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US 10,725,055 B1Granted
Compounds for carbonyl sulfide/carbon disulfide/hydrogen sulfide release and methods of making and using the same
AssigneeUniversity of Oregon
InventorsMichael D. Pluth, Andrea Steiger, Yu Zhao
Life of this patent
Estimating the term…
Abstract
Disclosed herein are embodiments of donor compounds that can be used to produce H2S from COS or CS2 released from the donor compounds. In some embodiments, the donor compounds can indirectly produce H2S after being exposed to a reactive component in a triggering event. In other embodiments, the donor compounds can indirectly regenerate H2S after reacting with an H2S analyte. The donor compounds disclosed herein can be used for analytical techniques, disease diagnostics, and/or therapeutic applications. Methods of making and using the donor compounds also are provided herein.
Claims21
A donor compound represented by Formula 1:
- wherein ring B is an aryl group or a heteroaryl group selected from pyridyl, pyrrole, or thiophene;
- each of W and Y independently is oxygen or sulfur;
- V is oxygen, sulfur, or nitrogen;
- wherein each of W, Y, and V are selected to provide a carbamodithioate, a carbonodithioate, a carbonothioate, a carbonotrithioate, a thiocarbamate, or a thiocarbonate;
- or wherein W is oxygen and Y and V are both sulfur or Y is oxygen and W and V are both sulfur;
- R1, if present, is hydrogen, aliphatic, heteroaliphatic, aryl, or heteroaryl;
- R2 is heteroaliphatic, aryl, heteroaryl, a saccharide, a targeting group, a detectable moiety, a drug molecule, or combinations thereof;
- each R3 independently is aliphatic, heteroaliphatic, aryl, heteroaryl, halogen, hydroxyl, thiol, amine, imine, azide, a boronate ester, a boronic acid, a disulfide, an ester, a heteroaliphatic ester group, nitro, a silyl ether, a phosphoric ester, a sulfuric ester, 3,5-dinitrobenzenesulfonic acid, or a combination thereof;
- and n is an integer selected from 1 to 5;
- provided that
- when ring B is an aryl or heteroaryl group selected from pyridyl, pyrrole, or thiophene, the aryl or heteroaryl group comprises at least one ortho- or para-positioned R3 group, relative to the
- group, wherein the ortho-positioned R3 group is a thiol;
- an amine of formula —NRbRc, wherein each of Rb and Rc independently is selected from hydrogen, alkenyl, alkynyl, aryl, heteroalkyl, heteroalkenyl, heteroalkynyl, heteroaryl, and any combination thereof;
- an imine;
- a boronate ester;
- a boronic acid;
- a disulfide;
- an ester;
- a heteroaliphatic ester group;
- a nitro group;
- a silyl ether;
- a phosphoric ester;
- a sulfuric ester;
- or 3,5-dinitrobenzenesulfonic acid;
- and/or wherein the para-positioned R3 group is a thiol;
- an amine, an imine, an azide, a boronate ester, a boronic acid, a disulfide, an ester, a heteroaliphatic ester group, a nitro group, a silyl ether, a phosphoric ester, a sulfuric ester, or 3,5-dinitrobenzenesulfonic acid;
- if R1 is hydrogen and R2 is aryl, then the aryl group is -phenyl-(R4)m wherein m is an integer selected from 0 to 5 and R4 is alkoxy, thioether, amide, amine, hydroxyl, thiol, acyloxy, azide, aliphatic, aryl, aldehyde, ketone, ester, carboxylic acid, acyl, acyl halide, cyano, sulfonate, nitro, quaternary amine, bromo, iodo, alkyl halide, heterocyclyl, pyridinyl, or pyridinyl wherein the nitrogen atom is functionalized with an aliphatic or aryl group;
- if R1 is hydrogen and V is N, then R2 is heteroaliphatic, aryl, heteroaryl, a saccharide, a targeting group, a detectable moiety, a drug molecule, or a combination thereof;
- and
- the donor compound is not or is other than
27 more elements
A donor compound represented by Formula 2A:
- wherein ring B is an aryl group or a heteroaryl group;
- R1 is hydrogen, aliphatic, heteroaliphatic, aryl, or heteroaryl;
- R2 is aliphatic, heteroaliphatic, aryl, heteroaryl, halogen, a saccharide, a targeting group, a detectable moiety, a drug molecule, or combinations thereof;
- each R3 independently is aliphatic, heteroaliphatic, aryl, heteroaryl, halogen, hydroxyl, thiol, amine, imine, azide, a boronate ester, a boronic acid, a disulfide, an ester, a phosphoric ester, a sulfuric ester, a heteroaliphatic ester group, nitro, a silyl ether, 3,5-dinitrobenzenesulfonic acid, or a combination thereof;
- and n is an integer selected from 1 to 5;
- provided that
- when ring B is an aryl or heteroaryl group, the aryl or heteroaryl group comprises at least one ortho- or para-positioned R3 group, relative to the
- group, wherein the ortho-positioned R3 group is a hydroxyl, a thiol, an amine, a heteroaliphatic group, an imine, a boronate ester, a boronic acid, a disulfide, an ester, a heteroaliphatic ester group, a nitro group, a silyl ether, a phosphoric ester, a sulfuric ester, or 3,5-dinitrobenzenesulfonic acid;
- and/or wherein the para-positioned R3 group is a hydroxyl, a thiol, an amine, a heteroaliphatic group, an imine, an azide, a boronate ester, a boronic acid, a disulfide, an ester, a heteroaliphatic ester group, a nitro group, a silyl ether, a phosphoric ester, a sulfuric ester, or 3,5-dinitrobenzenesulfonic acid;
- if R1 is hydrogen and R2 is aryl, then the aryl group is -phenyl-(R4)m wherein m is an integer selected from 0 to 5 and R4 is alkoxy, thioether, amide, amine, hydroxyl, thiol, acyloxy, azide, aliphatic, aryl, aldehyde, ketone, ester, carboxylic acid, acyl, acyl halide, cyano, sulfonate, nitro, quaternary amine, fluoro, bromo, iodo, alkyl halide, heterocyclyl, pyridinyl, or pyridinyl wherein the nitrogen atom is functionalized with an aliphatic or aryl group;
- if R1 is hydrogen then R2 is non-aromatic aliphatic;
- or heteroaliphatic, aryl, heteroaryl, a saccharide, a targeting group, a detectable moiety, a drug molecule, or a combination thereof;
- and
- the donor compound is not or is other than
11 more elements
A donor compound represented by any one or more of the following formulas:
- wherein
- each Z independently is CH or nitrogen;
- each X independently is O, S, or NR, wherein R is selected from hydrogen, aliphatic, aryl, heteroaliphatic, or heteroaryl;
- each R3 independently is aliphatic, heteroaliphatic, aryl, heteroaryl, halogen, hydroxyl, thiol, amine, azide, a boronate ester, a boronic acid, a disulfide, an ester, nitro, a phosphoric ester, a sulfuric ester, a silyl ether, 3,5-dinitrobenzenesulfonic acid, or a combination thereof;
- R4 is alkoxy, thioether, amide, amine, hydroxyl, thiol, acyloxy, aliphatic, aryl, aldehyde, ketone, ester, carboxylic acid, acyl, acyl halide, cyano, sulfonate, nitro, quaternary amine, fluoro, bromo, iodo, alkyl halide, pyridinyl, pyridinyl wherein the nitrogen atom is functionalized with an aliphatic or aryl group;
- and
- n is an integer selected from 1 to 3;
- and provided that the donor compound is not
5 more elements
Dependencies are inferred from the claim text.