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H2D3:  A Cationic Porphyrin Designed to Intercalate into B-Form DNA (H2D3 = trans-Di(N-methylpyridium-3-yl)porphyrin)
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    H2D3:  A Cationic Porphyrin Designed to Intercalate into B-Form DNA (H2D3 = trans-Di(N-methylpyridium-3-yl)porphyrin)
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    Department of Chemistry, Purdue University West Lafayette, Indiana 47907-1393
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2001, 123, 46, 11480–11481
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    https://doi.org/10.1021/ja010005b
    Published October 26, 2001
    Copyright © 2001 American Chemical Society
    Copyright © 2001 American Chemical Society

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    This article is cited by 37 publications.

    1. Srijana Ghimire, Phillip E. Fanwick, and David R. McMillin . DNA-Binding Studies of a Tetraalkyl-Substituted Porphyrin and the Mutually Adaptive Distortion Principle. Inorganic Chemistry 2014, 53 (20) , 11108-11118. https://doi.org/10.1021/ic501683t
    2. Abby J. Gaier, Srijana Ghimire, Sarah E. Fix, and David R. McMillin . Internal Versus External Binding of Cationic Porphyrins to Single-Stranded DNA. Inorganic Chemistry 2014, 53 (11) , 5467-5473. https://doi.org/10.1021/ic403105q
    3. Matthew A. Bork, Christopher G. Gianopoulos, Hanyu Zhang, Phillip E. Fanwick, Jong Hyun Choi, and David R. McMillin . Accessibility and External versus Intercalative Binding to DNA As Assessed by Oxygen-Induced Quenching of the Palladium(II)-Containing Cationic Porphyrins Pd(T4) and Pd(tD4). Biochemistry 2014, 53 (4) , 714-724. https://doi.org/10.1021/bi401610t
    4. Breeze N. Briggs, Abby J. Gaier, Phillip E. Fanwick, Dilek K. Dogutan, and David R. McMillin . Cationic Copper(II) Porphyrins Intercalate into Domains of Double-Stranded RNA. Biochemistry 2012, 51 (38) , 7496-7505. https://doi.org/10.1021/bi300828z
    5. Shaun T. Mutter and James A. Platts . Density Functional Theory Studies of Interactions of Ruthenium–Arene Complexes with Base Pair Steps. The Journal of Physical Chemistry A 2011, 115 (41) , 11293-11302. https://doi.org/10.1021/jp2049487
    6. Janet Manono, Patricia A. Marzilli and Luigi G. Marzilli. New Porphyrins Bearing Positively Charged Peripheral Groups Linked by a Sulfonamide Group to meso-Tetraphenylporphyrin: Interactions with Calf Thymus DNA. Inorganic Chemistry 2009, 48 (13) , 5636-5647. https://doi.org/10.1021/ic900385y
    7. Konstantinos Gkionis, James A. Platts and J. Grant Hill. Insights into DNA Binding of Ruthenium Arene Complexes: Role of Hydrogen Bonding and π Stacking. Inorganic Chemistry 2008, 47 (9) , 3893-3902. https://doi.org/10.1021/ic702459h
    8. Kim Andrews and, David R. McMillin. A Pared-Down Version of 5,10,15,20-Tetra(N-methylpyridinium-4-yl)porphyrin Intercalates into B-Form DNA Regardless of Base Composition:  Binding Studies of Tri(N-methylpyridinium-4-yl)porphyrins. Biochemistry 2008, 47 (4) , 1117-1125. https://doi.org/10.1021/bi7018755
    9. Guy A. Hembury,, Victor V. Borovkov, and, Yoshihisa Inoue. Chirality-Sensing Supramolecular Systems. Chemical Reviews 2008, 108 (1) , 1-73. https://doi.org/10.1021/cr050005k
    10. Alexander H. Shelton,, Alison Rodger, and, David R. McMillin. DNA Binding Studies of a New Dicationic Porphyrin. Insights into Interligand Interactions. Biochemistry 2007, 46 (31) , 9143-9154. https://doi.org/10.1021/bi700293g
    11. Stephanie A. Bejune,, Alexander H. Shelton, and, David R. McMillin. New Dicationic Porphyrin Ligands Suited for Intercalation into B-Form DNA. Inorganic Chemistry 2003, 42 (25) , 8465-8475. https://doi.org/10.1021/ic035092i
    12. Hugo Morales-Rojas and, Eric T. Kool. A Porphyrin C-Nucleoside Incorporated into DNA. Organic Letters 2002, 4 (25) , 4377-4380. https://doi.org/10.1021/ol0267376
    13. Pavel Kubát,, Kamil Lang,, Vladimír Král, and, Pavel Anzenbacher, Jr.. Preprogramming of Porphyrin−Nucleic Acid Assemblies via Variation of the Alkyl/Aryl Substituents of Phosphonium Tetratolylporphyrins. The Journal of Physical Chemistry B 2002, 106 (26) , 6784-6792. https://doi.org/10.1021/jp014405x
    14. N. S. Lebedeva, E. S. Yurina. Porphyrins as polyfunctional ligands for binding to DNA. Prospects for application. Биоорганическая химия 2024, 50 (6) , 707-719. https://doi.org/10.31857/S0132342324060015
    15. N. Sh. Lebedeva, E. S. Yurina. Porphyrins as Polyfunctional Ligands for Binding to DNA. Prospects for Application (A Review). Russian Journal of Bioorganic Chemistry 2024, 50 (6) , 2567-2579. https://doi.org/10.1134/S1068162024060360
    16. Jianming Zhao, Jirong Shi, Xiangdan Meng, Chenchen Gong, Peng Wu, Zhou Yang, Haifeng Dong. ROS-Activated nanoscale coordination polymers for enhanced ultrasound-mediated therapy for the treatment of cancer. Acta Biomaterialia 2022, 143 , 372-380. https://doi.org/10.1016/j.actbio.2022.02.030
    17. Srijana Ghimire, Matthew A. Bork, Hanyu Zhang, Phillip E. Fanwick, Matthias Zeller, Jong Hyun Choi, David R. McMillin. DNA binding of Pd(TC3), a conformable cationic porphyrin with a long-lived triplet state. Dalton Transactions 2016, 45 (36) , 14277-14284. https://doi.org/10.1039/C6DT01918H
    18. Ping Zhao, Jin-Wang Huang, Liang-Nian Ji. DNA Binding and Photocleavage Study of Cationic Metalloporphyrins by Spectral Methods. Spectroscopy Letters 2011, 44 (3) , 211-220. https://doi.org/10.1080/00387010.2010.498032
    19. Sudeshna Bhattacharya, Gopa Mandal, Tapan Ganguly. Detailed spectroscopic investigations to reveal the nature of interaction of anionic porphyrin with calf thymus DNA. Journal of Photochemistry and Photobiology B: Biology 2010, 101 (1) , 89-96. https://doi.org/10.1016/j.jphotobiol.2010.06.016
    20. Ping Zhao, Jin-Wang Huang, Wen-Jie Mei, Juan He, Liang-Nian Ji. DNA binding and photocleavage specificities of a group of tricationic metalloporphyrins. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2010, 75 (3) , 1108-1114. https://doi.org/10.1016/j.saa.2009.12.065
    21. Ping Zhao, Lian-Cai Xu, Jin-Wang Huang, Kang-Cheng Zheng, Jie Liu, Han-Cheng Yu, Liang-Nian Ji. DNA binding and photocleavage properties of a novel cationic porphyrin-anthraquinone hybrid. Biophysical Chemistry 2008, 134 (1-2) , 72-83. https://doi.org/10.1016/j.bpc.2008.01.009
    22. Lin Wu, Peng Hu, Ying Xiao, Ming Zhang, Lixia Zhang, Xiaocheng Weng, Xiaojun Wu, Xiang Zhou, Xiaoping Cao. Synthesis and DNA‐Recognition and ‐Cleavage Properties of Multiply Charged Porphyrin Esters. Chemistry & Biodiversity 2008, 5 (1) , 153-161. https://doi.org/10.1002/cbdv.200890005
    23. Takashi Murashima, Kazuyuki Hayata, Yumi Saiki, Jun Matsui, Daisuke Miyoshi, Takashi Yamada, Toshifumi Miyazawa, Naoki Sugimoto. Synthesis, structure and thermal stability of fully hydrophobic porphyrin–DNA conjugates. Tetrahedron Letters 2007, 48 (48) , 8514-8517. https://doi.org/10.1016/j.tetlet.2007.09.147
    24. Yong Qin, Wen‐Hua Chen, Ji‐Yan Pang, Zhong‐Zhen Zhao, Liang Liu, Zhi‐Hong Jiang. DNA‐Binding Affinities and Sequence Specificities of Protoberberine Alkaloids and Their Demethylated Derivatives: A Comparative Study. Chemistry & Biodiversity 2007, 4 (2) , 145-153. https://doi.org/10.1002/cbdv.200790019
    25. Bo Chen, Song Wu, Aixiao Li, Feng Liang, Xiang Zhou, Xiaoping Cao, Zhike He. Synthesis of some multi-β-substituted cationic porphyrins and studies on their interaction with DNA. Tetrahedron 2006, 62 (23) , 5487-5497. https://doi.org/10.1016/j.tet.2006.03.041
    26. Song Wu, Zheng Li, Lige Ren, Bo Chen, Feng Liang, Xiang Zhou, Tao Jia, Xiaoping Cao. Dicationic pyridium porphyrins appending different peripheral substituents: Synthesis and studies for their interactions with DNA. Bioorganic & Medicinal Chemistry 2006, 14 (9) , 2956-2965. https://doi.org/10.1016/j.bmc.2005.12.011
    27. Jean-Philipe Tremblay-Morin, Hasrat Ali, Johan E. van Lier. Palladium catalyzed coupling reactions of cationic porphyrins with organoboranes (Suzuki) and alkenes (Heck). Tetrahedron Letters 2006, 47 (18) , 3043-3046. https://doi.org/10.1016/j.tetlet.2006.03.018
    28. Diana P. N. Gonçalves, Sylvain Ladame, Shankar Balasubramanian, Jeremy K. M. Sanders. Synthesis and G-quadruplex binding studies of new 4-N-methylpyridinium porphyrins. Org. Biomol. Chem. 2006, 4 (17) , 3337-3342. https://doi.org/10.1039/B608494J
    29. Premaladha Poddutoori, Prashanth Kumar Poddutoori, Bhaskar G. Maiya. Nucleobase (A, T, G and C) appended tri-cationic water-soluble porphyrins: synthesis, characterization, binding and photocleavage studies with DNA. Journal of Porphyrins and Phthalocyanines 2006, 10 (01) , 1-12. https://doi.org/10.1142/S1088424606000028
    30. Jean-Philipe Tremblay-Morin, Hasrat Ali, Johan E. van Lier. First example of a palladium catalyzed coupling reaction between cationic porphyrins and alkynyls in aqueous medium. Tetrahedron Letters 2005, 46 (41) , 6999-7002. https://doi.org/10.1016/j.tetlet.2005.08.054
    31. David R. McMillin, Alexander H. Shelton, Stephanie A. Bejune, Phillip E. Fanwick, Rebecca K. Wall. Understanding binding interactions of cationic porphyrins with B-form DNA. Coordination Chemistry Reviews 2005, 249 (13-14) , 1451-1459. https://doi.org/10.1016/j.ccr.2004.11.016
    32. Charles Michael Drain, Giorgio Bazzan, Tatjana Milic, Mikki Vinodu, John C. Goeltz. Formation and applications of stable 10 nm to 500 nm supramolecular porphyrinic materials. Israel Journal of Chemistry 2005, 45 (3) , 255-269. https://doi.org/10.1560/9QTD-B1GJ-K8J7-7YJR
    33. Song Wu, Ping Wang, Tian Tian, Lin Wu, Hanping He, Xiang Zhou, Xiaolian Zhang, Xiaoping Cao. Peripheral substituents of di(pyridiumyl)porphyrins affected on their interactions with DNA. Bioorganic & Medicinal Chemistry Letters 2004, 14 (10) , 2575-2577. https://doi.org/10.1016/j.bmcl.2004.02.083
    34. Bo Chen, Wen Qin, Ping Wang, Tian Tian, Hongjuan Ma, Xiaoping Cao, Xiaojun Wu, Xiang Zhou, Xiao-Lian Zhang, Fang Liu, Fang Zheng, Xia Li. Synthesis of β-substituted cationic porphyrins and their interactions with DNA. Bioorganic & Medicinal Chemistry Letters 2003, 13 (21) , 3731-3733. https://doi.org/10.1016/j.bmcl.2003.08.016
    35. Tomoko Yamamoto, Daryono Hadi Tjahjono, Naoki Yoshioka, Hidenari Inoue. Interaction of Dicationic Bis(imidazoliumyl)porphyrinatometals with DNA. Bulletin of the Chemical Society of Japan 2003, 76 (10) , 1947-1955. https://doi.org/10.1246/bcsj.76.1947
    36. Daniel T. Gryko, Mariusz Tasior. Simple route to meso-substituted trans-A2B2-porphyrins bearing pyridyl units. Tetrahedron Letters 2003, 44 (16) , 3317-3321. https://doi.org/10.1016/S0040-4039(03)00620-8
    37. Heiko Ihmels, Daniela Otto. Intercalation of Organic Dye Molecules into Double-Stranded DNA -- General Principles and Recent Developments. , 161-204. https://doi.org/10.1007/b135804

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2001, 123, 46, 11480–11481
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja010005b
    Published October 26, 2001
    Copyright © 2001 American Chemical Society

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