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Phosphorothioates, Essential Components of Therapeutic Oligonucleotides

Eckstein, Fritz·2014·Nucleic Acid Therapeutics

DOI 10.1089/nat.2014.0506

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Abstract

Phosphorothioates have found their usefulness in the general area of oligonucleotide therapeutic applications. Initially this modification was introduced into the antisense methodology because of the nuclease resistance of the phosphorothioate linkage in comparison with that of the phosphate linkage. However, as experimental data accumulated, it was detected that this chemical modification also facilitates cellular uptake and bioavailibity in vivo. Thus, today the majority of therapeutic oligonucleotides contain this modification. This review will discuss the historical development of this modification and present some of its chemical properties where they differ from those of the phosphate group. The antisense application will be discussed in the original context with cleavage of the target mRNA, but other target RNAs such as microRNAs and long noncoding RNAs will also be covered. It continues with applications where the target RNA should not be cleaved. A brief presentation of decoy oligonucleotides will be included, as well as some miscellaneous applications. Cellular uptake is a crucial step for oligonucleotides to reach their target and will be briefly reviewed. Lastly, a most surprising recent observation is the presence of phosphorothioate groups in bacterial DNA where functions still remain to be fully determined.

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Untitled work
Bartel (2004) · doi:10.1016/s0092-8674(04)00045-5 · Cited by 34,714
The nature of the chemical bond—1992
Pauling, L. C. (1992) · Journal of Chemical Education · doi:10.1021/ed069p519 · Cited by 13,235
CpG motifs in bacterial DNA trigger direct B-cell activation
Krieg, A. M., Yi, A.-K., Matson, S., Waldschmidt, T. J., Bishop, G. A., Teasdale, R., Koretzky, G. A., & Klinman, D. M. (1995) · Nature · doi:10.1038/374546a0 · Cited by 3,508
miR-122 regulation of lipid metabolism revealed by in vivo antisense targeting
Esau, C., Davis, S., Murray, S. F., Yu, X. X., Pandey, S. K., Pear, M., Watts, L., Booten, S. L., Graham, M., McKay, R., et al. (2006) · Cell Metabolism · doi:10.1016/j.cmet.2006.01.005 · Cited by 2,082
Inhibition of Rous sarcoma virus replication and cell transformation by a specific oligodeoxynucleotide.
Zamecnik, P. C., & Stephenson, M. L. (1978) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.75.1.280 · Cited by 1,792
A Sequencing Method Based on Real-Time Pyrophosphate
Ronaghi, M., Uhlén, M., & Nyrén, P. (1998) · Science · doi:10.1126/science.281.5375.363 · Cited by 1,630
LNA-mediated microRNA silencing in non-human primates
Elmén, J., Lindow, M., Schütz, S., Lawrence, M., Petri, A., Obad, S., Lindholm, M., Hedtjärn, M., Hansen, H. F., Berger, U., et al. (2008) · Nature · doi:10.1038/nature06783 · Cited by 1,589
RNA Targeting Therapeutics: Molecular Mechanisms of Antisense Oligonucleotides as a Therapeutic Platform
Bennett, C. F., & Swayze, E. E. (2010) · The Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pharmtox.010909.105654 · Cited by 1,431
Conserved Function of lincRNAs in Vertebrate Embryonic Development despite Rapid Sequence Evolution
Ulitsky, I., Shkumatava, A., Jan, C. H., Sive, H. L., & Bartel, D. P. (2011) · Cell · doi:10.1016/j.cell.2011.11.055 · Cited by 1,197
A general two-metal-ion mechanism for catalytic RNA
Steitz, T. A., & Steitz, J. A. (1993) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.90.14.6498 · Cited by 1,171

Flagged first, then by citations

Show all 123 references

Research works printed but not linked: 5

Dias N, and Stein CA. (2002) Antisense oligonucleotides: Basic concepts and mechanisms. Mol Cancer Ther, 1:347–355.
Juliano RL. (2005). Peptide-oligonucleotide conjugatesfor the delivery of antisense and siRNA. Curr Opin Mel Ther, 7:132–136.
Manoharan M. (2013). RNAi therapeutics using GalNAc-siRNA conjugate delivery platform: New era of oligonucleotides. Presented at Oligonucleotide Therapeutics Society Ninth Annual Meeting, Naples, Italy, October 6–8, 2013.
Bhat B, , Neben S, , Tay J, , Liu K, , Chau N, , Hogan D, , MacKenna D, , Gibson N. (2014). RG-101, a GalNAC-conjugated anti-miR employing a unique mechanism of action by targeting host factor microRNA-122 (miR-122), demonstrates potent activity and reduction of HCV in preclinical studies. Hepatology, 58:1377A–1395A.
Hutchinson CAIII, , Smith HO, , Pfannkoch C, and Venter JC. (2005). Cell-free cloning using φ29 DNA polymerase. Proc Natl Acad Sci (USA), 102:17322–17336.

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Antibody-oligonucleotide conjugates: design principles, intracellular delivery, and translational opportunities
Li, Y., Liu, X. D., Zhang, F., Fu, R., Zhao, D., Ye, L., & Zhu, Y. Z. (2026) · Journal of Hematology & Oncology · doi:10.1186/s13045-026-01824-4 · Cited by 1
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Zhang, S., Ye, R., Shi, T., Deng, C., Chang, L., Ren, Q., Zhang, P., Xu, C., & Zhong, Z. (2026) · Journal of Controlled Release · doi:10.1016/j.jconrel.2026.115209 · Cited by 1
Multifunctional chiral bis(amidine) organocatalysts enable stereoselective synthesis of phosphorothioate oligonucleotides
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Phosphonomethyl (Thio)Phosphonamidite Reagents for the Construction of Phosphonylmethyl Phosphono(Di)Thioate Mono‐ and Diesters
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Development of Efficient Synthetic Methods of Boranophosphate Oligonucleotides
Sato, K., & Wada, T. (2020) · Journal of Synthetic Organic Chemistry Japan · doi:10.5059/yukigoseikyokaishi.78.421 · Cited by 1
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Sakiani, S., Asif, B., Yang, A. H., & Koh, C. (2020) · Current Hepatology Reports · doi:10.1007/s11901-020-00550-w · Cited by 1
Mesyl Phosphoramidate Oligonucleotides: A New Promising Type of Antisense Agents
Stetsenko, D. A. (2023) · Springer eBooks · doi:10.1007/978-981-16-1313-5_19-1 · Cited by 1
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Patrushev, D. E., Burakova, E. A., Bizyaev, S. N., Фокина, А. А., & Stetsenko, D. A. (2023) · Molecular Biology · doi:10.31857/s0026898423020180 · Cited by 1
Promoter-independent synthesis of chemically modified RNA by human DNA polymerase θ variants
Tredinnick, T., Kent, T., Станиславович, М. Л., Li, Z., Madžo, J., Chen, X. S., & Pomerantz, R. T. (2023) · RNA · doi:10.1261/rna.079396.122 · Cited by 1
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Otte, D.-M., Choukeife, M., Patwari, T., & Mayer, G. (2023) · Springer eBooks · doi:10.1007/978-981-19-9776-1_25 · Cited by 1
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Laina, A., Vlachogiannis, N. I., Stamatelopoulos, K. S., & Stellos, K. (2022) · Elsevier eBooks · doi:10.1016/b978-0-12-822546-2.00003-4 · Cited by 2
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Dirin, M., & Winkler, J. (2018) · Wiley eBooks · doi:10.1002/9781119070153.ch5 · Cited by 1
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Strzelecka, D., Śmietański, M., Sikorski, P. J., Warmiński, M., Kowalska, J., & Jemielity, J. (2020) · bioRxiv (Cold Spring Harbor Laboratory) · doi:10.1101/2020.07.02.184598 · Cited by 1
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Malong, L., Roskosch, J., Hager, C., Fortin, J., Schmucki, R., Callow, M. G., Weile, C., Romeo, V., Patsch, C., Martin, S. E., et al. (2024) · bioRxiv (Cold Spring Harbor Laboratory) · doi:10.1101/2024.12.17.628665 · Cited by 1
Immunomodulatory effects of CpG and other oligonucleotides
Herbáth, M. (2015) · Eötvös Loránd Tudományegyetem · doi:10.15476/elte.2015.068
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Bhaduri, S., Spano, M. N., & Arya, D. P. (2016) · Elsevier eBooks · doi:10.1016/b978-0-12-409547-2.12550-8
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Murakami, M. (2016) · Drug Discoveries & Therapeutics · doi:10.5582/ddt.2016.01073
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Aartsma-Rus, A. M., Jackson, A. L., & Levin, A. A. (2018) · Wiley eBooks · doi:10.1002/9781119070153.ch1
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Huang, X., Xue, J., Wang, F., & Li, J. (2019) · Analytical Biochemistry · doi:10.1016/j.ab.2019.01.003
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Yoshioka, K., Nishina, K., Nagata, T., & Yokota, T. (2019) · doi:10.1002/9783527823987.vol2_c12
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Nambiar, T. S. (2020) · doi:10.7916/d8-2xwd-td48
Nucleic acid structure and conjugation for drug design
Tan, D. J. Y. (2020) · DR-NTU (Nanyang Technological University) · doi:10.32657/10356/143056

Authors: Eckstein, F.
Affiliations: Max Planck Society (DE)
Corresponding author: Eckstein, Fritz
Venue: Nucleic Acid Therapeutics
Publisher: SAGE Publications
Published: 2014-12
Volume: 24
Issue: 6
Pages: 374-387
ISSN: 2159-3337 (ISSN-L)
2159-3345
DOI: 10.1089/nat.2014.0506
OpenAlex: W2316132657
Cited by: 684
References: 123
Citations by year: 2026: 69 · 2025: 87 · 2024: 86 · 2023: 75 · 2022: 81 · 2021: 69 · 2020: 64 · 2019: 49 · 2018: 39 · 2017: 25 · 2016: 20 · 2015: 20
FWCI: 2.04
Type: journal article
Language: en
Open access: closed
Licence: journals.sagepub.com/page/policies/text-and-data-mining-license (tdm)
Locations: Nucleic Acid Therapeutics (publishedVersion)
PubMed (publishedVersion)
MPG.PuRe (Max Planck Society) (submittedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA Interference and Gene Delivery
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
Keywords: phosphorothioate, oligonucleotide therapeutics, antisense oligonucleotides, nuclease resistance, cellular uptake, bioavailability, microRNA targeting, long non-coding RNA, decoy oligonucleotides, bacterial DNA
MeSH terms: Animals, Humans, Protein Binding, Rabbits, Transcription Factors, Oligonucleotides, Antisense, History, 20th Century, Mice, Phosphorothioate Oligonucleotides

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Phosphorothioates, Essential Components of Therapeutic Oligonucleotides

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