Department of Chemistry, Islamic Azad University, Central Tehran Branch (IAUCTB), Tehran, Iran.
J Photochem Photobiol B. 2012 Dec 5;117:207-13. doi: 10.1016/j.jphotobiol.2012.09.016. Epub 2012 Oct 11.
Homoisoflavonoids (3-benzylidenechroman-4-ones) are related to flavonoids and occur as natural products and exhibit biological activity. These compounds have been reported to possess antioxidant, antifungal, hypocholesterolemic, antimutagenic and antiviral activities. This study was designed to examine the interactions of four synthetic homoisoflavonoids (BMC, BPC, HBC and HBMC) with calf-thymus DNA in aqueous solution at physiological conditions, using constant DNA concentration (6.25 mM) and various homoisoflavonoids/polynucleotide (phosphate) ratios of 1/120, 1/80, 1/40, 1/20, 1/10 and 1/5. Fourier transform infrared (FTIR) and UV-Visible spectroscopic methods were used to determine the ligand binding modes, the binding constants and the stability of homoisoflavonoids-DNA complexes in aqueous solution. Spectroscopic evidence showed major binding of homoisoflavonoids to DNA with overall binding constants of K(BMC-DNA)=9.37(± 0.34)× 10(3)M(-1), K(BPC-DNA)=1.8(± 0.09)× 10(4)M(-1), K(HBC-DNA)=1.3(± 0.19)× 10(3)M(-1) and K(HBMC-DNA)=4.7(± 0.41)× 10(3)M(-1). The affinity of homoisoflavonoids-DNA binding is in the order of BPC>BMC>HBMC>HBC. No biopolymer secondary structural changes were observed upon homoisoflavonoids interaction and DNA remains in the B-family structure in these complexes.
同型异黄酮（3-亚苄基色满-4-酮）与类黄酮有关，作为天然产物存在，并具有生物活性。这些化合物已被报道具有抗氧化、抗真菌、降胆固醇、抗突变和抗病毒活性。本研究旨在在生理条件下，使用恒定的 DNA 浓度（6.25mM）和各种同型异黄酮/多核苷酸（磷酸盐）比为 1/120、1/80、1/40、1/20、1/10 和 1/5，检查四种合成同型异黄酮（BMC、BPC、HBC 和 HBMC）与小牛胸腺 DNA 在水溶液中的相互作用。傅里叶变换红外（FTIR）和紫外可见光谱法用于确定配体结合模式、结合常数和同型异黄酮-DNA 复合物在水溶液中的稳定性。光谱证据表明同型异黄酮主要与 DNA 结合，其总结合常数为 K（BMC-DNA）=9.37（±0.34）×10（3）M（-1），K（BPC-DNA）=1.8（±0.09）×10（4）M（-1），K（HBC-DNA）=1.3（±0.19）×10（3）M（-1）和 K（HBMC-DNA）=4.7（±0.41）×10（3）M（-1）。同型异黄酮-DNA 结合的亲和力顺序为 BPC>BMC>HBMC>HBC。同型异黄酮相互作用后未观察到生物聚合物二级结构发生变化，这些复合物中 DNA 仍保持 B 型结构。
