Dual Crosslinking Photo-Switches for Orthogonal Photo-Control of Hybridization Between Serinol Nucleic Acid and RNA.
XNA
crosslinking
nucleobase modification
photochemistry
serinol nucleic acid
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
08 Mar 2021
08 Mar 2021
Historique:
received:
29
07
2020
revised:
31
08
2020
pubmed:
8
9
2020
medline:
19
3
2021
entrez:
7
9
2020
Statut:
ppublish
Résumé
Wavelength-selective photo-regulation by multiple chromophores responding to different wavelengths can expand the variation of photo-manipulating systems. Herein, we report the orthogonal photo-regulation of duplex formation between serinol nucleic acid (SNA) and RNA using light-induced crosslinking reactions mediated by a new photo-reactive nucleobase 8-naphthylvinyladenine (
Identifiants
pubmed: 32893394
doi: 10.1002/chem.202003528
doi:
Substances chimiques
Nucleic Acids
0
Propanolamines
0
Propylene Glycols
0
RNA
63231-63-0
serinol
IC94L30J8M
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4599-4604Subventions
Organisme : Japan Agency for Medical Research and Development
ID : 19am0401007
Organisme : Japan Society for the Promotion of Science
ID : JP18H03933
Organisme : Japan Society for the Promotion of Science
ID : JP20K15399
Organisme : Japan Society for the Promotion of Science
ID : JP20J15414
Organisme : JSPS A3 Foresight Program
Organisme : Asahi Glass Foundation
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
M. A. C. Stuart, W. T. S. Huck, J. Genzer, M. Müller, C. Ober, M. Stamm, G. B. Sukhorukov, I. Szleifer, V. V. Tsukruk, M. Urban, F. Winnik, S. Zauscher, I. Luzinov, S. Minko, Nat. Mater. 2010, 9, 101-113;
C. de las Heras Alarcón, S. Pennadam, C. Alexander, Chem. Soc. Rev. 2005, 34, 276-285;
Y. Qiu, K. Park, Adv. Drug Delivery Rev. 2001, 53, 321-339;
E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. Int. Ed. 2007, 46, 72-191;
Angew. Chem. 2007, 119, 72-196.
G. Mayer, A. Heckel, Angew. Chem. Int. Ed. 2006, 45, 4900-4921;
Angew. Chem. 2006, 118, 5020-5042;
C. Brieke, F. Rohrbach, A. Gottschalk, G. Mayer, A. Heckel, Angew. Chem. Int. Ed. 2012, 51, 8446-8476;
Angew. Chem. 2012, 124, 8572-8604.
C. G. Bochet, Tetrahedron Lett. 2000, 41, 6341-6346;
P. Klán, T. Šolomek, C. G. Bochet, A. Blanc, R. Givens, M. Rubina, V. Popik, A. Kostikov, J. Wirz, Chem. Rev. 2013, 113, 119-191;
M. J. Hansen, W. A. Velema, M. M. Lerch, W. Szymanski, B. L. Feringa, Chem. Soc. Rev. 2015, 44, 3358-3377;
V. San Miguel, C. G. Bochet, A. del Campo, J. Am. Chem. Soc. 2011, 133, 5380-5388;
L. Fournier, I. Aujard, T. le Saux, S. Maurin, S. Beaupierre, J. B. Baudin, L. Jullien, Chem. Eur. J. 2013, 19, 17494-17507;
J. M. Amatrudo, J. P. Olson, G. Lur, C. Q. Chiu, M. J. Higley, G. C. R. Ellis-Davies, ACS Chem. Neurosci. 2014, 5, 64-70.
M. A. Priestman, L. Sun, D. S. Lawrence, ACS Chem. Biol. 2011, 6, 377-384;
W. A. Velema, J. P. van der Berg, W. Szymanski, A. J. M. Driessen, B. L. Feringa, ACS Chem. Biol. 2014, 9, 1969-1974.
X. Zhang, W. Xi, S. Huang, K. Long, C. N. Bowman, Macromolecules 2017, 50, 5652-5660;
L. García-Fernández, C. Herbivo, V. S. M. Arranz, D. Warther, L. Donato, A. Specht, A. del Campo, Adv. Mater. 2014, 26, 5012-5017;
H. Frisch, F. R. Bloesser, C. Barner-Kowollik, Angew. Chem. Int. Ed. 2019, 58, 3604-3609;
Angew. Chem. 2019, 131, 3642-3648;
H. Frisch, D. Kodura, F. R. Bloesser, L. Michalek, C. Barner-Kowollik, Macromol. Rapid Commun. 2020, 41, 1900414.
M. A. Azagarsamy, K. S. Anseth, Angew. Chem. Int. Ed. 2013, 52, 13803-13807;
Angew. Chem. 2013, 125, 14048-14052;
D. B. Pacardo, B. Neupane, S. M. Rikard, Y. Lu, R. Mo, S. R. Mishra, J. B. Tracy, G. Wang, F. S. Ligler, Z. Gu, Nanoscale 2015, 7, 12096-12103.
A. Rodrigues-Correia, X. M. M. Weyel, A. Heckel, Org. Lett. 2013, 15, 5500-5503;
A. Rodrigues-Correia, D. Knapp-Bühle, J. W. Engels, A. Heckel, Org. Lett. 2014, 16, 5128-5131.
K. Fujimoto, S. Sasago, J. Mihara, S. Nakamura, Org. Lett. 2018, 20, 2802-2805.
H. Nishioka, X. Liang, T. Kato, H. Asanuma, Angew. Chem. Int. Ed. 2012, 51, 1165-1168;
Angew. Chem. 2012, 124, 1191-1194.
M. W. Haydell, M. Centola, V. Adam, J. Valero, M. Famulok, J. Am. Chem. Soc. 2018, 140, 16868-16872.
M. Škugor, J. Valero, K. Murayama, M. Centola, H. Asanuma, M. Famulok, Angew. Chem. Int. Ed. 2019, 58, 6948-6951;
Angew. Chem. 2019, 131, 7022-7025.
H. Kashida, K. Murayama, T. Toda, H. Asanuma, Angew. Chem. Int. Ed. 2011, 50, 1285-1288;
Angew. Chem. 2011, 123, 1321-1324.
K. Murayama, Y. Yamano, H. Asanuma, J. Am. Chem. Soc. 2019, 141, 9485-9489.
Theoretically, photo-reaction of SNN should not proceed upon irradiation with 465 nm light because NVA has almost no absorption band around 465 nm. However, study of the quantum yield of the crosslinking reaction revealed that crosslinking between NVA residues was over 100 times faster than crosslinking of PVA and to PVA or NVA (Table S1). This high yield might facilitate photo-crosslinking in SNN by excitation with 465 nm light regardless of very slight absorbance at around 465 nm. Despite the unintended reaction of SNN by 465 nm light, clear difference in percent crosslinking of chromophores in SNN and SPN was observed after 20 min of irradiation.