Patent
US 10,493,170TARGETED GRAPHENE QUANTUM DOT-BASED THERANOSTICS
Yiru Qin
US
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Patent
Atlas literature
Patent
US 10,493,170Patent drawings and their descriptions. Click a drawing to enlarge it.
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
1-13. Canceled
Canceled
A method of making a plurality of conjugates, wherein each con j ugate comprising a graphene quantum dot (GQD), a targetin g moiety con iug ated to the GQD, and an active a q ent associated with the GQD, wherein the GQDs in the plurality of con iug ates have an avera g e diameter of about 3 nm and a span of about 1.5 or less, wherein the ta rq etin q moiety is folic acid or a derivative thereof, and wherein the active a q ent is a doxorubicin noncovalently associated with the GQD via r r-rr stackin g; the method comprising conjugating [[a]] the targeting moiety to each GQD in [[a]] the plurality of GQDs to form a plurality of first intermediates, wherein the targeting moiety is folic acid or a derivative thereof, and wherein the GQDs in the plurality of GQDs have an average diameter of about 3 nm and a span of about 1.5 or less; wherein con j ugatin g the targetin g moiety to each GQD comprises the steps of: reactin q each GQD with ammonium hydroxide and h y dro g en peroxide to introduce amine reactive coupling groups onto each of the GQDs; and reactin q the folic acid tar q etin q moiety with crosslinkin q aq ents to form a covalent bond with the amine reactive couplin q g roup to form the plurality of first intermediates; and associating a s the active agent to each first intermediate in the plurality of first intermediates to form the plurality of conjugates, wherein the active agent is a doxorubicin noncovalently associated with the GQD via r r-rr stacking. Currently amended
The method of claim 14, further comprising producing the plurality of GQDs by a method comprising the steps of combining a graphite with an oxidizing mixture comprising potassium permanganate (KM n O 4), sulfuric acid (H 2 SO 4), and nitric acid (HNO 3) to form a combination; and heating the combination to an elevated temperature of about 12 0 C to 18 0 C with respect to room temperature to produce the GQDs. Previously presented
The method of claim 14, wherein the c rosslinking agents comprise [[,]] N-hydroxysuccinimide (NHS) and 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide (ED C). Currently amended
The method of claim 14, wherein the GQDs have a monodisperse size distribution having a span of 1 or less, a coefficient of variation of 0.5 or less, or both. New
The method of claim 14, wherein at least 40% of the GQDs have a diameter within ± 0.5 nm of the average diameter of the GQDs. New
18-20. Canceled
Canceled
Materials described outside the worked examples.
graphene quantum dot
folic acid targeting moiety
doxorubicin
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
GQD average diameter | 3 nm | graphene quantum dot |
Patent
Atlas literature
Patent
US 10,493,170Patent drawings and their descriptions. Click a drawing to enlarge it.
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
1-13. Canceled
Canceled
A method of making a plurality of conjugates, wherein each con j ugate comprising a graphene quantum dot (GQD), a targetin g moiety con iug ated to the GQD, and an active a q ent associated with the GQD, wherein the GQDs in the plurality of con iug ates have an avera g e diameter of about 3 nm and a span of about 1.5 or less, wherein the ta rq etin q moiety is folic acid or a derivative thereof, and wherein the active a q ent is a doxorubicin noncovalently associated with the GQD via r r-rr stackin g; the method comprising conjugating [[a]] the targeting moiety to each GQD in [[a]] the plurality of GQDs to form a plurality of first intermediates, wherein the targeting moiety is folic acid or a derivative thereof, and wherein the GQDs in the plurality of GQDs have an average diameter of about 3 nm and a span of about 1.5 or less; wherein con j ugatin g the targetin g moiety to each GQD comprises the steps of: reactin q each GQD with ammonium hydroxide and h y dro g en peroxide to introduce amine reactive coupling groups onto each of the GQDs; and reactin q the folic acid tar q etin q moiety with crosslinkin q aq ents to form a covalent bond with the amine reactive couplin q g roup to form the plurality of first intermediates; and associating a s the active agent to each first intermediate in the plurality of first intermediates to form the plurality of conjugates, wherein the active agent is a doxorubicin noncovalently associated with the GQD via r r-rr stacking. Currently amended
The method of claim 14, further comprising producing the plurality of GQDs by a method comprising the steps of combining a graphite with an oxidizing mixture comprising potassium permanganate (KM n O 4), sulfuric acid (H 2 SO 4), and nitric acid (HNO 3) to form a combination; and heating the combination to an elevated temperature of about 12 0 C to 18 0 C with respect to room temperature to produce the GQDs. Previously presented
The method of claim 14, wherein the c rosslinking agents comprise [[,]] N-hydroxysuccinimide (NHS) and 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide (ED C). Currently amended
The method of claim 14, wherein the GQDs have a monodisperse size distribution having a span of 1 or less, a coefficient of variation of 0.5 or less, or both. New
The method of claim 14, wherein at least 40% of the GQDs have a diameter within ± 0.5 nm of the average diameter of the GQDs. New
18-20. Canceled
Canceled
Materials described outside the worked examples.
graphene quantum dot
folic acid targeting moiety
doxorubicin
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
GQD average diameter | 3 nm | graphene quantum dot |
Patent
Atlas literature
Patent
US 10,493,170Patent drawings and their descriptions. Click a drawing to enlarge it.
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
1-13. Canceled
Canceled
A method of making a plurality of conjugates, wherein each con j ugate comprising a graphene quantum dot (GQD), a targetin g moiety con iug ated to the GQD, and an active a q ent associated with the GQD, wherein the GQDs in the plurality of con iug ates have an avera g e diameter of about 3 nm and a span of about 1.5 or less, wherein the ta rq etin q moiety is folic acid or a derivative thereof, and wherein the active a q ent is a doxorubicin noncovalently associated with the GQD via r r-rr stackin g; the method comprising conjugating [[a]] the targeting moiety to each GQD in [[a]] the plurality of GQDs to form a plurality of first intermediates, wherein the targeting moiety is folic acid or a derivative thereof, and wherein the GQDs in the plurality of GQDs have an average diameter of about 3 nm and a span of about 1.5 or less; wherein con j ugatin g the targetin g moiety to each GQD comprises the steps of: reactin q each GQD with ammonium hydroxide and h y dro g en peroxide to introduce amine reactive coupling groups onto each of the GQDs; and reactin q the folic acid tar q etin q moiety with crosslinkin q aq ents to form a covalent bond with the amine reactive couplin q g roup to form the plurality of first intermediates; and associating a s the active agent to each first intermediate in the plurality of first intermediates to form the plurality of conjugates, wherein the active agent is a doxorubicin noncovalently associated with the GQD via r r-rr stacking. Currently amended
The method of claim 14, further comprising producing the plurality of GQDs by a method comprising the steps of combining a graphite with an oxidizing mixture comprising potassium permanganate (KM n O 4), sulfuric acid (H 2 SO 4), and nitric acid (HNO 3) to form a combination; and heating the combination to an elevated temperature of about 12 0 C to 18 0 C with respect to room temperature to produce the GQDs. Previously presented
The method of claim 14, wherein the c rosslinking agents comprise [[,]] N-hydroxysuccinimide (NHS) and 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide (ED C). Currently amended
The method of claim 14, wherein the GQDs have a monodisperse size distribution having a span of 1 or less, a coefficient of variation of 0.5 or less, or both. New
The method of claim 14, wherein at least 40% of the GQDs have a diameter within ± 0.5 nm of the average diameter of the GQDs. New
18-20. Canceled
Canceled
Materials described outside the worked examples.
graphene quantum dot
folic acid targeting moiety
doxorubicin
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
GQD average diameter | 3 nm | graphene quantum dot |
Patent
Atlas literature
Patent
US 10,493,170Patent drawings and their descriptions. Click a drawing to enlarge it.
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
1-13. Canceled
Canceled
A method of making a plurality of conjugates, wherein each con j ugate comprising a graphene quantum dot (GQD), a targetin g moiety con iug ated to the GQD, and an active a q ent associated with the GQD, wherein the GQDs in the plurality of con iug ates have an avera g e diameter of about 3 nm and a span of about 1.5 or less, wherein the ta rq etin q moiety is folic acid or a derivative thereof, and wherein the active a q ent is a doxorubicin noncovalently associated with the GQD via r r-rr stackin g; the method comprising conjugating [[a]] the targeting moiety to each GQD in [[a]] the plurality of GQDs to form a plurality of first intermediates, wherein the targeting moiety is folic acid or a derivative thereof, and wherein the GQDs in the plurality of GQDs have an average diameter of about 3 nm and a span of about 1.5 or less; wherein con j ugatin g the targetin g moiety to each GQD comprises the steps of: reactin q each GQD with ammonium hydroxide and h y dro g en peroxide to introduce amine reactive coupling groups onto each of the GQDs; and reactin q the folic acid tar q etin q moiety with crosslinkin q aq ents to form a covalent bond with the amine reactive couplin q g roup to form the plurality of first intermediates; and associating a s the active agent to each first intermediate in the plurality of first intermediates to form the plurality of conjugates, wherein the active agent is a doxorubicin noncovalently associated with the GQD via r r-rr stacking. Currently amended
The method of claim 14, further comprising producing the plurality of GQDs by a method comprising the steps of combining a graphite with an oxidizing mixture comprising potassium permanganate (KM n O 4), sulfuric acid (H 2 SO 4), and nitric acid (HNO 3) to form a combination; and heating the combination to an elevated temperature of about 12 0 C to 18 0 C with respect to room temperature to produce the GQDs. Previously presented
The method of claim 14, wherein the c rosslinking agents comprise [[,]] N-hydroxysuccinimide (NHS) and 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide (ED C). Currently amended
The method of claim 14, wherein the GQDs have a monodisperse size distribution having a span of 1 or less, a coefficient of variation of 0.5 or less, or both. New
The method of claim 14, wherein at least 40% of the GQDs have a diameter within ± 0.5 nm of the average diameter of the GQDs. New
18-20. Canceled
Canceled
Materials described outside the worked examples.
graphene quantum dot
folic acid targeting moiety
doxorubicin
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
GQD average diameter | 3 nm | graphene quantum dot |
potassium permanganate
KMnO₄
sulfuric acid
H₂SO₄
nitric acid
HNO₃
N-hydroxysuccinimide
1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide
graphite
ammonium hydroxide
NH₄OH
hydrogen peroxide
H₂O₂
GQD size distribution span (claim 14) |
| ≤ 1.5 dimensionless |
graphene quantum dot |
GQD monodisperse size distribution span (claim 21) | ≤ 1 dimensionless | graphene quantum dot |
GQD size distribution coefficient of variation (claim 21) | ≤ 0.5 dimensionless | graphene quantum dot |
Thickness | 425–475 nm | — |
Thickness | 500–530 nm | — |
Thickness | 552–617 nm | — |
Thickness | 1.5–5.5 nm | — |
Thickness | 10–12 nm | — |
Thickness | 3300–3500 cm | — |
Thickness | ≤ 365 nm | — |
Thickness | 1–1000 nm | — |
Thickness | 1–100 nm | — |
Thickness | 1–30 nm | — |
Thickness | 1–20 nm | — |
Thickness | 1–10 nm | — |
Thickness | 1–5 nm | — |
Voltage | 0.5–5 V | — |
Voltage | 0.9–3 V | — |
Voltage | 1–2.5 V | — |
Voltage | 1–2 V | — |
Voltage | 1–1.6 V | — |
Voltage | 1.2–1.6 V | — |
Thickness | 2–10 nm | — |
Thickness | 2–5 nm | — |
Thickness | 450–600 nm | — |
Thickness | 450–550 nm | — |
Thickness | 475–525 nm | — |
Duration | ≤ 2 hours | — |
Duration | ≤ 1.5 hours | — |
Duration | ≤ 1 hour | — |
potassium permanganate
KMnO₄
sulfuric acid
H₂SO₄
nitric acid
HNO₃
N-hydroxysuccinimide
1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide
graphite
ammonium hydroxide
NH₄OH
hydrogen peroxide
H₂O₂
GQD size distribution span (claim 14) |
| ≤ 1.5 dimensionless |
graphene quantum dot |
GQD monodisperse size distribution span (claim 21) | ≤ 1 dimensionless | graphene quantum dot |
GQD size distribution coefficient of variation (claim 21) | ≤ 0.5 dimensionless | graphene quantum dot |
Thickness | 425–475 nm | — |
Thickness | 500–530 nm | — |
Thickness | 552–617 nm | — |
Thickness | 1.5–5.5 nm | — |
Thickness | 10–12 nm | — |
Thickness | 3300–3500 cm | — |
Thickness | ≤ 365 nm | — |
Thickness | 1–1000 nm | — |
Thickness | 1–100 nm | — |
Thickness | 1–30 nm | — |
Thickness | 1–20 nm | — |
Thickness | 1–10 nm | — |
Thickness | 1–5 nm | — |
Voltage | 0.5–5 V | — |
Voltage | 0.9–3 V | — |
Voltage | 1–2.5 V | — |
Voltage | 1–2 V | — |
Voltage | 1–1.6 V | — |
Voltage | 1.2–1.6 V | — |
Thickness | 2–10 nm | — |
Thickness | 2–5 nm | — |
Thickness | 450–600 nm | — |
Thickness | 450–550 nm | — |
Thickness | 475–525 nm | — |
Duration | ≤ 2 hours | — |
Duration | ≤ 1.5 hours | — |
Duration | ≤ 1 hour | — |
potassium permanganate
KMnO₄
sulfuric acid
H₂SO₄
nitric acid
HNO₃
N-hydroxysuccinimide
1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide
graphite
ammonium hydroxide
NH₄OH
hydrogen peroxide
H₂O₂
GQD size distribution span (claim 14) |
| ≤ 1.5 dimensionless |
graphene quantum dot |
GQD monodisperse size distribution span (claim 21) | ≤ 1 dimensionless | graphene quantum dot |
GQD size distribution coefficient of variation (claim 21) | ≤ 0.5 dimensionless | graphene quantum dot |
Thickness | 425–475 nm | — |
Thickness | 500–530 nm | — |
Thickness | 552–617 nm | — |
Thickness | 1.5–5.5 nm | — |
Thickness | 10–12 nm | — |
Thickness | 3300–3500 cm | — |
Thickness | ≤ 365 nm | — |
Thickness | 1–1000 nm | — |
Thickness | 1–100 nm | — |
Thickness | 1–30 nm | — |
Thickness | 1–20 nm | — |
Thickness | 1–10 nm | — |
Thickness | 1–5 nm | — |
Voltage | 0.5–5 V | — |
Voltage | 0.9–3 V | — |
Voltage | 1–2.5 V | — |
Voltage | 1–2 V | — |
Voltage | 1–1.6 V | — |
Voltage | 1.2–1.6 V | — |
Thickness | 2–10 nm | — |
Thickness | 2–5 nm | — |
Thickness | 450–600 nm | — |
Thickness | 450–550 nm | — |
Thickness | 475–525 nm | — |
Duration | ≤ 2 hours | — |
Duration | ≤ 1.5 hours | — |
Duration | ≤ 1 hour | — |
potassium permanganate
KMnO₄
sulfuric acid
H₂SO₄
nitric acid
HNO₃
N-hydroxysuccinimide
1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide
graphite
ammonium hydroxide
NH₄OH
hydrogen peroxide
H₂O₂
GQD size distribution span (claim 14) |
| ≤ 1.5 dimensionless |
graphene quantum dot |
GQD monodisperse size distribution span (claim 21) | ≤ 1 dimensionless | graphene quantum dot |
GQD size distribution coefficient of variation (claim 21) | ≤ 0.5 dimensionless | graphene quantum dot |
Thickness | 425–475 nm | — |
Thickness | 500–530 nm | — |
Thickness | 552–617 nm | — |
Thickness | 1.5–5.5 nm | — |
Thickness | 10–12 nm | — |
Thickness | 3300–3500 cm | — |
Thickness | ≤ 365 nm | — |
Thickness | 1–1000 nm | — |
Thickness | 1–100 nm | — |
Thickness | 1–30 nm | — |
Thickness | 1–20 nm | — |
Thickness | 1–10 nm | — |
Thickness | 1–5 nm | — |
Voltage | 0.5–5 V | — |
Voltage | 0.9–3 V | — |
Voltage | 1–2.5 V | — |
Voltage | 1–2 V | — |
Voltage | 1–1.6 V | — |
Voltage | 1.2–1.6 V | — |
Thickness | 2–10 nm | — |
Thickness | 2–5 nm | — |
Thickness | 450–600 nm | — |
Thickness | 450–550 nm | — |
Thickness | 475–525 nm | — |
Duration | ≤ 2 hours | — |
Duration | ≤ 1.5 hours | — |
Duration | ≤ 1 hour | — |