Substituted fullerene compositions and their use as antioxidants
First Claim
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1. A substituted fullerene, comprising a fullerene core (Cn), wherein n is an even integer greater than or equal to 60, and at least one of i–
- iv;
(i) m (>
CX1X2) groups bonded to the fullerene core, wherein;
(i-a) m is an integer from 1 to 6, inclusive,(i-b) each X1 and X2 is independently selected from —
H;
—
COOH;
—
CONH2;
—
CONHR′
;
—
CONR′
2;
—
COOR′
;
—
CHO;
—
(CH2)dOH;
a peptidyl moiety;
—
R;
—
RCOOH;
—
RCONH2;
—
RCONHR′
;
—
RCONR′
2;
—
RCOOR′
;
—
RCHO;
—
R(CH2)dOH;
a heterocyclic moiety;
a branched moiety comprising one or more terminal —
OH, —
NH2, triazole, tetrazole, or sugar groups;
or a salt thereof, wherein each R is a hydrocarbon moiety having from 1 to about 6 carbon atoms and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol, and d is an integer from 0 to about 20; and
(i-c) when m is 3, at least one X1 or X2 is not —
COOH;
(ii) p —
X3 groups bonded to the fullerene core, wherein;
(ii-a) p is an integer from 1 to 18, inclusive; and
(ii-b) each —
X3 is independently selected from —
N+(R2)(R3)(R4), wherein R2, R3, and R4 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20;
—
N+(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
C(R5)(R6)(R7), wherein R5, R6, and R7 are independently —
COOH, —
H, —
CH(═
O), —
CH2OH, or a peptidyl moiety;
—
C(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
(CH2)e—
COOH, —
(CH2)e—
CONH2, —
(CH2)e—
COOR′
, wherein e is an integer from 1 to about 6 and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol;
a peptidyl moiety;
or an aromatic heterocyclic moiety containing a cationic nitrogen;
(iii) q —
X4—
groups bonded to the fullerene core, wherein(iii-a) q is an integer from 1 to 6, inclusive; and
(iii-b) each —
X4—
group is independently
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Abstract
This patent discloses a substituted fullerenes, compositions comprising the same, and their use as antioxidants. The substituted fullerenes comprise a fullerene core (Cn) and at least one of: (i) from 1 to 6 (>CX1X2) groups bonded to the fullerene core; (ii) from 1 to 18 —X3 groups bonded to the fullerene core; (iii) from 1 to 6 —X4— groups bonded to the fullerene core; or (iv) from 1 to 6 dendrons bonded to the fullerene core.
75 Citations
38 Claims
-
1. A substituted fullerene, comprising a fullerene core (Cn), wherein n is an even integer greater than or equal to 60, and at least one of i–
- iv;
(i) m (>
CX1X2) groups bonded to the fullerene core, wherein;(i-a) m is an integer from 1 to 6, inclusive, (i-b) each X1 and X2 is independently selected from —
H;
—
COOH;
—
CONH2;
—
CONHR′
;
—
CONR′
2;
—
COOR′
;
—
CHO;
—
(CH2)dOH;
a peptidyl moiety;
—
R;
—
RCOOH;
—
RCONH2;
—
RCONHR′
;
—
RCONR′
2;
—
RCOOR′
;
—
RCHO;
—
R(CH2)dOH;
a heterocyclic moiety;
a branched moiety comprising one or more terminal —
OH, —
NH2, triazole, tetrazole, or sugar groups;
or a salt thereof, wherein each R is a hydrocarbon moiety having from 1 to about 6 carbon atoms and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol, and d is an integer from 0 to about 20; and(i-c) when m is 3, at least one X1 or X2 is not —
COOH;(ii) p —
X3 groups bonded to the fullerene core, wherein;(ii-a) p is an integer from 1 to 18, inclusive; and (ii-b) each —
X3 is independently selected from —
N+(R2)(R3)(R4), wherein R2, R3, and R4 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20;
—
N+(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
C(R5)(R6)(R7), wherein R5, R6, and R7 are independently —
COOH, —
H, —
CH(═
O), —
CH2OH, or a peptidyl moiety;
—
C(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
(CH2)e—
COOH, —
(CH2)e—
CONH2, —
(CH2)e—
COOR′
, wherein e is an integer from 1 to about 6 and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol;
a peptidyl moiety;
or an aromatic heterocyclic moiety containing a cationic nitrogen;(iii) q —
X4—
groups bonded to the fullerene core, wherein(iii-a) q is an integer from 1 to 6, inclusive; and (iii-b) each —
X4—
group is independently - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
- iv;
-
12. A composition, comprising:
-
a carrier, and, a substituted fullerene, comprising a fullerene core (Cn), wherein n is an even integer greater than or equal to 60, and at least one of i-iv; (i) m (>
CX1X2) groups bonded to the fullerene core, wherein;(i-a) m is an integer from 1 to 6, inclusive, (i-b) each X1 and X2 is independently selected from —
H;
—
COOH;
—
CONH2;
—
CONHR′
;
—
CONR′
2;
—
COOR′
;
—
CHO;
—
(CH2)dOH;
a peptidyl moiety;
—
R;
—
RCOOH;
—
RCONH2;
—
RCONHR′
;
—
RCONR′
2;
—
RCOOR′
;
—
RCHO;
—
R(CH2)dOH;
a heterocyclic moiety;
a branched moiety comprising one or more terminal —
OH, —
NH2, triazole, tetrazole, or sugar groups;
or a salt thereof, wherein each R is a hydrocarbon moiety having from 1 to about 6 carbon atoms and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol, and d is an integer from 0 to about 20; and(i-c) when m is 3, at least one X1 or X2 is not —
COOH;(ii) p —
X3 groups bonded to the fullerene core, wherein;(ii-a) p is an integer from 1 to 18, inclusive; and (ii-b) each —
X3 is independently selected from —
N+(R2)(R3)(R4), wherein R2, R3, and R4 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20;
—
N+(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
C(R5)(R6)(R7), wherein R5, R6, and R7 are independently —
COOH, —
H, —
CH(═
O), —
CH2OH, or a peptidyl moiety;
—
C(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
(CH2)e—
COOH, —
(CH2)e—
CONH2, —
(CH2)e—
COOR′
, wherein e is an integer from 1 to about 6 and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol;
a peptidyl moiety;
or an aromatic heterocyclic moiety containing a cationic nitrogen;(iii) q —
X4—
groups bonded to the fullerene core, wherein(iii-a) q is an integer from 1 to 6, inclusive; and (iii-b) each —
X4—
group is independently - View Dependent Claims (13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23)
-
-
24. A method of ameliorating an oxidative stress disease, comprising:
-
administering to a mammal an effective amount of a composition comprising a substituted fullerene, wherein the substituted fullerene comprises a fullerene core (Cn), wherein n is an even integer greater than or equal to 60, and at least one of i-iv; (i) m (>
CX1X2) groups bonded to the fullerene core, wherein;(i-a) m is an integer from 1 to 6, inclusive, (i-b) each X1 and X2 is independently selected from —
H;
—
COOH;—
CONH2;
—
CONHR′
;
—
CONR′
2;
—
COOR′
;
—
CHO;
—
(CH2)dOH;
a peptidyl moiety;
—
R;
—
RCOOH;
—
RCONH2;
—
RCONHR′
;
—
RCONR′
2;
—
RCOOR′
;
—
RCHO;
—
R(CH2)dOH;
a heterocyclic moiety;
a branched moiety comprising one or more terminal —
OH, —
NH2, triazole, tetrazole, or sugar groups;
or a salt thereof, wherein each R is a hydrocarbon moiety having from 1 to about 6 carbon atoms and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol, and d is an integer from 0 to about 20; and(i-c) when m is 3, at least one X1 or X2 is not —
COOH;(ii) p —
X3 groups bonded to the fullerene core, wherein;(ii-a) p is an integer from 1 to 18, inclusive; and (ii-b) each —
X3 is independently selected from —
N+(R2)(R3)(R4), wherein R2, R3, and R4 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20;
—
N+(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
C(R5)(R6)(R7), wherein R5, R6, and R7 are independently —
COOH, —
H, —
CH(═
O), —
CH2OH, or a peptidyl moiety;
—
C(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
(CH2)e—
COOH, —
(CH2)e—
CONH2, —
(CH2)e—
COOR′
, wherein e is an integer from 1 to about 6 and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol;
a peptidyl moiety;
or an aromatic heterocyclic moiety containing a cationic nitrogen;(iii) q —
X4—
groups bonded to the fullerene core, wherein(iii-a) q is an integer from 1 to 6, inclusive; and (iii-b) each —
X4—
group is independently - View Dependent Claims (25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37)
-
-
38. A method of ameliorating damage to tissues for transplantation, ameliorating spoilage of food, inhibiting microbes, or reducing free radical levels in tobacco, comprising:
-
contacting the tissues for transplantation, the food, the microbes, or the tobacco with an effective amount of a composition comprising a substituted fullerene and a carrier, wherein the substituted fullerene comprises a fullerene core (Cn), wherein n is an even integer greater than or equal to 60, and at least one of i-iv; (i) m (>
CX1X2) groups bonded to the fullerene core, wherein;(i-a) m is an integer from 1 to 6, inclusive, (i-b) each X1 and X2 is independently selected from —
H;
—
COOH;
—
CONH2;
—
CONHR′
;
—
CONR′
2;
—
COOR′
;
—
CHO;
—
(CH2)dOH;
a peptidyl moiety;
—
R;
—
RCOOH;
—
RCONH2;
—
RCONHR′
;
—
RCONR′
2;
—
RCOOR′
;
—
RCHO;
—
R(CH2)dOH;
a heterocyclic moiety;
a branched moiety comprising one or more terminal —
OH, —
NH2, triazole, tetrazole, or sugar groups;
or a salt thereof, wherein each R is a hydrocarbon moiety having from 1 to about 6 carbon atoms and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol, and d is an integer from 0 to about 20; and(i-c) when m is 3, at least one X1 or X2 is not —
COOH;(ii) p —
X3 groups bonded to the fullerene core, wherein;(ii-a) p is an integer from 1 to 18, inclusive; and (ii-b) each —
X3 is independently selected from —
N+(R2)(R3)(R4), wherein R2, R3, and R4 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20;
—
N+(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
C(R5)(R6)(R7), wherein R5, R6, and R7 are independently —
COOH, —
H, —
CH(═
O), —
CH2OH, or a peptidyl moiety;
—
C(R2)(R3)(R8), wherein R2 and R3 are independently —
H or —
(CH2)d—
CH3, wherein d is an integer from 0 to about 20, and each R8 is independently —
(CH2)f—
SO3−
, —
(CH2)f—
PO4−
, or —
(CH2)f—
COO−
, wherein f is an integer from 1 to about 20;
—
(CH2)e—
COOH, —
(CH2)e—
CONH2, —
(CH2)e—
COOR′
, wherein e is an integer from 1 to about 6 and each R′
is independently a hydrocarbon moiety having from 1 to about 6 carbon atoms, an aryl-containing moiety having from 6 to about 18 carbon atoms, a hydrocarbon moiety having from 1 to about 6 carbon atoms and a terminal carboxylic acid or alcohol, or an aryl-containing moiety having from 6 to about 18 carbon atoms and a terminal carboxylic acid or alcohol;
a peptidyl moiety;
or an aromatic heterocyclic moiety containing a cationic nitrogen;(iii) q —
X4—
groups bonded to the fullerene core, wherein(iii-a) q is an integer from 1 to 6, inclusive; and (iii-b) each —
X4—
group is independently
-
Specification