IP Library Granted Patent US 9,233,177
Granted Patent B2
US 9,233,177 · App. 12/739,097 · Granted Jan 12, 2016

Metallofullerene contrast agents

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Quick Facts
Patent No.
US 9,233,177
App. No.
12/739,097
Granted
Jan 12, 2016
Kind
B2
Abstract

Endohedral metallofullerene compounds, which in water has a relaxivity of about 30 mM −1 S −1 to about 300 mM −1 S −1 and forms a dispersion in water with entities having an average hydrodynamic radius of less than about 20 nm.

Claims (18)

1. An endohedral metallofullerene compound represented by the formula (III): A k X n N i @C m ′,

wherein A and X represent identical or different elements in the periodic table of elements, provided that at least one of A and X is paramagnetic;

C m ′ represents a fullerene having one or more missing carbon atoms and/or bonds, wherein the fullerene is derived from C m , which may optionally be substituted;

C m represents a fullerene molecule having m carbon atoms;

k represents an integer from 1 to 3;

n represents an integer from 0 to 2, provided that 1≦k+n≦3;

i represents an integer of 0 or 1; and

m represents an even integer from about 60 to about 200.

2. The compound of claim 1 , which in water has a relaxivity of about 30 mM −1 ·S −1 to about 300 mM −1 ·S −1 and forms a dispersion in water with entities having an average hydrodynamic radius of less than 20 nm.

3. The endohedral metallofullerene compound of claim 1 , wherein at least one of A and X represents a rare earth element or a group IIIB element in the periodic table of elements.

4. The endohedral metallofullerene compound of claim 1 , wherein at least one of A and X is selected from the group consisting of scandium, yttrium, lanthanum, gadolimium, holmium, erbium, thulium, dysprosium, terbium and ytterbium.

5. The endohedral metallofullerene compound of claim 1 , wherein A k X n N i @C m ′ represents Gd@C 60 ′, Gd@ C 82 ′ or Gd 3 N@C 80 ′.

6. The endohedral metallofullerene compound of claim 1 , wherein the substituent(s) in C m ′ further comprise one or more targeting species selected from the group consisting of cholesterol, L-DOPA, tropane or its derivatives, tetrabenazine, urushiol, transferrin, muc-1, antibodies, cytokines, saccharides, polysaccharides, glutamate and aminolevulinic acid.

7. The endohedral metallofullerene compound of claim 1 , wherein the C m ′ is optionally substituted by:

(a) one or more groups which are directly bonded to C m via an atom selected from the group consisting of N, O, S and P, and/or

(b) one or more groups comprising a hydrophilic moiety.

8. The endohedral metallofullerene compound of claim 1 , wherein C m ′ is substituted with at least one selected from the group consisting of an oxygen atom and a —COOH group.

9. A composition comprising the endohedral metallofullerene compound of claim 1 .

Assignments (7)
RELEASE OF SECURITY INTEREST Recorded Jan 29, 2026
From: M&T BANK
To: LUNA LABS USA, LLC
Reel/Frame 073628/0060 →
RELEASE OF SECURITY INTEREST Recorded Mar 25, 2022
From: PNC BANK, NATIONAL ASSOCIATION
To: LUNA LABS USA, LLC
Reel/Frame 059396/0791 →
SECURITY INTEREST Recorded Mar 9, 2022
From: LUNA LABS USA, LLC
To: M&T BANK
Reel/Frame 059211/0861 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2022
From: LUNA INNOVATIONS INCORPORATED
To: LUNA LABS USA, LLC
Reel/Frame 059109/0181 →
SECURITY INTEREST Recorded Mar 4, 2021
From: LUNA INNOVATIONS INCORPORATED; FORMER LUNA SUBSIDIARY, INC.; GENERAL PHOTONICS CORP.
To: PNC BANK, NATIONAL ASSOCIATION
Reel/Frame 056455/0331 →
RELEASE OF SECURITY INTEREST Recorded Feb 6, 2015
From: HANSEN MEDICAL, INC.
To: LUNA INNOVATIONS INCORPORATED
Reel/Frame 034914/0407 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2011
From: MACFARLAND, DARREN K.; LENK, ROBERT P.; SHUKLA, RAJESH; WALKER, KENNETH L.; WILSON, STEPHEN R.; ZHOU, ZHIGUO
To: LUNA INNOVATIONS INCORPORATED
Reel/Frame 025731/0203 →