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Reprogramming the assembly of unmodified DNA with a small molecule
Abstract
The ability of DNA to store and encode information arises from base pairing of the four-letter nucleobase code to form a double helix. Expanding this DNA 'alphabet' by synthetic incorporation of new bases can introduce new functionalities and enable the formation of novel nucleic acid structures. However, reprogramming the self-assembly of existing nucleobases presents an alternative route to expand the structural space and functionality of nucleic acids. Here we report the discovery that a small molecule, cyanuric acid, with three thymine-like faces, reprogrammes the assembly of unmodified poly(adenine) (poly(A)) into stable, long and abundant fibres with a unique internal structure. Poly(A) DNA, RNA and peptide nucleic acid (PNA) all form these assemblies. Our studies are consistent with the association of adenine and cyanuric acid units into a hexameric rosette, which brings together poly(A) triplexes with a subsequent cooperative polymerization. Fundamentally, this study shows that small hydrogen-bonding molecules can be used to induce the assembly of nucleic acids in water, which leads to new structures from inexpensive and readily available materials.
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“Additionally, as alternative chemistries emerge, including unnatural nucleotides147 and small molecules that can modulate the structure of DNA,148 the parameter space for structure- and sequence-based DNA data storage is continually expanding.”
From Emerging Approaches to DNA Data Storage: Challenges and Prospects (2022) · cites this paper as [148]
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Cites
Molecular Structure of Nucleic Acids: A Structure for Deoxyribose Nucleic Acid
WATSON, J. D., & CRICK, F. H. C. (1953) · Nature · doi:10.1038/171737a0 · Cited by 13,584
de Greef, T. F. A., Smulders, M. M. J., Wolffs, M., Schenning, A. P. H. J., Sijbesma, R. P., & Meijer, E. W. (2009) · Chemical Reviews · doi:10.1021/cr900181u · Cited by 2,495
Circular dichroism: Principles and applications
Jones, C. (1995) · FEBS Letters · doi:10.1016/0014-5793(95)90057-8 · Cited by 2,472
PNA hybridizes to complementary oligonucleotides obeying the Watson–Crick hydrogen-bonding rules
Egholm, M., Buchardt, O., Christensen, L., Behrens, C., Freier, S. M., Driver, D. A., Berg, R. H., Kim, S. K., Norden, B., & Nielsen, P. E. (1993) · Nature · doi:10.1038/365566a0 · Cited by 2,079
Targeting G-quadruplexes in gene promoters: a novel anticancer strategy?
Balasubramanian, S., Hurley, L. H., & Neidle, S. (2011) · Nature Reviews Drug Discovery · doi:10.1038/nrd3428 · Cited by 1,720
Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA
Pyle, A., Rehmann, J. P., Meshoyrer, R., Kumar, C. V., TURRO, N. J., & Barton, J. K. (1989) · Journal of the American Chemical Society · doi:10.1021/ja00190a046 · Cited by 1,463
Circular Dichroism: Principles and Applications
Berova, N. D., 中西, 香., & Woody, R. W. (1994) · Cited by 1,264
Noncovalent Synthesis: Using Physical-Organic Chemistry To Make Aggregates
Whitesides, G. M., Simanek, E. E., Mathias, J. P., Seto, C. T., Chin, D. N., Mammen, M., & Gordon, D. M. (1995) · Accounts of Chemical Research · doi:10.1021/ar00049a006 · Cited by 1,030
Assembling Materials with DNA as the Guide
Aldaye, F. A., Palmer, A. L., & Sleiman, H. F. (2008) · Science · doi:10.1126/science.1154533 · Cited by 989
Self-citationPeptide nucleic acids (PNA). Oligonucleotide analogs with an achiral peptide backbone
Egholm, M., Buchardt, O., Nielsen, P. E., & Berg, R. H. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00031a062 · Cited by 739
Mechanisms and Consequences of Alternative Polyadenylation
Di Giammartino, D. C., Nishida, K., & Manley, J. L. (2011) · Molecular Cell · doi:10.1016/j.molcel.2011.08.017 · Cited by 737
Molecular structure of nucleic acids
Watson, J. D., & Crick, F. H. C. (2004) · Resonance · doi:10.1007/bf02834980 · Cited by 660
Enzymatic incorporation of a new base pair into DNA and RNA extends the genetic alphabet
Piccirilli, J. A., Benner, S. A., Krauch, T., Moroney, S. E., & Benner, S. A. (1990) · Nature · doi:10.1038/343033a0 · Cited by 636
A semi-synthetic organism with an expanded genetic alphabet
Malyshev, D. A., Dhami, K., Lavergne, T., Chen, T., Dai, N., Foster, J. M., Junior, I. R. C., & Romesberg, F. E. (2014) · Nature · doi:10.1038/nature13314 · Cited by 614
Nucleic Acid Based Molecular Devices
Krishnan, Y., & Simmel, F. C. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.200907223 · Cited by 575
Building Programmable Jigsaw Puzzles with RNA
Chworoś, A., Severcan, I., Koyfman, A. Y., Weinkam, P., Oroudjev, E., Hansma, H. G., & Jaeger, L. (2004) · Science · doi:10.1126/science.1104686 · Cited by 506
The molecular structure of polyadenylic acid
Rich, A., Davies, D. R., Crick, F. H. C., & Watson, J. D. (1961) · Journal of Molecular Biology · doi:10.1016/s0022-2836(61)80009-0 · Cited by 459
Conformational changes of non-B DNA
Choi, J., & Majima, T. (2011) · Chemical Society Reviews · doi:10.1039/c1cs15153c · Cited by 383
Programmable molecular recognition based on the geometry of DNA nanostructures
Woo, S., & Rothemund, P. W. K. (2011) · Nature Chemistry · doi:10.1038/nchem.1070 · Cited by 375
A single-stranded architecture for cotranscriptional folding of RNA nanostructures
Geary, C. W., Rothemund, P. W. K., & Andersen, E. S. (2014) · Science · doi:10.1126/science.1253920 · Cited by 369
A Novel Copper-Mediated DNA Base Pair
Meggers, E., Holland, P. L., Tolman, W. B., Romesberg, F. E., & Schultz, P. G. (2000) · Journal of the American Chemical Society · doi:10.1021/ja0025806 · Cited by 344
Teo, Y. N., & Kool, E. T. (2012) · Chemical Reviews · doi:10.1021/cr100351g · Cited by 330
Translational control by changes in poly(A) tail length: recycling mRNAs
Weill, L., Belloc, E., Bava, F.-A., & Méndez, R. (2012) · Nature Structural & Molecular Biology · doi:10.1038/nsmb.2311 · Cited by 328
Zerkowski, J. A., Seto, C. T., & Whitesides, G. M. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00039a096 · Cited by 306
An unnatural base pair system for efficient PCR amplification and functionalization of DNA molecules
Kimoto, M., Kawai, R., Mitsui, T., Yokoyama, S., & Hirao, I. (2008) · Nucleic Acids Research · doi:10.1093/nar/gkn956 · Cited by 192
Yang, H. S., McLaughlin, C. K., Aldaye, F. A., Hamblin, G. D., Rys, A. Z., Rouiller, I., & Sleiman, H. F. (2009) · Nature Chemistry · doi:10.1038/nchem.290 · Cited by 168
Self-citationOgawa, A. K., Wu, Y., McMinn, D. L., Liu, J., Schultz, P. G., & Romesberg, F. E. (2000) · Journal of the American Chemical Society · doi:10.1021/ja9940064 · Cited by 162
Efficient self-assembly in water of long noncovalent polymers by nucleobase analogues
Cafferty, B. J., Gállego, I., Chen, M. C., Farley, K. I., Eritja, R., & Hud, N. V. (2013) · Journal of the American Chemical Society · doi:10.1021/ja312155v · Cited by 157
The poly dA helix: a new structural motif for high performance DNA-based molecular switches
Chakraborty, S., Sharma, S., Maiti, P. K., & Krishnan, Y. (2009) · Nucleic Acids Research · doi:10.1093/nar/gkp133 · Cited by 152
Functionalized base-pairs: versatile scaffolds for self-assembly
Sessler, J. L., & Jayawickramarajah, J. (2005) · Chemical Communications · doi:10.1039/b418526a · Cited by 152
A DNA pentaplex incorporating nucleobase quintets
Chaput, J. C., & Switzer, C. (1999) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.96.19.10614 · Cited by 130
Supramolecular assembly of melamine and its derivatives: nanostructures to functional materials
Roy, B., Bairi, P., & Nandi, A. K. (2013) · RSC Advances · doi:10.1039/c3ra44524k · Cited by 123
Expanded Genetic Alphabets in the Polymerase Chain Reaction
Yang, Z., Chen, F., Chamberlin, S. G., & Benner, S. A. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200905173 · Cited by 122
Efforts toward Expansion of the Genetic Alphabet: Optimization of Interbase Hydrophobic Interactions
Wu, Y., Ogawa, A. K., Berger, M., McMinn, D. L., Schultz, P. G., & Romesberg, F. E. (2000) · Journal of the American Chemical Society · doi:10.1021/ja0009931 · Cited by 116
Marsh, A., Silvestri, M. G., & Lehn, J. (1996) · Chemical Communications · doi:10.1039/cc9960001527 · Cited by 116
Polak, M. (2002) · Nucleic Acids Research · doi:10.1093/nar/30.4.983 · Cited by 116
Assembly of an Antiparallel Homo-Adenine DNA Duplex by Small-Molecule Binding
Çetinkol, Ö. P., Santai, C. T., Jain, S. S., & Hud, N. V. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0492891 · Cited by 110
Jain, S. S. (2003) · Nucleic Acids Research · doi:10.1093/nar/gkg648 · Cited by 107
Chen, M. C., Cafferty, B. J., Mamajanov, I., Gállego, I., Khanam, J., Krishnamurthy, R., & Hud, N. V. (2014) · Journal of the American Chemical Society · doi:10.1021/ja410124v · Cited by 94
Zeng, Y., Pratumyot, Y., Piao, X., & Bong, D. T.-Y. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2099326 · Cited by 90
Timmerman, P., Weidmann, J.-L., Jolliffe, K. A., Prins, L. J., Reinhoudt, D. N., Shinkai, S., Frish, L., & Cohen, Y. (2000) · Journal of the Chemical Society Perkin Transactions 2 · doi:10.1039/b003968n · Cited by 88
Construction of RNA nanocages by re-engineering the packaging RNA of Phi29 bacteriophage
Hao, C., Li, X., Tian, C., Jiang, W., Wang, G., & Mao, C. (2014) · Nature Communications · doi:10.1038/ncomms4890 · Cited by 84
Çetinkol, Ö. P., & Hud, N. V. (2008) · Nucleic Acids Research · doi:10.1093/nar/gkn977 · Cited by 74
Determinants of Cyanuric Acid and Melamine Assembly in Water
Ma, M., & Bong, D. T.-Y. (2011) · Langmuir · doi:10.1021/la201415d · Cited by 69
Artificial Genetic Sets Composed of Size‐Expanded Base Pairs
Winnacker, M., & Kool, E. T. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201305267 · Cited by 59
Jiang, D., & Seela, F. (2010) · Journal of the American Chemical Society · doi:10.1021/ja910020n · Cited by 54
Structure of the Parallel Duplex of Poly(A) RNA: Evaluation of a 50 Year‐Old Prediction
Safaee, N., Noronha, A. M., Rodionov, D., Kozlov, G., Wilds, C. J., Sheldrick, G. M., & Gehring, K. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201303461 · Cited by 52
Base pairing equilibria between polynucleotides and complementary monomers
Davies, R. J. H., & Davidson, N. (1971) · Biopolymers · doi:10.1002/bip.360100904 · Cited by 50
A Janus-Wedge DNA Triplex with A-W1-T and G-W2-C Base Triplets
Chen, H., Meena, M., & McLaughlin, L. W. (2008) · Journal of the American Chemical Society · doi:10.1021/ja804607v · Cited by 47
Bifacial Nucleoside as a Surrogate for Both T and A in Duplex DNA
Shin, D., & Tor, Y. (2011) · Journal of the American Chemical Society · doi:10.1021/ja201397e · Cited by 41
Park, K. S., & Park, H. G. (2014) · Biosensors and Bioelectronics · doi:10.1016/j.bios.2014.10.003 · Cited by 33
Shionoya, M., & Tanaka, K. G. (2000) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.73.1945 · Cited by 28
Martín‐Ortiz, M., Gómez‐Gallego, M., de Arellano, C. R., & Sierra, M. Á. (2012) · Chemistry - A European Journal · doi:10.1002/chem.201202327 · Cited by 27
Janus-type AT nucleosides: synthesis, solid and solution state structures
Pan, M.-Y., Hang, W., Zhao, X., Zhao, H., Deng, P., Xing, Z., Qing, Y., & He, Y. (2011) · Organic & Biomolecular Chemistry · doi:10.1039/c1ob05577a · Cited by 27
Hydrogen-bond self-assembly of DNA-analogues into hexameric rosettes
Rakotondradany, F., Palmer, A., Toader, V., Chen, B., Whitehead, M. A., & Sleiman, H. F. (2005) · Chemical Communications · doi:10.1039/b511984g · Cited by 25
Self-citationSynthesis of Janus type nucleoside analogues and their preliminary bioactivity
Yang, H.-Z., Pan, M.-Y., Jiang, D., & He, Y. (2010) · Organic & Biomolecular Chemistry · doi:10.1039/c0ob00495b · Cited by 24
Complexes of Poly(adenylic Acid) with Complementary Monomers
Davies, R. J. H. (1976) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1976.tb10015.x · Cited by 14
Largy, E., Liu, W., Hasan, A., & Perrin, D. M. (2013) · ChemBioChem · doi:10.1002/cbic.201300250 · Cited by 14
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Xu, F., & Feringa, B. L. (2022) · Advanced Materials · doi:10.1002/adma.202204413 · Cited by 331
Single-stranded DNA and RNA origami
Han, D., Qi, X., Myhrvold, C., Wang, B., Dai, M., Jiang, S., Bates, M., Liu, Y., An, B., Zhang, F., et al. (2017) · Science · doi:10.1126/science.aao2648 · Cited by 300
Emerging Approaches to DNA Data Storage: Challenges and Prospects
Doricchi, A., Platnich, C. M., Gimpel, A., Horn, F., Earle, M., Lanzavecchia, G., Cortajarena, A. L., Liz-Marzán, L. M., Liu, N., Heckel, R., et al. (2022) · ACS Nano · doi:10.1021/acsnano.2c06748 · Cited by 235
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Metadata
- Authors
- Avakyan, N., Greschner, A. A., Aldaye, F., Serpell, C. J., Toader, V., Petitjean, A., & Sleiman, H. F.
- Affiliations
- McGill University (CA)
- Institut National de la Recherche Scientifique (CA)
- University of Kent (GB)
- Queen's University (CA)
- Corresponding author
- Sleiman, Hanadi F.
- ORCID
- Venue
- Nature Chemistry
- Published
- 2016-02-22
- Volume
- 8
- Issue
- 4
- Pages
- 368-376
- ISSN
- 1755-4330 (ISSN-L)
- 1755-4349
- OpenAlex
- W2283133204
- Cited by
- 148
- References
- 58
- Citations by year
- 2026: 10 · 2025: 12 · 2024: 10 · 2023: 10 · 2022: 21 · 2021: 17 · 2020: 17 · 2019: 15 · 2018: 15 · 2017: 10 · 2016: 11
- FWCI
- 8.84
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- www.springer.com/tdm (tdm)
- Locations
- Nature Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Kent Academic Repository (University of Kent) (acceptedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Advanced biosensing and bioanalysis techniques
- Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
- Keywords
- cyanuric acid, nucleic acid self-assembly, triplex DNA, peptide nucleic acid, nucleic acid nanostructures
- MeSH terms
- Circular Dichroism, DNA, Hydrogen Bonding, Poly A, Triazines, Peptide Nucleic Acids
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