A series of meso-tris(N-methyl-pyridiniumyl)-(4-alkylamidophenyl) porphyrins: Synthesis,interaction with DNA and antibacterial activity |
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| Institution: | 1. Department of Chemistry, University of Idaho, Moscow, ID 83844, USA;2. Department of Microbiology, Molecular Biology and Biochemistry, University of Idaho, Moscow, ID 83844, USA;3. Institute of Bioorganic Chemistry, Siberian Division of Russian Academy of Sciences, 630090 Novosibirsk, Russia;1. College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China;2. School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang 110016, China;3. PDT Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Republic of Korea;4. Department of Biomedicinal Chemistry and Institute of Basic Science, Inje University, Gimhae 621-749, Republic of Korea;1. Department of Food Technology, University Putra Malaysia, 43400 Serdang, Selangor, Malaysia;2. Department of Food Science, University Putra Malaysia, 43400 Serdang, Selangor, Malaysia;3. Laboratory of Natural Products, Institute of Bioscience, University Putra Malaysia, 43400 Serdang, Selangor, Malaysia;1. State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Microelectronics and Solid-State Electronics, University of Electronic Science and Technology of China, Chengdu 610054, PR China;2. School of Physical Electronics, University of Electronic Science and Technology of China, Chengdu 610054, PR China;3. State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China;1. College of Science, Hebei University of Engineering, Handan 056038, China;2. Department of Composite Materials and Engineering, College of Equipment Manufacturing, Hebei University of Engineering, Handan 056038, China;1. Augustana College, 2001 S. Summit Ave., Sioux Falls, SD 57197, United States;2. University of South Dakota, 414 E. Clark St., Vermillion, SD 57069, United States |
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| Abstract: | A series of meso-5,10,15-tris(N-methyl-4-pyridiniumyl)-20-(4-alkylamidophenyl) porphyrins were synthesized by derivatizing the amino group on the phenyl ring with the following hydrophobic groups: –C(O)C7F15, –C(O)CHCH2, C(O)CH3, –C(O)C7H15, and –C(O)C15H31. The cationic tris-pyridiumyl porphyrin core serves as a DNA binding motif and a photosensitizer to photomodify DNA molecules. The changes of the UV–Vis absorption spectra during the titration of these porphyrins with calf thymus DNA revealed a large bathochromic shift (up to 14 nm) and a hypochromicity (up to 55%) of the porphyrins Soret bands, usually considered as proof of porphyrin intercalation into DNA. Association constants (K) calculated according to the McGhee and von Hippel model, were in the range of 106–107 M−1. An increase in hydrophobicity of the substituents at the 20−meso-position produced higher binding affinity. These porphyrins caused photomodification of the supercoiled plasmid DNA when a green laser beam at 532 nm was applied. Those with higher surface activity acted more efficiently as DNA photomodifiers. The porphyrin with a perfluorinated alkyl chain (–COC7F15) at the meso-20-position inhibited the growth of gram-positive bacteria (S. aureus, or S. epidermidis). Other porphyrins exhibited moderate activity against both gram-negative and gram-positive organisms. |
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