This content will become publicly available on Thu Oct 31 00:00:00 EDT 2024
Enhanced Photo-Cross-Linking of Thymines in DNA Holliday Junction-Templated Squaraine Dimers
Abstract
Programmable self-assembly of dyes using DNA templates to promote exciton delocalization in dye aggregates is gaining considerable interest. New methods to improve the rigidity of the DNA scaffold and thus the stability of the molecular dye aggregates to encourage exciton delocalization are desired. In these dye–DNA constructs, one potential way to increase the stability of the aggregates is to create an additional covalent bond via photo-cross-linking reactions between thymines in the DNA scaffold. Specifically, we report an approach to increase the yield of photo-cross-linking reaction between thymines in the core of a DNA Holliday junction while limiting the damage from UV irradiation to DNA. We investigated the effect of the distance between thymines on the photo-cross-linking reaction yields by using linkers with different lengths to tether the dyes to the DNA templates. By comprehensively evaluating the photo-cross-linking reaction yields of dye–DNA aggregates using linkers with different lengths, we conclude that interstrand thymines tend to photo-cross-link more efficiently with short linkers. A higher cross-linking yield was achieved due to the shorter intermolecular distance between thymines influenced by strong dye–dye interactions. Furthermore, our method establishes the possibility of improving the stability of DNA-scaffolded dye aggregates, thereby expanding their use in exciton-based applicationsmore »
- Authors:
-
- Boise State University, ID (United States)
- Publication Date:
- Research Org.:
- Boise State Univ., ID (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Materials Sciences & Engineering Division (MSE)
- OSTI Identifier:
- 2234021
- Grant/Contract Number:
- SC0020089
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Biochemistry
- Additional Journal Information:
- Journal Volume: 62; Journal Issue: 22; Journal ID: ISSN 0006-2960
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Adjacent thymines; Interstrand photo−crosslinking; Short linker length; Squaraine dye; Dye−dye interactions; Dyes and pigments; Genetics; Nucleic acid structure; Oligomers; Thymine
Citation Formats
Basu, Shibani, Roy, Simon K., Barcenas, German, Li, Lan, Yurke, Bernard, Knowlton, William B., and Lee, Jeunghoon. Enhanced Photo-Cross-Linking of Thymines in DNA Holliday Junction-Templated Squaraine Dimers. United States: N. p., 2023.
Web. doi:10.1021/acs.biochem.3c00471.
Basu, Shibani, Roy, Simon K., Barcenas, German, Li, Lan, Yurke, Bernard, Knowlton, William B., & Lee, Jeunghoon. Enhanced Photo-Cross-Linking of Thymines in DNA Holliday Junction-Templated Squaraine Dimers. United States. https://doi.org/10.1021/acs.biochem.3c00471
Basu, Shibani, Roy, Simon K., Barcenas, German, Li, Lan, Yurke, Bernard, Knowlton, William B., and Lee, Jeunghoon. Tue .
"Enhanced Photo-Cross-Linking of Thymines in DNA Holliday Junction-Templated Squaraine Dimers". United States. https://doi.org/10.1021/acs.biochem.3c00471.
@article{osti_2234021,
title = {Enhanced Photo-Cross-Linking of Thymines in DNA Holliday Junction-Templated Squaraine Dimers},
author = {Basu, Shibani and Roy, Simon K. and Barcenas, German and Li, Lan and Yurke, Bernard and Knowlton, William B. and Lee, Jeunghoon},
abstractNote = {Programmable self-assembly of dyes using DNA templates to promote exciton delocalization in dye aggregates is gaining considerable interest. New methods to improve the rigidity of the DNA scaffold and thus the stability of the molecular dye aggregates to encourage exciton delocalization are desired. In these dye–DNA constructs, one potential way to increase the stability of the aggregates is to create an additional covalent bond via photo-cross-linking reactions between thymines in the DNA scaffold. Specifically, we report an approach to increase the yield of photo-cross-linking reaction between thymines in the core of a DNA Holliday junction while limiting the damage from UV irradiation to DNA. We investigated the effect of the distance between thymines on the photo-cross-linking reaction yields by using linkers with different lengths to tether the dyes to the DNA templates. By comprehensively evaluating the photo-cross-linking reaction yields of dye–DNA aggregates using linkers with different lengths, we conclude that interstrand thymines tend to photo-cross-link more efficiently with short linkers. A higher cross-linking yield was achieved due to the shorter intermolecular distance between thymines influenced by strong dye–dye interactions. Furthermore, our method establishes the possibility of improving the stability of DNA-scaffolded dye aggregates, thereby expanding their use in exciton-based applications such as light harvesting, nanoscale computing, quantum computing, and optoelectronics.},
doi = {10.1021/acs.biochem.3c00471},
journal = {Biochemistry},
number = 22,
volume = 62,
place = {United States},
year = {Tue Oct 31 00:00:00 EDT 2023},
month = {Tue Oct 31 00:00:00 EDT 2023}
}
Works referenced in this record:
Perspective: Detecting and measuring exciton delocalization in photosynthetic light harvesting
journal, March 2014
- Scholes, Gregory D.; Smyth, Cathal
- The Journal of Chemical Physics, Vol. 140, Issue 11
Nanoscale Resonance Energy Transfer-Based Devices for Probabilistic Computing
journal, September 2015
- Wang, Siyang; Lebeck, Alvin R.; Dwyer, Chris
- IEEE Micro, Vol. 35, Issue 5
Oxygen Toxicity and Reactive Oxygen Species: The Devil Is in the Details
journal, August 2009
- Auten, Richard L.; Davis, Jonathan M.
- Pediatric Research, Vol. 66, Issue 2
Squaraine dyes: The hierarchical synthesis and its application in optical detection
journal, June 2017
- Xia, Guomin; Wang, Hongming
- Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Vol. 31
DNA Damage and Interstrand Cross-Link Formation upon Irradiation of Aryl Iodide C-Nucleotide Analogues
journal, January 2010
- Ding, Hui; Greenberg, Marc M.
- The Journal of Organic Chemistry, Vol. 75, Issue 3
Theory of exciton-vibrational dynamics in molecular dimers
journal, March 1996
- Kühn, Oliver; Renger, Thomas; May, Volkhard
- Chemical Physics, Vol. 204, Issue 1
DNA single-strand breaks during repair of UV damage in human fibroblasts and abnormalities of repair in xeroderma pigmentosum.
journal, January 1976
- Fornace, A. J.; Kohn, K. W.; Kann, H. E.
- Proceedings of the National Academy of Sciences, Vol. 73, Issue 1
Exciton Delocalization in a DNA-Templated Organic Semiconductor Dimer Assembly
journal, January 2022
- Wang, Xiao; Sha, Ruojie; Knowlton, William B.
- ACS Nano, Vol. 16, Issue 1
Photochemical modifications for DNA/RNA oligonucleotides
journal, January 2022
- Tavakoli, Amirrasoul; Min, Jung-Hyun
- RSC Advances, Vol. 12, Issue 11
Arylamine-Based Squaraine Donors for Use in Organic Solar Cells
journal, October 2011
- Wei, Guodan; Xiao, Xin; Wang, Siyi
- Nano Letters, Vol. 11, Issue 10
Complete Photochemical Regulation of 8–17 DNAzyme Activity by Using Reversible DNA Photo‐crosslinking
journal, July 2020
- Watanabe, Yasuha; Fujimoto, Kenzo
- ChemBioChem, Vol. 21, Issue 22
Organic photoconductive materials: recent trends and developments
journal, January 1993
- Law, Kock Yee.
- Chemical Reviews, Vol. 93, Issue 1
Photocrosslinking Probes Proximity of Thymine Modifiers Tethering Excitonically Coupled Dye Aggregates to DNA Holliday Junction
journal, June 2022
- Basu, Shibani; Cervantes-Salguero, Keitel; Yurke, Bernard
- Molecules, Vol. 27, Issue 13
Coherent interactions of dyes assembled on DNA
journal, June 2012
- Asanuma, Hiroyuki; Fujii, Taiga; Kato, Tomohiro
- Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Vol. 13, Issue 2
Oxidative Stress: Harms and Benefits for Human Health
journal, January 2017
- Pizzino, Gabriele; Irrera, Natasha; Cucinotta, Mariapaola
- Oxidative Medicine and Cellular Longevity, Vol. 2017
Influence of Hydrophobicity on Excitonic Coupling in DNA-Templated Indolenine Squaraine Dye Aggregates
journal, February 2022
- Mass, Olga A.; Wilson, Christopher K.; Barcenas, German
- The Journal of Physical Chemistry C, Vol. 126, Issue 7
Exciton Chirality Inversion in Dye Dimers Templated by DNA Holliday Junction
journal, November 2022
- Mass, Olga A.; Basu, Shibani; Patten, Lance K.
- The Journal of Physical Chemistry Letters, Vol. 13, Issue 46
Organic Optoelectronic Materials: Mechanisms and Applications
journal, October 2016
- Ostroverkhova, Oksana
- Chemical Reviews, Vol. 116, Issue 22
Fluorescent Labeling of Biomolecules with Organic Probes
journal, January 2009
- Gonçalves, M. Sameiro T.
- Chemical Reviews, Vol. 109, Issue 1
DNA Photo-Cross-Linking Using 3-Cyanovinylcarbazole Modified Oligonucleotide with Threoninol Linker
journal, February 2015
- Sakamoto, Takashi; Tanaka, Yuya; Fujimoto, Kenzo
- Organic Letters, Vol. 17, Issue 4
DNA Assembly of Dye Aggregates—A Possible Path to Quantum Computing
book, January 2023
- Yurke, Bernard
- Natural Computing Series
Preparation of interstrand cross-linked DNA oligonucleotide duplexes
journal, January 2004
- Noll, David, M.
- Frontiers in Bioscience, Vol. 9, Issue 1-3
Extracting single and two-exciton couplings in photosynthetic complexes by coherent two-dimensional electronic spectra
journal, February 2009
- Abramavicius, Darius; Palmieri, Benoit; Mukamel, Shaul
- Chemical Physics, Vol. 357, Issue 1-3
Molecular Mechanisms of Ultraviolet Radiation-Induced DNA Damage and Repair
journal, January 2010
- Rastogi, Rajesh P.; Kumar, Ashok
- Journal of Nucleic Acids, Vol. 2010
The DNA three-way junction as a mould for tripartite chromophore assembly
journal, January 2012
- Probst, Markus; Wenger, Daniel; Biner, Sarah M.
- Org. Biomol. Chem., Vol. 10, Issue 4
Efficient Far Red Sensitization of Nanocrystalline TiO 2 Films by an Unsymmetrical Squaraine Dye
journal, August 2007
- Yum, Jun-Ho; Walter, Pablo; Huber, Simon
- Journal of the American Chemical Society, Vol. 129, Issue 34
Near-Infrared Squaraine Dye Encapsulated Micelles for in Vivo Fluorescence and Photoacoustic Bimodal Imaging
journal, May 2015
- Sreejith, Sivaramapanicker; Joseph, James; Lin, Manjing
- ACS Nano, Vol. 9, Issue 6
Alkyne–Alkene [2 + 2] cycloaddition based on visible light photocatalysis
journal, May 2020
- Ha, Sujin; Lee, Yeji; Kwak, Yoonna
- Nature Communications, Vol. 11, Issue 1
Effects of combinations of ROS scavengers on oxidative DNA damage caused by visible‐light‐activated camphorquinone/N,N‐dimethyl‐p‐toluidine
journal, April 2007
- Lee, Seungbum; Pagoria, Dustin; Raigrodski, Ariel
- Journal of Biomedical Materials Research Part B: Applied Biomaterials, Vol. 83B, Issue 2
NIH Image to ImageJ: 25 years of image analysis
journal, June 2012
- Schneider, Caroline A.; Rasband, Wayne S.; Eliceiri, Kevin W.
- Nature Methods, Vol. 9, Issue 7
Resonance Energy Transfer in DNA Duplexes Labeled with Localized Dyes
journal, December 2014
- Cunningham, Paul D.; Khachatrian, Ani; Buckhout-White, Susan
- The Journal of Physical Chemistry B, Vol. 118, Issue 50
Large Davydov Splitting and Strong Fluorescence Suppression: An Investigation of Exciton Delocalization in DNA-Templated Holliday Junction Dye Aggregates
journal, February 2018
- Cannon, Brittany L.; Patten, Lance K.; Kellis, Donald L.
- The Journal of Physical Chemistry A, Vol. 122, Issue 8
Differential biologic effects of CPD and 6-4PP UV-induced DNA damage on the induction of apoptosis and cell-cycle arrest
journal, October 2005
- Lo, Hsin-Lung; Nakajima, Satoshi; Ma, Lisa
- BMC Cancer, Vol. 5, Issue 1
5-Methylcytosine Selective Photoligation Using Photoresponsive Oligonucleotides Containing Various 5-Vinyl-2′-deoxyuridines Having an Aromatic Group
journal, January 2012
- Sakamoto, Takashi; Ami, Takehiro; Fujimoto, Kenzo
- Chemistry Letters, Vol. 41, Issue 1
Molecular Aggregate Photophysics beyond the Kasha Model: Novel Design Principles for Organic Materials
journal, January 2017
- Hestand, Nicholas J.; Spano, Frank C.
- Accounts of Chemical Research, Vol. 50, Issue 2
Superradiance and Exciton Delocalization in Bacterial Photosynthetic Light-Harvesting Systems
journal, September 1997
- Monshouwer, René; Abrahamsson, Malin; van Mourik, Frank
- The Journal of Physical Chemistry B, Vol. 101, Issue 37
Synthesis and properties of squaraine-modified DNA
journal, January 2012
- Markova, Larysa I.; Malinovskii, Vladimir L.; Patsenker, Leonid D.
- Organic & Biomolecular Chemistry, Vol. 10, Issue 45
Photoswitchable Formation of a DNA Interstrand Cross‐Link by a Coumarin‐Modified Nucleotide
journal, May 2014
- Haque, Mohammad Mojibul; Sun, Huabing; Liu, Shuo
- Angewandte Chemie International Edition, Vol. 53, Issue 27
Unsymmetrical Squaraines Incorporating Quinoline for Near Infrared Responsive Dye-Sensitized Solar Cells
journal, October 2012
- Li, Jheng-Ying; Chen, Chia-Yuan; Ho, Wen-Chein
- Organic Letters, Vol. 14, Issue 21
Exciton Delocalization in Indolenine Squaraine Aggregates Templated by DNA Holliday Junction Scaffolds
journal, October 2020
- Mass, Olga A.; Wilson, Christopher K.; Roy, Simon K.
- The Journal of Physical Chemistry B, Vol. 124, Issue 43
Unraveling the Molecular Pathway from Sunlight to Skin Cancer
journal, March 1994
- Taylor, John Stephen
- Accounts of Chemical Research, Vol. 27, Issue 3
Squaraine as a bright, stable and environment-sensitive far-red label for receptor-specific cellular imaging
journal, January 2015
- Karpenko, I. A.; Klymchenko, A. S.; Gioria, S.
- Chemical Communications, Vol. 51, Issue 14
Squaraine Dyes: Molecular Design for Different Applications and Remaining Challenges
journal, July 2019
- Ilina, Kristina; MacCuaig, William M.; Laramie, Matthew
- Bioconjugate Chemistry, Vol. 31, Issue 2
The Cartography of UV ‐induced DNA Damage Formation and DNA Repair
journal, January 2017
- Hu, Jinchuan; Adar, Sheera
- Photochemistry and Photobiology, Vol. 93, Issue 1
Programmable materials and the nature of the DNA bond
journal, February 2015
- Jones, M. R.; Seeman, N. C.; Mirkin, C. A.
- Science, Vol. 347, Issue 6224
On the design of molecular excitonic circuits for quantum computing: the universal quantum gates
journal, January 2020
- Castellanos, Maria A.; Dodin, Amro; Willard, Adam P.
- Physical Chemistry Chemical Physics, Vol. 22, Issue 5
DNA-Assisted Self-Assembly of Pyrene Foldamers
journal, June 2009
- Häner, Robert; Samain, Florent; Malinovskii, Vladimir L.
- Chemistry - A European Journal, Vol. 15, Issue 23
Extended dipole model for aggregates of dye molecules
journal, August 1970
- Czikklely, V.; Forsterling, H. D.; Kuhn, H.
- Chemical Physics Letters, Vol. 6, Issue 3
DNA Self-Assembly of Single Molecules with Deterministic Position and Orientation
journal, September 2022
- Adamczyk, Aleksandra K.; Huijben, Teun A. P. M.; Sison, Miguel
- ACS Nano, Vol. 16, Issue 10
Application of electronic circular dichroism in configurational and conformational analysis of organic compounds
journal, January 2007
- Berova, Nina; Bari, Lorenzo Di; Pescitelli, Gennaro
- Chemical Society Reviews, Vol. 36, Issue 6
Molecular Dynamic Studies of Dye–Dye and Dye–DNA Interactions Governing Excitonic Coupling in Squaraine Aggregates Templated by DNA Holliday Junctions
journal, February 2023
- Barcenas, German; Biaggne, Austin; Mass, Olga A.
- International Journal of Molecular Sciences, Vol. 24, Issue 4
Photo-Cross-Linking-Assisted Thermal Stability of DNA Origami Structures and Its Application for Higher-Temperature Self-Assembly
journal, September 2011
- Rajendran, Arivazhagan; Endo, Masayuki; Katsuda, Yousuke
- Journal of the American Chemical Society, Vol. 133, Issue 37
Optical Properties of Vibronically Coupled Cy3 Dimers on DNA Scaffolds
journal, April 2018
- Cunningham, Paul D.; Kim, Young C.; Díaz, Sebastián A.
- The Journal of Physical Chemistry B, Vol. 122, Issue 19
Exciton delocalization, charge transfer, and electronic coupling for singlet excitation energy transfer between stacked nucleobases in DNA: An MS-CASPT2 study
journal, March 2014
- Blancafort, Lluís; Voityuk, Alexander A.
- The Journal of Chemical Physics, Vol. 140, Issue 9
Analysis of Coherent Heteroclustering of Different Dyes by Use of Threoninol Nucleotides for Comparison with the Molecular Exciton Theory
journal, October 2009
- Fujii, Taiga; Kashida, Hiromu; Asanuma, Hiroyuki
- Chemistry - A European Journal, Vol. 15, Issue 39
Beneficial and Detrimental Effects of Reactive Oxygen Species on Lifespan: A Comprehensive Review of Comparative and Experimental Studies
journal, February 2021
- Shields, Hazel J.; Traa, Annika; Van Raamsdonk, Jeremy M.
- Frontiers in Cell and Developmental Biology, Vol. 9
DNA−Dye Conjugates for Controllable H* Aggregation 1
journal, February 2003
- Asanuma, Hiroyuki; Shirasuka, Kenji; Takarada, Tohru
- Journal of the American Chemical Society, Vol. 125, Issue 8
A DNA-Based Light-Harvesting Antenna
journal, December 2011
- Garo, Florian; Häner, Robert
- Angewandte Chemie International Edition, Vol. 51, Issue 4
Coherent Multidimensional Optical Spectroscopy of Excitons in Molecular Aggregates; Quasiparticle versus Supermolecule Perspectives
journal, June 2009
- Abramavicius, Darius; Palmieri, Benoit; Voronine, Dmitri V.
- Chemical Reviews, Vol. 109, Issue 6
Hybridization-Sensitive On–Off DNA Probe: Application of the Exciton Coupling Effect to Effective Fluorescence Quenching
journal, June 2008
- Ikeda, Shuji; Okamoto, Akimitsu
- Chemistry – An Asian Journal, Vol. 3, Issue 6
Directional Photonic Wire Mediated by Homo-Förster Resonance Energy Transfer on a DNA Origami Platform
journal, September 2017
- Nicoli, Francesca; Barth, Anders; Bae, Wooli
- ACS Nano, Vol. 11, Issue 11
Squaraine‐Doped Functional Nanoprobes: Lipophilically Protected Near‐Infrared Fluorescence for Bioimaging
journal, September 2010
- Lee, Yong‐Deok; Lim, Chang‐Keun; Kim, Sehoon
- Advanced Functional Materials, Vol. 20, Issue 17
Coherent Exciton Delocalization in a Two-State DNA-Templated Dye Aggregate System
journal, September 2017
- Cannon, Brittany L.; Kellis, Donald L.; Patten, Lance K.
- The Journal of Physical Chemistry A, Vol. 121, Issue 37
Nanomaterials Based on DNA
journal, June 2010
- Seeman, Nadrian C.
- Annual Review of Biochemistry, Vol. 79, Issue 1
Engineering couplings for exciton transport using synthetic DNA scaffolds
journal, March 2021
- Hart, Stephanie M.; Chen, Wei Jia; Banal, James L.
- Chem, Vol. 7, Issue 3
Triplex-directed covalent cross-linking of a DNA nanostructure
journal, January 2012
- Rusling, David A.; Nandhakumar, Iris S.; Brown, Tom
- Chemical Communications, Vol. 48, Issue 77
Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions
journal, March 2016
- Poplata, Saner; Tröster, Andreas; Zou, You-Quan
- Chemical Reviews, Vol. 116, Issue 17
Sequence-programmable covalent bonding of designed DNA assemblies
journal, August 2018
- Gerling, Thomas; Kube, Massimo; Kick, Benjamin
- Science Advances, Vol. 4, Issue 8
Exciton Delocalization and Scaffold Stability in Bridged Nucleotide-Substituted, DNA Duplex-Templated Cyanine Aggregates
journal, December 2021
- Roy, Simon K.; Mass, Olga A.; Kellis, Donald L.
- The Journal of Physical Chemistry B, Vol. 125, Issue 50