US009932443B2  c12)  United States Patent  Haynie  (IO)  Patent No.:  US 9,932,443 B2  (45)  Date of Patent:  Apr. 3, 2018  (54)  PEPTIDE-BASED MATERIALS  (71)  Applicant:  Donald T Haynie,  Tampa, FL (US)  (72)  Inventor:  Donald T Haynie,  Tampa, FL (US)  (73)  Assignee:  University of South Florida,  Tampa,  FL (US)  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 166 days.  (21)  Appl. No.:  14/561,413  (22)  Filed:  Dec. 5, 2014  (51)  Int. Cl.  (52)  U.S. Cl.  CPC  C08G 69/14  (2013.01);  A0lN  37118  (2013.01);  C08G 69/10  (2013.01);  C08G  69/16  (2013.01);  C08J  5100  (2013.01);  C08J  5118  (2013.01);  C08J 9/00  (2013.01);  C08L  89/00  (2013.01);  C09D  177102  (2013.01);  C09D  177104  (2013.01);  D0lF  4100  (2013.01);  D0lF 6/68  (2013.01);  C08J  2377/02  (2013.01);  C08J 2389/00  (2013.01);  D0JD 5/003  (2013.01)  ( 58)  Field of Classification Search  CPC ...... C09D 177/04; C09D 177/02; C07K 5/07;  C07K 14/78; A01N 37/18; C08G 69/10;  C08G 69/14; C08G 69/16; C08J 2377/02;  C08J 2389/00; C08J 5/00; C08J 5/18;  C08J 9/00; C08L 89/00; D0lD 5/003;  D01F 4/00; D01F 6/68; C08K 5/07  USPC .................. 521/183; 524/606, 607; 525/432;  528/323, 325; 514/21.3, 1.1; 530/300,  530/324, 353  See application file for complete search history.  US 2016/0159981 Al  Jun. 9, 2016  The subject invention pertains to peptide-based materials  comprising cross-linked peptides with random amino acid  sequences that are soluble in water or ethanol before cross› linking but insoluble in water after crosslinking.  Primary Examiner  - Julie Ha  (74)  Attorney, Agent, or Firm  - Saliwanchik, Lloyd &  Eisenschenk  (Continued)  Haynie et al., "Biomimetic nanostructured materials: inherent  reversible stabilization of polypeptide microcapsules,"  Langmuir,  2005, pp. 1136-1138, vol. 21, No. 3.  Haynie et al., "Polypeptide multilayer films: role of molecular  structure and charge,"  Langmuir,  2004, pp. 4540-4547, vol. 20, No.  11.  Haynie et al., "Mechanisms of stability of fibers electrospun from  peptides with ionized side chains,"  Macromolecular Materials and  Engineering,  2013, pp. 529-540, vol. 298.  Haynie et al., "Physical properties of polypeptide electrospun  nanofiber cell culture scaffolds on a wettable substrate,"  Polymers,  2012, pp. 1535-1553, vol. 4.  Haynie et al., "Structural energetics of the molten globule state,"  Proteins: Structure, Function, and Genetics,  1993, pp. 115-140, vol.  16.  Gill et al., "Calculation of protein extinction coefficients from amino  acid sequence data,"  Analytical Biochemistry,  1989, pp. 319-326,  vol. 182.  Fasman et al., "High molecular weight Poly-L-Proline: synthesis  and physical-chemical studies,"  Biopolymers,  1963, pp. 3-14, vol. 1.  Fudge et al. "Molecular design of the a-keratin composite: insights  from a matrix-free model, hagfish slime threads,"  Proceedings of  the Royal Society of London B,  2004, pp. 291-299, vol. 271.  Elvin et al., "Synthesis and properties of crosslinked recombinant  pro-resilin,"  Nature,  Oct. 13, 2005, pp. 999-1002, vol. 437.  Deming et al., "Chain initiation efficiency in cobalt-and nickel› mediated polypeptide synthesis,"  Journal of American Chemical  Society,  2000, pp. 5710-5717, vol. 122, No. 24.  Cuff et al., "ProtEST: protein multiple sequence alignments from  expressed sequence tags,"  Bioinformatics,  2000, pp. 111-116, vol.  16, No. 2.  Bray, "Large-scale manufacture of peptide therapeutics by chemical  synthesis,"  Nature Reviews: Drug Discovery,  Jul. 2003, pp. 587- 593, vol. 2.  Cambridge, UK: Cambridge University Press.  Boal, D. (2012). Polymers. In  Mechanics of the Cell  (pp. 65-104).  Berger et al., "Poly-L-proline,"  Journal of the American Chemical  Society,  Nov. 5, 1954, pp. 5552-5554, vol. 76.  Aliferis et al., "Living polypeptides,"  Biomacromolecules,  2004, pp.  1653-1656, vol. 5.  Acharya et al., "Refined structure of baboon a-lactalbumin at 1 •7  A  resolution: comparison with C-type lysozyme,"  Journal of Molecu› lar Biology,  1989, pp. 99-127, vol. 208, No. 1.  Huang et al., "Generation of Synthetic Elastin-Mimetic Small  Diameter Fibers and Fiber Networks," Macromolecules, 2000,  33:2989-2997. *  Haynie et al., "Mechanisms of Stability of Fibers Electro spun from  Peptides with Ionized Side Chains," from Macromolecular Mate› rials and Engineering, 2013, 298, pp. 529-540.*  WO  WO 2014014613 A2 *  1/2014  C07K 14/78  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (65)  Prior Publication Data  (57)  ABSTRACT  (56)  References Cited  U.S. PATENT DOCUMENTS  2014/0364371 Al* 12/2014 Setton .  A61K 9/0024  514/16.8  C07K  14178  (2006.01)  A0lN  37118  (2006.01)  C08G 69/14  (2006.01)  C08G 69/16  (2006.01)  C08J  5100  (2006.01)  C08J 9/00  (2006.01)  C09D  177102  (2006.01)  C08J  5118  (2006.01)  C08L 89/00  (2006.01)  D0lF  4100  (2006.01)  D0lF 6/68  (2006.01)  C09D  177104  (2006.01)  C08G 69/10  (2006.01)  D0JD5/00  (2006.01)  15 Claims, 17 Drawing Sheets 