Anthraquinone and its derivatives

Chemistry: molecular biology and microbiology – Measuring or testing process involving enzymes or...

Reexamination Certificate

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C435S006120, C514S644000, C552S236000, C552S237000, C552S249000

Reexamination Certificate

active

07060427

ABSTRACT:
There is disclosed a compound of formula (I) wherein each of X1and X2are independently NH—A—NR1R2, and wherein A is A C2-8alkylene and R1and R2are independently selected from hydrogen, C1-4alkyl, C2-4hydroxy-alkyl and C2-4aminoalkyl, or R1and R2together form a C2-6alkylene group which with the nitrogen atom to which R1and R2are attached forms a heterocyclic ring, or an N-oxide derivative thereof, and wherein the compound (I) or its N-oxide derivative is optionally in the form of an acid salt derived from an organic or inorganic acid. Also disclosed is a method of its production and its uses, including its use in analyzing a cell or biological material and detecting the emitted fluorescence signal.

REFERENCES:
patent: 4410524 (1983-10-01), Murdock
patent: 5132327 (1992-07-01), Patterson
patent: 6468753 (2002-10-01), Smith et al.
patent: 2 237 283 (1991-05-01), None
patent: WO 91 05824 (1991-05-01), None
Paul J. Smith et al., “Flow Cytometric Analysis and Confocal Imaging of Anticancer Alkylaminoathraquinones and Their N-Oxides in Intact Human Cells Using 647-nm Krypton Laser Excitation,” Cytometry, vol. 27, No. 1, 1997, pp. 43-53.
Paul J. Smith et al., “DNA topoisomerase II-dependent cytotoxicity of alkylaminoanthraquinones and their N-oxides,” Cancer Chemotherapy and Pharmacology, vol. 39, No. 5, 1997, pp. 455-461.
Laurence H. Patterson, “Rationale for use of aliphatic N-oxides of cytotoxic anthraquinones as prodrug DNA binding agents: a new class of bioreductive agent,” Cancer and Metastatis Reviews, vol. 12, 1993, pp. 119-134.
WR Wilson et al., “Tertiary anime N-oxides as bioreductive drugs: DACA N-oxide, nitracine N-oxide and AQ4N,” British Journal of Cancer, vol. 74, 1996, pp. 43-47.
Laurence H. Patterson et al., “Aliphatic Amine N-oxides of DNA Binding Agents as Bioreductive Drugs,” Oncology Research, V. 6, 1994, pp. 533-538.
SR McKeown et al, “AQ4N: an Alkylaminoanthraquinone N-oxide Showing Bioreductive Potential and Positive Interaction with Radiation in vivo,” British Journal of Cancer, 72, 1995 pp. 76-81.
SR McKeown et al., “Evidence for a Therapeutic Gain when AQ4N or Tirapazamine is Combined with Radiation,” British Journal of Cancer, 74, 1996, pp. S39-S42.
MV Hejmadi et al., “DNA Damage Following Combination of Radiation with the Bioreductive Drug AQ4N: Possible Selective Toxicity to Oxic and Hypoxic Tumour Cells,” British Journal of Cancer, 73, 1996, pp. 499-505.

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