Molecular Recognition of DNA Intercalators at Nanomolar Concentration in Water

• Published in: Journal of the American Chemical Society Vol. 123; no. 26; pp. 6459 - 6460
• Main Authors: Mizutani, Tadashi, Wada, Kenji, Kitagawa, Susumu
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 04.07.2001
• Subjects: Acridines - chemistry; Catalysis; Cations - chemistry; DNA - chemistry; Intercalating Agents - chemistry; Ligands; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Conformation; Molecular Structure; Palladium - chemistry; Porphyrins - chemistry; Spectrophotometry, Ultraviolet; Water - chemistry; Zinc - chemistry
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja015641o

The development of artificial receptors capable of binding to biologically active molecules with high affinity and high selectivity, and understanding the underlying principles of recognition are an intriguing subject of chemistry. For rational design of receptor/ligand interactions, there have been several attempts to evaluate contributions of functional groups or constituent atoms to the binding free energy, using compiled data of enzyme inhibitor, antibody-antigen, and protein-ligand binding. To gain deeper insight into recognition interactions, studies using synthetic receptors are desirable since systematic variation of the functional groups is possible while controlling conformation of the receptors. Although our knowledge of the recognition mechanism is still limited, a number of studies suggested that a larger receptor-guest contact surface area would result in a greater driving force from receptor/guest interactions and desolvation processes. We report here that bisporphyrin-based synthetic receptors, having a large contact surface area with guest, bind to DNA intercalators such as acridine orange, DAPI, and ethidium bromide with unprecedented affinity in water.