Effect of binding mode on the photoluminescence of CTMA–DNA doped with (E)-2-(2-(4-(diethylamino)styryl)-4H-pyran-4-ylidene)malononitrile

Abstract Purified natural DNA extracted from Salmon sperm can only be dissolved in water; it is not soluble in any other organic solvent. Therefore, in this study, the structure of DNA was modified and its solubility was changed. The preparation of organic-soluble DNA was carried out by precipitating the purified DNA in water with the cationic surfactant cetyltrimethylammonium chloride (CTMA). The resulting DNA–lipid complex shows good solubility in alcohol, which allows the fabrication of thin films for studying the photophysical properties of DNA in a solid state. The absorption and photoluminescence (PL) behaviors of CTMA–DNA and polymethylmethacrylate (PMMA) doped with ( E )-2-(2-(4-(diethylamino)styryl)-4 H -pyran-4-ylidene)malononitrile (DCM) were investigated. In addition, different PL spectral behaviors with differing concentrations of DCM in two different host materials were observed. These behaviors were explained by a mechanism based on intercalation or groove binding of fluorescent dye into the base pairs or aliphatic side-chain moieties of CTMA–DNA.

[1]  Emily M. Heckman,et al.  DNA Photonics [Deoxyribonucleic Acid] , 2005 .

[2]  ANDREW J. STECKL,et al.  DNA – a new material for photonics? , 2007 .

[3]  F. Crick,et al.  Molecular Structure of Nucleic Acids: A Structure for Deoxyribose Nucleic Acid , 1953, Nature.

[4]  James G. Grote,et al.  Organic field-effect transistors and memory elements using deoxyribonucleic acid (DNA) gate dielectric , 2007 .

[5]  Chulhun Kang,et al.  Fluorescent Hydrophobic Probes Based on Intramolecular Charge Transfer State for Sensitive Protein Detection in Solution , 2004 .

[6]  L. A. Lipscomb,et al.  Structure of DNA-porphyrin complex. , 1996, Biochemistry.

[7]  M R Arkin,et al.  Fast photoinduced electron transfer through DNA intercalation. , 1994, Proceedings of the National Academy of Sciences of the United States of America.

[8]  D. Odom,et al.  Recognition and reaction of metallointercalators with DNA. , 1999, Chemical reviews.

[9]  Hoi Sing Kwok,et al.  Molecular packing and aggregation-induced emission of 4-dicyanomethylene-2,6-distyryl-4H-pyran derivatives , 2006 .

[10]  J. Barton,et al.  On demonstrating DNA intercalation , 1990 .

[11]  Anne Condon,et al.  Designed DNA molecules: principles and applications of molecular nanotechnology , 2006, Nature Reviews Genetics.

[12]  F. Fraternali,et al.  The p73 DNA binding domain displays enhanced stability relative to its homologue, the tumor suppressor p53, and exhibits cooperative DNA binding. , 2008, Biochemistry.

[13]  James G. Grote,et al.  Enhanced emission efficiency in organic light-emitting diodes using deoxyribonucleic acid complex as an electron blocking layer , 2006 .

[14]  Jacqueline K. Barton,et al.  LONG-RANGE TRIPLET ENERGY TRANSFER BETWEEN METALLOINTERCALATORS TETHERED TO DNA : IMPORTANCE OF INTERCALATION, STACKING, AND DISTANCE , 1998 .

[15]  A. Steckl,et al.  Photoluminescence and lasing from deoxyribonucleic acid (DNA) thin films doped with sulforhodamine. , 2007, Applied optics.

[16]  David J. S. Birch,et al.  The fluorescence properties of DCM , 1991 .

[17]  Robert Langer,et al.  Tumor-targeted gene delivery using molecularly engineered hybrid polymers functionalized with a tumor-homing peptide. , 2008, Bioconjugate chemistry.