Photo-physical behavior of some antitumor anthracycline in solvent media with different polarity M.S. Zakerhamidi a,⇑ , M. Johari-Ahar b , S.M. Seyed Ahmadian c , R. Kian a,c a Research Institute for Applied Physics and Astronomy, University of Tabriz, Tabriz, Iran b Research Center for Pharmaceutical Nanotechnology, Tabriz University of Medical Science, Tabriz, Iran c Department of Chemistry, Faculty of Basic Sciences, Azarbaijan Shahid Madani University, BP 5375171379 Tabriz, Iran highlights  Self-aggregation of aglycone moiety show main change in solvatochromism of anthracycline.  Intramolecular charge-transfer takes place in all three anthracycline samples.  Reorientation of doxorubicin and epirubicin molecular functions in polar environment increases.  Idarubicin’s functional groups reorientation increases in hydrogen bond donor media. graphical abstract article info Article history: Received 22 January 2014 Received in revised form 30 March 2014 Accepted 7 April 2014 Available online 21 April 2014 Keywords: Anthracycline Stereoisomer Linear solvation energy relationship Solvent polarity scale Dipole moment Intramolecular hydrogen bonding abstract Absorption and emission spectra of three antitumour anthracyclines, with various substituent and stereoisomer groups, were studied in different solvents. The solute’s photo-physical behavior strongly depends on solvent–solute interactions and solvent’s nature. Solvatochromic method was used to inves- tigate dipole moments of these materials in ground and excited states. Spectral variations were analyzed via means of linear solvation energy relationships concept, proposed by Kamlet and Taft. The results explain the nature of specific and non-specific solvent–solute interactions and functional groups’ reorientation of studied anthracyclines in different media. Ó 2014 Elsevier B.V. All rights reserved. Introduction Anthraquinones (AQ) are one of the largest and most important classes of organic compounds in nature [1]. Anthraquinones deriv- atives have several industrial, biological and pharmaceutical appli- cations [1–9]. The hydroxy anthraquinone chromophore has biological activity in several antitumour anthracyclines [2–4]. Antitumour anthracycline is the most useful group of cytotoxic anticancer drugs, which are commonly used in cancer chemother- apy. They have anthraquinone skeleton and aglycone ring coupled with amino sugar. The disparate substitute in these materials creates unique properties, such as intercalate between DNA, interfering in transcription and replication [5–8]. The molecular activity and medicinal properties of anthracy- cline derivatives can be determined through stereoisomerism and http://dx.doi.org/10.1016/j.saa.2014.04.048 1386-1425/Ó 2014 Elsevier B.V. All rights reserved. ⇑ Corresponding author. Tel.: +98 411 3393003; fax: +98 411 3347050. E-mail address: Zakerhamidi@tabrizu.ac.ir (M.S. Zakerhamidi). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 130 (2014) 257–262 Contents lists available at ScienceDirect Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy journal homepage: www.elsevier.com/locate/saa