Electrochemically active ligand for sequence-specific...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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07863455

ABSTRACT:
The purpose of the present invention is to provide a compound that specifically binds to the base sequence of a double-stranded nucleic acid molecule. The compound can reduce the electrochemical signal
oise ratio (S/N) in electrochemical detection, and as a result, the detection sensitivity (precision) will be greatly improved so as to enable the determination of an ultratrace amount of nucleic acid molecule. The present invention relates to a ferrocene compound represented by the following general formula (I):wherein “A” represents a divalent ferrocene-containing linker or ferrocene-1,1′-yl, R2represents a hydrogen atom or alkyl; “n” and “m” represent any natural numbers; and “V” and “X” represent the pyrrole-imidazole-polyamide (PIPA); to a ligand consisting of said ferrocene compound for sequence-specific detection of double-stranded nucleic acid molecules; to a method for electrochemical detection of double-stranded nucleic acid molecules 8 with the use of said ligand; and to an apparatus or device for the electrochemical detection with the use of said ligand.

REFERENCES:
patent: 2002/0068294 (2002-06-01), Takenaka
patent: 2002/0117396 (2002-08-01), Pak et al.
patent: 2003-000300 (2003-01-01), None
patent: 2003-83968 (2003-03-01), None
patent: WO-00/31750 (2000-06-01), None
Kohji Seio et al.; Synthesis and Properties of a Pyrrole-imidazole Polyamide Having a Ferrocene Dicarboxilic Amide Linker; Tetrahedron Letters, 2004, 45 (36); pp. 1-4.
Markus Scherer et al.; A bridged pyrrolic ansa-ferrocene. A new type of anion receptor, Chemical Communications, 1998, 1, pp. 85-86.
Jahyo Kang et al.; Preparation of bis [palladacycles[ and application to asymmetric aza-Claisen rearrangement of allylic imidates, Tetrahedron Letters, 2002, 43 (52), 9509-9512.
Chunhai Fan et al.; Electrochemical interrogation of conformational changes as a reagentless method for the sequence-specific detection of DNA; A. J. Proc. Natl. Acad. Sci., Aug. 5, 2003, vol. 100, No. 16, pp. 9134-9137.
Milan Mrksich; Hairpin Peptide Motif. A New Class of Oligopeptides for Sequence-Specific Recognition in the Minor Groove of Double-Helical DNA; J. Am. Chem. Soc., 1994, No. 116, pp. 7983-7988.
Victor C. Rucker et al.; Sequence Specific Fluorescence Detection of Double Strand DNA; J. Am. Chem. Soc., 2003, No. 125, pp. 1195-1202.
Yong-Dong Wang et al.; DNA crosslinking and biological activity of a hairpin polyamidechlorambucil conjugate; Nucleic Acids Research, vol. 31, No. 4, 2003.
Shane Foister et al.; Shape Selective Recognition of T-A Base Pairs by Hairpin Polyamides Containing N-Terminal 3-Methoxy (and 3-Chloro) Thiophene Residues; Bioorganic & Medicinal Chemistry, No. 11, 2003, pp. 4333-4340.

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