecule across a biological membrane into a cell, wherein the biologically active molecule is one selected from the group consisting of a peptide, a nucleic acid, a therapeutic molecule, and a diagnostic agent, which comprises the step of employing a compound selected from the group consisting of the compounds of formula (1) or (4) as a molecular transporter:
wherein, R 1 , R 2 and R 3 are the same as defined in claim 1 , or
Wherein, R 1 is the same as defined in claim 3 ,
for delivery with the biologically active molecule.