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(12) United States Patent (10) Patent No.: US 6,616,858 B2 Fahy Et Al

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(12) United States Patent (10) Patent No.: US 6,616,858 B2 Fahy Et Al USOO6616858B2 (12) United States Patent (10) Patent No.: US 6,616,858 B2 Fahy et al. (45) Date of Patent: Sep. 9, 2003 (54) PREVENTION OF ICE NUCLEATION BY 4,565,643 A 1/1986 Arai et al. .................... 252/70 POLYGLYCEROL 5,104,415 A * 4/1992 5,710,350 A * 1/1998 Jeromin et al. ............. 568/868 (76) Inventors: Greg Fahy, 880 Via Blairo, Corona, 5,904,944 A 5/1999 Battermann et al. ........ 426/281 CA (US) 92879; Brian Wowk, 848 5,952,168 A 9/1999 Wowk et al. ................ 435/1.3 Montague Dr., Corona, CA (US) 92879 FOREIGN PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this DE 212768O * 4/1971 patent is extended or adjusted under 35 EP O 291 O73 11/1988 U.S.C. 154(b) by 0 days. WO WO 97/16062 5/1997 OTHER PUBLICATIONS (21) Appl. No.: 09/726,857 Database WPI, XP-002172967 (abstract of Japanese Patent (22) Filed: Nov.30, 2000 Specification 58-91775 (5/83). (65) Prior Publication Data * cited by examiner US 2002/0063235 A1 May 30, 2002 Primary Examiner Anthony J. Green (74) Attorney, Agent, or Firm-Foley & Lardner Related U.S. Application Data (60) Provisional application No. 60/167.963, filed on Nov.30, (57) ABSTRACT 1999. Linear polymers of glycerol can prevent or delay ice nucle (51) Int. Cl." ............................ C09K3/18: A01N 1/00; ation in a variety of contexts. Polyglycerol can also be AO1N 1/02 employed in combination with other ice control agents, Such (52) U.S. Cl. ................................. 252/70, 47/2; 106/13; as polyvinyl alcohol/polyvinyl acetate copolymers and anti 252/71; 252/73; 252/77; 435/11; 435/13; freeze proteins, to provide antinucleation effects that are 435/260 Superior to those of either polyglycerol or the (58) Field of Search .............................. 252/70, 71, 73 co-antinucleator alone. Polyglycerol has a number of advan 252/77; 106/13: 47/2; 435/11 1.3 260 tageous physical and toxicological properties, Such as s s s s u-8-1s extreme water Solubility, non-toxicity to human beings, (56) References Cited non-toxicity to animal tissues and organs in vitro even at extreme concentrations, minimal foaming tendency, mini U.S. PATENT DOCUMENTS mal retention on hydrophobic Surfaces, and Stability in Solution without the need for periodic heating to reactivate 2,373,727 A * 4/1945 West et al. ................... 106/13 3,968,169 A * 7/1976 Seiden et al. ........ ... 549/347 its antinucleation properties. 4,077.895 A 3/1978 Langdon et al. .............. 252/76 4,388,203 A 6/1983 Nimerick et al. ............. 252/70 29 Claims, 12 Drawing Sheets U.S. Patent Sep. 9, 2003 Sheet 1 of 12 US 6,616,858 B2 Reduction Of the CPA ConCentration Needed for Stable Supercooling using Decaglycerol (dG) and dG + X1 OOO glucose O.5% X1000 + O.5% dG - A - RPS-2 + 1% dG -C- RPS-T + O.5% X1 OOO + O.5% dG -A- RPS-T + 1% dG O 20 22 24 26 28 30 32 34 Concentration of Veg Solutes (% w/v) FIG. 1 U.S. Patent Sep. 9, 2003 Sheet 2 of 12 US 6,616,858 B2 Enhanced Supercooling by Polyglycerol (22 ml samples cooling from O'C) 120 Soln T H20 1% w/v. Dextrose H2O -7.35 --- 100 deX -7.6O >0.5 dG -9.26 0.004 dG VS. dex: 0.018 tG -9.1 O O.OO2 tG VS. dex: 0.012 X1k -7.18 nS 60 40 -8 -9 -10 -11 - 12 - 13 Temperature (C) FIG. 2 U.S. Patent Sep. 9, 2003 Sheet 3 of 12 US 6,616,858 B2 Enhanced Supercooling by Polyglycerol (22 ml samples cooling from O'C) 120 Soln n p H2O 3.32 -- 100 - dex 4.18 0.13 dG 5.88 0.007 dG VS. dex: 0.09 tG 5.22 O.OO5 8O tG vs. dex: 0.17 OO 60 40 20 O 1 2 3 4 5 6 7 8 9 1 0 1 1 12 Time Below 0°C (Hr) FIG. 3 U.S. Patent Sep. 9, 2003 Sheet 4 of 12 US 6,616,858 B2 2 1 1%tG+1% 1%dG glucose O H +1% - 1 glucose 1% X1000 10% DMSO O- -2 1. DMSO+ Q- -3 5% decaglycerol CD (no freezing peak) S- -4 -5 O E -6 CD H -7 CD 2 -8 d5 -9 - 10 -11 -12 -13 180 240 300 360 420 480 540 600 Time Below 0°C (Minutes) FIG. 4 U.S. Patent Sep. 9, 2003 Sheet 5 of 12 US 6,616,858 B2 Enhanced Supercooling of Automobile Antifreeze by Tetraglycerol (22 ml samples cooling from O'C) 100 80 C C) S.S 60 c) CD o 40 S 5 20 SS -O- H0 O -C- 1% Tetraglycerol -O- 5% PrestOne -A- 5% PrestOne + -20 0.2% Tetraglycerol -3 -4 -5 -6 -7 -8 -9 - 10 - 11 - 12-13 - 14-15 Temperature (C) FIG. 5 U.S. Patent Sep. 9, 2003 Sheet 6 of 12 US 6,616,858 B2 22 ml samples immersed in cold bath 100 80 c) N O i 60 CD O E 3 40 -O- %H2O as 1% dG S 1%X1000 O 20 56-5600xtrS 5%. Prestone 15% PreStone 5%PreSt.2tG O 60 120 180 240 300 360 420 480 540 600 Time to Nucleate (min) FIG. 6 U.S. Patent Sep. 9, 2003 Sheet 7 of 12 US 6,616,858 B2 Nucleation. After Direct immersion in a 60% w/v Ethylene Glycol Bath at ~-15°C 1 OO SOIn T H0 -8.53 - 10CG -110 0.012 PEG -9.6O 0.16 80 60 40 20 is -O-H-0 H 10% dG -C)- 10% PEG O KHK-K-K 1 OOO -4 -5 -6 - 7 -8 -9 - 10 - 11 - 12 - 13 - 14 Temperature (C) FIG. 7 U.S. Patent Sep. 9, 2003 Sheet 8 of 12 US 6,616,858 B2 Glucose Decaglycerol PEG-1000 Hexaglycerol SuCrOSe O 1 2 3 4 5 Days of Storage at ~ O'C FIG. 8 U.S. Patent Sep. 9, 2003 Sheet 9 of 12 US 6,616,858 B2 4 3 2 1 O O 2 4 6 8 10 12 14 16 Postoperative Day FIG. 9 U.S. Patent Sep. 9, 2003 Sheet 10 of 12 US 6,616,858 B2 OOO1% PGL O.01% PGL - 1000 0.1% PGL O 19 PGL SP 100 10 -16 -14 - 12 - 10 -8 -6 -4 Temperature (C) FIG 10 U.S. Patent Sep. 9, 2003 Sheet 11 of 12 US 6,616,858 B2 0.1% PVA 0.19, PGL 1000 NO Ya St.2N 1 OO -24 -22 -20 - 18 -16 -14 -12 Temperature (C) FIG 11 U.S. Patent Sep. 9, 2003 Sheet 12 of 12 US 6,616,858 B2 wia wia wia wia soic white party mostly perfectly wit is cloudy citear tear (vitrified FG, 12 US 6,616,858 B2 1 2 PREVENTION OF ICE NUCLEATION BY freeze proteins thus act as non-colligative antifreeze agents, POLYGLYCEROL and very Small concentrations (less than 1%) are able to SuppreSS the temperature at which ice forms, in Some cases RELATED APPLICATIONS by Several degrees. Soon after the original discovery of antifreeze proteins, it was Speculated that “many polymeric This application is related to U.S. provisional patent molecules (not just proteins) ought to be able to inhibit application No. 60/167.963, filed Nov.30, 1999, from which nucleation (of ice) in this way” (Klotz, I. M. in “The Frozen priority is claimed. Cell” pp. 5–26. J. & A. Churchill, London, 1970). These Speculations opened the door to the possibility that inexpen FIELD OF THE INVENTION Sive Synthetic compounds might be found with non This invention relates to methods of inhibiting ice forma colligative antifreeze activity. tion using polyglycerol and related molecules. In 1983, Caple et al (“Polymeric Inhibition of Ice Nuclei Active Sites” Cryo-Letters 4, pp. 51–58, 1983 and U.S. Pat. BACKGROUND OF THE INVENTION No. 4,484.409) reported significant enhancement of water Preventing the freezing of water, and Solutions that con 15 Supercooling tendency by adding Small quantities of methyl tain water, is a problem of Substantial environmental, acrylate-co-Vinyl pyrrollidone polymer or methyl agricultural, industrial, and biomedical interest. Ice on methacrylate-co-Vinyl pyrrollidone polymer. While showing walkways, roads and aircraft wings constitutes an environ proof of concept, these observations were limited in a mental hazard to transportation. Ice formation on and inside number of important respects. First, these copolymers were plants causes expensive damage to crops and gardens. not tested for toxicity and may be toxic. Second, release of Freezing of antifreeze Solutions, pipeline contents, paints, these polymers into the environment, or their inclusion in wet concrete and other aqueous Solutions Subjected to cold foods, may not be permissible. Third, the polymerS required temperatures are issueS of concern for industry. Avoiding ice substantial hydrophobicity for effectiveness, which limits formation during cold Storage of proteins, viruses, cells, their utility in water Solutions. Fourth, the nature of these 25 polymers and of the methods for their Synthesis may make tissues, and organs is an important problem in cryobiology. them too expensive for practical use. Finally, their perfor Below a critical temperature (the equilibrium freezing mance was not fully characterized, and may be limited in a point), the crystallization of water into ice becomes thermo variety of ways. In any case, no commercial use of Caple's dynamically favored. The equilibrium freezing point of polymerS has appeared in the 16 years Since their water can be lowered by adding Solutes that lower the vapor publication, implying unreported deficiencies of these poly preSSure of water Such that it becomes equivalent to the merS for practical ice antinucleation applications.
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