IP Library Granted Patent US 12,534,468
Granted Patent B2
US 12,534,468 · App. 18/156,306 · Granted Jan 27, 2026

Nanomaterial compositions, synthesis, and assembly

Inventors: Qian Chen (Barrington, RI); Hongchuan Yu (Mansfield, MA); Yupeng Chen (Mansfield, MA)
Assignee: Rhode Island Hospital
C07D487/04A61K45/06A61K47/542A61K47/545A61K47/6925A61L27/20A61L27/227A61L27/50A61L27/52A61L27/54C07D471/04C07D519/00A61F2/30756A61L2300/252A61L2300/406A61L2300/414A61L2400/12
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,534,468
App. No.
18/156,306
Granted
Jan 27, 2026
Kind
B2
Abstract

Compositions or an assembly of a series of biomimetic compounds include chemical structures that mimic or structurally resemble a nucleic acid base pair. Complexes of nanotubes and agents are useful to deliver agents into the cells or bodily tissues of individuals for therapeutic and diagnostic purposes. Exemplary compounds include those of Formula (I), (III), (V) or (VII), or of Formula (II), (IV), (VI) or (VIII).

Claims (30)

1 . A composition comprising a compound of formula (I):

or a pharmaceutically acceptable salt or ester thereof wherein,

n is an integer of 0, 1, 2, 3, 4, 5 or 6;

R 1 is selected from an α-amino acid, a β-amino acid, an α-polypeptide,

a β-polypeptide,

j, k, m and p are each independently an integer of 0 to 20;

R x is aliphatic or H;

R y is H or

q, s and t are each independently an integer of 0 to 20;

R 2 is selected from H, CH 3 , or NHR z ;

R z is selected from H or aliphatic; and

wherein the compound is operative to self-assemble to form a nanotube.

2 . The composition of claim 1 , comprising a compound of formula (I)

wherein the compound of Formula (I) is Compound A,

3 . The composition of claim 1 , wherein

n is an integer of 1, 2, 3, 4, 5 or 6;

j, k, m and p are each independently an integer of 1 to 20; and

q, s and t are each independently an integer of 1 to 20.

4 . The composition of claim 1 , wherein R 1 is selected from an α-amino acid comprising a covalent bond between an α-amino group and (CH 2 ) n , a β-amino acid comprising a covalent bond between a β-amino group and (CH 2 ) n , an α-polypeptide comprising a covalent bond between an α-amino group and (CH 2 ) n , a β-polypeptide comprising a covalent bond between a β-amino group and (CH 2 ) n ,

5 . The composition of claim 2 , wherein R 1 is an α-amino acid comprising a covalent bond between an α-amino group and (CH 2 ) n or a β-amino acid comprising a covalent bond between a β-amino group and (CH 2 ) n .

6 . The composition of claim 5 , wherein R 1 in Formula (I) is

7 . The composition of claim 1 , wherein the compounds are provided in the form of a nanotube.

8 . The composition of claim 7 , wherein said nanotube further comprises one or more therapeutic agents.

9 . The composition of claim 8 , wherein said therapeutic agent comprises a nucleic acid, a peptide or a molecule.

10 . The composition of claim 8 , further comprising matrilin.

11 . The composition of claim 10 , wherein said matrilin comprises Matrilin-3.

12 . The composition of claim 8 , further comprising a bioactive agent.

13 . The composition of claim 12 , wherein the bioactive agent comprises a bone morphogenetic protein (BMP), vascular endothelial growth factor (VEGF), connective tissue growth factor (CTGF), osteoprotegerin, growth differentiation factor (GDF), cartilage-derived morphogenetic protein (CDMP), LIM mineralization protein (LMP), transforming growth factor beta (TGF-β), antibiotic, immunosuppressive agent, or a combination thereof.

14 . The composition of claim 10 , further comprising an immunosuppressive agent.

15 . The composition of claim 14 , wherein the immunosuppressive agent is selected from the group consisting of steroids, cyclosporine, cyclosporine analogs, cyclophosphamide, methylprednisolone, prednisone, azathioprine, FK-506, and er-15-deoxyspergualin.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 8, 2023
From: CHEN, QIAN; YU, HONGCHUAN; CHEN, YUPENG
To: RHODE ISLAND HOSPITAL
Reel/Frame 062914/0195 →
Continuity (3)
Continuation 15527283
Provisional Application 62080685 · Nov 17, 2014
Related Publication 20230183253A1 · Jun 15, 2023
References Cited (45)
US 9775842B2 · Chen et al. · 2017 [cited by applicant]
US 10344300B2 · Chen et al. · 2019 [cited by applicant]
US 10364440B2 · Webster et al. · 2019 [cited by applicant]
US 11608340B2 · Chen · 2023 [cited by examiner]
US 20100075904A1 · Laurencin et al. · 2010 [cited by applicant]
US 20110027339A1 · Mao · 2011 [cited by applicant]
US 20110136838A1 · Atkinson et al. · 2011 [cited by applicant]
US 20120171121A1 · Webster · 2012 [cited by applicant]
US 20120258094A1 · Cohen et al. · 2012 [cited by applicant]
US 20130059359A1 · Wagner · 2013 [cited by applicant]
US 20130129788A1 · Webster et al. · 2013 [cited by applicant]
US 20130288972A1 · Chen et al. · 2013 [cited by applicant]
US 20140171482A1 · Webster et al. · 2014 [cited by applicant]
US 20150258094A1 · Chen et al. · 2015 [cited by applicant]
US 20150258213A1 · Chen et al. · 2015 [cited by applicant]
JP 2012500204A · 2012 [cited by applicant]
JP 2013528405A · 2013 [cited by applicant]
JP 6836989B2 · 2021 [cited by applicant]
WO 2011116085A1 · 2011 [cited by applicant]
WO 2012094304A1 · 2012 [cited by applicant]
WO 2012094511A2 · 2012 [cited by applicant]
WO 2012153576A1 · 2012 [cited by applicant]
WO 2013142382A1 · 2013 [cited by applicant]
Extended European Search Report received for European Patent Application No. 15861300.0, mailed on Oct. 8, 2018, 10 pages. [cited by applicant]
Extended European Search Report received for European Patent Application No. 20193864.4, mailed on Jun. 9, 2021, 11 pages. [cited by applicant]
GenBank Accession No. NM_002379.3. [cited by applicant]
GenBank Accession No. NM_002380.3. [cited by applicant]
GenBank Accession No. NM_002381.4. [cited by applicant]
GenBank Accession No. NM_003833.3. [cited by applicant]
GenBank Accession No. NM_030583.2. [cited by applicant]
GenBank Accession No. NM_030590.2. [cited by applicant]
GenBank Accession No. NM_030592.2. [cited by applicant]
GenBank Accession No. NP_002372.1. [cited by applicant]
International Search Report and Written Opinion received for PCT Patent Application No. PCT/US2015/061193, mailed on Mar. 28, 2016, 16 pages. [cited by applicant]
Partial Search Report received for European Patent Application No. 20193864.4, mailed on Mar. 4, 2021, 12 pages. [cited by applicant]
Partial Supplementary European Search Report received for European Patent Application No. 15861300.0, mailed on Jul. 4, 2018, 10 pages. [cited by applicant]
PubChem-CID-11974489, Jan. 3, 2007. [cited by applicant]
PubChem-CID-16103534, Jun. 18, 2007. [cited by applicant]
Asadi, et al., Janus-AT Bases: Synthesis, Self-Assembly, and Solid State Structures, The Journal of Organic Chemistry, vol. 72, 2007, pp. 466-475. [cited by applicant]
Fenniri, et al., “Helical Rosette Nanotubes: Design, Self-Assembly, and Characterization”, Journal of Am Chem Society, vol. 123, No. 16, 2001, pp. 3854-3855. [cited by applicant]
Mascal, et al., “Synthesis of the G-C DNA Base Hybrid with a Functional Tail”, The Journal of Organic Chemistry, vol. 71, No. 21, 2006, pp. 8146-8150. [cited by applicant]
Moralez, et al., “Helical Rosette Nanotubes With Tunable Stability and Hierarchy”, Journal of American Chemical Society, vol. 127, No. 23, Jun. 15, 2005, pp. 8307-8309. [cited by applicant]
Song, et al., “Self-Assembled Rosette Nanotubes for Incorporating Hydrophobic Drugs in Physiological Environments”, International Journal of Nanomedicine, Issue 6, Jan. 10, 2011, pp. 101-107. [cited by applicant]
Zhang, et al., “Arginine-Glycine-Aspartic Acid Modified Rosette Nanotube-Hydrogel Composites for Bone Tissue Engineering”, Biomaterials, vol. 30, No. 7, Mar. 1, 2009, pp. 1309-1320. [cited by applicant]
Zhao, et al., “Micro-Flowers Changing to Nano-Bundle Aggregates by Translocation of the Sugar Moiety in Janus TA Nucleosides”, Chemical Communications, vol. 49, 2013, pp. 3742-3744. [cited by applicant]