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Title: Playing supramolecular dominoes with light: building and breaking a photoreversible G-quadruplex made from guanosine, boric acid and an azobenzene

Abstract

Addition of an azo dye triggers a cascade of photoreversible intermolecular recognition processes in a mixture of simple guanosine derivatives.

Authors:
 [1];  [1]; ORCiD logo [2]; ORCiD logo [3];  [2]; ORCiD logo [1]
  1. Dipartimento di Chimica “Giacomo Ciamician”, Università di Bologna, v. S. Giacomo, 11-40126 Bologna, Italy
  2. Dipartimento di Scienze della Vita e dell'Ambiente, Università Politecnica delle Marche, 60131 Ancona, Italy
  3. Dept. of Chemistry and Biochemistry, University of Maryland, College Park, USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1495245
Grant/Contract Number:  
DEFG02-98ER14888
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Organic and Biomolecular Chemistry
Additional Journal Information:
Journal Name: Organic and Biomolecular Chemistry Journal Volume: 17 Journal Issue: 10; Journal ID: ISSN 1477-0520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Pieraccini, Silvia, Campitiello, Marilena, Carducci, Federica, Davis, Jeffery T., Mariani, Paolo, and Masiero, Stefano. Playing supramolecular dominoes with light: building and breaking a photoreversible G-quadruplex made from guanosine, boric acid and an azobenzene. United Kingdom: N. p., 2019. Web. doi:10.1039/C9OB00193J.
Pieraccini, Silvia, Campitiello, Marilena, Carducci, Federica, Davis, Jeffery T., Mariani, Paolo, & Masiero, Stefano. Playing supramolecular dominoes with light: building and breaking a photoreversible G-quadruplex made from guanosine, boric acid and an azobenzene. United Kingdom. doi:https://doi.org/10.1039/C9OB00193J
Pieraccini, Silvia, Campitiello, Marilena, Carducci, Federica, Davis, Jeffery T., Mariani, Paolo, and Masiero, Stefano. Wed . "Playing supramolecular dominoes with light: building and breaking a photoreversible G-quadruplex made from guanosine, boric acid and an azobenzene". United Kingdom. doi:https://doi.org/10.1039/C9OB00193J.
@article{osti_1495245,
title = {Playing supramolecular dominoes with light: building and breaking a photoreversible G-quadruplex made from guanosine, boric acid and an azobenzene},
author = {Pieraccini, Silvia and Campitiello, Marilena and Carducci, Federica and Davis, Jeffery T. and Mariani, Paolo and Masiero, Stefano},
abstractNote = {Addition of an azo dye triggers a cascade of photoreversible intermolecular recognition processes in a mixture of simple guanosine derivatives.},
doi = {10.1039/C9OB00193J},
journal = {Organic and Biomolecular Chemistry},
number = 10,
volume = 17,
place = {United Kingdom},
year = {2019},
month = {3}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: https://doi.org/10.1039/C9OB00193J

Citation Metrics:
Cited by: 4 works
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Works referenced in this record:

Photomobile Polymer Materials: Towards Light-Driven Plastic Motors
journal, June 2008

  • Yamada, Munenori; Kondo, Mizuho; Mamiya, Jun-ichi
  • Angewandte Chemie International Edition, Vol. 47, Issue 27
  • DOI: 10.1002/anie.200800760

Small-Angle X-ray Scattering Study of Self-Assembling Lipophilic Guanines in Organic Solvents: G-Quadruplex Formation and Cation Effects in Cyclohexane
journal, January 2013

  • Gonnelli, A.; Ortore, M. G.; Baldassarri, E. J.
  • The Journal of Physical Chemistry B, Vol. 117, Issue 4
  • DOI: 10.1021/jp3121929

A G 4 ·K + Hydrogel Stabilized by an Anion
journal, August 2014

  • Peters, Gretchen Marie; Skala, Luke P.; Plank, Taylor N.
  • Journal of the American Chemical Society, Vol. 136, Issue 36
  • DOI: 10.1021/ja507506c

On the structural stability of guanosine-based supramolecular hydrogels
journal, January 2018

  • Carducci, Federica; Yoneda, Juliana S.; Itri, Rosangela
  • Soft Matter, Vol. 14, Issue 15
  • DOI: 10.1039/C8SM00299A

Expanding the Toolbox of Photoswitches for DNA Nanotechnology Using Arylazopyrazoles
journal, January 2018

  • Adam, Volker; Prusty, Deepak K.; Centola, Mathias
  • Chemistry - A European Journal, Vol. 24, Issue 5
  • DOI: 10.1002/chem.201705500

G-quadruplexes in Prague: A Bohemian Rhapsody
journal, April 2018


UV and pH-responsive supra-amphiphiles driven by combined interactions for controlled self-assembly behaviors
journal, January 2018

  • Li, Shangyang; Hao, Aiyou; Shen, Jian
  • Soft Matter, Vol. 14, Issue 11
  • DOI: 10.1039/C8SM00118A

Artificial muscle-like function from hierarchical supramolecular assembly of photoresponsive molecular motors
journal, December 2017

  • Chen, Jiawen; Leung, Franco King-Chi; Stuart, Marc C. A.
  • Nature Chemistry, Vol. 10, Issue 2
  • DOI: 10.1038/nchem.2887

Light-Induced Reversible Reconfiguration of DNA-Based Constitutional Dynamic Networks: Application to Switchable Catalysis
journal, May 2018

  • Wang, Shan; Yue, Liang; Li, Zi-Yuan
  • Angewandte Chemie International Edition, Vol. 57, Issue 27
  • DOI: 10.1002/anie.201803371

Light-driven conformational regulation of human telomeric G-quadruplex DNA in physiological conditions
journal, January 2011

  • Xing, Xiwen; Wang, Xiaoling; Xu, Liang
  • Org. Biomol. Chem., Vol. 9, Issue 19
  • DOI: 10.1039/C1OB05939D

Chemical Probe for Glycosidic Conformation in Telomeric DNAs
journal, May 1994

  • Dias, Eric; Battiste, John L.; Williamson, James R.
  • Journal of the American Chemical Society, Vol. 116, Issue 10
  • DOI: 10.1021/ja00089a048

Classification of G-Quadruplex DNA on the Basis of the Quadruplex Twist Angle and Planarity of G-Quartets
journal, December 2010


A non-empirical chromophoric interpretation of CD spectra of DNA G-quadruplex structures
journal, January 2010

  • Masiero, Stefano; Trotta, Roberta; Pieraccini, Silvia
  • Organic & Biomolecular Chemistry, Vol. 8, Issue 12
  • DOI: 10.1039/c003428b

c-di-GMP can form remarkably stable G-quadruplexes at physiological conditions in the presence of some planar intercalators
journal, January 2011

  • Nakayama, Shizuka; Kelsey, Ilana; Wang, Jingxin
  • Chemical Communications, Vol. 47, Issue 16
  • DOI: 10.1039/c0cc05432a

G4-Quartet·M + Borate Hydrogels
journal, April 2015

  • Peters, Gretchen Marie; Skala, Luke P.; Plank, Taylor N.
  • Journal of the American Chemical Society, Vol. 137, Issue 17
  • DOI: 10.1021/jacs.5b02753

Small Angle X-ray Scattering Analysis of Deoxyguanosine 5′-Monophosphate Self-Assembing in Solution: Nucleation and Growth of G-Quadruplexes
journal, June 2009

  • Mariani, Paolo; Spinozzi, Francesco; Federiconi, Francesco
  • The Journal of Physical Chemistry B, Vol. 113, Issue 22
  • DOI: 10.1021/jp809734p

Self-assembly of Natural and Unnatural Nucleobases at Surfaces and Interfaces
journal, October 2015


Reversible Photoswitching of a G-Quadruplex
journal, August 2009

  • Ogasawara, Shinzi; Maeda, Mizuo
  • Angewandte Chemie International Edition, Vol. 48, Issue 36
  • DOI: 10.1002/anie.200902183

Co-existence of Distinct Supramolecular Assemblies in Solution and in the Solid State
journal, December 2016

  • Reddy, G. N. Manjunatha; Huqi, Aida; Iuga, Dinu
  • Chemistry - A European Journal, Vol. 23, Issue 10
  • DOI: 10.1002/chem.201604832

Bottom-up approaches for material and device designing using practical aspects of self-assembled molecular architectures
journal, January 2018

  • Ohtake, Toshihiro
  • Molecular Systems Design & Engineering, Vol. 3, Issue 5
  • DOI: 10.1039/C8ME00020D

Conformational Switching of G-Quadruplex DNA by Photoregulation
journal, June 2010

  • Wang, Xiaolin; Huang, Jing; Zhou, Yangyang
  • Angewandte Chemie International Edition, Vol. 49, Issue 31
  • DOI: 10.1002/anie.201002290

Photo-responsive systems and biomaterials: photochromic polymers, light-triggered self-assembly, surface modification, fluorescence modulation and beyond
journal, January 2010

  • Ercole, Francesca; Davis, Thomas P.; Evans, Richard A.
  • Polymer Chemistry, Vol. 1, Issue 1, p. 37-54
  • DOI: 10.1039/B9PY00300B

Photoresponsive Formation of an Intermolecular Minimal G-Quadruplex Motif
journal, January 2016

  • Thevarpadam, Julie; Bessi, Irene; Binas, Oliver
  • Angewandte Chemie International Edition, Vol. 55, Issue 8
  • DOI: 10.1002/anie.201510269

Thiazole Orange-Induced c-di-GMP Quadruplex Formation Facilitates a Simple Fluorescent Detection of This Ubiquitous Biofilm Regulating Molecule
journal, April 2011

  • Nakayama, Shizuka; Kelsey, Ilana; Wang, Jingxin
  • Journal of the American Chemical Society, Vol. 133, Issue 13
  • DOI: 10.1021/ja1091062

Triggering of Guanosine Self-Assembly by Light
journal, April 2010

  • Lena, Stefano; Neviani, Paolo; Masiero, Stefano
  • Angewandte Chemie International Edition, Vol. 49, Issue 21
  • DOI: 10.1002/anie.201000805

Light-enabled reversible self-assembly and tunable optical properties of stable hairy nanoparticles
journal, January 2018

  • Chen, Yihuang; Wang, Zewei; He, Yanjie
  • Proceedings of the National Academy of Sciences, Vol. 115, Issue 7
  • DOI: 10.1073/pnas.1714748115

A Molecular Chaperone for G4-Quartet Hydrogels
journal, December 2015

  • Peters, Gretchen Marie; Skala, Luke P.; Davis, Jeffery T.
  • Journal of the American Chemical Society, Vol. 138, Issue 1
  • DOI: 10.1021/jacs.5b08769