# US 11,993,670 B2 · Zwitterionic biocompatible polymers, methods, and uses thereof

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- Number: US 11,993,670 B2
- Document ID: US11993670B2
- Status: Granted
- Kind: B2
- Application number: 15/734,686
- Filed: 2019-06-06
- Published: 2021-07-29
- Granted: 2024-05-28
- Earliest claimed: 2018-06-06
- Assignees: The Board of Trustees of the University of Illinois
- Applicants: The Board of Trustees of the University of Illinois
- Inventors: Gang Cheng; Huifeng Wang
- Web page: https://patentgrep.com/patent/US11993670B2

## CPC

- C08F 220/36: containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate}
- A61K 47/6939: {the polymer being a polysaccharide, e.g. starch, chitosan, chitin, cellulose or pectin}
- C08G 73/0226: {Quaternisation of polyalkylene(poly)amines}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Provided herein are biocompatible polymers having a polymer backbone and one or more repeating units, and methods of making and using the same. The repeating units can each be individually selected from a zwitterionic precursor repeating unit of Formula (1). Also provided are systems for nucleic acid delivery including the biocompatible polymers, the systems having a cationic core and a polysaccharide-anionic peptide conjugate adsorbed to the cationic core.

## Claims

### Claim 1

A biocompatible polymer, comprising:
a polymer backbone comprising one or more repeating units, wherein the one or more repeating units are each individually selected from a zwitterionic precursor repeating unit of Formula (I):
wherein R1 is —(CH2)n—, —(CH2)nO(CH2)m—, —(CH2CH2OCH2CH2)n—, —(CH2CH2O)nCH2CH2—, —(CH2CH2O)n(CH2)m—, —(CH2)n(CH2CH2O)m(CH2)p—, —((CH2)1-8C(O)O)n(CH2)m—, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)p-, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)p-, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —((CH2)nOC(O)O)(CH2CH2)m, —(CH2)nNHC(O)(CH2)m—, —(CH2)nC(O)NH(CH2)m, —(CH2)nS(O2)(CH2)m—, —(CH2)nS(O2)(CH2)mO(CH2)t—, —(CH2)nO—, —(CH2)nO(CH2)mO—, —(CH2CH2OCH2CH2)nO—, —(CH2CH2O)nCH2CH2O—, —(CH2CH2O)n(CH2)mO—, —(CH2)n(CH2CH2O)m(CH2)pO—, —((CH2)1-8C(O)O)n(CH2)mO—, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pO—, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)pO—, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pO—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pO—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pO—, —((CH2)nOC(O)O)(CH2CH2)mO—, —(CH2)nNHC(O)(CH2)mO—, —(CH2)nC(O)NH(CH2)mO—, —(CH2)nS(O2)(CH2)mO—, or —(CH2)nS(O2)(CH2)mO(CH2)tO—;
R2 is C, P(OR7), or S(═O);
R3 is O, NH, or OC(═O);
R4, R5 and R7 are each independently H, —CH3, —(CH2)nCH3, —(CH2CH2O)nCH3, —(CH2CH2O)n(CH2)mCH3, —(CH2CH2O)n(CH2)mOH, —((CH2)nO)m((CH2)pO)q(CH2)rOH, —(CH2CH2O)nH, —(CH2)nOH, —(CH2)nO(CH2)mOH, —(CH2CH2OCH2CH2)nOH, —(CH2CH2O)nCH2CH2OH, —((CH2)1-8C(O)O)n(CH2)mOH, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pOH, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)pOH, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pOH, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pOH, —((CH2)nOC(O)O)(CH2CH2)mOH, —(CH2)nNHC(O)(CH2)mOH, —(CH2)nC(O)NH(CH2)m OH, C1-n alkenyl, C1-n alkynyl, C6-10 aryl, pentafluorophenyl, or succinimidyl;
R6 is F, Cl, Br, I, acetate, citrate, bicarbonate, carbonate, chlorate, dihydrogen phosphate, hydrogen phosphate, hydrogen sulfate, hydroxide, nitrate, nitride, nitrite, phosphate, sulfate, sulfide, sulfite, thiocyanate, thiosulfate, oxalate, perchlorate, chlorite, hypochlorite, periodate, iodate, hypoiodate, bromate, hypobromate, hypobromite, hydrogen carbonate, hydrogen sulfate, hydrogen sulfite, hydrogen oxalate, borate, tetraborate, hexafluorosilicate, tartrate, silicate, selenite, arsenate, ethanedioate, oxoethanoate, 2-hydroxyethanoate, propanoate, butanoate, pentanoate, butyrate, formate, lactate, maleate, oleate, oxalate, stearate, tartrate, urate, acrylate, glutamate, malonate, phthalate, barbiturate, cinnamate, hexanoate, folate, propionate, stearate, ascorbate, glutarate, azelate, benzilate, fumarate, gluconate, propiolate, tannate, gallate, titanate, trifluoroacetate, or diuranate;
each n, m, p, q, and r is independently 1 to 10,000; and,
t is 0 to 10,000,
wherein the polymer further comprises a functional group capable of conjugating to a peptide, a protein, a monosaccharide, a disaccharide, an oligo/polysaccharide, a lipid, a nucleic acid, a polymer, a target ligand molecule, a prodrug, a small molecule drug, or any combination thereof, wherein the functional group is selected from the group consisting of acyl halide, alcohol, aldehyde, amide, amine, azo, anhydride, azide, hydrazide, toluene derivative, biotin, disulfide, carbonate, carboxylic acid, cyanate, haloalkane, ether, ester, hydroperoxide, hydrazone, isocyanide, imine, isocyanate, ketone, nitrate, nitrile, nitrite, nitro, nitroso, peroxide, benzyl, phosphodiester, vinylsulfone, thiol, hydroxyl, imidoester, pyridyldithiol, phosphonic acid, phosphate, pyridinyl, sulfide, sulfone, sulfonic acid, sulfoxide, thiol, azide, alkene, alkyne, nitrone, hydrazide, maleimide, acrylate, methacrylate, acrylamide, methacrylamide, lipoamide, difluorobenzocyclooctyne, tetrazine, pentafluorophenyl ester, or succinimidyl ester, any derivative of the any foregoing, and any combination of any of the foregoing.

### Claim 2 (depends on 1)

The biocompatible polymer of claim 1, wherein one or more of the zwitterionic precursor repeating unit is a zwitterionic repeating unit and the zwitterionic repeating unit has a structure of Formula (II):

### Claim 3 (depends on 2)

The biocompatible polymer of claim 2, wherein the polymer is a copolymer comprising alternating zwitterionic precursor repeating units having a structure of Formula (I) and zwitterionic repeating units having a structure of Formula (II).

### Claim 4 (depends on 3)

The biocompatible polymer of claim 3, wherein the polymer is a block copolymer comprising alternating blocks of one or more zwitterionic precursor repeating units having a structure of Formula (I) and blocks of one or more zwitterionic repeating units having a structure of Formula (II).

### Claim 5 (depends on 1)

The biocompatible polymer of claim 1, wherein R3 is O.

### Claim 6 (depends on 1)

The biocompatible polymer of claim 1, wherein R2 is C.

### Claim 7 (depends on 1)

The biocompatible polymer of claim 1, wherein R1 is —(CH2)n—, —(CH2)nO(CH2)m—, —(CH2CH2OCH2CH2)n—, —(CH2CH2O)nCH2CH2—, —(CH2CH2O)n(CH2)m—, —(CH2)n(CH2CH2O)m(CH2)p—, —((CH2)1-8C(O)O)n(CH2)m—, —((CH2)1- 8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)p—, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)p—, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —((CH2)nOC(O)O)(CH2CH2)m, —(CH2)nNHC(O)(CH2)m—, —(CH2)nC(O)NH(CH2)m, —(CH2)nS(O2)(CH2)m—, or —(CH2)nS(O2)(CH2)mO(CH2)t—.

### Claim 8 (depends on 1)

The biocompatible polymer of claim 1, wherein the polymer comprises one or more zwitterionic repeating units having a structure selected from the group consisting of:
and any combination thereof.

### Claim 9 (depends on 1)

The biocompatible polymer according to claim 1, further comprising one or more secondary repeating units, wherein the one or more secondary repeating units have a structure according to Formula (III):
wherein R11 is H, —CH3, —(CH2)nCH3, —(CH2CH2O)nCH3, —(CH2CH2O)n(CH2)mCH3, —(CH2CH2O)n(CH2)mOH, —((CH2)nO)m((CH2)pO)q(CH2)rOH, —(CH2CH2O)nH, —(CH2)nOH, —(CH2)nO(CH2)mOH, —(CH2CH2OCH2CH2)nOH, —(CH2CH2O)nCH2CH2OH, —((CH2)1-8C(O)O)n(CH2)mOH, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pOH, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)pOH, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pOH, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pOH, —((CH2)nOC(O)O)(CH2CH2)mOH, —(CH2)nNHC(O)(CH2)mOH, —(CH2)nC(O)NH(CH2)mOH, C1-n alkenyl, C1-n alkynyl, C6-10 aryl, pentafluorophenyl, or succinimidyl.

### Claim 10 (depends on 1)

The biocompatible polymer of claim 1, wherein the polymer is of Formula (IV):
wherein R8 is —CH3, —CH2CH═CH2, —(CH2)nCH═CH2, —(CH2)nCH═CH2(CH2)tCH3, —CH2C≡CH, —(CH2)nC≡CH, —(CH2)nC≡C(CH2)tCH3, —(CH2)nCH3, —(CH2)nCH2N3, —(CH2)nNH2, —(CH2)nCH2SH, —(CH2CH2O)nCH3, —(CH2CH2O)n(CH2)mCH3, —(CH2CH2O)n(CH2)mN3, —(CH2CH2O)n(CH2)mSH, —(CH2CH2O)n(CH2)mOH, —((CH2)nO)m((CH2)pO)q(CH2)rOH, —(CH2CH2O)nH, —(CH2)nOH, —(CH2)nO(CH2)mOH, —(CH2CH2OCH2CH2)nOH, —(CH2CH2O)nCH2CH2OH, —((CH2)1-8C(O)O)n(CH2)mOH, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pOH, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)pOH, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pOH, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pOH, —((CH2)nOC(O)O)(CH2CH2)mOH, —(CH2)nNHC(O)(CH2)mOH, —(CH2)nC(O)NH(CH2)mOH, C1-n alkenyl, C1-n alkynyl, C6-10 aryl, or a compound containing acyl halide, alcohol, aldehyde, amide, amine, azo, anhydride, azide, hydrazide, toluene derivative, biotin, disulfide, carbonate, carboxylic acid, cyanate, haloalkane, ether, ester, hydroperoxide, hydrazone, isocyanide, imine, isocyanate, ketone, nitrate, nitrile, nitrite, nitro, nitroso, peroxide, benzyl, phosphodiester, vinylsulfone, thiol, hydroxyl, imidoester, pyridyldithiol, phosphonic acid, phosphate, pyridinyl, sulfide, sulfone, sulfonic acid, sulfoxide, thiol, azide, alkene, alkyne, nitrone, hydrazide, maleimide, acrylate, methacrylate, acrylamide, methacrylamide, lipoamide, difluorobenzocyclooctyne, tetrazine, pentafluorophenyl ester, or succinimidyl ester;
R9 is O, NH, S, Se, CH2, or —N═N—,
R10 is —H, —N, —CH3, —CH2CH═CH2, —(CH2)nCH═CH2, —(CH2)nCH═CH2(CH2)tCH3, —CH2C≡CH, —(CH2)nC≡CH, —(CH2)nC≡C(CH2)tCH3, —(CH2)nCH3, —(CH2)nCH2N3, —(CH2CH2O)nCH3, —(CH2CH2O)n(CH2)mCH3, —(CH2CH2O)n(CH2)mN3, —(CH2CH2O)n(CH2)mOH, —((CH2)nO)m((CH2)pO)q(CH2)rOH, —(CH2CH2O)nH, —(CH2)nOH, —(CH2)nO(CH2)mOH, —(CH2CH2OCH2CH2)nOH, —(CH2CH2O)nCH2CH2OH, —((CH2)1-8C(O)O)n(CH2)mOH, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pOH, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)pOH, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pOH, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pOH, —((CH2)nOC(O)O)(CH2CH2)mOH, —(CH2)nNHC(O)(CH2)mOH, —(CH2)nC(O)NH(CH2)mOH, vinyl sulfone, succinimidyl ester, pentafluorophenyl ester, —SH, —(CH2)nNH2, —(CH2)nCOOH, —(CH2)nSH, —(CH2)nNH(CH2)mCH3, —(CH2)nNHCH3, —(CH2CH2O)n(CH2)mNH2, —(CH2CH2O)n(CH2)mSH, —(CH2CH2O)n(CH2)mCOOH, C1-n alkenyl, C1-n alkynyl, C6-10 aryl, C1-n alkylene-SH,
or a compound containing acyl halide, alcohol, aldehyde, amide, amine, azo, anhydride, azide, hydrazide, toluene derivative, biotin, disulfide, carbonate, carboxylic acid, cyanate, haloalkane, ether, ester, hydroperoxide, hydrazone, isocyanide, imine, isocyanate, ketone, nitrate, nitrile, nitrite, nitre, nitroso, peroxide, benzyl, phosphodiester, vinylsulfone, thiol, hydroxyl, imidoester, pyridyldithiol, phosphonic acid, phosphate, pyridinyl, sulfide, sulfone, sulfonic acid, sulfoxide, thiol, azide, alkene, alkyne, nitrone, hydrazide, maleimide, acrylate, methacrylate, acrylamide, methacrylamide, lipoamide, difluorobenzocyclooctyne, tetrazine, pentafluorophenyl ester, or succinimidyl ester; and,
x is 1 to 10,000.

### Claim 11 (depends on 10)

The biocompatible polymer of claim 10, wherein the polymer is hydrolyzed, and the hydrolyzed polymer has a structure of Formula (V):

### Claim 12 (depends on 10)

The biocompatible polymer of claim 10, wherein R8 is CH3, R9 is O, and R10 is H.

### Claim 13 (depends on 10)

The biocompatible polymer of claim 10, wherein R8 is CH3, R9 is O, and R10 has a structure of:

### Claim 14 (depends on 1)

The biocompatible polymer of claim 1, wherein the polymer has a structure of:
wherein y is 1 to 10,000.

### Claim 15 (depends on 1)

The biocompatible polymer of claim 1, wherein the polymer is conjugated to a peptide, a protein, a monosaccharide, a disaccharide, an oligo/polysaccharide, a lipid, a nucleic acid, a polymer, a targeting ligand molecule, a prodrug, a small molecule drug, or any combination thereof.

### Claim 16 (depends on 1)

The biocompatible polymer of claim 1, wherein the polymer has a solubility in water at 20-50° C. in a range of about 1 pg/mL to about 500 mg/mL.

### Claim 17 (depends on 1)

A nanoparticle comprising:
the biocompatible polymer according to claim 1 and a drug,
wherein the drug is selected from the group consisting of a peptide, a protein, a nucleic acid, a small molecule drug, a prodrug, and any combination thereof.

### Claim 18

A method comprising:
(i) reacting a polyethyleneimine having a structure of
with an α,β-unsaturated ester having a structure of
to form an N-alkylated polyethyleneimine having a structure of
wherein n is from 1 to 10,000 and R is H, —CH3, —(CH2)nCH3, —(CH2CH2O)nCH3, —(CH2CH2O)n(CH2)mCH3, —(CH2CH2O)n(CH2)mOH, —((CH2)nO)m((CH2)pO)q(CH2)rOH, —(CH2CH2O)nH, —(CH2)nOH, —(CH2)nO(CH2)mOH, —(CH2CH2OCH2CH2)nOH, —(CH2CH2O)nCH2CH2OH, —((CH2)1-8C(O)O)n(CH2)mOH, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pOH, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)pOH, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pOH, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pOH, —((CH2)nOC(O)O)(CH2CH2)mOH, —(CH2)nNHC(O)(CH2)mOH, —(CH2)nC(O)NH(CH2)mOH, C1-n alkenyl, C1-n alkynyl, C6-10 aryl, pentafluorophenyl ester or succinimidyl;
(ii) hydrolyzing the N-alkylated polyethyleneimine to provide a zwitterionic N-alkylated polyethyleneimine; and
(iii) reacting the zwitterionic N-alkylated polyethyleneimine with a compound having a functional group capable of conjugating to a peptide, a protein, a monosaccharide, a disaccharide, an oligo/polysaccharide, a lipid, a nucleic acid, a polymer, a targeting ligand molecule, a prodrug, a small molecule drug, or any combination thereof to form a biocompatible zwitterionic polymer.

### Claim 19 (depends on 1)

A system for nucleic acid delivery comprising:
a cationic core comprising a cationic compound and nucleic acid; and,
a polysaccharide-anionic peptide conjugate comprising an anionic peptide physically bound to a polysaccharide,
wherein the polysaccharide-anionic peptide conjugate is adsorbed to the cationic core,
and the biocompatible polymer of claim 1 is associated with the cationic core or the polysaccharide-anionic peptide conjugate.

### Claim 20

A biocompatible polymer, comprising a polymer backbone comprising
one or more repeating units selected from a zwitterionic precursor repeating unit of Formula (I):
and
one or more repeating units selected from a zwitterionic repeating unit of Formula (II):
wherein each R1 is independently —(CH2)n—, —(CH2)nO(CH2)m—, —(CH2CH2OCH2CH2)n—, —(CH2CH2O)nCH2CH2—, —(CH2CH2O)n(CH2)m—, —(CH2)n(CH2CH2O)m(CH2)p—, —((CH2)1-8C(O)O)n(CH2)m—, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)p-, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)p-, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —((CH2)nOC(O)O)(CH2CH2)m, —(CH2)nNHC(O)(CH2)m—, —(CH2)nC(O)NH(CH2)m, —(CH2)nS(O2)(CH2)m—, —(CH2)nS(O2)(CH2)mO(CH2)t—, —(CH2)nO—, —(CH2)nO(CH2)mO—, —(CH2CH2OCH2CH2)nO—, —(CH2CH2O)nCH2CH2O—, —(CH2CH2O)n(CH2)mO—, —(CH2)n(CH2CH2O)m(CH2)pO—, —((CH2)1-8C(O)O)n(CH2)mO—, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pO—, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)pO—, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pO—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pO—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pO—, —((CH2)nOC(O)O)(CH2CH2)mO—, —(CH2)nNHC(O)(CH2)mO—, —(CH2)nC(O)NH(CH2)mO—, —(CH2)nS(O2)(CH2)mO—, or —(CH2)nS(O2)(CH2)mO(CH2)tO—;
each R2 is independently C, P(OR7), or S(═O);
each R3 is independently O, NH, or OC(═O);
each R4, R5 and R7 is independently H, —CH3, —(CH2)nCH3, —(CH2CH2O)nCH3, —(CH2CH2O)n(CH2)mCH3, —(CH2CH2O)n(CH2)mOH, —((CH2)nO)m((CH2)pO)q(CH2)rOH, —(CH2CH2O)nH, —(CH2)nOH, —(CH2)nO(CH2)mOH, —(CH2CH2OCH2CH2)nOH, —(CH2CH2O)nCH2CH2OH, —((CH2)1-8C(O)O)n(CH2)mOH, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pOH, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)pOH, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pOH, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pOH, —((CH2)nOC(O)O)(CH2CH2)mOH, —(CH2)nNHC(O)(CH2)mOH, —(CH2)nC(O)NH(CH2)mOH, C1-n alkenyl, C1-n alkynyl, C6-10 aryl, pentafluorophenyl, or succinimidyl;
R6 is F, Cl, Br, I, acetate, citrate, bicarbonate, carbonate, chlorate, dihydrogen phosphate, hydrogen phosphate, hydrogen sulfate, hydroxide, nitrate, nitride, nitrite, phosphate, sulfate, sulfide, sulfite, thiocyanate, thiosulfate, oxalate, perchlorate, chlorite, hypochlorite, periodate, iodate, hypoiodate, bromate, hypobromate, hypobromite, hydrogen carbonate, hydrogen sulfate, hydrogen sulfite, hydrogen oxalate, borate, tetraborate, hexfluorosilicate, tartrate, silicate, selenite, arsenate, ethanedioate, oxoethanoate, 2-hydroxyethanoate, propanoate, butanoate, pentanoate, butyrate, formate, lactate, maleate, oleate, oxalate, stearate, tartrate, urate, acrylate, glutamate, malonate, phthalate, barbiturate, cinnamate, hexanoate, folate, propionate, stearate, ascorbate, glutarate, azelate, benzilate, fumarate, gluconate, propiolate, tannate, gallate, titanate, trifluoroacetate, or diuranate;
each n, m, p, q, and r is independently 1 to 10,000; and,
t is 0 to 10,000.