Triazine-based detoxification agents and their use
View Patent ↗An affinity ligand-matrix conjugate comprises the matrix and conjugated thereto by the group Z, a ligand having general formula (I): wherein one X is N and the other X is N, CCL or CCn; A 1 and A 2 are each independently O, S or N—R 1 and R 1 is H, C 1-6 alkyl, C 1-6 hydroxyalkyl, benzyl or β-phenylethyl; B 1 and B 2 are each independently an optionally substituted hydrocarbon linkage containing from 1 to 10 carbon atoms; D 1 is H or a primary amino, secondary amino, tertiary amino, quaternary ammonium, imidazole, guanidine or amidino group; and D 2 is a secondary amino, tertiary amino, quaternary ammonium, imidazole, guanidine or amidino group; or B 2 —D 2 is —CHCOOH—(CH 2 ) 3-4 —NH 2 ; and p is 0 or 1. Such conjugates are useful for the separation, isolation, purification, characterization, identification or quantification of an endotoxin.
1. An affinity ligand-matrix conjugate comprising the matrix and, conjugated thereto by the group Z, a ligand having the general formula (I):
wherein one X is N and the other X is N, CCl or CCN;
A 1 is O, S or N—R 1 and R 1 is H, C 1-6 alkyl, C 1-6 hydroxyalkyl, benzyl or β-phenylethyl;
A 2 is NH;
B 1 is an optionally substituted hydrocarbon linkage containing from 1 to 10 carbon atoms;
B 2 is —CHCOOH—(CH 2 ) 1-4 —;
D 1 is H or a primary amino, secondary amino, tertiary amino, quaternary ammonium, imidazole, guanidine or amidino group; and
D 2 is a secondary amino, tertiary amino, quaternary ammonium, imidazole, guanidine or amidino group; or
B 2 —D 2 is —CHCOOH—(CH 2 ) 3-4 —NH 2 ; and
p is 0 or 1.
2. The conjugate according to claim 1 , wherein A 1 is N—R 1 wherein R 1 is H, C 1-6 alkyl, C 1-6 hydroxyalkyl, benzyl or β-phenylethyl.
3. The conjugate according to claim 1 , wherein B 1 is —CHCOOH—(CH 2 ) 1-4 — or a divalent ethyl, propyl, 2-hydroxypropyl, butyl, pentyl, hexyl, phenyl, naphthyl or cyclohexyl group.
4. The conjugate according to claim 1 , wherein D 1 is H, amino, imidazolyl, guanidine, aminidino, trimethylammonium, triethylammonium, dimethylamino, diethylamino, methylamino or ethylamino.
5. The conjugate according to claim 1 , wherein p is 1.
6. The conjugate according to claim 1 , wherein Z is
—T—[L—V] m — (II)
wherein T is O, S or NR 2 and R 2 is H or C 1-6 alkyl;
V is O, S, —COO—, CONH, NHCO, —PO 3 H—, NH-arylene-SO 2 —CH 2 —CH 2 — or N—R 3 and R 3 is H or C 1-6 alkyl;
L is an optionally substituted hydrocarbon linkage containing from 2 to 20 carbon atoms; and
m is 0 or 1.
7. The conjugate according to claim 6 , wherein T is O or NH.
8. The conjugate according to claim 6 , wherein m is 1 and V is O, —CONH—, —NHCO— or N—R 3 .
9. The conjugate according to claim 8 , wherein Z—M (M being the matrix) is —NH—(CH 2 ) 4-10 —NH—M.
10. The conjugate, according to claim 1 , wherein P is 1, A 1 is NH and B 1 is —CHCOOH—(CH 2 ) 1-4 .
11. An affinity ligand-matrix conjugate comprising the matrix and, conjugated thereto by the group Z, a ligand having the general formula (I):
wherein one X is N and the other X is N, CCl or CCN;
A 1 is NH;
A 2 is NH;
B 1 is —CHCOOH—(CH 2 ) 1-4 —;
B 2 is —CHCOOH—(CH 2 ) 1-4 —;
D 1 is H or a primary amino, secondary amino, tertiary amino, quaternary ammonium, imidazole, guanidine or amidino group; and
D 2 is a secondary amino, tertiary amino, quaternary ammonium, imidazole, guanidine or amidino group; or
B 2 —D 2 is —CHCOOH—(CH 2 ) 3-4 —NH 2 ; and
p is 1.