Compositions and methods for reducing ice crystal formation
Inventors
Assignees
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Publication Number
US-10694739-B2
Publication Date
2020-06-30
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 provides a peptoid-peptide hybrid comprising a peptoid polymer according to formula (I), including a tautomer thereof or a stereoisomer thereof. The peptoid polymer is defined by variable substituents R1, R2, and R3, by X and Y that are independently selected or alternatively taken together to form a covalent bond, and by a subscript n between 8 and 50, with at least 2 instances of R1 independently selected from optionally substituted C1-18 hydroxyalkyl groups.
The hybrid further includes one or more amino acids located at one or both ends of the peptoid polymer and/or in between any of the peptoid monomers. The peptoid polymer includes optional substitution of cycloalkyl, heterocycloalkyl, aryl, and heteroaryl groups with one or more R3 groups, and the disclosure describes multiple specific peptoid-peptide hybrid compounds and associated structural variants as chemical structures.
In the disclosed embodiments, the peptoid-peptide hybrids include helical polyproline-like structures promoted by N-aryl side chain features, including Nep. The document also connects these hybrids to ice crystal formation inhibition and anti-icing/antifreeze behavior over subzero temperature ranges, and describes cryoprotectant solution compositions containing the peptoid/peptoid-peptide hybrids.
Claims Coverage
The independent claims cover peptoid-peptide hybrids centered on a formula (I) peptoid polymer and the location of amino acids relative to the peptoid backbone. Four inventive features are recited in the consolidated claim language.
Formula-defined peptoid polymer with tautomer or stereoisomer forms
A peptoid polymer according to formula (I), including a tautomer thereof or a stereoisomer thereof, with substituents R1, R2, R3, and X and Y defined within the listed group selections.
Hydroxyalkyl frequency constraint on R1
At least 2 instances of R1 are independently selected from optionally substituted C1-18 hydroxyalkyl groups.
Constrained peptoid monomer count
The subscript n, representing the number of peptoid monomers in the peptoid polymer, is between 8 and 50.
Terminal and/or internal amino acids linked to the peptoid polymer
One or more amino acids are located at one or both ends of the peptoid polymer and/or in between any of the peptoid monomers.
Overall, the claims cover peptoid-peptide hybrids defined by a formula (I) peptoid polymer with specified substituent classes, a requirement that at least two R1 substituents are optionally substituted C1-18 hydroxyalkyl groups, a monomer count n between 8 and 50, and inclusion of one or more amino acids at terminal positions and/or between peptoid monomers.
Stated Advantages
Inhibits ice crystal formation at subzero temperatures, including cryogenic ranges.
Inhibits ice crystal formation over a subzero temperature range from about 0°C to about −120°C.
Improves vitrification and cell survival while reducing cryoprotectant concentration.
Provides cryoprotectant solution compositions with anti-icing/antifreeze behavior.
Documented Applications
Cryoprotectant/antifreeze solutions and products.
Preservation methods for tissues, organs, cells, and biological macromolecules by contacting with the compositions.
Cryopreservation by preserving a tissue, organ, or cells by contacting them with the peptoid-peptide hybrid.
Preserving organs, tissues, cells, and biological macromolecules.
Cosmetic care product use and antifreeze/deicing product use.
Frozen food product use.
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