1-Amino-4-hydroxy-9,10-anthraquinone – An analogue of anthracycline anticancer drugs, interacts with DNA and induces apoptosis in human MDA-MB-231 breast adinocarcinoma cells: Evaluation of structure–activity relationship using computational, spectroscopic and biochemical studies

Abstract

The X-ray diffraction and spectroscopic properties of 1-amino-4-hydroxy-9,10-anthraquinone (1-AHAQ), a simple analogue of anthracycline chemotherapeutic drugs were studied by adopting experimental and computational methods. The optimized geometrical parameters obtained from computational methods were compared with the results of X-ray diffraction analysis and the two were found to be in reasonably good agreement. X-ray diffraction study, Density Functional Theory (DFT) and natural bond orbital (NBO) analysis indicated two types of hydrogen bonds in the molecule. The IR spectra of 1-AHAQ were studied by Vibrational Energy Distribution Analysis (VEDA) using potential energy distribution (PED) analysis. The electronic spectra were studied by TDDFT computation and compared with the experimental results. Experimental and theoretical results corroborated each other to a fair extent. To understand the biological efficacy of 1-AHAQ, it was allowed to interact with calf thymus DNA and human breast adino-carcinoma cell MDA-MB-231. It was found that the molecule induces apoptosis in this adinocarcinoma cell, with little, if any, cytotoxic effect in HBL-100 normal breast epithelial cell.

Synthesis of Diamino Benzoquinones using Facile and One-Pot Chemical Oxidative Method

“…Quinones based amino derivatives, considered as the critical constituents in synthesizing a wide variety of natural products, medicinal compounds [1][2][3][4] applying antitumor and antimalarial activities [5][6][7][8] are typically supplied by alternative, multistep synthetic pathways 9 .…”

A Co(III) Complex of 1-Amino-4-hydroxy-9,10-anthraquinone Exhibits Apoptotic Action against MCF-7 Human Breast Cancer Cells

“…The absorption spectrum of QH (Figure a) in 30% ethanol , shows four absorption bands (at 250, 290, 530, and 565 nm) due to π–π* and n−π* transitions of its various tautomeric forms in rapid equilibrium in aqueous solution. ,, From the UV–vis spectrum of CoQ 3 (Figure b), it is clear that the absorption peaks at 250, 290, 530, and 565 nm remain almost unaltered, which indicate that the electronic absorption spectrum of CoQ 3 depends weakly on the nature of the metal and is primarily defined by the ligand (QH) . However, the appearance of a new peak at 600 nm is characteristic of the complex (CoQ 3 ).…”

“…Anthracycline drugs are anticancer agents used in treating different forms of human carcinoma. − Although they enjoy wide acceptance in chemotherapy, their use is often questioned for the associated cardiotoxicity and high cost involved, particularly for people from economically weaker sections of the society. Hence, there is an effort worldwide − to find alternative cheaper analogues that are less cardiotoxic. − These are either derivatives of anthracyclines that are less costly or their simpler analogues. − …”

Solubility of Cinnarizine in (Transcutol + Water) Mixtures: Determination, Hansen Solubility Parameters, Correlation, and Thermodynamics

“…The mathematical correlation of experimental data of pharmaceutical compounds is important for practical predictions/validations [20,33,39,40]. As a result, the measured solubility values of CNZ were predicted using the modified "Apelblat, van't Hoff, Yalkowsky-Roseman, Jouyban-Acree, and Jouyban-Acree-van't Hoff models" [18][19][20][24][25][26][27].…”