Peptides comprising thioester groups, including depsipeptide thioesters, methods of making, and use thereof
AssigneeBrandeis University
InventorsBing XU, Weiyi TAN
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Abstract
The present invention relates to a compound of formula (I) or formula (II) as defined herein: Also disclosed are compositions that include compounds of formula (I) or formula (II) in an aqueous medium or a pharmaceutically acceptable carrier. Use of the compounds of formula (I) or formula (II) for delivering a drug moiety into the Golgi apparatus, imaging a cell, or treating a patient having a cancerous condition are also disclosed.
Claims28
A compound according to formula (I)
- where
- Z1 is an aromatic-containing group, preferably an arylacyl;
- NH-Q-C(O) is a dipeptide containing natural or unnatural amino acids, which can be the same or different;
- n is an integer from 1 to 12, such as 1 to 6, preferably 1 or 2;
- Z2 is a C1-C6 alkyl, C1-C6 alkenyl, C1-C6 alkynyl, —N(CH3)2, —CH2OC(O)CH3, —CH2C(O)OCH3,
- a therapeutic agent (drug moiety), or a fluorophore;
- R1, R2, and R3 are independently selected at each occurrence from the group consisting of H, halogen, C1-4 alkyl, —OC1-4 alkyl, and —NO2;
- and
- m is 0, 1, 2, 3, 4, 5, or 6.
3-6. (canceled)
-18. (canceled)
-27. (canceled)
-30. (canceled)
A compound according to formula (II)
- where
- Z3 is H or an aromatic-containing group, preferably an arylacyl;
- NH-Q2-C(O) is a peptide containing at least three amino acid residues, including at least two aromatic amino acid residues and at least one cysteine residue, wherein the cysteine residue is optionally a modified cysteine residue having a phosphate (—PO3H2) group or the group —C(O)(CH2)pCH3, where p is an integer from 0 to 5, attached to the sidechain sulfur group;
- Z4 is —O(CH2)qCH3 where q is an integer from 0 to 5, a therapeutic agent (drug moiety), or a fluorophore, optionally with the group —NH(CH2)rNH— or —NH(CH2)rC(O)— between the therapeutic agent or fluorophore and the C-terminal amino acid group, where r is an integer from 0 to 5.
-40. (canceled)
(canceled)
(canceled)
-50. (canceled)
-53. (canceled)
Dependencies are inferred from the claim text.