Biomimetic, Smart, and Multivalent Ligands for G-Quadruplex Isolation and Bioorthogonal Imaging

G-quadruplexes (G4s) continue to gather wide attention in the field of chemical biology as their prevalence in the human genome and transcriptome strongly suggests that they play key regulatory roles in cell biology. G4-specific, cell-permeable small molecules (G4-ligands) innovatively permit the in...

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Published inACS chemical biology Vol. 16; no. 5; pp. 905 - 914
Main Authors Sperti Rota, Francesco, Charbonnier, Thibaut, Lejault, Pauline, Zell, Joanna, Bernhard, Claire, Valverde, Ibai E, Monchaud, David
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 21.05.2021
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Abstract G-quadruplexes (G4s) continue to gather wide attention in the field of chemical biology as their prevalence in the human genome and transcriptome strongly suggests that they play key regulatory roles in cell biology. G4-specific, cell-permeable small molecules (G4-ligands) innovatively permit the interrogation of cellular circuitries in order to assess to what extent G4s influence cell fate and functions. Here, we report on multivalent, biomimetic G4-ligands referred to as TASQs that enable both the isolation and visualization of G4s in human cells. Two biotinylated TASQs, and , are indeed efficient molecular tools to isolate G4s from mixtures of nucleic acids through simple affinity capture protocols and to image G4s in cells via a biotin/avidin pretargeted imaging system first applied here to G4s, found to be a reliable alternative to in situ click chemistry.
AbstractList G-quadruplexes (G4s) continue to gather wide attention in the field of chemical biology as their prevalence in the human genome and transcriptome strongly suggests that they play key regulatory roles in cell biology. G4-specific, cell-permeable small molecules (G4-ligands) innovatively permit the interrogation of cellular circuitries in order to assess to what extent G4s influence cell fate and functions. Here, we report on multivalent, biomimetic G4-ligands referred to as TASQs that enable both the isolation and visualization of G4s in human cells. Two biotinylated TASQs, BioTASQ and BioCyTASQ, are indeed efficient molecular tools to isolate G4s from mixtures of nucleic acids through simple affinity capture protocols and to image G4s in cells via a biotin/avidin pretargeted imaging system first applied here to G4s, found to be a reliable alternative to in situ click chemistry.
G-quadruplexes (G4s) continue to gather wide attention in the field of chemical biology as their prevalence in the human genome and transcriptome strongly suggests that they play key regulatory roles in cell biology. G4-specific, cell-permeable small molecules (G4-ligands) innovatively permit the interrogation of cellular circuitries in order to assess to what extent G4s influence cell fate and functions. Here, we report on multivalent, biomimetic G4-ligands referred to as TASQs that enable both the isolation and visualization of G4s in human cells. Two biotinylated TASQs, and , are indeed efficient molecular tools to isolate G4s from mixtures of nucleic acids through simple affinity capture protocols and to image G4s in cells via a biotin/avidin pretargeted imaging system first applied here to G4s, found to be a reliable alternative to in situ click chemistry.
Author Zell, Joanna
Charbonnier, Thibaut
Sperti Rota, Francesco
Lejault, Pauline
Valverde, Ibai E
Monchaud, David
Bernhard, Claire
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Cites_doi 10.1038/nmeth.3965
10.1039/c2ob25601k
10.1039/c0cc04960c
10.1016/j.ymeth.2012.03.020
10.1016/j.trechm.2019.07.002
10.1101/cshperspect.a032284
10.1093/nar/gkab187
10.1038/s41570-018-0030-x
10.1093/nar/gkt001
10.1038/s41588-020-0672-8
10.1038/nbt.3295
10.1093/nar/gki553
10.1021/jo9001245
10.1038/nprot.2017.150
10.1093/nar/gkaa841
10.2174/0929867325666171229132619
10.1038/srep32141
10.1038/s41570-019-0132-0
10.1021/ja405100z
10.1038/s41570-017-0041
10.1016/j.biochi.2011.05.012
10.7554/eLife.52283
10.1002/ejoc.201900870
10.1021/ja208145d
10.1016/S0169-409X(98)00101-X
10.1002/anie.198905353
10.1021/acs.jmedchem.5b01835
10.1038/srep33888
10.1038/nchem.842
10.1093/nar/gki609
10.1039/C9CC09107F
10.1093/nar/gkw006
10.1038/nmeth.2019
10.1002/chem.200903456
10.1093/nar/gkz215
10.1093/nar/gkv862
10.1002/(SICI)1097-0282(199609)39:3<297::AID-BIP3>3.0.CO;2-J
10.1038/ng.3662
10.1016/j.tetlet.2011.02.017
10.1038/s41580-020-0236-x
10.1002/chem.201300791
10.1021/jacs.5b03413
10.1021/ja506331x
10.1002/ejoc.200901183
10.1080/15548627.2020.1769991
10.1016/j.tibtech.2017.06.012
10.1016/0040-4039(94)02481-P
10.1021/ja310056y
10.1074/jbc.RA120.014332
10.1021/ja00075a029
10.1002/anie.199614821
10.1002/cbic.201200262
10.1016/S0014-5793(98)01043-6
10.1016/j.bbamcr.2019.118539
10.1517/17425241003677749
10.1002/cmdc.201300526
10.1016/j.ymeth.2006.10.004
10.3390/molecules24132416
10.1016/j.jmb.2019.03.010
10.2967/jnumed.117.189944
10.15252/embr.201540607
10.1002/anie.200704199
10.1002/chem.201003556
10.1038/s41467-018-07224-8
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References ref9/cit9
ref45/cit45
ref3/cit3
ref27/cit27
ref63/cit63
ref56/cit56
ref16/cit16
ref52/cit52
ref23/cit23
ref8/cit8
ref31/cit31
ref59/cit59
ref2/cit2
ref34/cit34
ref37/cit37
ref20/cit20
ref48/cit48
ref60/cit60
ref17/cit17
ref10/cit10
ref35/cit35
ref53/cit53
ref19/cit19
ref21/cit21
ref42/cit42
ref49/cit49
ref13/cit13
ref61/cit61
ref24/cit24
ref38/cit38
ref50/cit50
ref64/cit64
ref54/cit54
ref6/cit6
ref36/cit36
ref18/cit18
ref65/cit65
ref11/cit11
ref25/cit25
ref29/cit29
ref32/cit32
ref39/cit39
ref14/cit14
ref57/cit57
ref5/cit5
ref51/cit51
ref43/cit43
ref28/cit28
Monchaud D. (ref46/cit46) 2020
ref40/cit40
ref26/cit26
ref55/cit55
ref12/cit12
ref15/cit15
ref62/cit62
ref41/cit41
ref58/cit58
ref22/cit22
ref33/cit33
ref4/cit4
ref30/cit30
ref47/cit47
ref1/cit1
ref44/cit44
ref7/cit7
References_xml – ident: ref52/cit52
  doi: 10.1038/nmeth.3965
– ident: ref21/cit21
  doi: 10.1039/c2ob25601k
– ident: ref7/cit7
  doi: 10.1039/c0cc04960c
– ident: ref32/cit32
  doi: 10.1016/j.ymeth.2012.03.020
– ident: ref48/cit48
  doi: 10.1016/j.trechm.2019.07.002
– ident: ref53/cit53
  doi: 10.1101/cshperspect.a032284
– ident: ref44/cit44
  doi: 10.1093/nar/gkab187
– ident: ref50/cit50
  doi: 10.1038/s41570-018-0030-x
– ident: ref41/cit41
  doi: 10.1093/nar/gkt001
– ident: ref59/cit59
  doi: 10.1038/s41588-020-0672-8
– ident: ref51/cit51
  doi: 10.1038/nbt.3295
– ident: ref54/cit54
  doi: 10.1093/nar/gki553
– ident: ref5/cit5
  doi: 10.1021/jo9001245
– ident: ref58/cit58
  doi: 10.1038/nprot.2017.150
– ident: ref60/cit60
  doi: 10.1093/nar/gkaa841
– ident: ref62/cit62
  doi: 10.2174/0929867325666171229132619
– ident: ref28/cit28
  doi: 10.1038/srep32141
– ident: ref17/cit17
  doi: 10.1038/s41570-019-0132-0
– ident: ref13/cit13
  doi: 10.1021/ja405100z
– ident: ref15/cit15
  doi: 10.1038/s41570-017-0041
– ident: ref18/cit18
  doi: 10.1016/j.biochi.2011.05.012
– ident: ref39/cit39
  doi: 10.7554/eLife.52283
– ident: ref8/cit8
  doi: 10.1002/ejoc.201900870
– ident: ref20/cit20
  doi: 10.1021/ja208145d
– ident: ref36/cit36
  doi: 10.1016/S0169-409X(98)00101-X
– ident: ref1/cit1
  doi: 10.1002/anie.198905353
– ident: ref14/cit14
  doi: 10.1021/acs.jmedchem.5b01835
– ident: ref26/cit26
  doi: 10.1038/srep33888
– ident: ref35/cit35
  doi: 10.1038/nchem.842
– ident: ref55/cit55
  doi: 10.1093/nar/gki609
– ident: ref49/cit49
  doi: 10.1039/C9CC09107F
– ident: ref56/cit56
  doi: 10.1093/nar/gkw006
– ident: ref65/cit65
  doi: 10.1038/nmeth.2019
– ident: ref16/cit16
  doi: 10.1002/chem.200903456
– ident: ref30/cit30
  doi: 10.1093/nar/gkz215
– ident: ref61/cit61
  doi: 10.1093/nar/gkv862
– ident: ref9/cit9
  doi: 10.1002/(SICI)1097-0282(199609)39:3<297::AID-BIP3>3.0.CO;2-J
– ident: ref57/cit57
  doi: 10.1038/ng.3662
– ident: ref12/cit12
  doi: 10.1016/j.tetlet.2011.02.017
– ident: ref34/cit34
  doi: 10.1038/s41580-020-0236-x
– ident: ref23/cit23
  doi: 10.1002/chem.201300791
– ident: ref27/cit27
  doi: 10.1021/jacs.5b03413
– ident: ref25/cit25
  doi: 10.1021/ja506331x
– start-page: 133
  volume-title: Annu. Rep. Med. Chem.
  year: 2020
  ident: ref46/cit46
  contributor:
    fullname: Monchaud D.
– ident: ref31/cit31
  doi: 10.1002/ejoc.200901183
– ident: ref40/cit40
  doi: 10.1080/15548627.2020.1769991
– ident: ref47/cit47
  doi: 10.1016/j.tibtech.2017.06.012
– ident: ref10/cit10
  doi: 10.1016/0040-4039(94)02481-P
– ident: ref22/cit22
  doi: 10.1021/ja310056y
– ident: ref43/cit43
  doi: 10.1074/jbc.RA120.014332
– ident: ref4/cit4
  doi: 10.1021/ja00075a029
– ident: ref2/cit2
  doi: 10.1002/anie.199614821
– ident: ref6/cit6
  doi: 10.1002/cbic.201200262
– ident: ref19/cit19
  doi: 10.1016/S0014-5793(98)01043-6
– ident: ref63/cit63
  doi: 10.1016/j.bbamcr.2019.118539
– ident: ref37/cit37
  doi: 10.1517/17425241003677749
– ident: ref24/cit24
  doi: 10.1002/cmdc.201300526
– ident: ref33/cit33
  doi: 10.1016/j.ymeth.2006.10.004
– ident: ref45/cit45
  doi: 10.3390/molecules24132416
– ident: ref42/cit42
  doi: 10.1016/j.jmb.2019.03.010
– ident: ref38/cit38
  doi: 10.2967/jnumed.117.189944
– ident: ref64/cit64
  doi: 10.15252/embr.201540607
– ident: ref3/cit3
  doi: 10.1002/anie.200704199
– ident: ref11/cit11
  doi: 10.1002/chem.201003556
– ident: ref29/cit29
  doi: 10.1038/s41467-018-07224-8
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Snippet G-quadruplexes (G4s) continue to gather wide attention in the field of chemical biology as their prevalence in the human genome and transcriptome strongly...
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SubjectTerms Biochemistry, Molecular Biology
Biomimetic Materials - chemical synthesis
Biomimetic Materials - isolation & purification
Biophysics
Biotinylation
Cell Membrane Permeability
Chemical Sciences
Click Chemistry
G-Quadruplexes
Humans
Life Sciences
Ligands
MCF-7 Cells
Molecular Structure
Nucleic Acids - chemistry
Optical Imaging
Organic chemistry
Title Biomimetic, Smart, and Multivalent Ligands for G-Quadruplex Isolation and Bioorthogonal Imaging
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