IP Library › Patent Application 18238687
Patent Application
App. No. 18/238,687

Ferroptosis-HDAC Inhibitor Hybrid Anticancer Agents

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Quick Facts
Patent No.
US None
App. No.
18/238,687
Abstract

Hybrid molecules having pharmacophores of a ferrotoptosis inducer and an HDAC inhibitor, as well as ferroptosis inducers and HDAC inhibitors, and methods of making and using the same, are described.

Claims (40)

1 . A composition comprising a hybrid molecule having both a ferroptotic pharmacophore and a histone deacetylase (HDAC) inhibitor pharmacophore.

2 . The composition of claim 1 , wherein the ferroptotic pharmacophore comprises a terminal alkyne attached to a thiazole.

3 . The composition of claim 1 , wherein the HDAC inhibitor pharmacophore comprises a hydroxamic acid metal-binding group.

4 . The composition of claim 1 , wherein the hybrid molecule has Formula A:

wherein:

R is alkyl, alkenyl, amidoalkyl, amidoalkenyl, arylalkyl, arylalkenyl, or amidoarylalkenyl;

and salts, stereoisomers, racemates, solvates, hydrates, and polymorphs thereof.

5 . The composition of claim 4 , wherein R is (C1-C6)alkyl or (C1-C6)alkenyl.

6 . The composition of claim 1 , wherein the hybrid molecule is HY-1:

7 . The composition of claim 1 , wherein the hybrid molecule is HY-2:

8 . The composition of claim 1 , wherein the hybrid molecule is HY-3:

9 . The composition of claim 1 , wherein the hybrid molecule is HY-4:

10 . The composition of claim 1 , wherein the hybrid molecule is HY-5:

11 . A composition comprising a histone deacetylase (HDAC) inhibitor having Formula C:

wherein:

X is a halide, and

R is an alkyl, alkenyl, alkynyl, amidoalkyl, amidoalkenyl, arylalkyl, arylalkenyl, or amidoarylalkenyl group;

and salts, stereoisomers, racemates, solvates, hydrates, and polymorphs thereof.

12 . The composition of claim 11 , wherein X is Br, and R includes an aliphatic chain of from 4 to 6 carbons.

13 . The composition of claim 11 , wherein X is Br, and R includes an alkenyl group.

14 . The composition of claim 11 , wherein the HDAC inhibitor is HC-1:

15 . The composition of claim 11 , wherein the HDAC inhibitor is HC-2:

16 . The composition of claim 11 , wherein the HDAC inhibitor is HC-3:

17 . The composition of claim 11 , wherein the HDAC inhibitor is HC-4:

18 . The composition of claim 11 , wherein the HDAC inhibitor is HC-5:

19 . A method of killing cancer cells, the method comprising contacting cancer cells with an effective amount of a composition comprising Formula A, Formula B, or Formula C, and killing the cancer cells:

wherein:

R is alkyl, alkenyl, amidoalkyl, amidoalkenyl, arylalkyl, arylalkenyl, or amidoarylalkenyl;

X is a halide;

R 1 is alkyl, alkenyl, amidoalkyl, amidoalkenyl, arylalkyl, arylalkenyl, or amidoarylalkenyl; and

R 2 is alkyl.

20 . The method of claim 19 , wherein the cancer is triple negative breast cancer, renal cancer, leukemia, colon cancer, ovarian cancer, breast cancer, lung cancer, melanoma, or CNS cancer.

21 . A method of treating a cancer, the method comprising administering to a subject having cancer an effective amount of a composition comprising Formula A or Formula C, and treating the cancer:

wherein:

R is alkyl, alkenyl, amidoalkyl, amidoalkenyl, arylalkyl, arylalkenyl, or amidoarylalkenyl; and

X is a halide.

22 . A method of inhibiting histone deacetylase (HDAC) in a subject, the method comprising administering to the subject an effective amount of a composition comprising Formula A or Formula C, and inhibiting HDAC in the subject:

wherein:

R is alkyl, alkenyl, amidoalkyl, amidoalkenyl, arylalkyl, arylalkenyl, or amidoarylalkenyl; and

X is a halide.