An anthraquinone compound of formula I (such as the compounds of formulae II to X) and processes for making the same are provided. Pharmaceutical compositions for use in the treatment of cancer, optionally in combination with an agent capable of reducing the level of oxygenation of a tumor, are also provided. Additionally, an option for combination with chemotherapeutic and radiotherapeutic modalities to enhance overall tumor cell kill is provided. Methods for the detection of cellular hypoxia, both in vivo and in vitro, are additionally provided. ##STR00001##

An anthraquinone compound of formula I (such as the compounds of formulae II to X) and processes for making the same are provided. Pharmaceutical compositions for use in the treatment of cancer, optionally in combination with an agent capable of reducing the level of oxygenation of a tumor, are also provided. Additionally, an option for combination with chemotherapeutic and radiotherapeutic modalities to enhance overall tumor cell kill is provided. Methods for the detection of cellular hypoxia, both in vivo and in vitro, are additionally provided. ##STR00001##

The present invention provides di-substituted acetalanthraquinone-based compounds of the Formulae (l)-(IV) that are useful for cellular staining and for light-based detection of biological material, e.g. fluorescence-based detection of biological material. These compounds may be used in hydrolysed or non-hydrolysed form. Also provided is a fluorescent complex that comprises a nucleic acid and an acetalanthraquinone-based compound of the invention; and a method of staining a biological sample comprising cells or other biological material containing nucleic acid, which method comprises contacting the biological sample with an acetalanthraquinone-based compound of the invention. In the Formulae (l)-(IV), A and B are each independently of formula R.sup.aCH.sub.2CH(OR.sup.b).sub.2; or one of A and B is of formula R.sup.aCH.sub.2CH(OR.sup.b).sub.2 and the other one is of formula: NR.sup.b.sub.2.

##STR00001##

An anthraquinone compound represented by formula (1): (where R.sub.1 and R.sub.4 represent H, a C1-C12 alkyl group, a C1-C12 alkyl group, a halogen atom, CO.sub.2R.sub.9, OCOR.sub.9, COR.sub.9, a cyano group, or CF.sub.3, R.sub.2, R.sub.3, R.sub.5 and R.sub.6 represent H, a C1-C4 alkyl group, a C1-C4 alkoxy group, a halogen atom, CO.sub.2R.sub.9, OCOR.sub.9, COR.sub.9, a cyano group, or CF.sub.3. R.sub.7 and R.sub.8 represent H, a C1-C12 alkyl group, or a C1-C12 alkoxy group. R.sub.9 represents a C1-C12 alkyl group, or a substituent represented by formula (a) (where R.sub.10 represents H, a C1-C8 alkyl group, or a C1-C8 alkoxy group) or formula (b) (where R.sub.11 represents H or a C1-C8 alkyl group); however, at least one of R.sub.1 through R.sub.6 represents a halogen atom, CO.sub.2R.sub.9, COR.sub.9, a cyano group, or CF.sub.3).

##STR00001##

An anthraquinone compound represented by formula (1) (In the formula, R.sub.1 and R.sub.4 represent a hydrogen atom, a C1-12 alkyl group, a C1-12 alkoxy group, a halogen atom, CO.sub.2R.sub.9, OCOR.sub.9, COR.sub.9, a cyano group, or a trifluoromethyl group. R.sub.2, R.sub.3, R.sub.5, and R.sub.6 represent a hydrogen atom, a C1-4 alkyl group, a C1-4 alkoxy group, a halogen atom, CO.sub.2R.sub.9, OCOR.sub.9, COR.sub.9, a cyano group, or a trifluoromethyl group, R.sub.7 and R.sub.8 represent a hydrogen atom or a C1-8 alkyl group. R.sub.9 represents a C1-12 alkyl group, a substituent represented by formula (a) (in the formula, R.sub.10 represents a hydrogen atom, a C1-8 alkyl group, or a C1-8 alkoxy group), or a substituent represented by formula (b) (in the formula, R.sub.11 represents a hydrogen atom or a C1-8 alkyl group)).

##STR00001##

Disclosed are near IR emitting fluorescent compounds; methods of making and kits containing the described compounds; and their use in fluorescence-based detection of biological materials.