IP Library › Granted Patent US 11,141,495
Granted Patent B2
US 11,141,495 · App. 16/791,068 · Granted Oct 12, 2021

MRI imaging of amyloid plaque using liposomes

Inventors: Ananth V. Annapragada (Manvel, TX); Eric A. Tanifum (Katy, TX); Mayank Srivastava (Pearland, TX)
Assignee: Texas Children's Hospital
A61K49/1812A61K49/0034A61K49/0084A61K49/10A61K49/126
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Quick Facts
Patent No.
US 11,141,495
App. No.
16/791,068
Granted
Oct 12, 2021
Kind
B2
Abstract

Provided are aromatic compounds, phospholipid-polymer-aromatic conjugates comprising the aromatic compounds, and liposome compositions including the phospholipid-polymer-aromatic conjugates. The liposomal compositions may be useful for imaging of Alzheimer's Disease, for example, imaging of the amyloid-β plaque deposits characteristic of Alzheimer's Disease.

Claims (51)

1. A liposomal composition, comprising:

a membrane, comprising:

a phospholipid-polymer-aromatic conjugate, the aromatic moiety in the phospholipid-polymer-aromatic conjugate comprising:

2. The liposomal composition of claim 1 , further comprising a nonradioactive magnetic resonance imaging (MRI) contrast enhancing agent that is at least one of encapsulated by or bound to the membrane.

3. The liposomal composition of claim 1 , the membrane further comprising a first phospholipid and a second phospholipid, the second phospholipid being derivatized with a hydrophilic polymer.

4. The liposomal composition of claim 1 , the membrane further comprising:

a phospholipid;

cholesterol;

a nonradioactive MM contrast enhancing agent comprising gadolinium; and

1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000].

5. The liposomal composition of claim 1 , the phospholipid-polymer moiety in the phospholipid-polymer-aromatic conjugate being represented by the following structural formula:

or a salt thereof, wherein m is one of 12, 13, 14, 15, 16, 17, or 18, and wherein n is an integer between 60 and 100.

6. The liposomal composition of claim 5 , wherein m is 16.

7. The liposomal composition of claim 5 , wherein n is an integer between 70 and 90.

8. The liposomal composition of claim 5 , wherein n is 79.

9. A kit for imaging amyloid deposits in a patient, the kit comprising: a liposomal composition, the liposomal composition comprising:

a membrane, comprising:

a phospholipid-polymer-aromatic conjugate, the aromatic moiety in the phospholipid-polymer-aromatic conjugate comprising:

a nonradioactive magnetic resonance imaging (MM) contrast enhancing agent at least one of encapsulated by or bound to the membrane; and

instructions, the instructions directing a user to:

introduce into the patient a detectable quantity of the liposomal composition;

allow sufficient time for the liposomal composition to be associated with one or more amyloid deposits; and

detect the liposomal composition associated with the one or more amyloid deposits.

10. The kit of claim 9 , the phospholipid-polymer moiety in the phospholipid-polymer-aromatic conjugate being represented by the following structural formula:

or a salt thereof, wherein m is one of 12, 13, 14, 15, 16, 17, or 18, and wherein n is an integer between 60 and 100.

11. The kit of claim 10 , wherein m is 16.

12. The kit of claim 10 , wherein n is an integer between 70 and 90.

13. The kit of claim 10 , the membrane further comprising:

a phospholipid;

cholesterol; and

1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000].

14. A method for imaging amyloid deposits in a patient, the method comprising:

introducing into the patient a detectable quantity of a liposomal composition, the liposomal composition comprising:

a membrane, comprising:

a phospholipid-polymer-aromatic conjugate, the aromatic moiety in the phospholipid-polymer-aromatic conjugate comprising:

a nonradioactive magnetic resonance imaging (MM) contrast enhancing agent at least one of encapsulated by or bound to the membrane;

allowing sufficient time for the liposomal composition to be associated with one or more amyloid deposits; and

detecting the liposomal composition associated with the one or more amyloid deposits.

15. The method of claim 14 , the detecting comprising detecting using magnetic resonance imaging.

16. The method of claim 14 , the MRI contrast enhancing agent comprising gadolinium.

17. The method of claim 16 , the liposomal composition characterized by per-particle relaxivity in mM-1 s-1 at 1 T of at least about: 190,000.

18. The method of claim 14 , the membrane further comprising:

a phospholipid;

cholesterol;

a nonradioactive MRI contrast enhancing agent comprising gadolinium; and

1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000].

19. The method of claim 14 , further comprising diagnosing the patient with Alzheimer's disease according to detecting the liposomal composition associated with the one or more amyloid deposits.

20. The method of claim 14 , further comprising:

identifying the patient as potentially having Alzheimer's disease according to detecting the liposomal composition associated with the one or more amyloid deposits;

subjecting the patient to an analysis for tau neurofibrillary tangles; and

upon determining the presence of tau neurofibrillary tangles in conjunction with detecting the liposomal composition associated with the one or more amyloid deposits, diagnosing the patent with Alzheimer's disease.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2020
From: ANNAPRAGADA, ANANTH; TANIFUM, ERIC; SRIVASTAVA, MAYANK
To: TEXAS CHILDREN'S HOSPITAL
Reel/Frame 051922/0118 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2020
From: TEXAS CHILDREN'S PHYSICIAN SERVICES ORGANIZATION
To: ANNAPRAGADA, ANANTH; SRIVASTAVA, MAYANK; TANIFUM, ERIC
Reel/Frame 051922/0198 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2020
From: ANNAPRAGADA, ANANTH
To: ALZECA BIOSCIENCES, LLC
Reel/Frame 051922/0548 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2020
From: SRIVASTAVA, MAYANK
To: ALZECA BIOSCIENCES, LLC
Reel/Frame 051922/0615 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2020
From: TANIFUM, ERIC
To: ALZECA BIOSCIENCES, LLC
Reel/Frame 051922/0782 →
Continuity (6)
Continuation 16677751 · Nov 8, 2019
Continuation 15366667 · Dec 1, 2016
Continuation 14878745 · Oct 8, 2015
Provisional Application 62111057 · Feb 2, 2015
Provisional Application 62061514 · Oct 8, 2014
Related Publication 20200179540A1 · Jun 11, 2020