Compositions and methods for reducing ice crystal formation
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Publication Number
US-11510407-B2
Publication Date
2022-11-29
Expiration Date
Abstract
The present invention provides peptoid polymers capable of reducing or inhibiting the formation of ice crystals at sub 0° C. temperatures. Also provided are peptoid-peptide hybrids comprising the peptoid polymers provided herein. The peptoid polymers and peptoid-peptide hybrids provided herein are useful for making cryoprotectant solutions. The peptoid polymers, peptoid-peptide hybrids, and cryoprotectant solutions provided herein are useful for making antifreeze solutions, frozen food products, and cosmetic care products. Also provided herein are methods for preserving a tissue, an organ, a cell, or a biological macromolecule using the compositions described herein.
Core Innovation
The invention relates to a peptoid polymer according to formula (I), including a tautomer thereof or stereoisomer thereof. The polymer contains monomer units with side-chain substituents R1, R2, and R3 that are independently selected from defined chemical groups, and at least 2 instances of R1 are independently selected from C1-18 hydroxyalkyl groups. The terminal substituents X and Y are independently selected from defined groups, or alternatively X and Y are taken together to form a covalent bond.
The polymer definition further specifies that R2 is independently selected from H and a set of optionally substituted groups, and that R3 is independently selected from halogen, oxo, thioxo, —OH, —SH, amino, and defined C1-8 alkyl, hydroxyalkyl, alkylamino, and alkylthio groups. The number of monomers n is between 6 and 50, subject to a proviso regarding hydroxyethyl when n is between 6 and 7.
The peptoid polymer is described in relation to reducing or inhibiting ice crystal formation. The disclosed use includes cryoprotectant solution contexts and preservation of biological samples and biological macromolecules, including cryoprotection for crystallized proteins in x-ray crystallography to reduce ice-mediated diffraction background and crystal dissolving.
Claims Coverage
The independent claim identified is clm-00001, directed to a peptoid polymer defined by formula (I), with detailed substituent selection rules, terminal substituent options, and a proviso on hydroxyethyl substitution. The claim coverage also includes a cryoprotectant solution including the defined peptoid polymer.
Peptoid polymer according to formula (I) with defined R1, R2, R3, X and Y substituents
A peptoid polymer according to formula (I), including a tautomer thereof or a stereoisomer thereof, wherein each R1 is independently selected from defined optionally substituted groups with at least 2 instances of R1 being independently selected as C1-18 hydroxyalkyl groups; each R2 is independently selected from defined substituent options; each R3 is independently selected from halogen, oxo, thioxo, —OH, —SH, amino, and C1-8 substituent options; and X and Y are independently selected from defined options or alternatively X and Y are taken together to form a covalent bond.
Polymerization degree range n and hydroxyethyl proviso
The subscript n, representing the number of monomers in the polymer, is between 6 and 50, provided that all instances of R1 are not hydroxyethyl when n is between 6 and 7.
Cryoprotectant solution including the defined peptoid polymer
A cryoprotectant solution that includes the peptoid polymer as defined in claim 1.
Overall, the claim coverage is anchored by clm-00001 and specifies the formula (I) peptoid polymer via constrained R1, R2, R3, X, and Y selections, with n between 6 and 50 and a restriction on complete hydroxyethyl substitution when n is 6-7. The formulation context is a cryoprotectant solution that includes the defined peptoid polymer for reducing or inhibiting ice crystal formation.
Stated Advantages
Reducing or inhibiting ice crystal formation.
Reducing ice-mediated diffraction background in x-ray crystallography and reducing crystal dissolving.
Cryoprotection for preserving biological samples and biological macromolecules.
Documented Applications
Cryoprotectant solutions and antifreeze applications for reducing or inhibiting ice crystal formation at subzero/cryogenic temperatures.
Preservation of tissues, organs, cells, biological samples, and biological macromolecules, including nucleic acids and proteins.
Cryoprotection for crystallized proteins in x-ray crystallography.
Cosmetics.
Deicing or ice-inhibiting products.
Frozen food products.
Organ transplantation.
Supercooling.
Slow freezing and cryogenic freezing, including liquid nitrogen.
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