Design and Synthesis of an Expanded Porphyrin That Has Selectivity for the c-MYC G-Quadruplex Structure
Abstract
Cationic porphyrins are known to bind to and stabilize different types of G-quadruplexes. Recent studies have shown the biological relevance of the intramolecular parallel G-quadruplex as a transcriptional silencer in the c-MYC promoter. TMPyP4 also binds to this G-quadruplex and most likely converts it to a mixed parallel/antiparallel G-quadruplex with two external lateral loops and one internal propeller loop, suppressing c-MYC transcriptional activation. To achieve therapeutic selectivity by targeting G-quadruplexes, it is necessary to synthesize drugs that can differentiate among the different types of G-quadruplexes. We have designed and synthesized a core-modified expanded porphyrin analogue, 5,10,15,20-[tetra(N-methyl-3-pyridyl)]-26,28-diselenasapphyrin chloride (Se2SAP). Se2SAP converts the parallel c-MYC G-quadruplex into a mixed parallel/antiparallel G-quadruplex with one external lateral loop and two internal propeller loops, resulting in strong and selective binding to this G-quadruplex. A Taq polymerase stop assay was used to evaluate the binding of TMPyP4 and Se2SAP to G-quadruplex DNA. Compared to TMPyP4, Se2SAP shows a greater selectivity for and a 40-fold increase in stabilization of the single lateral-loop hybrid. Surface plasmon resonance and competition experiments with duplex DNA and other G-quadruplexes further confirmed the selectivity of Se2SAP for the c-MYC G-quadruplex. Significantly, Se2SAP was found to be less photoactive and noncytotoxic in comparison to TMPyP4. From this study, we have identified an expanded porphyrin that selectively binds with the c-MYC G-quadruplex in the presence of duplex DNA and other G-quadruplexes.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Se2SAP selectively binds the c-Myc G4 in the presence of duplex DNA and other G4s.
“Se2SAP selectively binds with the c-Myc G4 in the presence of duplex DNA and other G4s, offering a potential approach to selectively target undruggable Myc.583”
From Recent advances in targeting the “undruggable” proteins: from drug discovery to clinical trials (2023) · cites this paper as [583]
Hurley's group designed and synthesized Se2SAP based on modeling and comparative analysis of the binding of a G4 stabilizer TMPyP4 and telomestatin to c-Myc G4.
“In 2005, Hurley’s group designed and synthesized Se2SAP (5,10,15,20-[tetra(N-methyl-3-pyridyl)]-26,28-diselenasapphyrin chloride) (248), a selenium-substituted expanded porphyrin analog based on the modeling and comparative analysis of the binding of a G4 stabilizer TMPyP4 and a natural product telomestatin to c-Myc G4.”
From Recent advances in targeting the “undruggable” proteins: from drug discovery to clinical trials (2023) · cites this paper as [583]
Cites
Comparison of simple potential functions for simulating liquid water
Jorgensen, W. L., Chandrasekhar, J., Madura, J., Impey, R., & Klein, M. (1983) · The Journal of Chemical Physics · doi:10.1063/1.445869 · Cited by 38,335 · see citing works
A Second Generation Force Field for the Simulation of Proteins, Nucleic Acids, and Organic Molecules
Cornell, W. D., Cieplak, P., Bayly, C. I., Gould, I. R., Merz, K. M., Ferguson, D. M., Spellmeyer, D. C., Fox, T., Caldwell, J. W., & Kollman, P. A. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00124a002 · Cited by 13,111 · see citing works
A simplified synthesis for meso-tetraphenylporphine
Adler, A. D., Longo, F. R., Finarelli, J. D., Goldmacher, J. E., Assour, J. M., & Korsakoff, L. (1967) · The Journal of Organic Chemistry · doi:10.1021/jo01288a053 · Cited by 2,696 · see citing works
Siddiqui-Jain, A., Grand, C., Bearss, D., & Hurley, L. (2002) · Proceedings of the National Academy of Sciences of the United States of America · doi:10.1073/pnas.182256799 · Cited by 2,069 · see citing works
Self-citationCrystal structure of parallel quadruplexes from human telomeric DNA
Parkinson, G., Lee, M. P. H., & Neidle, S. (2002) · Nature · doi:10.1038/nature755 · Cited by 1,863 · see citing works
DNA and its associated processes as targets for cancer therapy
Hurley, L. H. (2002) · Nature reviews. Cancer · doi:10.1038/nrc749 · Cited by 1,350 · see citing works
Self-citationMarcu, K. B., Bossone, S., & Patel, A. J. (1992) · Annual Review of Biochemistry · doi:10.1146/annurev.bi.61.070192.004113 · Cited by 799 · see citing works
Inhibition of Human Telomerase by a G-Quadruplex-Interactive Compound
Sun, D., Thompson, B., Cathers, B. E., Salazar, M., Kerwin, S. M., Trent, J. O., Jenkins, T. C., Neidle, S., & Hurley, L. H. (1997) · Journal of Medicinal Chemistry · doi:10.1021/jm970199z · Cited by 794 · see citing works
Self-citationPhotocleavage of Nucleic Acids
Armitage, B. A. (1998) · Chemical Reviews · doi:10.1021/cr960428+ · Cited by 684 · see citing works
Telomere maintenance as a target for anticancer drug discovery
Neidle, S., & Parkinson, G. N. (2002) · Nature Reviews Drug Discovery · doi:10.1038/nrd793 · Cited by 623 · see citing works
DNA tetraplex formation in the control region of c-myc
Simonsson, T. (1998) · Nucleic Acids Research · doi:10.1093/nar/26.5.1167 · Cited by 598 · see citing works
Wheelhouse, R. T., Sun, D., Han, H., Han, F. X., & Hurley, L. H. (1998) · Journal of the American Chemical Society · doi:10.1021/ja973792e · Cited by 448 · see citing works
Self-citationSiebenlist, U. K., Hennighausen, L. G., Battey, J., & Leder, P. (1984) · Cell · doi:10.1016/0092-8674(84)90368-4 · Cited by 423 · see citing works
Three-dimensional Solution Structure of the Thrombin-binding DNA Aptamer d(GGTTGGTGTGGTTGG)
Schultze, P., Macaya, R. F., & Feigon, J. F. (1994) · Journal of Molecular Biology · doi:10.1006/jmbi.1994.1105 · Cited by 410 · see citing works
Biophysical and biological properties of quadruplex oligodeoxyribonucleotides
Dapic, V. (2003) · Nucleic Acids Research · doi:10.1093/nar/gkg316 · Cited by 397 · see citing works
The Dynamic Character of the G-Quadruplex Element in the c-MYC Promoter and Modification by TMPyP4
Seenisamy, J., Rezler, E. M., Powell, T. J., Tye, D., Gokhale, V. M., Joshi, C. S., Siddiqui-Jain, A., & Hurley, L. H. (2004) · Journal of the American Chemical Society · doi:10.1021/ja040022b · Cited by 390 · see citing works
Self-citationThe molecular role of Myc in growth and transformation: recent discoveries lead to new insights
Facchini, L. M., & Penn, L. Z. (1998) · The FASEB Journal · doi:10.1096/fasebj.12.9.633 · Cited by 376 · see citing works
(1985) · Elsevier eBooks · doi:10.1016/b978-0-7236-0722-9.50057-2 · Cited by 355 · see citing works
Bossone, S., Asselin, C., Patel, A. J., & Marcu, K. B. (1992) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.89.16.7452 · Cited by 326 · see citing works
Ying, L., Green, J. J., Li, H., Klenerman, D., & Balasubramanian, S. (2003) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.2433350100 · Cited by 304 · see citing works
Telomerase and the maintenance of chromosome ends
Bryan, T. M., & Cech, T. R. (1999) · Current Opinion in Cell Biology · doi:10.1016/s0955-0674(99)80043-x · Cited by 301 · see citing works
Porphyrins in Photodynamic Therapy - A Search for Ideal Photosensitizers
Pushpan, S. K., Venkatraman, S., Anand, V. G., Sankar, J., Parmeswaran, D., Ganesan, S., & Chandrashekar, T. K. (2002) · Anti-Cancer Agents in Medicinal Chemistry · doi:10.2174/1568011023354137 · Cited by 230 · see citing works
Gowan, S. M., Heald, R. A., Stevens, M. F. G., & Kèlland, L. R. (2001) · Molecular Pharmacology · doi:10.1124/mol.60.5.981 · Cited by 229 · see citing works
2,7-Disubstituted Amidofluorenone Derivatives as Inhibitors of Human Telomerase
Perry, P. J., Read, M. A., Davies, R. T., Gowan, S. M., Reszka, A. P., Wood, A. A., Kèlland, L. R., & Neidle, S. (1999) · Journal of Medicinal Chemistry · doi:10.1021/jm990084q · Cited by 226 · see citing works
Porphyrin Binding to Quadruplexed T4G4
Anantha, N. V., Azam, M., & Sheardy, R. D. (1998) · Biochemistry · doi:10.1021/bi973009v · Cited by 216 · see citing works
Action of Myc in vivo — proliferation and apoptosis
Pelengaris, S., Rudolph, B., & Littlewood, T. D. (2000) · Current Opinion in Genetics & Development · doi:10.1016/s0959-437x(99)00046-5 · Cited by 207 · see citing works
Activating transcription from single stranded DNA.
Tomonaga, T., & Levens, D. (1996) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.93.12.5830 · Cited by 199 · see citing works
Reconciliation of the X-ray and NMR Structures of the Thrombin-Binding Aptamer d(GGTTGGTGTGGTTGG)
Kelly, J. A., Feigon, J. F., & Yeates, T. O. (1996) · Journal of Molecular Biology · doi:10.1006/jmbi.1996.0097 · Cited by 198 · see citing works
Davis, T. M., & Wilson, W. D. (2000) · Analytical Biochemistry · doi:10.1006/abio.2000.4726 · Cited by 185 · see citing works
Self-citationS1-hypersensitive sites in eukaryotic promoter regions
Evans, T., Schon, E. A., Gora-Maslak, G., Patterson, J. A. K., & Efstratiadis, A. (1984) · Nucleic Acids Research · doi:10.1093/nar/12.21.8043 · Cited by 161 · see citing works
Functional and dysfunctional roles of quadruplex DNA in cells
Arthanari, H., & Bolton, P. H. (2001) · Chemistry & Biology · doi:10.1016/s1074-5521(01)00007-2 · Cited by 159 · see citing works
Schriemer, D. C., Bundle, D. R., Li, L., & Hindsgaul, O. (1998) · Angewandte Chemie International Edition · doi:10.1002/(sici)1521-3773(19981231)37:24 · Cited by 138 · see citing works
A thermodynamic and structural analysis of DNA minor-groove complex formation 1 1Edited by I. Tinoco
Mazur, S., Tanious, F. A., Ding, D., Kumar, A., Boykin, D. W., Simpson, I. J., Neidle, S., & Wilson, W. D. (2000) · Journal of Molecular Biology · doi:10.1006/jmbi.2000.3869 · Cited by 138 · see citing works
Self-citationSolution Structure of theOxytrichaTelomeric Repeat d[G4(T4G4)3] G-tetraplex
Wang, Y., & Patel, D. J. (1995) · Journal of Molecular Biology · doi:10.1006/jmbi.1995.0417 · Cited by 135 · see citing works
Postel, E. H., Berberich, S. J., Rooney, J. W., & Kaetzel, D. M. (2000) · Journal of Bioenergetics and Biomembranes · doi:10.1023/a:1005541114029 · Cited by 134 · see citing works
Redon, S. (2003) · Nucleic Acids Research · doi:10.1093/nar/gkg259 · Cited by 125 · see citing works
Telomere Inhibition and Telomere Disruption as Processes for Drug Targeting
Rezler, E. M., Bearss, D. J., & Hurley, L. H. (2003) · The Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pharmtox.43.100901.135733 · Cited by 125 · see citing works
Self-citationStructures of the potassium-saturated, 2:1, and intermediate, 1:1, forms of a quadruplex DNA
Marathias, V. M., & Bolton, P. H. (2000) · Nucleic Acids Research · doi:10.1093/nar/28.9.1969 · Cited by 122 · see citing works
Determinants of DNA Quadruplex Structural Type: Sequence and Potassium Binding
Marathias, V. M., & Bolton, P. H. (1999) · Biochemistry · doi:10.1021/bi982604+ · Cited by 117 · see citing works
Matsugami, A., Okuizumi, T., Uesugi, S., & Katahira, M. (2003) · Journal of Biological Chemistry · doi:10.1074/jbc.m303694200 · Cited by 116 · see citing works
Murchie, A. I. H., & Lilley, D. M. J. (1992) · Nucleic Acids Research · doi:10.1093/nar/20.1.49 · Cited by 114 · see citing works
Hilmey, D. G., Abe, M., Nelen, M. I., Stilts, C. E., Baker, G. A., Baker, S. N., Bright, F. V., Davies, S. R., Gollnick, S. O., Oseroff, A. R., et al. (2001) · Journal of Medicinal Chemistry · doi:10.1021/jm0103662 · Cited by 90 · see citing works
Unusual DNA structures in the adenovirus genome.
Kilpatrick, M. W., Torri, A. F., Kang, D. S., Engler, J. A., & Wells, R. D. (1986) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)67390-9 · Cited by 84 · see citing works
Stilts, C. E., Nelen, M. I., Hilmey, D. G., Davies, S. R., Gollnick, S. O., Oseroff, A. R., Gibson, S. L., Hilf, R., & Detty, M. R. (2000) · Journal of Medicinal Chemistry · doi:10.1021/jm000044i · Cited by 84 · see citing works
Influence of a Terminal Formamido Group on the Sequence Recognition of DNA by Polyamides
Lacy, E. R., Le, N. M., Price, C. A., Lee, M., & Wilson, W. D. (2002) · Journal of the American Chemical Society · doi:10.1021/ja016154b · Cited by 79 · see citing works
Self-citationElucidating cell signaling mechanisms using antisense technology
Koller, E., Gaarde, W. A., & Monia, B. P. (2000) · Trends in Pharmacological Sciences · doi:10.1016/s0165-6147(00)01448-6 · Cited by 78 · see citing works
Petraccone, L., Erra, E., Esposito, V., Randazzo, A., Mayol, L., Nasti, L., Barone, G., & Giancola, C. (2004) · Biochemistry · doi:10.1021/bi0300985 · Cited by 74 · see citing works
Structure—activity relationships for DNA photocleavage by cationic porphyrins
Croke, D. T., Perrouault, L., Sari, M., BATTIONI, J. ‐., Mansuy, D., Hélène, C., & Ledoan, T. (1993) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/1011-1344(93)80039-c · Cited by 71 · see citing works
Nguyen, B., Tardy, C., Bailly, C., Colson, P., Houssier, C., Kumar, A., Boykin, D. W., & Wilson, W. D. (2002) · Biopolymers · doi:10.1002/bip.10073 · Cited by 56 · see citing works
Self-citationErratum: corrigendum: MEC-2 regulates C. elegans DEG/ENaC channels needed for mechanosensation
Goodman, M. B., Ernstrom, G. G., Chelur, D. S., O’Hagan, R., Yao, C. A., & Chalfie, M. (2002) · Nature · doi:10.1038/nature00853 · Cited by 50 · see citing works
Nuclear transport of photosensitizers during photosensitization and oxidative stress
Patito, I. A., Rothmann, C., & Malik, Z. (2001) · Biology of the Cell · doi:10.1016/s0248-4900(01)01118-2 · Cited by 44 · see citing works
The Chicken β-Globin Gene Promoter Forms a Novel “Cinched” Tetrahelical Structure
Howell, R. M., Woodford, K. J., Weitzmann, M. N., & Usdin, K. (1996) · Journal of Biological Chemistry · doi:10.1074/jbc.271.9.5208 · Cited by 44 · see citing works
Sakatsume, O., Tsutsui, H., Wang, Y., Gao, H., Tang, X., Yamauchi, T., Murata, T., Itakura, K., & Yokoyama, K. K. (1996) · Journal of Biological Chemistry · doi:10.1074/jbc.271.49.31322 · Cited by 42 · see citing works
Carrasco, C. (2002) · Nucleic Acids Research · doi:10.1093/nar/30.8.1774 · Cited by 42 · see citing works
Nussbaum, J. M., Newport, M. E. A., Mackie, M., & Leontis, N. B. (1994) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1994.tb02977.x · Cited by 18 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Patel, D. J., Phan, A. T., & Kuryavyi, V. (2007) · Nucleic Acids Research · doi:10.1093/nar/gkm711 · Cited by 879 · see citing works
A hitchhiker's guide to G-quadruplex ligands.
Monchaud, D., & Teulade-Fichou, M. (2008) · Organic and biomolecular chemistry · doi:10.1039/b714772b · Cited by 707 · see citing works
Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities
Saito, S., & Osuka, A. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201003909 · Cited by 699 · see citing works
Conjugated Macrocycles: Concepts and Applications
Iyoda, M., Yamakawa, J., & Rahman, M. J. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201006198 · Cited by 574 · see citing works
Phan, A. T., Kuryavyi, V., Gaw, H. Y., & Patel, D. J. (2005) · Nature Chemical Biology · doi:10.1038/nchembio723 · Cited by 519 · see citing works
Survey of the year 2003 commercial optical biosensor literature
Rich, R. L., & Myszka, D. G. (2004) · Journal of Molecular Recognition · doi:10.1002/jmr.726 · Cited by 505 · see citing works
Interaction of Metal Complexes with G‐Quadruplex DNA
Georgiades, S. N., Karim, N. H. A., Suntharalingam, K., & Vilar, R. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200906363 · Cited by 482 · see citing works
G‐Quadruplexes: Targets in Anticancer Drug Design
Ou, T., Lu, Y., Tan, J., Huang, Z., Wong, K., & Gu, L. (2008) · ChemMedChem · doi:10.1002/cmdc.200700300 · Cited by 482 · see citing works
Qin, Y. W., & Hurley, L. H. (2008) · Biochimie · doi:10.1016/j.biochi.2008.02.020 · Cited by 451 · see citing works
Self-citationRecent advances in targeting the “undruggable” proteins: from drug discovery to clinical trials
Xie, X., Yu, T., Li, X., Zhang, N., Foster, L. J., Peng, C., Huang, W., & He, G. (2023) · Signal Transduction and Targeted Therapy · doi:10.1038/s41392-023-01589-z · Cited by 396 · see citing works
Bioactive Luminescent Transition‐Metal Complexes for Biomedical Applications
Ma, D., He, H., Leung, K., Chan, D. S., & Leung, C. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201208414 · Cited by 388 · see citing works
Dexheimer, T. S., Sun, D., & Hurley, L. H. (2006) · Journal of the American Chemical Society · doi:10.1021/ja0563861 · Cited by 383 · see citing works
Self-citationThe new models of the human telomere d[AGGG(TTAGGG)3] in K+ solution
Xu, Y., Noguchi, Y., & Sugiyama, H. (2006) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2006.04.033 · Cited by 372 · see citing works
Rezler, E. M., Seenisamy, J., Sridevi, B., Kim, M.-Y., White, E. W., Wilson, W. D., & Hurley, L. H. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0505088 · Cited by 336 · see citing works
Self-citationChemistry in human telomere biology: structure, function and targeting of telomere DNA/RNA
Xu, Y. (2011) · Chemical Society Reviews · doi:10.1039/c0cs00134a · Cited by 322 · see citing works
Aromaticity and photophysical properties of various topology-controlled expanded porphyrins
Shin, J., Kim, K. S., Yoon, M., Lim, J. M., Yoon, Z. S., Osuka, A., & Kim, D. (2010) · Chemical Society Reviews · doi:10.1039/b925417j · Cited by 317 · see citing works
Stabilization of G-Quadruplex DNA and Down-Regulation of Oncogene c-myc by Quindoline Derivatives
Ou, T., Lu, Y., Zhang, C., Huang, Z., Wang, X., Tan, J., Chen, Y., Ma, D., Wong, K., Tang, J. C. O., et al. (2007) · Journal of Medicinal Chemistry · doi:10.1021/jm0610088 · Cited by 289 · see citing works
Surface plasmon resonance sensing of nucleic acids: A review
Šípová, H., & Homola, J. (2013) · Analytica Chimica Acta · doi:10.1016/j.aca.2012.12.040 · Cited by 258 · see citing works
Guo, K., Pourpak, A., Beetz-Rogers, K., Gokhale, V. M., Sun, D., & Hurley, L. H. (2007) · Journal of the American Chemical Society · doi:10.1021/ja072185g · Cited by 257 · see citing works
Self-citationSmall Molecules Targeting c-Myc Oncogene: Promising Anti-Cancer Therapeutics
Chen, B.-J., Wu, Y., Tanaka, Y., & Zhang, W. (2014) · International Journal of Biological Sciences · doi:10.7150/ijbs.10190 · Cited by 247 · see citing works
Expandierte Porphyrine: überraschende Strukturen, elektronische Eigenschaften und Reaktivitäten
Saito, S., & Osuka, A. (2011) · Angewandte Chemie · doi:10.1002/ange.201003909 · Cited by 231 · see citing works
Monchaud, D., Allain, C., & Teulade‐Fichou, M. (2006) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2006.06.067 · Cited by 224 · see citing works
The c‐myc Promoter: Still MysterY and Challenge
(2008) · Advances in Cancer Research · doi:10.1016/s0065-230x(07)99004-1 · Cited by 211 · see citing works
White, E. W., Tanious, F. A., Ismail, M. A., Reszka, A. P., Neidle, S., Boykin, D. W., & Wilson, W. D. (2006) · Biophysical Chemistry · doi:10.1016/j.bpc.2006.06.006 · Cited by 199 · see citing works
Self-citationLi, T., Wang, E., & Dong, S. (2010) · Analytical Chemistry · doi:10.1021/ac1019446 · Cited by 198 · see citing works
Sun, D., Liu, W., Guo, K., Rusche, J. J., Ebbinghaus, S., Gokhale, V. M., & Hurley, L. H. (2008) · Molecular Cancer Therapeutics · doi:10.1158/1535-7163.mct-07-2119 · Cited by 188 · see citing works
Self-citationAptamer-Based Au Nanoparticles-Enhanced Surface Plasmon Resonance Detection of Small Molecules
Wang, J., & Zhou, H. S. (2008) · Analytical Chemistry · doi:10.1021/ac801281c · Cited by 185 · see citing works
Bhadra, K., & Kumar, G. S. (2011) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2011.01.011 · Cited by 181 · see citing works
Cogoi, S., Paramasivam, M., Spolaore, B., & Xodo, L. (2008) · Nucleic Acids Research · doi:10.1093/nar/gkn120 · Cited by 158 · see citing works
Carabet, L. A., Rennie, P. S., & Cherkasov, A. (2018) · International Journal of Molecular Sciences · doi:10.3390/ijms20010120 · Cited by 172 · see citing works
Macrocyclic and Helical Oligoamides as a New Class of G-Quadruplex Ligands
Shirude, P. S., Gillies, E. R., Ladame, S., Godde, F., Shin‐ya, K., Huc, I., & Balasubramanian, S. (2007) · Journal of the American Chemical Society · doi:10.1021/ja073775h · Cited by 171 · see citing works
Self-citationCancer therapeutics: Targeting the dark side of Myc
Ponzielli, R., Katz, S., Baršytė-Lovejoy, D., & Penn, L. Z. (2005) · European Journal of Cancer · doi:10.1016/j.ejca.2005.08.017 · Cited by 166 · see citing works
Wu, P., Ma, D., Leung, C., Yan, S., Zhu, N., Abagyan, R. A., & Che, C. (2009) · Chemistry - A European Journal · doi:10.1002/chem.200901943 · Cited by 161 · see citing works
G‐Quadruplex Structures and Their Interaction Diversity with Ligands
Zhang, S., Wu, Y., & Zhang, W. (2014) · ChemMedChem · doi:10.1002/cmdc.201300566 · Cited by 160 · see citing works
Diarylethynyl Amides That Recognize the Parallel Conformation of Genomic Promoter DNA G-Quadruplexes
Dash, J., Shirude, P. S., Hsu, S. D., & Balasubramanian, S. (2008) · Journal of the American Chemical Society · doi:10.1021/ja8046552 · Cited by 159 · see citing works
Lim, J. M., Yoon, Z. S., Shin, J., Kim, K. S., Yoon, M., & Kim, D. (2008) · Chemical Communications · doi:10.1039/b810718a · Cited by 154 · see citing works
Freyer, M. W., Buscaglia, R., Kaplan, K. A., Cashman, D. J., Hurley, L. H., & Lewis, E. A. S. (2006) · Biophysical Journal · doi:10.1529/biophysj.106.097246 · Cited by 144 · see citing works
Self-citationKonjugierte Makrocyclen: Konzepte und Anwendungen
Iyoda, M., Yamakawa, J., & Rahman, M. J. (2011) · Angewandte Chemie · doi:10.1002/ange.201006198 · Cited by 143 · see citing works
9-Substituted berberine derivatives as G-quadruplex stabilizing ligands in telomeric DNA
Zhang, W., Ou, T., Lu, Y., Huang, Y.-Y., Wu, W., Huang, Z., Zhou, J.-L., Wong, K., & Gu, L. (2007) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2007.05.050 · Cited by 135 · see citing works
Zhi-yin, S., Wang, X., Cheng, S.-Q., Su, X., & Ou, T. (2019) · Molecules · doi:10.3390/molecules24030396 · Cited by 135 · see citing works
Macrocyclic Hexaoxazoles as Sequence‐ and Mode‐Selective G‐Quadruplex Binders
Tera, M., Ishizuka, H., Takagi, M., Suganuma, M., Shin‐ya, K., & Nagasawa, K. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200801235 · Cited by 133 · see citing works
Self-citationTopologies of G-quadruplex: Biological functions and regulation by ligands
Ma, Y., Iida, K., & Nagasawa, K. (2020) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2019.12.103 · Cited by 131 · see citing works
Wang, X., Ou, T., Lu, Y., Zeng, L. Q., Zheng, X., Chen, X., Tan, J., Huang, S., An, L., Li, D., et al. (2010) · Journal of Medicinal Chemistry · doi:10.1021/jm100445e · Cited by 127 · see citing works
Self-assembly of supramolecular aptamer structures for optical or electrochemical sensing
Freeman, R., Li, Y., Tel‐Vered, R., Sharon, E., Elbaz, J., & Willner, I. (2009) · The Analyst · doi:10.1039/b822836c · Cited by 127 · see citing works
Recent Update on Targeting c-MYC G-Quadruplexes by Small Molecules for Anticancer Therapeutics
Chaudhuri, R., Bhattacharya, S., Dash, J., & Bhattacharya, S. (2020) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.0c01145 · Cited by 127 · see citing works
Oxazole-Based Peptide Macrocycles: A New Class of G-Quadruplex Binding Ligands
Jantos, K., Rodriguez, R., Ladame, S., Shirude, P. S., & Balasubramanian, S. (2006) · Journal of the American Chemical Society · doi:10.1021/ja064713e · Cited by 126 · see citing works
Liu, L., Shao, Y., Peng, J., Huang, C., Liu, H., & Zhang, L. (2014) · Analytical Chemistry · doi:10.1021/ac403326m · Cited by 126 · see citing works
Wang, P., Leung, C., Ma, D., Yan, S., & Che, C. (2010) · Chemistry - A European Journal · doi:10.1002/chem.201000167 · Cited by 120 · see citing works
Ma, Y., Ou, T., Hou, J., Lu, Y., Tan, J., Gu, L., & Huang, Z. (2008) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2008.07.029 · Cited by 119 · see citing works
Sun, D., Liu, Y., Liu, D., Zhang, R., Yang, X., & Liu, J. (2012) · Chemistry - A European Journal · doi:10.1002/chem.201103156 · Cited by 115 · see citing works
Self-citationHu, M.-H., Wu, T.-Y., Huang, Q., & Jin, G. (2019) · Nucleic Acids Research · doi:10.1093/nar/gkz835 · Cited by 115 · see citing works
Survey of the year 2005 commercial optical biosensor literature
Rich, R. L., & Myszka, D. G. (2006) · Journal of Molecular Recognition · doi:10.1002/jmr.808 · Cited by 115 · see citing works
Phthalocyanines: a new class of G-quadruplex-ligands with many potential applications
Yaku, H., Fujimoto, T., Murashima, T., Miyoshi, D., & Sugimoto, N. (2012) · Chemical Communications · doi:10.1039/c2cc31037f · Cited by 114 · see citing works
Ou, T., Lin, J., Lu, Y., Hou, J., Tan, J., Chen, S., Li, Z., Li, Y., Li, D., Gu, L., et al. (2011) · Journal of Medicinal Chemistry · doi:10.1021/jm200062u · Cited by 112 · see citing works
Evidence for the binding mode of porphyrins to G-quadruplex DNA
Wei, C., Jia, G., Zhou, J., Han, G., & Li, C. (2009) · Physical Chemistry Chemical Physics · doi:10.1039/b901027k · Cited by 103 · see citing works
Hu, M.-H., Wang, Y.-Q., Yu, Z.-Y., Hu, L.-N., Ou, T.-M., Chen, S.-B., Huang, Z.-S., & Tan, J.-H. (2018) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.7b01697 · Cited by 101 · see citing works
Chan, D. S., Yang, H., Kwan, M. H., Cheng, Z., Lee, P., Bai, L., Jiang, Z., Wong, C., Fong, W. F., Leung, C., et al. (2011) · Biochimie · doi:10.1016/j.biochi.2011.02.013 · Cited by 97 · see citing works
Recognition and regulation of unique nucleic acid structures by small molecules
Song, G., & Ren, J. (2010) · Chemical Communications · doi:10.1039/c0cc01312a · Cited by 96 · see citing works
G‐Quadruplex DNA Structures and Organic Chemistry: More Than One Connection
Franceschin, M. (2009) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200801196 · Cited by 94 · see citing works
Zhao, X. R., Zhang, K., Wang, Y., Jiang, W., Cheng, H., Wang, Q., Xiang, T., Zhang, Z., Liu, J., & Shi, J. (2022) · Advanced Functional Materials · doi:10.1002/adfm.202108883 · Cited by 93 · see citing works
Matsugami, A., Xu, Y., Noguchi, Y., Sugiyama, H., & Katahira, M. (2007) · FEBS Journal · doi:10.1111/j.1742-4658.2007.05881.x · Cited by 90 · see citing works
Chemical biology of non-canonical structures of nucleic acids for therapeutic applications
Tateishi‐Karimata, H., & Sugimoto, N. (2020) · Chemical Communications · doi:10.1039/c9cc09771f · Cited by 90 · see citing works
Ghosh, S., Mendoza, Ó., Cubo, L., Rosu, F., Gabelica, V., White, A. J. P., & Vilar, R. (2014) · Chemistry - A European Journal · doi:10.1002/chem.201304905 · Cited by 89 · see citing works
Wechselwirkung von Metallkomplexen mit G‐Quadruplex‐DNA
Georgiades, S. N., Karim, N. H. A., Suntharalingam, K., & Vilar, R. (2010) · Angewandte Chemie · doi:10.1002/ange.200906363 · Cited by 89 · see citing works
Yuan, L., Tian, T., Chen, Y., Yan, S., Xing, X., Zhang, Z., Zhai, Q., Xu, L., Wang, S., Weng, X., et al. (2013) · Scientific Reports · doi:10.1038/srep01811 · Cited by 88 · see citing works
A platinum–quinacridine hybrid as a G-quadruplex ligand
Bertrand, H. C., Bombard, S., Monchaud, D., & Teulade‐Fichou, M. (2007) · JBIC Journal of Biological Inorganic Chemistry · doi:10.1007/s00775-007-0273-3 · Cited by 88 · see citing works
Zeng, D.-Y., Kuang, G., Wang, S., Peng, W., Lin, S., Zhang, Q., Su, X., Hu, M.-H., Wang, H., Tan, J., et al. (2017) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.7b00016 · Cited by 87 · see citing works
Yuan, G., Zhang, Q., Zhou, J., & Li, H. (2011) · Mass Spectrometry Reviews · doi:10.1002/mas.20315 · Cited by 86 · see citing works
Cyclo[n]pyrroles: Size and Site-Specific Binding to G-Quadruplexes
Baker, E. S., Lee, J. T., Sessler, J. L., & Bowers, M. T. (2006) · Journal of the American Chemical Society · doi:10.1021/ja0564968 · Cited by 83 · see citing works
Wang, P., Ren, L., He, H., Liang, F., Zhou, X., & Tan, Z. (2006) · ChemBioChem · doi:10.1002/cbic.200600036 · Cited by 83 · see citing works
Unfolding Thermodynamics of Intramolecular G-Quadruplexes: Base Sequence Contributions of the Loops
Olsen, C. M., Lee, H.-T., & Marky, L. A. (2008) · The Journal of Physical Chemistry B · doi:10.1021/jp806853n · Cited by 82 · see citing works
Function and targeting of G-quadruplexes.
Wong, H. M., Payet, L., & Huppert, J. L. (2009) · PubMed · Cited by 80 · see citing works
Triarylpyridines: a versatile small molecule scaffold for G-quadruplex recognition
Waller, Z. A. E., Shirude, P. S., Rodriguez, R., & Balasubramanian, S. (2008) · Chemical Communications · doi:10.1039/b718854d · Cited by 79 · see citing works
Panda, D., Saha, P., Das, T., & Dash, J. (2017) · Nature Communications · doi:10.1038/ncomms16103 · Cited by 77 · see citing works
Human MYC G-quadruplex: From discovery to a cancer therapeutic target
Wang, W., Hu, S., Gu, Y., Yan, Y., Stovall, D. B., Li, D., & Sui, G. (2020) · Biochimica et Biophysica Acta (BBA) - Reviews on Cancer · doi:10.1016/j.bbcan.2020.188410 · Cited by 77 · see citing works
The role of G-quadruplex/i-motif secondary structures as cis-acting regulatory elements
Kendrick, S., & Hurley, L. (2010) · Pure and applied chemistry. Chimie pure et appliquee · doi:10.1351/pac-con-09-09-29 · Cited by 69 · see citing works
Self-citationNovel Molecular Mechanism for Actinomycin D Activity as an Oncogenic Promoter G-Quadruplex Binder
Kang, H.-J., & Park, H. (2009) · Biochemistry · doi:10.1021/bi9006836 · Cited by 74 · see citing works
Monchaud, D., Granzhan, A., Saettel, N., Guédin, A., Mergny, J., & Teulade‐Fichou, M. (2010) · Journal of Nucleic Acids · doi:10.4061/2010/525862 · Cited by 73 · see citing works
G-quadruplex recognition by bis-indole carboxamides
Dash, J., Shirude, P. S., & Balasubramanian, S. (2008) · Chemical Communications · doi:10.1039/b806042h · Cited by 72 · see citing works
Dhamodharan, V., Harikrishna, S., Jagadeeswaran, C., Halder, K., & Pradeepkumar, P. (2012) · Journal of Organic Chemistry · doi:10.1021/jo201816g · Cited by 63 · see citing works
Targeting c-MYC G-Quadruplexes for Cancer Treatment with Small Molecules
Thumpati, P., Rai, S. N., Prajapati, C., Ramakrishna, K., & Singh, S. K. (2025) · Scientia Pharmaceutica · doi:10.3390/scipharm93010006 · Cited by 69 · see citing works
Porphyrins in complex with DNA: Modes of interaction and oxidation reactions
Pratviel, G. (2015) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2015.07.003 · Cited by 70 · see citing works
Synthesis of a Potent G‐Quadruplex‐Binding Macrocyclic Heptaoxazole
Tera, M., Iida, K., Ishizuka, H., Takagi, M., Suganuma, M., Doi, T., Shin‐ya, K., & Nagasawa, K. (2009) · ChemBioChem · doi:10.1002/cbic.200800563 · Cited by 68 · see citing works
Self-citationLe, H. T., Miller, M. C., Buscaglia, R., Dean, W. L., Holt, P. A., Chaires, J. B., & Trent, J. O. (2012) · Organic & Biomolecular Chemistry · doi:10.1039/c2ob26504d · Cited by 66 · see citing works
Dhamodharan, V., Harikrishna, S., Bhasikuttan, A. C., & Pradeepkumar, P. I. (2014) · ACS Chemical Biology · doi:10.1021/cb5008597 · Cited by 64 · see citing works
Panda, D., Debnath, M., Mandal, S., Bessi, I., Schwalbe, H., & Dash, J. (2015) · Scientific Reports · doi:10.1038/srep13183 · Cited by 63 · see citing works
Wilson, T., Williamson, M. P., & Thomas, J. A. (2010) · Organic & Biomolecular Chemistry · doi:10.1039/b924263e · Cited by 63 · see citing works
DNA Loop Sequence as the Determinant for Chiral Supramolecular Compound G-Quadruplex Selectivity
Yu, H., Zhao, C., Chen, Y., Fu, M., Ren, J., & Qu, X. (2009) · Journal of Medicinal Chemistry · doi:10.1021/jm9014795 · Cited by 63 · see citing works
Aminoglycoside Binding toOxytricha novaTelomeric DNA
Ranjan, N., Andreasen, K. F., Kumar, S., Hyde-Volpe, D., & Arya, D. P. (2010) · Biochemistry · doi:10.1021/bi101517e · Cited by 63 · see citing works
Redman, J. E. (2007) · Methods · doi:10.1016/j.ymeth.2007.05.008 · Cited by 63 · see citing works
Neomycin-capped aromatic platforms: quadruplex DNA recognition and telomerase inhibition
Kaiser, M., Cian, A. D., Sainlos, M., Renner, C., Mergny, J., & Teulade‐Fichou, M. (2006) · Organic & Biomolecular Chemistry · doi:10.1039/b516378a · Cited by 63 · see citing works
Synthetic strategies towards ruthenium–porphyrin conjugates for anticancer activity
Gianferrara, T., Bratsos, I., Iengo, E., Milani, B., Ostric, A., Spagnul, C., Zangrando, E., & Alessio, E. (2009) · Dalton Transactions · doi:10.1039/b911393b · Cited by 62 · see citing works
Zhao, C., Geng, J., Feng, L., Ren, J., & Qu, X. (2011) · Chemistry - A European Journal · doi:10.1002/chem.201100272 · Cited by 61 · see citing works
Diveshkumar, K. V., Sakrikar, S., Rosu, F., Harikrishna, S., Gabelica, V., & Pradeepkumar, P. I. (2016) · Biochemistry · doi:10.1021/acs.biochem.6b00120 · Cited by 61 · see citing works
Liu, H., Chen, A.-C., Yin, Q., Li, Z., Huang, S.-M., Du, G., He, J., Zan, L.-P., Wang, S., Xu, Y., et al. (2017) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.7b00099 · Cited by 60 · see citing works
Spectroscopic study on the binding of porphyrins to (G4T4G4)4 parallel G-quadruplex
Wei, C., Wang, J., & Zhang, M. (2010) · Biophysical Chemistry · doi:10.1016/j.bpc.2010.02.009 · Cited by 59 · see citing works
Ma, D., Lin, S., Leung, K., Zhong, H., Liu, L., Chan, D. S., Bourdoncle, A., Mergny, J., Wang, H., & Leung, C. (2014) · Nanoscale · doi:10.1039/c4nr00541d · Cited by 58 · see citing works
Recognition and discrimination of DNA quadruplexes by acridine-peptide conjugates
Redman, J. E., Granadino‐Roldán, J. M., Schouten, J. A., Ladame, S., Reszka, A. P., Neidle, S., & Balasubramanian, S. (2008) · Organic & Biomolecular Chemistry · doi:10.1039/b814682a · Cited by 56 · see citing works
Singh, K., Sharma, A. K., Zhang, J., Xu, W., & Zhu, D. (2010) · Chemical Communications · doi:10.1039/c0cc03974h · Cited by 54 · see citing works
Role of c-Myc in intestinal tumorigenesis of the Apc min/+ mouse1
Ignatenko, N. A., Holubec, H., Besselsen, D. G., Blohm-Mangone, K. A., Padilla‐Torres, J., Nagle, R. B., de Alborán, I. M., Guillen-Rodriguez, J., & Gerner, E. W. (2006) · Cancer Biology & Therapy · doi:10.4161/cbt.5.12.3376 · Cited by 54 · see citing works
- Authors
- Seenisamy, J., Bashyam, S., Gokhale, V., Vankayalapati, H., Sun, D., Siddiqui-Jain, A., Streiner, N., Shin-ya, K., White, E., Wilson, W. D., & Hurley, L. H.
- Affiliations
- University of Arizona (US)
- Contribution from the College of Pharmacy, The University of Arizona, 1703 East Mabel, Tucson, Arizona 85721, Arizona Cancer Center, 1515 North Campbell Avenue, Tucson, Arizona 85724, Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, Cylene Pharmaceuticals, 11045 Roselle Street, Suite C, San Diego, California 92121, Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan, and Department of Chemistry, Georgia State...
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-02-05
- Volume
- 127
- Issue
- 9
- Pages
- 2944-2959
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2041730421
- Cited by
- 319
- References
- 55
- Citations by year
- 2026: 2 · 2025: 7 · 2024: 5 · 2023: 6 · 2022: 14 · 2021: 7 · 2020: 14 · 2019: 5 · 2018: 21 · 2017: 7 · 2016: 14 · 2015: 15 · 2014: 27 · 2013: 19 · 2012: 12
- FWCI
- 10.29
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Cancer Institute (CA94166, R01CA094166, R01CA088310, CA95060, CA88310, P50CA095060)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
- Health Sciences › Medicine › Oncology › Metal complexes synthesis and properties
- Keywords
- expanded porphyrins, cationic porphyrins, TMPyP4, transcriptional silencing, G-quadruplex stabilization, photoactivity, cytotoxicity, anticancer drug design
- MeSH terms
- Binding, Competitive, DNA, DNA, Single-Stranded, Guanine, HeLa Cells, Humans, Models, Molecular, Nucleic Acid Conformation, Oxazoles, Porphyrins, Promoter Regions, Genetic, Substrate Specificity, Genes, myc, Telomere, Selenium Compounds, Surface Plasmon Resonance, G-Quadruplexes
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
