Building siRNAs with Cubes: Synthesis and Evaluation of Cubane-Modified siRNAs.

Gene Silencing HeLa Cells Humans Molecular Structure Organophosphorus Compounds / chemistry RNA, Small Interfering / chemical synthesis
cubanes gene-silencing phosphoramidite siRNA strand selection

Journal

Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360

Informations de publication

Date de publication:
13 10 2021
Historique:
revised: 27 07 2021
received: 08 07 2021
pubmed: 29 7 2021
medline: 22 2 2022
entrez: 28 7 2021
Statut: ppublish

Résumé

Cubane molecules hold great potential for medicinal chemistry applications due to their inherent stability and low toxicity. In this study, we report the synthesis of a cubane derivative phosphoramidite for the incorporation of cubane into small interfering RNAs (siRNAs). Synthetic siRNAs rely on chemical modifications to improve their pharmacokinetic profiles. However, they are still able to mediate sequence-specific gene silencing via the endogenous RNA interference pathway. We designed a library of siRNAs bearing cubane at different positions within the sense and antisense strands. All siRNAs showed excellent gene-silencing activity, with IC

Identifiants

DOI: 10.1002/cbic.202100334 PMID: 34319643
pubmed: 34319643
doi: 10.1002/cbic.202100334
doi:

Substances chimiques

Organophosphorus Compounds 0
RNA, Small Interfering 0
phosphoramidite 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

2981-2985

Subventions

Organisme : Natural Sciences and Engineering Research Council

Informations de copyright

© 2021 Wiley-VCH GmbH.

Références

A. Fire, S. Xu, M. K. Montgomery, S. A. Kostas, S. E. Driver, C. C. Mello, Nature 1998, 391, 806-811.
 
C. Matranga, Y. Tomari, C. Shin, D. P. Bartel, P. D. Zamore, Cell 2005, 123, 607-620;
A. Khvorova, A. Reynolds, S. D. Jayasena, Cell 2003, 115, 209-216.
 
P. R. de Paula Brandão, S. S. Titze-de-Almeida, R. Titze-de-Almeida, Mol. Diagn. Ther. 2020, 24, 61-68;
J. Rüger, S. Ioannou, D. Castanotto, C. A. Stein, Trends Pharmacol. Sci. 2020, 41, 27-41.
 
M. Manoharan, Biochim. Biophys. Acta 1999, 1489, 117-130;
P. S. Pallan, E. M. Greene, P. A. Jicman, R. K. Pandey, M. Manoharan, E. Rozners, M. Egli, Nucleic Acids Res. 2011, 39, 3482-3495.
J. Wang, Z. Lu, M. G. Wientjes, J. L. Au, AAPS J. 2010, 12, 492-503.
X. Shen, D. R. Corey, Nucleic Acids Res. 2017, 46, 1584-1600.
 
F. Eckstein, Nucleic Acid Ther. 2014, 24, 374-387;
A. H. Hall, J. Wan, E. E. Shaughnessy, B. Ramsay Shaw, K. A. Alexander, Nucleic Acids Res. 2004, 32, 5991-6000.
D. Mutisya, C. Selvam, B. D. Lunstad, P. S. Pallan, A. Haas, D. Leake, M. Egli, E. Rozners, Nucleic Acids Res. 2014, 42, 6542-6551.
 
T. C. Efthymiou, B. Peel, V. Huynh, J.-P. Desaulniers, Bioorg. Med. Chem. Lett. 2012, 22, 5590-5594;
T. C. Efthymiou, V. Huynh, J. Oentoro, B. Peel, J. P. Desaulniers, Bioorg. Med. Chem. Lett. 2012, 22, 1722-1726.
K. Tsubaki, M. L. Hammill, A. J. Varley, M. Kitamura, T. Okauchi, J.-P. Desaulniers, ACS Med. Chem. Lett. 2020, 11, 1457-1462.
 
M. L. Hammill, C. Isaacs-Trépanier, J.-P. Desaulniers, ChemistrySelect 2017, 2, 9810-9814;
M. L. Hammill, G. Islam, J.-P. Desaulniers, Org. Biomol. Chem. 2020, 18, 41-46;
J. P. Desaulniers, G. Hagen, J. Anderson, C. McKim, B. Roberts, RSC Adv. 2017, 7, 3450-3454.
T. A. Reekie, C. M. Williams, L. M. Rendina, M. Kassiou, J. Med. Chem. 2019, 62, 1078-1095.
P. E. Eaton, Angew. Chem. Int. Ed. Engl. 1992, 31, 1421-1436.
Y.-W. Cheung, P. Röthlisberger, A. E. Mechaly, P. Weber, F. Levi-Acobas, Y. Lo, A. W. C. Wong, A. B. Kinghorn, A. Haouz, G. P. Savage, M. Hollenstein, J. A. Tanner, Proc. Nat. Acad. Sci. USA 2020, 117, 16790-16798.
B. A. Chalmers, H. Xing, S. Houston, C. Clark, S. Ghassabian, A. Kuo, B. Cao, A. Reitsma, C.-E. P. Murray, J. E. Stok, G. M. Boyle, C. J. Pierce, S. W. Littler, D. A. Winkler, P. V. Bernhardt, C. Pasay, J. J. De Voss, J. McCarthy, P. G. Parsons, G. H. Walter, M. T. Smith, H. M. Cooper, S. K. Nilsson, J. Tsanaktsidis, G. P. Savage, C. M. Williams, Angew. Chem. Int. Ed. 2016, 55, 3580-3585;
Angew. Chem. 2016, 128, 3644-3649.
 
M. J. Falkiner, S. W. Littler, K. J. McRae, G. P. Savage, J. Tsanaktsidis, Org. Process Res. Dev. 2013, 17, 1503-1509;
M. Bliese, J. Tsanaktsidis, Aust. J. Chem. 1997, 50, 189-192.
H. Addepalli, Meena, C. G. Peng, G. Wang, Y. Fan, K. Charisse, K. N. Jayaprakash, K. G. Rajeev, R. K. Pandey, G. Lavine, L. Zhang, K. Jahn-Hofmann, P. Hadwiger, M. Manoharan, M. A. Maier, Nucleic Acids Res. 2010, 38, 7320-7331.
 
J. Lisowiec-Wąchnicka, N. Bartyś, A. Pasternak, Sci. Rep. 2019, 9, 2477;
C. L. Noland, J. A. Doudna, RNA 2013, 19, 639-648;
A. J. Varley, J.-P. Desaulniers, RSC Adv. 2021, 11, 2415-2426.
A. Varley, M. L. Hammill, L. Salim, J.-P. Desaulniers, Nucleic Acid Ther. 2020, 30, 229-236.

Auteurs

Matthew L Hammill (ML)

Faculty of Science, University of Ontario Institute of Technology, 2000 Simcoe Street North, Oshawa, Ontario, L1G 0C5, Canada.

Lidya Salim (L)

Faculty of Science, University of Ontario Institute of Technology, 2000 Simcoe Street North, Oshawa, Ontario, L1G 0C5, Canada.

Kouta Tsubaki (K)

Faculty of Science, University of Ontario Institute of Technology, 2000 Simcoe Street North, Oshawa, Ontario, L1G 0C5, Canada.
Department of Applied Chemistry, Graduate School of Engineering, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata, Kitakyushu, 804-8550, Japan.

Andrew J Varley (AJ)

Faculty of Science, University of Ontario Institute of Technology, 2000 Simcoe Street North, Oshawa, Ontario, L1G 0C5, Canada.

Mitsuru Kitamura (M)

Department of Applied Chemistry, Graduate School of Engineering, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata, Kitakyushu, 804-8550, Japan.

Tatsuo Okauchi (T)

Department of Applied Chemistry, Graduate School of Engineering, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata, Kitakyushu, 804-8550, Japan.
ORCID: 0000-0002-0143-149X

Jean-Paul Desaulniers (JP)

Faculty of Science, University of Ontario Institute of Technology, 2000 Simcoe Street North, Oshawa, Ontario, L1G 0C5, Canada.
ORCID: 0000-0002-9596-4552

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Classifications MeSH

questionsmedicales.fr › Phénomènes génétiques › Régulation de l'expression des gènes › Épigenèse génétique › Extinction de l'expression des gènes › Building siRNAs with Cubes: Synthesis and...
questionsmedicales.fr › Cellules › Cellules épithéliales › Cellules HeLa › Building siRNAs with Cubes: Synthesis and...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Building siRNAs with Cubes: Synthesis and...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Building siRNAs with Cubes: Synthesis and...
questionsmedicales.fr › Composés chimiques organiques › Composés organiques du phosphore › Building siRNAs with Cubes: Synthesis and...
questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Acides nucléiques › ARN › ARN non traduit › Petit ARN non traduit › Petit ARN interférent › Building siRNAs with Cubes: Synthesis and...