| US 7,576,205 B2 | ||
| Detectable threading intercalator | ||
| Zhiqiang Gao, Singapore (Singapore); Hong Xie, Singapore (Singapore); and Fang Xie, Sydney (Australia) | ||
| Assigned to Agency for Science, Technology & Research, Singapore (Singapore) | ||
| Filed on Jun. 13, 2005, as Appl. No. 11/152,495. | ||
| Prior Publication US 2006/0281922 A1, Dec. 14, 2006 | ||
| Int. Cl. C07F 15/00 (2006.01); C12Q 1/68 (2006.01) | ||
| U.S. Cl. 546—10 [435/6; 546/2; 546/66] | 17 Claims |
| 1. A threading intercalator of general formula I:
IG1-DG-IG2-(DG-IG3)n (I)
wherein
IG1, IG2 and IG3 are the same or different and each of IG1, IG2 and IG3 is an intercalating group that is a naphthalene imide derivative or a naphthalene diimide derivative, with at least one of
IG1, IG2 and IG3 being a napthalene diimide derivative having a structure of formula V:
 R1 is a group which is capable of forming a coordinative bond with the detectable group and has a structure of formula IV:
—R6-AG (IV)
wherein
R6 is a branched or unbranched, saturated or unsaturated C1-C10 alkylene; or a branched or unbranched, saturated or unsaturated C1-C10 heteroalkylene having from 1 to 3 heteroatoms selected from the group consisting of N, O, S and P; and
AG is a saturated or unsaturated 5 to 10-membered heterocyclic group having from 1 to 3 heteroatoms selected from the groups
consisting of N, O, S and P;
R2 is H, NR3R4, CONR3R4, COOR5, an optionally branched C1-C10 alkyl or an optionally branched C2-C10 alkene, which C1-C10 alkyl and C2-C10 alkene are optionally substituted by one or more substituents selected from the group consisting of (i) a 5 to 10 membered
heterocyclic group having from 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P; (ii) a C5-C14 saturated or unsaturated cyclic group; (iii) a C6-C14 aryl group; (iv) NR3R4; (v) CONR3R4; and (vi) COOR5;
R3, R4 and R5 are each independently selected from the group consisting of H, C1-C6 alkyl and C2-C6 alkene, and when the R2 group contains a N atom, R2 optionally forms a salt;
DG is a catalytic, electrochemical, a chemiluminescent or an electrochemiluminescent detectable group having a structure of
formula II:
-M[(L)n′]- (II)
wherein
M represents a metal selected from the group consisting of Ru, Fe, Co, Cu and Os;
L is a coordinative binding ligand that is a C5-C30 heterocyclic group comprising from 1 to 6 heteroatoms selected from the group consisting of N, O, S and P, optionally substituted
by 1 to 6 groups independently selected from C1-C6 alkyl, C2-C6 alkene and halogen; and
n′ is an integer from 1 to 6; and
n is 0 or 1.
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