(12) United States Patent (10) Patent N0.: US 8,748,569 B2 Stupp Et A]
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USOO8748569B2 (12) United States Patent (10) Patent N0.: US 8,748,569 B2 Stupp et a]. (45) Date of Patent: Jun. 10, 2014 (54) PEPTIDE AMPHIPHILES AND METHODS TO Berendsen, A Glimpae of the Holy Grail?, Science, 1998, 282, pp. ELECTROSTATICALLY CONTROL 642-643.* BIOACTIVITY OF THE IKVAV PEPTIDE Voet et al, Biochemistry, John Wiley & Sons Inc., 1995, pp. 235 EPITOPE 241.* Ngo et al, Computational Complexity, Protein Structure Protection, (75) Inventors: Samuel I. Stupp, Chicago, IL (US); and the Levinthal Paradox, 1994, pp. 491-494.* Bradley et al., Limits of Cooperativity in a Structurally Modular Joshua E. Goldberger, Columbus, OH Protein: Response of the Notch Ankyrin Domain to Analogous (US); Eric J. Berns, Chicago, IL (US) Alanine Substitutions in Each Repeat, J. M01. BIoL (2002) 324, 373-386.* (73) Assignee: Northwestern University, Evanston, IL Tysseling et al., “Self-assembling peptide amphiphile promotes plas (Us) ticity of serotonergic ?bers following spinal cord injury,” J Neurosci Res, 2010, 88: 3161-3170. ( * ) Notice: Subject to any disclaimer, the term of this Tysseling-Mattiace et al., “Self-assembling nano?bers inhibit glial patent is extended or adjusted under 35 scar formation and promote axon elongation after spinal cord injury,” U.S.C. 154(b) by 0 days. JNeurosci, 2008, 28: 3814-3823. Wheeler et al., “Microcontact printing for precise control of nerve (21) Appl.No.: 13/442,210 cell growth in culture,” J Biomech Eng, 1999, 121: 73-78. Yamada et al., “Ile-Lys-Val-Ala-Val (IKVAV)-containing laminin (22) Filed: Apr. 9, 2012 alphal chain peptides form amyloid-like ?brils,” FEBS Lett, 2002, 530: 48-52. (65) Prior Publication Data Yeung et al., “Modulation of the growth and guidance of rat brain stem neurons using patterned extracellular matrix proteins,” US 2012/0294902 A1 Nov. 22,2012 Neurosci Lett, 2001, 301: 147-150. Yoshida et al., “Identi?cation of a heparin binding site and the bio logical activities of the laminin alphal chain carboxy-terminal globu Related US. Application Data lar domain,” JCell Physiol, 1999, 179: 18-28. Zhang et al., “Compatibility of neural stem cells With functionalized (60) Provisional application No. 61/473,593, ?led on Apr. self-assembling peptide scaffold in vitro,” Biotech Bioprocess Engi 8,2011. neering, 2010, 15: 545-551. Zou et al., “Growth of rat dorsal root ganglion neurons on a novel (51) 1111.0. self-assembling scaffold containing IKVAV sequence,” Mater Sci A61K38/02 (2006.01) Engineering: C, 2009, 29(7)o: 2099-2103. C07K2/00 (2006.01) Zustiak et al., “In?uence of cell-adhesive peptide ligands on poly A61K38/00 (2006.01) (ethylene glycol) hydrogel physical, mechanical and transport prop A61K 9/51 (2006.01) erties,” Acta Biomater, 2010, 6: 3404-3414. B82Y5/00 (2011.01) Adams et al., “Growth cones turn and migrate up an immobilized gradient of the laminin IKVAV peptide,” J Neurobiol, 2005, 62: 134 (52) U.S.Cl. 147. CPC . A61K38/00 (2013.01); C07K2/00 (2013.01); Agheli et al., “Large area protein nanopatterning for biological appli C07K 2319/735 (2013.01); A61K 9/5169 cations,” Nano Lett, 2006, 6: 1165-1171. (2013.01); B82Y5/00 (2013.01); YIOS 977/795 Agius et al., “Antibodies directed against the beta l-integrin subunit (2013.01) and peptides containing the IKVAV sequence of laminin perturb USPC .......................... .. 530/300; 530/345; 977/795 neurite outgrowth of peripheral neurons on immature spinal cord (58) Field of Classi?cation Search substrata,” Neurosci, 1996, 71:773-786. CPC A61K 38/00; A61K 9/0019; A61K 9/0024; A61K 9/5169; C07K 14/78; C07K 2319/735; (Continued) C07K 2/00; B82Y 5/00 See application ?le for complete search history. Primary Examiner * Julie Ha Assistant Examiner * Li Ni Komatsu (56) References Cited (74) Attorney, Agent, or Firm * Casimir Jones, SC. U.S. PATENT DOCUMENTS 2006/0247165 A1 11/2006 Stupp et al. (57) ABSTRACT OTHER PUBLICATIONS The present invention is directed to peptide amphiphile com pounds, compositions and methods of use, wherein nano?ber Cui et al, Spontaneous and X-rayiTriggered Crystallization at Long bundling or epitope aggregation is inhibited. In certain Range in Self-Assembling Filament Networks, Science, 2010, 327, embodiments, the peptide amphiphiles of the present inven pp. SSS-559* tion have increased solubility and reduced nano?ber bun Cui et al, Spontaneous and X-rayiTriggered Crystallization at Long Range in Self-Assembling Filament Networks, Science, 2010, 327, dling. The molecules may be used in pharmaceutical appli supporting materials, pp. 1-47.* cations, for example for in vivo administration to human Angeloni et al, Regeneration of the cavernous nerve by Sonic hedge patients, by increasing biological activity of the compositions hog using aligned peptide amphiphile nano?bers, Biomaterials, toward neurite outgrowth and nerve regeneration. 2011, 32, pp. 1091-1101.* Rudinger, Peptide Hormones, JA Parsons, Ed., 1976, pp. 1-7.* SIGMA, 2004, pp. 1-2.* 5 Claims, 17 Drawing Sheets US 8,748,569 B2 Page 2 (56) References Cited Nakamura et al., “Construction of a multi-functional extracellular matrix protein that increases number of N1E-115 neuroblast cells OTHER PUBLICATIONS having neurites,” J Biomed Mater Res B Appl Biomater, 2009, 91:425-432. 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