Conjugated lipomers and uses thereof

1. A conjugated lipomer of the Formula (II):

or a salt thereof; wherein:

each instance of L 1 is independently formula:

provided that at least one L 1 is formulae (iii);

n is an integer between 5 and 25, inclusive;

each instance of R 2 is independently hydrogen; acyl; silyl; sulfonyl; an amino protecting group; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted heteroalkyl; substituted or unsubstituted heteroalkenyl; substituted or unsubstituted heteroalkynyl; substituted or unsubstituted carbocyclyl; substituted or unsubstituted heterocyclyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; a substituted or unsubstituted polyethyleneimine; or a group of the formula (iii′):

or the two R 2 groups are joined to form a substituted or unsubstituted heterocyclyl;

each instance of R 3 is independently substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted heteroalkyl; substituted or unsubstituted heteroalkenyl; substituted or unsubstituted heteroalkynyl; substituted or unsubstituted carbocyclyl; substituted or unsubstituted heterocyclyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; or a hydrophilic polymer;

each instance of R 4 is independently hydrogen, acyl; silyl; a hydroxyl protecting group; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted heteroalkyl; substituted or unsubstituted heteroalkenyl; substituted or unsubstituted heteroalkynyl; substituted or unsubstituted carbocyclyl; substituted or unsubstituted heterocyclyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl;

A is —N(R 5 ) 2 , wherein each instance of R 5 is independently hydrogen; acyl; silyl; sulfonyl; an amino protecting group; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted heteroalkyl; substituted or unsubstituted heteroalkenyl; substituted or unsubstituted heteroalkynyl; substituted or unsubstituted carbocyclyl; substituted or unsubstituted heterocyclyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; or a group of the formula (iii′):

or two R 5 groups are joined to form a substituted or unsubstituted heterocyclyl; and

Z is hydrogen; acyl; silyl; sulfonyl; an amino protecting group; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted heteroalkyl; substituted or unsubstituted heteroalkenyl; substituted or unsubstituted heteroalkynyl; substituted or unsubstituted carbocyclyl; substituted or unsubstituted heterocyclyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl, or a group of the formula (iii′):

or Z and the nitrogen atom to which it is attached form a substituted or unsubstituted heterocyclyl group;

wherein the conjugated lipomer is prepared from a polyethyleneimine polymer having a number average molecule weight (Mn) of less than 1200 g/mol.

2. The conjugated lipomer of claim 1 , wherein the conjugated lipomer is prepared from a polyethyleneimine polymer having a number average molecule weight (Mn) of less than 800 g/mol.

3. The conjugated lipomer of claim 1 , wherein each instance of R 5 is independently hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted heteroalkyl; or a group of the formula (iii′).

4. The conjugated lipomer of claim 1 , wherein Z is hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted heteroalkyl; or a group of the formula (iii′).

5. The conjugated lipomer of claim 1 , wherein n is an integer between 5 and 20, inclusive.

6. The conjugated lipomer of claim 1 , wherein each instance of R 2 is independently hydrogen; a substituted or unsubstituted polyethyleneimine; or a group of the formula (iii′).

7. The conjugated lipomer of claim 1 , wherein each instance of R 3 is independently substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted heteroalkyl; or a hydrophilic polymer.

8. The conjugated lipomer of claim 7 , wherein the hydrophilic polymer is a polyethyleneglycol (PEG) polymer.

9. The conjugated lipomer of claim 1 , wherein the lipomer is selected from the group consisting of:

(i)

(ii)

(iii)

(iii)

1

—

—

2

—

3

4

—

5

—

—

6

—

7

8

—

9

—

—

10

—

11

12

—

13

—

—

14

—

15

16

—

17

—

—

18

—

19

20

—

21

—

—

22

—

23

24

—

25

—

—

26

—

27

28

—

29

—

—

30

—

31

32

—

33

—

—

34

—

35

36

—

and salts thereof.

10. The conjugated lipomer of claim 1 , wherein the lipomer is selected from the group consisting of:

(i)

(iii)

(iii)

1

—

—

2

—

3

4

—

5

—

—

6

—

7

8

—

9

—

—

10

—

11

12

—

13

—

—

14

—

15

16

—

17

—

—

18

—

19

20

—

21

—

—

22

—

23

24

—

25

—

—

26

—

27

28

—

29

—

—

30

—

31

32

—

33

—

—

34

—

35

36

—

and salts thereof.

11. A composition comprising one or more conjugated lipomers of claim 1 , and, optionally, an excipient.

12. The composition of claim 11 , wherein the composition is a pharmaceutical composition or a cosmetic composition.

13. The composition of claim 11 , wherein the composition further comprises an agent.

14. The composition of claim 13 , wherein the agent is an organic molecule or inorganic molecule.

15. A method of treating hepatocellular cancer comprising administering to a subject in need thereof an effective amount of a conjugated lipomer, or salt thereof, of claim 1 .

16. The conjugated lipomer of claim 1 , wherein n is an integer between 5 and 15, inclusive.

17. The conjugated lipomer of claim 1 , wherein at least one L 1 group is of the formula (ii).

18. The conjugated lipomer of claim 1 , wherein at least one instance of R 3 is unsubstituted C 8-20 alkyl or unsubstituted C 8-20 alkenyl.

19. The conjugated lipomer of claim 1 , wherein at least one instance of R 3 is —C 10 H 21 , —C 11 H 23 , —C 12 H 25 , —C 13 H 27 , —C 14 H 29 , —C 15 H 31 , or —C 16 H 33 .

20. The conjugated lipomer of claim 1 , wherein the conjugated lipomer is prepared from a polyethyleneimine polymer having a number average molecule weight (Mn) of less than 800 g/mol.

21. The composition of claim 14 , wherein the agent is a polynucleotide, and the polynucleotide is DNA or RNA.

22. The composition of claim 14 , wherein the RNA is RNAi, dsRNA, siRNA, shRNA, miRNA, or antisense RNA.

23. The composition of claim 14 , wherein the agent is a polynucleotide that encodes a protein or peptide.

24. The composition of claim 13 , where the agent is a nucleic acid or polynucleotide.

25. The composition of claim 13 , where the agent is a protein or peptide.

26. The composition of claim 13 , where the agent is a targeting agent.

27. The composition of claim 13 , where the agent is an isotopically labeled chemical compound.

28. The composition of claim 13 , where the agent is a vaccine.

29. The composition of claim 13 , where the agent is an immunological agent.