content_image/930651.jpg content_image/930604.jpg
# c12) United States Patent Haynie 

# (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 

## (65) Prior Publication Data 

US 2016/0159981 Al Jun. 9, 2016 

(51) Int. Cl. 

<img src='content_image/930651.jpg'>

(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. 

## (56) References Cited 

2014/0364371 Al* 12/2014 Setton . A61K 9/0024 514/16.8 

## U.S. PATENT DOCUMENTS 

<img src='content_image/930604.jpg'>

# (IO) Patent No.: US 9,932,443 B2 

# (45) Date of Patent: Apr. 3, 2018 

WO WO 2014014613 A2 * 1/2014 C07K 14/78 

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.* 

Huang et al., "Generation of Synthetic Elastin-Mimetic Small Diameter Fibers and Fiber Networks," Macromolecules, 2000, 33:2989-2997. * 

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. 

Aliferis et al., "Living polypeptides," Biomacromolecules, 2004, pp. 1653-1656, vol. 5. 

Berger et al., "Poly-L-proline," Journal of the American Chemical Society, Nov. 5, 1954, pp. 5552-5554, vol. 76. 

Boal, D. (2012). Polymers. In Mechanics of the Cell (pp. 65-104). 

Cambridge, UK: Cambridge University Press. 

Bray, "Large-scale manufacture of peptide therapeutics by chemical synthesis," Nature Reviews: Drug Discovery, Jul. 2003, pp. 587- 593, vol. 2. 

Cuff et al., "ProtEST: protein multiple sequence alignments from expressed sequence tags," Bioinformatics, 2000, pp. 111-116, vol. 16, No. 2. 

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. 

Elvin et al., "Synthesis and properties of crosslinked recombinant pro-resilin," Nature, Oct. 13, 2005, pp. 999-1002, vol. 437. 

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. 

Gill et al., "Calculation of protein extinction coefficients from amino acid sequence data," Analytical Biochemistry, 1989, pp. 319-326, vol. 182. 

Haynie et al., "Structural energetics of the molten globule state," Proteins: Structure, Function, and Genetics, 1993, pp. 115-140, vol. 16. 

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., "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., "Polypeptide multilayer films: role of molecular structure and charge," Langmuir, 2004, pp. 4540-4547, vol. 20, No. 11. 

Haynie et al., "Biomimetic nanostructured materials: inherent reversible stabilization of polypeptide microcapsules," Langmuir, 2005, pp. 1136-1138, vol. 21, No. 3. 

Primary Examiner - Julie Ha 

(74) Attorney, Agent, or Firm - Saliwanchik, Lloyd & Eisenschenk 

## (57) ABSTRACT 

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. 

US009932443B2 

## FOREIGN PATENT DOCUMENTS 

## OTHER PUBLICATIONS 

(Continued) 

## 15 Claims, 17 Drawing Sheets 

