A Janus-Type Phthalocyanine for the Assembly of Photoactive DNA Origami Coatings

Asma Rahali; Ahmed Shaukat; Verónica Almeida-Marrero; Bassem Jamoussi; Andrés de la Escosura; Tomás Torres; Mauri A. Kostiainen; Eduardo Anaya-Plaza

doi:10.1021/acs.bioconjchem.1c00176

A Janus-Type Phthalocyanine for the Assembly of Photoactive DNA Origami Coatings

Asma Rahali, Ahmed Shaukat, Verónica Almeida-Marrero, Bassem Jamoussi, Andrés de la Escosura, Tomás Torres^*, Mauri A. Kostiainen^*, Eduardo Anaya-Plaza^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

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Abstract

Design and synthesis of novel photosensitizer architectures is a key step toward new multifunctional molecular materials. Photoactive Janus-type molecules provide interesting building blocks for such systems by presenting two well-defined chemical functionalities that can be utilized orthogonally. Herein a multifunctional phthalocyanine is reported, bearing a bulky and positively charged moiety that hinders their aggregation while providing the ability to adhere on DNA origami nanostructures via reversible electrostatic interactions. On the other hand, triethylene glycol moieties render a water-soluble and chemically inert corona that can stabilize the structures. This approach provides insight into the molecular design and synthesis of Janus-type sensitizers that can be combined with biomolecules, rendering optically active biohybrids.

Original language	English
Pages (from-to)	1123–1129
Number of pages	7
Journal	Bioconjugate Chemistry
Volume	32
Issue number	6
Early online date	24 May 2021
DOIs	https://doi.org/10.1021/acs.bioconjchem.1c00176
Publication status	Published - 16 Jun 2021
MoE publication type	A1 Journal article-refereed

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CHEM_Rahali_et_al_A_Janus-Type_Phthalocyanine_2021_Bioconjugate_ChemistryFinal published version, 3.69 MBLicence: CC BY

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title = "A Janus-Type Phthalocyanine for the Assembly of Photoactive DNA Origami Coatings",

abstract = "Design and synthesis of novel photosensitizer architectures is a key step toward new multifunctional molecular materials. Photoactive Janus-type molecules provide interesting building blocks for such systems by presenting two well-defined chemical functionalities that can be utilized orthogonally. Herein a multifunctional phthalocyanine is reported, bearing a bulky and positively charged moiety that hinders their aggregation while providing the ability to adhere on DNA origami nanostructures via reversible electrostatic interactions. On the other hand, triethylene glycol moieties render a water-soluble and chemically inert corona that can stabilize the structures. This approach provides insight into the molecular design and synthesis of Janus-type sensitizers that can be combined with biomolecules, rendering optically active biohybrids.",

author = "Asma Rahali and Ahmed Shaukat and Ver{\'o}nica Almeida-Marrero and Bassem Jamoussi and {de la Escosura}, Andr{\'e}s and Tom{\'a}s Torres and Kostiainen, {Mauri A.} and Eduardo Anaya-Plaza",

note = "| openaire: EC/H2020/794536/EU//BiHyOMat Funding Information: We acknowledge the provision of facilities and technical support by Aalto University Bioeconomy Facilities and OtaNano – Nanomicroscopy Center (Aalto-NMC) and funding from the Jane and Aatos Erkko Foundation. The authors also thank Sofia Julin and Heini Ij{\"a}s from Department of Bioproducts and Biosystems, Aalto University, for providing DNA origami samples. IMDEA Nanociencia also acknowledges support from the “Severo Ochoa” Programme for Centres of Excellence in R&D (MINECO, grant SEV-2016-0686). Funding Information: We acknowledge the Academy of Finland (286845, 308578), the Magnus Ehrnrooth Foundation, and the Marie Sklodowska-Curie grant (794536). MINECO-Feder funds (CTQ2017-85393-P (TT), CTQ-2014-53673-P and CTQ-2017-89539-P (AdlE), and PCIN-2017-042/EuroNanoMed2017-191, TEMPEAT (TT)). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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AU - Shaukat, Ahmed

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AU - Jamoussi, Bassem

AU - de la Escosura, Andrés

AU - Torres, Tomás

AU - Kostiainen, Mauri A.

AU - Anaya-Plaza, Eduardo

N1 - | openaire: EC/H2020/794536/EU//BiHyOMat Funding Information: We acknowledge the provision of facilities and technical support by Aalto University Bioeconomy Facilities and OtaNano – Nanomicroscopy Center (Aalto-NMC) and funding from the Jane and Aatos Erkko Foundation. The authors also thank Sofia Julin and Heini Ijäs from Department of Bioproducts and Biosystems, Aalto University, for providing DNA origami samples. IMDEA Nanociencia also acknowledges support from the “Severo Ochoa” Programme for Centres of Excellence in R&D (MINECO, grant SEV-2016-0686). Funding Information: We acknowledge the Academy of Finland (286845, 308578), the Magnus Ehrnrooth Foundation, and the Marie Sklodowska-Curie grant (794536). MINECO-Feder funds (CTQ2017-85393-P (TT), CTQ-2014-53673-P and CTQ-2017-89539-P (AdlE), and PCIN-2017-042/EuroNanoMed2017-191, TEMPEAT (TT)). Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/6/16

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N2 - Design and synthesis of novel photosensitizer architectures is a key step toward new multifunctional molecular materials. Photoactive Janus-type molecules provide interesting building blocks for such systems by presenting two well-defined chemical functionalities that can be utilized orthogonally. Herein a multifunctional phthalocyanine is reported, bearing a bulky and positively charged moiety that hinders their aggregation while providing the ability to adhere on DNA origami nanostructures via reversible electrostatic interactions. On the other hand, triethylene glycol moieties render a water-soluble and chemically inert corona that can stabilize the structures. This approach provides insight into the molecular design and synthesis of Janus-type sensitizers that can be combined with biomolecules, rendering optically active biohybrids.

AB - Design and synthesis of novel photosensitizer architectures is a key step toward new multifunctional molecular materials. Photoactive Janus-type molecules provide interesting building blocks for such systems by presenting two well-defined chemical functionalities that can be utilized orthogonally. Herein a multifunctional phthalocyanine is reported, bearing a bulky and positively charged moiety that hinders their aggregation while providing the ability to adhere on DNA origami nanostructures via reversible electrostatic interactions. On the other hand, triethylene glycol moieties render a water-soluble and chemically inert corona that can stabilize the structures. This approach provides insight into the molecular design and synthesis of Janus-type sensitizers that can be combined with biomolecules, rendering optically active biohybrids.

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A Janus-Type Phthalocyanine for the Assembly of Photoactive DNA Origami Coatings

Abstract

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BiHyOMat: BioHybrid Optoelectronic Materials

SYNVIRO: Synthetic Virology Toolbox for the Encapsulation of Therapeutic Polyelectrolytes (SYNVIRO)

Rationally designed molecular devices through nucleic acid nanotechnology

OtaNano

OtaNano - Nanomicroscopy Center

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A Janus-Type Phthalocyanine for the Assembly of Photoactive DNA Origami Coatings

Abstract

Access to Document

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Projects

BiHyOMat: BioHybrid Optoelectronic Materials

SYNVIRO: Synthetic Virology Toolbox for the Encapsulation of Therapeutic Polyelectrolytes (SYNVIRO)

Rationally designed molecular devices through nucleic acid nanotechnology

Equipment

OtaNano

OtaNano - Nanomicroscopy Center

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