Although generation of reactive oxygen species (ROS) by anthracycline anticancer drugs is essential for anti-tumor activity, they make these drugs cardiotoxic.

Anthracycline drugs show anticancer activity, an ability to inhibit DNA replication and RNA transcription but are costly. This study attempts to see if cheaper hydroxy‐9,10‐anthraquinones (1,2,4‐trihydroxy‐9,10‐anthraquinone) that structurally resemble anthracyclines mimic its biological interactions and whether it can be a suitable substitute. Proton dissociation at 298 K for THA, pK1 = 4.82 ± 0.05 (phenolic OH at C2) and particularly pK2 = 9.22 ± 0.05 (phenolic OH at C1 and C4) closely resemble those of the anthracyclines. THA undergoes a single step two‐electron reduction in aqueous media (pH 7.36) having E1/2 = −0.69 V and two successive single‐electron reduction in DMF having E1/2 values −0.70 V and −1.06 V, respectively. CV data showed quasi‐reversible nature of THA in aqueous media. E1/2 values of THA were comparable to anthracycline drugs suggesting similarity in redox behavior. Binding studies of THA to ct DNA using UV–Vis and fluorescence spectroscopy were analyzed. Intrinsic binding constant and site size of interaction were (4.80 ± 0.2) × 104 M−1 and (5.96 ± 0.3) bases, respectively. THA, approximately three to five times weaker in binding ct DNA than anthracycline anticancer drugs suggests a role for sugar moieties present in anthracyclines. Anti‐leukemic activity studies of THA on cultured MOLT‐4 cell lines were performed and apoptosis measured by MTT assay. Result indicates THA to be a potent inducer of apoptosis in MOLT‐4 cell line having an IC50 value of 33.8 µM. THA therefore possesses anti‐leukemic activity that is comparable to anthracyclines on P388 leukemia and the study reveals that 1,2,4‐trihydroxy‐9,10‐anthraquinone to be a suitable substitute to the costlier anthracyclines. Copyright © 2011 John Wiley & Sons, Ltd.

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