Controlled Monofunctionalization of Molecular Spherical Nucleic Acids on a Buckminster Fullerene Core

Vijay Gulumkar; Antti Äärelä; Olli Moisio; Jani Rahkila; Ville Tähtinen; Laura Leimu; Niko Korsoff; Heidi Korhonen; Päivi Poijärvi-Virta; Satu Mikkola; Victor Nesati; Elina Vuorimaa-Laukkanen; Tapani Viitala; Marjo Yliperttula; Anne Roivainen; Pasi Virta

doi:10.1021/acs.bioconjchem.1c00187

Controlled Monofunctionalization of Molecular Spherical Nucleic Acids on a Buckminster Fullerene Core

Vijay Gulumkar, Antti Äärelä, Olli Moisio, Jani Rahkila, Ville Tähtinen, Laura Leimu, Niko Korsoff, Heidi Korhonen, Päivi Poijärvi-Virta, Satu Mikkola, Victor Nesati, Elina Vuorimaa-Laukkanen, Tapani Viitala, Marjo Yliperttula, Anne Roivainen, Pasi Virta^*

^*Corresponding author for this work

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

9 Citations (Scopus)

40 Downloads (Pure)

Abstract

An azide-functionalized 12-armed Buckminster fullerene has been monosubstituted in organic media with a substoichiometric amount of cyclooctyne-modified oligonucleotides. Exposing the intermediate products then to the same reaction (i.e., strain-promoted alkyne-azide cycloaddition, SPAAC) with an excess of slightly different oligonucleotide constituents in an aqueous medium yields molecularly defined monofunctionalized spherical nucleic acids (SNAs). This procedure offers a controlled synthesis scheme in which one oligonucleotide arm can be functionalized with labels or other conjugate groups (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid, DOTA, and Alexa-488 demonstrated), whereas the rest of the 11 arms can be left unmodified or modified by other conjugate groups in order to decorate the SNAs' outer sphere. Extra attention has been paid to the homogeneity and authenticity of the C60-azide scaffold used for the assembly of full-armed SNAs.

Original language	English
Pages (from-to)	1130-1138
Number of pages	9
Journal	Bioconjugate Chemistry
Volume	32
Issue number	6
DOIs	https://doi.org/10.1021/acs.bioconjchem.1c00187
Publication status	Published - 16 Jun 2021
MoE publication type	A1 Journal article-refereed

Access to Document

10.1021/acs.bioconjchem.1c00187

acs.bioconjchem.1c00187Final published version, 2.97 MBLicence: Publisher rights policy

https://urn.fi/URN:NBN:fi-fe2022120168463

Cite this

Gulumkar, V., Äärelä, A., Moisio, O., Rahkila, J., Tähtinen, V., Leimu, L., Korsoff, N., Korhonen, H., Poijärvi-Virta, P., Mikkola, S., Nesati, V., Vuorimaa-Laukkanen, E., Viitala, T., Yliperttula, M., Roivainen, A., & Virta, P. (2021). Controlled Monofunctionalization of Molecular Spherical Nucleic Acids on a Buckminster Fullerene Core. Bioconjugate Chemistry, 32(6), 1130-1138. https://doi.org/10.1021/acs.bioconjchem.1c00187

@article{b19869063f8f45e08d079f5b0c4183d2,

title = "Controlled Monofunctionalization of Molecular Spherical Nucleic Acids on a Buckminster Fullerene Core",

abstract = "An azide-functionalized 12-armed Buckminster fullerene has been monosubstituted in organic media with a substoichiometric amount of cyclooctyne-modified oligonucleotides. Exposing the intermediate products then to the same reaction (i.e., strain-promoted alkyne-azide cycloaddition, SPAAC) with an excess of slightly different oligonucleotide constituents in an aqueous medium yields molecularly defined monofunctionalized spherical nucleic acids (SNAs). This procedure offers a controlled synthesis scheme in which one oligonucleotide arm can be functionalized with labels or other conjugate groups (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid, DOTA, and Alexa-488 demonstrated), whereas the rest of the 11 arms can be left unmodified or modified by other conjugate groups in order to decorate the SNAs' outer sphere. Extra attention has been paid to the homogeneity and authenticity of the C60-azide scaffold used for the assembly of full-armed SNAs. ",

author = "Vijay Gulumkar and Antti {\"A}{\"a}rel{\"a} and Olli Moisio and Jani Rahkila and Ville T{\"a}htinen and Laura Leimu and Niko Korsoff and Heidi Korhonen and P{\"a}ivi Poij{\"a}rvi-Virta and Satu Mikkola and Victor Nesati and Elina Vuorimaa-Laukkanen and Tapani Viitala and Marjo Yliperttula and Anne Roivainen and Pasi Virta",

note = "Publisher Copyright: {\textcopyright} ",

year = "2021",

month = jun,

day = "16",

doi = "10.1021/acs.bioconjchem.1c00187",

language = "English",

volume = "32",

pages = "1130--1138",

journal = "Bioconjugate Chemistry",

issn = "1043-1802",

publisher = "American Chemical Society",

number = "6",

}

Gulumkar, V, Äärelä, A, Moisio, O, Rahkila, J, Tähtinen, V, Leimu, L, Korsoff, N, Korhonen, H, Poijärvi-Virta, P, Mikkola, S, Nesati, V, Vuorimaa-Laukkanen, E, Viitala, T, Yliperttula, M, Roivainen, A & Virta, P 2021, 'Controlled Monofunctionalization of Molecular Spherical Nucleic Acids on a Buckminster Fullerene Core', Bioconjugate Chemistry, vol. 32, no. 6, pp. 1130-1138. https://doi.org/10.1021/acs.bioconjchem.1c00187

TY - JOUR

T1 - Controlled Monofunctionalization of Molecular Spherical Nucleic Acids on a Buckminster Fullerene Core

AU - Gulumkar, Vijay

AU - Äärelä, Antti

AU - Moisio, Olli

AU - Rahkila, Jani

AU - Tähtinen, Ville

AU - Leimu, Laura

AU - Korsoff, Niko

AU - Korhonen, Heidi

AU - Poijärvi-Virta, Päivi

AU - Mikkola, Satu

AU - Nesati, Victor

AU - Vuorimaa-Laukkanen, Elina

AU - Viitala, Tapani

AU - Yliperttula, Marjo

AU - Roivainen, Anne

AU - Virta, Pasi

PY - 2021/6/16

Y1 - 2021/6/16

N2 - An azide-functionalized 12-armed Buckminster fullerene has been monosubstituted in organic media with a substoichiometric amount of cyclooctyne-modified oligonucleotides. Exposing the intermediate products then to the same reaction (i.e., strain-promoted alkyne-azide cycloaddition, SPAAC) with an excess of slightly different oligonucleotide constituents in an aqueous medium yields molecularly defined monofunctionalized spherical nucleic acids (SNAs). This procedure offers a controlled synthesis scheme in which one oligonucleotide arm can be functionalized with labels or other conjugate groups (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid, DOTA, and Alexa-488 demonstrated), whereas the rest of the 11 arms can be left unmodified or modified by other conjugate groups in order to decorate the SNAs' outer sphere. Extra attention has been paid to the homogeneity and authenticity of the C60-azide scaffold used for the assembly of full-armed SNAs.

AB - An azide-functionalized 12-armed Buckminster fullerene has been monosubstituted in organic media with a substoichiometric amount of cyclooctyne-modified oligonucleotides. Exposing the intermediate products then to the same reaction (i.e., strain-promoted alkyne-azide cycloaddition, SPAAC) with an excess of slightly different oligonucleotide constituents in an aqueous medium yields molecularly defined monofunctionalized spherical nucleic acids (SNAs). This procedure offers a controlled synthesis scheme in which one oligonucleotide arm can be functionalized with labels or other conjugate groups (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid, DOTA, and Alexa-488 demonstrated), whereas the rest of the 11 arms can be left unmodified or modified by other conjugate groups in order to decorate the SNAs' outer sphere. Extra attention has been paid to the homogeneity and authenticity of the C60-azide scaffold used for the assembly of full-armed SNAs.

UR - http://www.scopus.com/inward/record.url?scp=85108081415&partnerID=8YFLogxK

U2 - 10.1021/acs.bioconjchem.1c00187

DO - 10.1021/acs.bioconjchem.1c00187

M3 - Article

C2 - 33998229

AN - SCOPUS:85108081415

SN - 1043-1802

VL - 32

SP - 1130

EP - 1138

JO - Bioconjugate Chemistry

JF - Bioconjugate Chemistry

IS - 6

ER -

Controlled Monofunctionalization of Molecular Spherical Nucleic Acids on a Buckminster Fullerene Core

Abstract

Access to Document

Other files and links

Fingerprint

Cite this