Granted Patent
B2
US 12,370,255 · App. 16/500,762 · Granted Jul 29, 2025
Peptide-based vaccines, methods of manufacturing, and uses thereof for inducing an immune response
Assignees:
BARINTHUS BIOTHERAPEUTICS NORTH AMERICA, INC.; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, OFFICE OF TECHNOLOGY TRANSFER—NATIONAL INSTITUTES OF HEALTH
A61K39/385A61K31/33A61K31/395A61K31/40A61K31/435A61K38/02A61K38/03A61K39/0011A61K39/12A61K39/39C07K4/00C07K17/00C07K17/06C07K17/08A61K38/10A61K38/26A61K2039/55555A61K2039/57A61K2039/6093A61K2039/627A61K2039/64A61K2039/70C07K2318/00
View Patent ↗
Loading inventors, assignments & file history…
Abstract
The present disclosure relates to novel peptide-based vaccines, methods of manufacturing the novel peptide-based vaccines and uses thereof for delivering peptide antigens to induce an immune response, and in particular a T cell response to a subject.
Claims (1)
1. A peptide antigen conjugate comprising a hydrophobic molecule represented by Formula (1):
Assignments (5)
CHANGE OF NAME
Recorded Feb 9, 2024
From: VACCITECH NORTH AMERICA, INC.
To: BARINTHUS BIOTHERAPEUTICS NORTH AMERICA, INC.
Reel/Frame 066550/0917 →
CHANGE OF NAME
Recorded Apr 15, 2022
From: VA MERGER SUB 2 INC.
To: VACCITECH NORTH AMERICA, INC.
Reel/Frame 059615/0026 →
MERGER
Recorded Mar 25, 2022
From: AVIDEA TECHNOLOGIES, INC.
To: VA MERGER SUB 2 INC.
Reel/Frame 059405/0680 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Oct 4, 2019
From: LYNN, GEOFFREY MARTIN
To: AVIDEA TECHNOLOGIES, INC.
Reel/Frame 050623/0140 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Oct 4, 2019
From: ISHIZUKA, ANDREW SCOTT
To: THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES
Reel/Frame 050623/0154 →
Continuity (3)
Provisional Application
62617519
· Jan 15, 2018
Provisional Application
62481432
· Apr 4, 2017
References Cited (244)
US 5312620A
· Ribi
· 1994
[cited by applicant]
US 6573245B1
· Marciani
· 2003
[cited by applicant]
US 6747137B1
· Weinstock
· 2004
[cited by examiner]
US 6858396B2
· Dix
· 2005
[cited by examiner]
US 9115402B2
· Hacohen et al.
· 2015
[cited by applicant]
US 9120841B2
· Hauser et al.
· 2015
[cited by applicant]
US 9682934B2
· Stafford et al.
· 2017
[cited by applicant]
US 9962453B2
· Georges
· 2018
[cited by applicant]
US 20040057958A1
· Waggoner et al.
· 2004
[cited by applicant]
US 20080139481A1
· Dix
· 2008
[cited by examiner]
US 20080160089A1
· Vitiello et al.
· 2008
[cited by applicant]
US 20100028381A1
· Gorski et al.
· 2010
[cited by applicant]
US 20120114699A1
· Mistrello
· 2012
[cited by examiner]
US 20120141409A1
· Seymour et al.
· 2012
[cited by applicant]
US 20130330367A1
· Song et al.
· 2013
[cited by applicant]
US 20170112923A1
· Seymour et al.
· 2017
[cited by applicant]
US 20170304420A1
· Fisher et al.
· 2017
[cited by applicant]
US 20210000934A1
· Fisher et al.
· 2021
[cited by applicant]
US 20210113705A1
· Lynn
· 2021
[cited by examiner]
US 20210393523A1
· Lynn et al.
· 2021
[cited by applicant]
US 20230381112A1
· Lynn et al.
· 2023
[cited by applicant]
US 20240269269A1
· Lynn et al.
· 2024
[cited by applicant]
US 20240382614A1
· Lynn et al.
· 2024
[cited by applicant]
CA 2627903A1
· 2009
[cited by applicant]
EP 0324455A2
· 1989
[cited by applicant]
JP H10509038A
· 1998
[cited by applicant]
JP 2001294636A
· 2001
[cited by applicant]
JP 2002526436A
· 2002
[cited by applicant]
JP 2005532405A
· 2005
[cited by applicant]
JP 2006523185A
· 2006
[cited by applicant]
JP 2013544074A
· 2013
[cited by applicant]
JP 2014139139A
· 2014
[cited by applicant]
JP 2015500229A
· 2015
[cited by applicant]
KR 20090002946A
· 2009
[cited by applicant]
WO 9322338A1
· 1993
[cited by applicant]
WO 9615249A1
· 1996
[cited by applicant]
WO 1998001558A2
· 1998
[cited by applicant]
WO 1998019710A2
· 1998
[cited by applicant]
WO 0016746A2
· 2000
[cited by applicant]
WO 2000074722A2
· 2000
[cited by applicant]
WO 0118035A2
· 2001
[cited by applicant]
WO 0152614A2
· 2001
[cited by applicant]
WO 02070006A2
· 2002
[cited by applicant]
WO 02094994A2
· 2002
[cited by applicant]
WO 03075956A2
· 2003
[cited by applicant]
WO 2004007525A3
· 2004
[cited by applicant]
WO 2005007789A2
· 2005
[cited by applicant]
WO 2005099752A2
· 2005
[cited by applicant]
WO 2006083874A2
· 2006
[cited by applicant]
WO 2006084319A1
· 2006
[cited by applicant]
WO 2007075502A2
· 2007
[cited by applicant]
WO 2004071457A3
· 2007
[cited by applicant]
WO 2007149802A2
· 2007
[cited by applicant]
WO 2009043165A1
· 2009
[cited by applicant]
WO 2009051837A2
· 2009
[cited by applicant]
WO 2009104001A2
· 2009
[cited by applicant]
WO 2010067041A1
· 2010
[cited by applicant]
WO 2010128303A1
· 2010
[cited by applicant]
WO WO2011101332A1
· 2011
[cited by examiner]
WO 2011150240A1
· 2011
[cited by applicant]
WO 2012049317A3
· 2012
[cited by applicant]
WO 2012090002A1
· 2012
[cited by applicant]
WO 2012139094A3
· 2012
[cited by applicant]
WO 2013006050A9
· 2013
[cited by applicant]
WO 2013019669A2
· 2013
[cited by applicant]
WO 2013080187A1
· 2013
[cited by applicant]
WO 2013051936A9
· 2013
[cited by applicant]
WO 2013151771A1
· 2013
[cited by applicant]
WO 2013154774A1
· 2013
[cited by applicant]
WO 2014142653A1
· 2014
[cited by applicant]
WO 2015033140A1
· 2015
[cited by applicant]
WO 2015082905A1
· 2015
[cited by applicant]
WO 2015085233A1
· 2015
[cited by applicant]
WO 2016055812A1
· 2016
[cited by applicant]
WO 2016146143A1
· 2016
[cited by applicant]
WO 2016146260A1
· 2016
[cited by applicant]
WO 2017044803A1
· 2017
[cited by applicant]
WO 2017083963A1
· 2017
[cited by applicant]
WO 2017147597A1
· 2017
[cited by applicant]
WO 2017157964A1
· 2017
[cited by applicant]
WO 2017173321A1
· 2017
[cited by applicant]
WO 2018055060A1
· 2018
[cited by applicant]
WO 2018148671A1
· 2018
[cited by applicant]
WO 2018187356A2
· 2018
[cited by applicant]
WO 2018187515A1
· 2018
[cited by applicant]
WO 2019126186A1
· 2019
[cited by applicant]
WO 2019126371A1
· 2019
[cited by applicant]
WO 2019195626A1
· 2019
[cited by applicant]
WO 2019204663A1
· 2019
[cited by applicant]
WO 2019094642A1
· 2019
[cited by applicant]
WO 2019241306A2
· 2019
[cited by applicant]
WO 2019246315A1
· 2019
[cited by applicant]
WO WO2020190762A1
· 2020
[cited by examiner]
WO 2020191305A3
· 2020
[cited by applicant]
WO 2021156404A3
· 2021
[cited by applicant]
The Biology Project, “Tyrosine”, Department of Biochemistry and Molecular Biophysics, University of Arizona, available online at http://www.biology.arizona.edu/biochemistry/problem_sets/aa/tyrosine.html, 2 pages (2003) …
[cited by examiner]
“Amino acids molecular weights,” available online at: http://fortiusbio.com/Aa_MW.html, 2 pages (accessed on Dec. 22, 2021) (Year: 2021).
[cited by examiner]
U.S. Appl. No. 17/638,576, filed Feb. 2022, Stoidl et al.
[cited by examiner]
U.S. Appl. No. 17/517,597, filed Nov. 2021, Seder; Robert.
[cited by examiner]
Yadav et al., Nature 515:572-578 (2014) (Year: 2014).
[cited by examiner]
Brito et al., J. Controlled Rel. 190:563-579 (2014) (Year: 2014).
[cited by examiner]
Perrie et al., Intl. J. Pharmaceutics 364:272-280 (2008) (Year: 2008).
[cited by examiner]
“Amino Acid Structures, Codes, and Reference Information,” available online at www.promega.com/resources/tools/amino-acid-chart-amino-acid-structure/, 14 pages (accessed on Apr. 21, 2022) (Year: 2022).
[cited by examiner]
“Tyrosine”, available online at www.russelllab.org/aas/Tyr.html#:˜: text=Substitutions%3A%20As%20Tyrosine%20is%20an,position%20on%20the%20benzene%20ring, 2 pages (accessed on Apr. 21, 2022) (Year: 2022).
[cited by examiner]
Mitsui et al., J. Investigative Dermatol. 126:1804-1812 (2006) (Year: 2006).
[cited by examiner]
Carr et al., Ind. Eng. Chem. Res. 49:11991-11995 (2010) (Year: 2010).
[cited by examiner]
“How to Enhance the Solubility of L-Tyrosine in Cell Culture Media Applications,” Evonik, available online at https://healthcare.evonik.com/en/biopharma/cell-culture/common-challenges/performance-improvement, 2 pages (a…
[cited by examiner]
Klein et al., Prot. Eng. Des. Selection 27:325-330 (2014) (Year: 2014).
[cited by examiner]
“Chemistry of Crosslinking,” Thermo Fisher Scientific, available online at www.thermofisher.com/us/en/home/life-science/protein-biology/protein-biology-learning-center/protein-biology-resource-library/pierce-protein-met…
[cited by examiner]
Ji et al., Ind. Eng. Chem. Res. 47:6275-6279 (2008) (Year: 2008).
[cited by examiner]
“Peptide Mimetics” Biosyn, available online at www.biosyn.com/tew/peptide-mimetics.aspx, 7 pages (2012) (Year: 2012).
[cited by examiner]
Wagner et al., New Naturally Occurring Amino Acids, Anew. Chem. Int. Ed. Engl. 22:816-828 (1983) (Year: 1983).
[cited by examiner]
Chruszcz et al., Serum albumins-unusual allergens. Biochim Biophys Acta. Dec. 2013;1830(12):5375-81. doi: 10.1016/j.bbagen.2013.06.016. Epub Jun. 26, 2013. PMID: 23811341; PMCID: PMC4419372 (Year: 2013).
[cited by examiner]
Alexander et al., A Simple Method for Improving Protein Solubility and Long-Term Stability, Journal of the American Chemical Society 2004 126 (29), 8933-8939 DOI: 10.1021/ja049297h (Year: 2004).
[cited by examiner]
Dehsorkhi et al., Self-assembling amphiphilic peptides. J Pept Sci. Jul. 2014;20(7):453-67. doi: 10.1002/psc.2633. Epub Apr. 13, 2014. PMID: 24729276; PMCID: PMC4237179 (Year: 2014).
[cited by examiner]
National Center for Biotechnology Information. “PubChem Compound Summary for CID 12391, Pentadecane” PubChem, https://pubchem.ncbi.nlm.nih.gov/compound/Pentadecane. Accessed Oct. 12, 2023 (Year: 2023).
[cited by examiner]
NCBI Protein database, NCBI Reference Sequence: WP_047111413.1, DNA methyltransferase [Brachyspira hyodysenteriae], earliest reference of 1986, attached as 2 pages, also available at https://www.ncbi.nlm.nih.gov/. Acces…
[cited by examiner]
Zang et al., Tunable diblock copolypeptide hydrogel depots for local delivery of hydrophobic molecules in healthy and injured central nervous system, Biomaterials 35 (2014) 1989e2000 (Year: 2014).
[cited by examiner]
Pina et al., Tryptophan tags and de novo designed complementary affinity ligands for the expression and purification of recombinant proteins, Journal of Chromatography A, 1472 (2016) 55-65 (Year: 2016).
[cited by examiner]
Fexby et al., Hydrophobic peptide tags as tools in bioseparation, TRENDS in Biotechnology vol. 22 No. Oct. 10, 2004 (Year: 2004).
[cited by examiner]
Guo et al., Cell-penetrating peptides: Possible transduction mechanisms and therapeutic applications (Review), Biomedical Reports 4: 528-534, 2016 (Year: 2016).
[cited by examiner]
Collins et al., Self-assembly of peptides into spherical nanoparticles for delivery of hydrophilic moieties to the cytosol. ACS Nano. May 25, 2010;4(5):2856-64. doi: 10.1021/nn901414q. PMID: 20408581 (Year: 2010).
[cited by examiner]
International Search Report and Written Opinion dated Sep. 24, 2018 and received in PCT/US2018/026145.
[cited by applicant]
Wilson et al., “pH-Responsive Nanoparticle Vaccines for Dual-Delivery of Antigens and Immunostimulatory Oligonucleotides”, ACS Nano, vol. 7, No. 5, pp. 3912-3925, (2013).
[cited by applicant]
International Preliminary Report of Patentability mailed Oct. 17, 2019 and received in PCT/US2018/026145.
[cited by applicant]
Fujita et al., “6-(4-Amino-2-butyl-imidazoquinolyl)-norleucine: Toll-like receptor 7 and 8 agonist amino add for self-adjuvanting peptide vaccine,” Amino Acids (20(6) 48; 1319-1329, 2016.
[cited by applicant]
Gerster, J. et al., “Synthesis and Structure-Activity-Relationships of 1H-Imidazo[4,5-c]Quinolines that Induce Interferon Production”, Journal of Medicinal Chemistry, vol. 48, No. 10, pp. 3481-3491, (2005).
[cited by applicant]
Ghendon Y. et al., “Chitosan as an Adjuvant for Parenterally Administered Inactivated Influenza Vaccines”, Arch Virol, vol. 153, pp. 831-837, (2008).
[cited by applicant]
Grela, F. et al., “The TLR7 Agonist R848 Alleviates Allergic Inflammation by Targeting Invariant NKT Cells To Produce IFN-y”, The Journal of Immunology, vol. 186, No. 1, pp. 284-290, (2010).
[cited by applicant]
Harris et al., “Rapid and general profiling of protease specificity by using combinatorial fluorogenic substrate libraries,” PNAS, Jul. 5, 2000, vol. 97, No. 14, pp. 7754-7759.
[cited by applicant]
Harris et al., “Substrate specificity of the human proteasome,” Chemistry & Biology 8 (2001) 1131-1141.
[cited by applicant]
Heuking, S. et al., “Stimulation of Human Macrophages (THP-1) Using Toll-like Receptor-2 (TLR-2) Agonist Decorated Nanocarriers”, Journal of Drug Targeting, vol. 17, No. 8, pp. 662-670, (2009).
[cited by applicant]
Heuking, S. et al., “Toll-Like Receptor-2 Agonist Functionalized Biopolymer for Mucosal Vaccination,” International Journal of Pharmaceutics, vol. 381, pp. 97-105, (2009).
[cited by applicant]
Huber et al., “Immuno- and Constitutive Proteasome Crystal Structures Reveal Differences in Substrate and Inhibitor Specificity,” Cell 148, 727-738, Feb. 17, 2012.
[cited by applicant]
Seder et al., U.S. Appl. No. 16/079,972, filed Aug. 24, 2018.
[cited by applicant]
International Preliminary Examination Report dated Sep. 13, 2011 received in PCT/GB2010/000915.
[cited by applicant]
International Preliminary Report of Patentability and Written Opinion mailed Dec. 3, 2020 and received in PCT/US19/33612.
[cited by applicant]
Pola et al., “Click chemistry as a powerful and chemoselective tool for the attachment of targeting ligands to polymer drug carriers,” Polym. Chem., 2014, 5, 1340-1350.
[cited by applicant]
International Search Report and Written Opinion dated Aug. 30, 2019 and received in PCT/US2019/033612.
[cited by applicant]
International Search Report dated Aug. 19, 2010 received in PCT/GB2010/000915.
[cited by applicant]
Raissi, A. et al., “Enhanced Potency of the Metalloprotease Inhibitor TAPI-2 by Multivalent Display”, Bioorganic & Medicinal Chemistry Letters, vol. 24, No. 8, pp. 2002-2007, (2014).
[cited by applicant]
International Search Report, and Written Opinion dated Dec. 5, 2019 and received in PCT/US2019/033612.
[cited by applicant]
Iuurovskii, T., et al., “Artificial Peptide and Carbohydrate Antigens. Immobilization of Haptens and Adjuvant (MDP) on Polyacrylamide”, Bioorganicheskaia Khimiia., vol. 12, No. 1, pp. 100-105, (1986).
[cited by applicant]
Rihova, B., et al., “HPMA-Based Biodegradable Hydrogels Containing Different Forms of Doxorubicin -Antitumor Effects and Biocompatibility”, Ann. New York Academy Sciences, vol. 831, pp. 57-71, (1997).
[cited by applicant]
Jackson, D. et al., “A Totally Synthetic Vaccine of Generic Structure That Targets Toll-Like Receptor 2 on Dendritic Cells and Promotes Antibody or Cytotoxic T Cell Responses”, Proc. Natl. Acad. Sci. USA, vol. 101, No. …
[cited by applicant]
Joshi, N. et al., “Inflammation Directs Memory Precursor and Short-Lived Effector CD8+ T Cell Fates via the Graded Expression of T-bet Transcription Factor”, Immunity, vol. 27, pp. 281-295, (2007).
[cited by applicant]
Moynihan et al., “Eradication of large established tumors in mice by combination immunotherapy that engages innate and adaptive immune responses,” Nature Medicine, vol. 22, No. 12, Dec. 2016, pp. 1402-1410.
[cited by applicant]
Kleine, B. et al., “Lipopeptide-Polyoxyethylene Conjugates as Mitogens and Adjuvants”, Immunobiol., vol. 190, pp. 53-66, (1994).
[cited by applicant]
Levina, A. et al., “Synthesis of Polyamine-Containing Oligonucleotides”, Russian Journal of Bioorganic Chemistry, vol. 34, No. 1, pp. 80-86, (2008).
[cited by applicant]
Liras et al., “Thermo-Responsive Allyl-Functionalized 2-(2-Methoxyethoxy)ethyl Methacrylate-Based Polymers as Versatile Precursors for Smart Polymer Conjugates and Conetworks”, Macromolecules, vol. 44, pp. 3739-3745, (2…
[cited by applicant]
Lynn, G. et al., “In Vivo Characterization of the Physicochemical Properties of Polymer-Linked TLR Agonists that Enhance Vaccine Immunogenicity”, Nature Biotechnology, vol. 33, No. 11, pp. 1201-1213, (2015).
[cited by applicant]
Liu et al., “Structure-based programming of lymph-node targeting in molecular vaccines,” Nature, vol. 507; Mar. 27, 2014; pp. 519-522 and extended figures, 11 pages.
[cited by applicant]
Maurer, T. et al., “CpG-DNA Aided Cross-Presentation of Soluble Antigens By Dendritic Cells.” Eur. J. Immunol., vol. 32, pp. 2356-2364, (2002).
[cited by applicant]
Morelli et al., “Self-Assembled or Mixed Peptide Amphiphile Micelles from Herpes Simplex Virus Glycoproteins as Potential Immunomodulatory Treatment”, International Journal of Nanomedicine, pp. 2137-2148, (2014).
[cited by applicant]
Morgan, S. et al., “Evaluation of N -(2-Hydroxypropyl)Methacrylamide Copolymer-Peptide Conjugates as Potential Oral Vaccines. Studies on their Degradation by Isolated Rat Small Intestinal Peptidases and their Uptake by …
[cited by applicant]
Moyle et al., “Self-Adjuvanting Lipopeptide Vaccines,” Current Medicinal Chemistry, vol. 15, No. 5, pp. 506-516, 2008).
[cited by applicant]
“Acrylamide”, Wikipedia, the Free Encyclopedia, https://en.wikipedia.org/wiki/Acrylamide[Jun. 4, 2016 12:28:13]. (2016).
[cited by applicant]
“Adjuvant Therapy”, Wikipedia, the Free Encyclopedia, http://en.wikipedia.org/wiki/Adjuvant_therapy[May 28, 2012; 10:22:52]. (2012).
[cited by applicant]
“CD40—Tumor Necrosis Factor Receptor Superfamily Member 5 Precursor . . . ”, UniProtKB—P25942 (TNR5_HUMAN) UniProt P25942—TNR5_HUMAN, http://www.uniprot.org/uniprot/P25942. (1992).
[cited by applicant]
“CD40 (Protein)”, Wikipedia, the Free Encyclopedia, https://en.wikipedia.org/w/index.php?title=CD40_(protein)&oldid=7 42991040, (2016).
[cited by applicant]
“ChitoClear—A Natural and Functional Ingredient for Personal Care Products/ LipoSan—The Natural Way of Weight Loss”, Primex—Products: ChitoClear the Purest Chitosan & LipoSan Ultra, http://www.primex.is/Products/, (2013…
[cited by applicant]
“Chitosan”, Wikipedia, the Free Encyclopedia, http://en.wikipedia.org/wiki/Chitosan[Aug. 29, 2014 14:50:23], (2014).
[cited by applicant]
“CSF2—Granulocyte-Macrophage Colony-Stimulating Factor Precursor—. . . ”, UniProtKB—P04141 (CSF2_HUMAN) UniProt P04141—CSF2_HUMAN, http://www.uniprot.org/uniprot/P04141, (1986).
[cited by applicant]
“Guidelines on Adjuvants in Vaccines for Human Use”, EMEA Adjuvants Guidance, The European Medicines Agency Evaluation of Medicines for Human Use, (2005).
[cited by applicant]
“Methacrylamide”, Wikipedia, the Free Encyclopedia, https://en.wikipedia.org/wiki/Methacrylamide[Jun. 4, 2016; 11:54:24], (2016).
[cited by applicant]
“Particulate Contamination—Risk Prevention in Infusion Therapy”, B. Braun Melsungen AG, No. 6069091, Edition: 03, 2011 ).
[cited by applicant]
“Polyacrylamide” Wikipedia, the Free Encyclopedia, https://en.wikipedia.org/wiki/Polyacrylamide[Jun. 4, 2016 11:51:51], (2016).
[cited by applicant]
'TNFSF4 - Tumor Necrosis Factor Ligand Superfamily Member 4—Homo . . . , UniProtKB—P23510 (TNFL4_HUMAN) UniProt P23510—TNFL4_HUMAN, http://www.uniprot.org/uniprot/P23510, (1991).
[cited by applicant]
“Toll-Like Receptor”, Wikipedia, the Free Encyclopedia, http://en.wikipedia.org/wiki/Toll-like_receptor[May 28, 2012; 13:57:51]. (2012).
[cited by applicant]
Arnon, R. et al., “Antiviral Response Elicited by a Completely Synthetic Antigen with Built-in Adjuvanticity”, Proc. National Acad. Sci. USA, vol. 77, No. 11, pp. 6769-6772, (1980).
[cited by applicant]
Audibert, F., et al., “Successful Immunization with a Totally Synthetic Diphtheria Vaccine”, Proc. Natl. Acad. Sci., vol. 79, pp. 5042-5046, (1982).
[cited by applicant]
Bachmann et al., “Vaccine Delivery: a Matter of Size, Geometry, Kinetics and Molecular Patterns”, Nature Reviews Immunology, vol. 10, No. 11, pp. 787-796, (2010).
[cited by applicant]
Barrios et al., “TriVax-HPV: an improved peptide-based therapeutic vaccination strategy against human papillomavirus-induced cancers,” Cancer Immunol Immunother (2012) 61:1307-1317.
[cited by applicant]
Basalp, A. et al., “Immune Response to 17[Beta]-Estradiol Involved in Polymer Gels: Antigen Specificity and Affinity of Hybridoma Clones,” Hybridoma, vol. 19, No. 6, pp. 495-499, (2000).
[cited by applicant]
Belnoue et al., “Enhancing Antitumor Immune Responses by Optimized Combinations of Cell-penetrating Peptide-based Vaccines and Adjuvants,” Molecular Therapy vol. 24 No. 9, 1675-1685, 2016.
[cited by applicant]
Belnoue et al., “Targeting self-and neoepitopes with a modular self-adjuvanting cancer vaccine,” JCI Insight. 2019;4 (11), pp. 1-17.
[cited by applicant]
Black et al., “Self-Assembled Peptide Amphiphile Micelles Containing a Cytotoxic T-Cell Epitope Promote a Protective Immune Response In Vivo”, Advanced Materials, vol. 24, No. 28, p. 3848, (2012).
[cited by applicant]
Bogyo et al., “Substrate binding and sequence preference of the proteasome revealed by active-site-directed affinity probes,” Chemistry & Biology Jun. 1998, 5:307-320.
[cited by applicant]
Brito et al., “Designing and Building the Next Generation of Improved Vaccine Adjuvants”, Journal of Controlled Release, vol. 190, pp. 563-579, (2014).
[cited by applicant]
Choe et al., “Substrate Profiling of Cysteine Proteases Using a Combinatorial Peptide Library Identifies Functionally Unique Specificities,” The Journal of Biological Chemistry vol. 281, No. 18, pp. 12824-12832, May 5, …
[cited by applicant]
Chan et al., “Synthesis and Immunological Characterization of Toll-Like Receptor 7 Agonistic Conjugates,” Bioconjugate Chem. 2009, 20, pp. 1194-1200.
[cited by applicant]
Chaudhuri et al., “High-Throughput Biophysical Analysis of Protein Therapeutics to Examine Interrelationships Between Aggregate Formation and Conformational Stability”, The AAPS Journal, vol. 16, No. 1, pp. 48-64, (2013…
[cited by applicant]
Chedid, L., et al., “Enhancement of Certain Biological Activities of Muramyl Dipeptide Derivatives After Conjugation to a Multi-Poly(DL-Alanine)-Poly(L-Lysine) Carrier”, Proc. Natl. Acad. Sci., vol. 76, No. 12, pp. 6557…
[cited by applicant]
Cho et al., “BiVax: a peptide/poly-IC subunit vaccine that mimics an acute infection elicits vast and effective anti-tumor CD8 T-cell responses,” Cancer Immunol Immunother (2013) 62:787-799.
[cited by applicant]
Etrych, T. et al., “Synthesis of HPMA Copolymers Containing Doxorubicin Bound via a Hydrazone Linkage. Effect of Spacer on Drug Release and In Vitro Cytotoxicity”, Macromolecular Bioscience, vol. 2, No. 1, pp. 43-52, (2…
[cited by applicant]
Cristofaro et al., “The Toll-Like Receptors and their Role in Septic Shock”, Expert Opinion on Therapeutic Targets, vol. 7, No. 5, pp. 603-612, (2003).
[cited by applicant]
Dane et al., “Big Thinking for Adjuvants. Particles Formed by Polymeric Adjuvants Preferentially Localize to the Lymph Node and Elicit Robust Immunity”, Nature Biotechnology, vol. 33, No. 11, pp. 1146-1148, (2015).
[cited by applicant]
Francica et al., “Thermoresponsive Polymer Nanoparticles Co-deliver RSV F Trimers with a TLR-7/8 Adjuvant,” Bioconjugate Chem. 2016, 27, 2372-2385.
[cited by applicant]
Dintzis, H. et al., “Molecular Determinants of Immunogenicity: The Immunon Model of Immune Response”, Proceedings of the National Academy of Science USA, vol. 73, No. 10, pp. 3671-3675, (1976).
[cited by applicant]
Duncan, R. et al., “Anticancer Agents Coupled to N-(2-Hydroxypropyl)Methacrylamide Copolymers. II. Evaluation of Daunomycin Conjugates in Vivo Against L 1210 Leukaemia”, Br. J_ Cancer, vol. 57, pp. 147-156, (1988).
[cited by applicant]
Duncan, R. et al., “Do HPMA Copolymer Conjugates Have a Future as Clinically Useful Nanomedicines? A Critical Overview of Current Status and Future Opportunities”, Advanced Drug Delivery Reviews, vol. 62, pp. 272-282, (…
[cited by applicant]
Ryu, K. et al., “Stimulation of Innate Immune Cells by Light-Activated TLR7/8 Agonists”, Journal of the American Chemical Society, vol. 136, pp. 10823-10825, (2014).
[cited by applicant]
Shakya et al., “Characterization of Chemically Defined Poly-N-Isopropylacrylamide Based Copolymeric Adjuvants”, Magazine, vol. 31, pp. 3519-3527 (2013).
[cited by applicant]
Shukla et al., Toward self-adjuvanting subunit vaccines: Model peptide and protein antigens incorporating covalently pound toll-like receptor-7 agonistic imidazoquinolines, Bioorganic & Medicinal Chemistry Letters 21 (2…
[cited by applicant]
Subr, V., et al., “Coating of Adenovirus Type 5 With Polymers Containing Quaternary Amines Prevents Binding to Blood Components,” Journal of Controlled Release, vol. 135, No. 2, pp. 152-158, (2009).
[cited by applicant]
Tanji, H., et al., “Structural Reorganization of the Toll-Like Receptor 8 Dimer Induced by Agonistic Ligands”, Science, vol. 339, No. 6126, pp. 1426-1429, (2013).
[cited by applicant]
Trent et al., “Peptide Amphiphile Micelles Self-Adjuvant Group A Streptococcal Vaccination”, The AAPS Journal, vol. 17, No. 2, pp. 380-388, (2014).
[cited by applicant]
Trzcinska et al., “Bioactive Mesoglobules of Poly(di(ethylene glycol) monomethyl ether methacrylate)-Peptide Conjugate”, Polymer Chemistry vol. 50, pp. 3104-3115, (2012).
[cited by applicant]
Wu et al., “Immunotherapeutic activity of a conjugate of a Toll-like receptor 7 ligand,” PNAS, Mar. 6, 2007, vol. 104, No. 10, pp. 3990-3995.
[cited by applicant]
Zeng et al., “A Modular Approach to Assembly of Totally Synthetic Self-adjuvanting Lipopeptide-based Vaccines Allows Conformational Epitope Building,” The Journal of Biological Chemistry vol. 286, No. 15, pp. 12944-1295…
[cited by applicant]
Zhu et al., “Albumin/vaccine nanocomplexes that assemble in vivo for combination cancer immunotherapy,” Nature Communications, 2017, 8:1954, pp. 1-15.
[cited by applicant]
Zom et al., “Efficient Induction of Antitumor Immunity by Synthetic Toll-like Receptor Ligand-Peptide Conjugates,” Cancer Immunol Res; 2(8) Aug. 2014, pp. 756-764.
[cited by applicant]
Wang et al., “Aggregation of Therapeutic Proteins Passage”, 5.3.6 Turbidimetry and Nephelometry, pp. 235-237, p. 236, second and third paragraphs, (2010).
[cited by applicant]
Weterings et al., “Synthesis of 2-alkoxy-8-hydroxyadenylpeptides: Towards synthetic epitope-based vaccines,” Bioorganic & Medicinal Chemistry Letters 16 (2006) 3258-3261.
[cited by applicant]
Weterings, J. et al., “Synthesis of 2-Alkoxy-8-Hydroxyadenylpeptides: Towards Synthetic Epitope-Based Vaccines.” Bioorganic & Medicinal Chemistry Letters, vol. 16, pp. 3258-3261, (2006).
[cited by applicant]
Wille-Reece et al., “Immunization with HIV-1 Gag Protein Conjugated to a TLR7/8 Agonist Results in the Generation of HIV-1 Gag-Specific Th1 and CD8+ T Cell Responses,” The Journal of Immunology, 2005, 174: 7676-7683.
[cited by applicant]
Wille-Reece, U. et al., “HIV Gag Protein Conjugated to a Toll-Like Receptor 7/8 Agonist Improves the Magnitude and Quality of Th1 and CD8+ T Cell Responses in Nonhuman Primates.” Proc. Natl. Acad. Sci. USA, vol. 102, No…
[cited by applicant]
Wille-Reece, U. et al., “Immunization with HIV-1 Gag Protein Conjugated to a TLR7/8 Agonist Results in the Generation of HIV-1 Gag-Specific Th1 and CD8+ T Cell Responses”, The Journal of Immunology, vol. 174, pp. 7676-7…
[cited by applicant]
Wille-Reece, U. et al., “Toll-Like Receptor Agonists Influence the Magnitude and Quality of Memory T Cell Responses After Prime-Boost Immunization in Nonhuman Primates”, The Journal of Experimental Medicine, vol. 203, N…
[cited by applicant]
Oradd et al., “Effects of peptide hydrophobicity on its incorporation in phospholipid membrane—an NMR and ellipsometry study,” Biochimica et Biophysica Acta 1808 (2011) 244-252.
[cited by applicant]
U.S. Appl. No. 16/907,912, filed Jun. 22, 2020, Polymer Adjuvant, Abandoned.
[cited by applicant]
U.S. Appl. No. 18/970,451, filed Dec. 5, 2024, Polymer Adjuvant, Pending.
[cited by applicant]
U.S. Appl. No. 18/570,579, filed Dec. 14, 2023, Self-Assembing Nanoparticles Based on Amphiphilic Peptides for Drug Delivery Applications, Published as US 2024/0382614 A1.
[cited by applicant]
Hein et al. Click Chemistry, A Powerful Tool for Pharmaceutical Sciences. Pharmaceutical Research. 2008; 25 (10):2216-2230.
[cited by applicant]
Co-pending U.S. Appl. No. 18/970,451, filed Dec. 5, 2024.
[cited by applicant]
U.S. Appl. No. 13/318,844, filed Feb. 21, 2012, Multi-Valent Adjuvant Display, Abandoned.
[cited by applicant]
U.S. Appl. No. 15/299,936, filed Oct. 21, 2016, Multi-Valent Adjuvant Display, Abandoned.
[cited by applicant]
U.S. Appl. No. 15/517,121, filed Apr. 5, 2017, Polymer Adjuvant, Abandoned.
[cited by applicant]
U.S. Appl. No. 16/907,912, filed Jun. 22, 2020, Polymer Adjuvant, Published as US 2021/0000934 A1.
[cited by applicant]
U.S. Appl. No. 17/057,658, filed Nov. 21, 2020, Improved Methods of Manufacturing Peptide-Based Vaccines, Published as US 2021/0113705 A1.
[cited by applicant]
U.S. Appl. No. 17/282,447, filed Apr. 2, 2021, Aromatic Ring Substituted Amphiphilic Polymers as Drug Delivery Systems, Published as US 2021/0393523 A1.
[cited by applicant]
U.S. Appl. No. 17/604,227, filed Oct. 15, 2021, Compositions and Methods of Manufacturing Star Polymers for Ligang Display and/or Drug Delivery, Published as US 2023/0026627 A1.
[cited by applicant]
U.S. Appl. No. 18/277,220, filed Aug. 14, 2023, Self-Assembling Nanoparticles Based on Amphiphilic Peptides, Pending.
[cited by applicant]
U.S. Appl. No. 18/570,579, filed Dec. 14, 2023, Self-Assembling Nanoparticles Based on Amphiphilic Peptides for Drug Delivery Applications, Pending.
[cited by applicant]
U.S. Appl. No. 18/027,346, filed Mar. 20, 2023, Compositions and Methods of Manufacturing Amphiphilic Block, Published as US 2023/0381112 A1.
[cited by applicant]
U.S. Appl. No. 18/032,538, filed Apr. 18, 2023, Star Polymer Drug Conjugates, Published as US 2023/0390406 A1.
[cited by applicant]
U.S. Appl. No. 17/638,576, filed Feb. 25, 2022, Methods for Inducing an Immune Response Against Neoantigens, Published as 202210305099 A1.
[cited by applicant]
U.S. Appl. No. 18/494,491, filed Oct. 25, 2023, Self-Assebling Nanoparticles, Published as US 2024/0269269 A1.
[cited by applicant]
Heuking & Borchard. Toll-like receptor-7 agonist decoration enhances the adjuvanticity of chitosan-DNA nanoparticles. J Pharm Sci. 2012; 101(3):1166-1177.
[cited by applicant]
Luo et al. Synthetic nanovaccines for immunotherapy. J Control Release. 2017;263:200-210.
[cited by applicant]
Segura & Hubbell. Synthesis and in vitro characterization of an ABC triblock copolymer for siRNA delivery. Bioconjug Chem. 2007;18(3):736-745.
[cited by applicant]
Fuks et al. Biohybrid block copolymers: towards functional micelles and vesicles. Chem Soc Rev. 2011;40 (5):2475-2493.
[cited by applicant]
Duong et al. Pronounced peptide selectivity for melanoma through tryptophan end-tagging. Sci Rep. 2016;6:24952.
[cited by applicant]
Co-pending U.S. Appl. No. 18/277,220, filed Aug. 14, 2023.
[cited by applicant]
Co-pending U.S. Appl. No. 18/570,579, filed Dec. 14, 2023.
[cited by applicant]