Drawing with Iron on a Gel Containing a Supramolecular Siderophore

Xiao, Songjun; Paukstelis, Paul J.; Ash, Richard D.; Zavalij, Peter Y.; Davis, Jeffery T.

doi:10.1002/ange.201910872

Title: Drawing with Iron on a Gel Containing a Supramolecular Siderophore

Journal Article · 04 November 2019 · Angewandte Chemie

DOI: https://doi.org/10.1002/ange.201910872 · OSTI ID:1573078

Xiao, Songjun ^[1]; Paukstelis, Paul J. ^[1]; Ash, Richard D. ^[2]; Zavalij, Peter Y. ^[1];

^[1]

Department of Chemistry and Biochemistry University of Maryland College Park MD 20742 USA
Department of Geology University of Maryland College Park MD 20742 USA

Abstract Guanosine‐5′‐hydroxamic acid ( 3 ) forms hydrogels when mixed with guanosine ( 1 ) and KCl. The 5′‐hydroxamic acid (HA) unit is pH‐responsive and also chelates Fe ³⁺ . When gels are prepared under basic conditions, the 5′‐HA groups are deprotonated and the anionic hydrogel binds cationic thiazole orange (TO), signaled by enhanced fluorescence. The HA nucleoside 3 , when immobilized in the G‐quartet gel, acts as a supramolecular siderophore to form red complexes with Fe ³⁺ . We patterned the hydrogel's surface with FeCl ₃ , by hand and by using a 3D printer. Patterns form instantly, are visible by eye, and can be erased using vitamin C. This hydrogel, combining self‐assembled G‐quartet and siderophore–Fe ³⁺ motifs, is strong, can be molded into different shapes, and is stable on the bench or under salt water.

View Accepted Manuscript (Publisher)

Cite

Export

Save

Sponsoring Organization:: USDOE

OSTI ID:: 1573078

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Vol. 131 Journal Issue: 51; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (47)

Surface Patterning of Hydrogels for Programmable and Complex Shape Deformations by Ion Inkjet Printing Peng, Xin; Liu, Tianqi; Zhang, Qin Advanced Functional Materials, Vol. 27, Issue 33 https://doi.org/10.1002/adfm.201701962	journal	July 2017
Coordination Chemistry of Microbial Iron Transport Raymond, Kenneth N.; Allred, Benjamin E.; Sia, Allyson K. Accounts of Chemical Research, Vol. 48, Issue 9 https://doi.org/10.1021/acs.accounts.5b00301	journal	August 2015
Amplification and Transcription of the Dynamic Supramolecular Chirality of the Guanine Quadruplex Arnal-Hérault, Carole; Banu, Andreea; Barboiu, Mihail Angewandte Chemie, Vol. 119, Issue 23 https://doi.org/10.1002/ange.200700787	journal	June 2007
Shaping and structuring supramolecular gels Chivers, Phillip R. A.; Smith, David K. Nature Reviews Materials, Vol. 4, Issue 7 https://doi.org/10.1038/s41578-019-0111-6	journal	May 2019
A G ₄ ·K ⁺ Hydrogel Stabilized by an Anion Peters, Gretchen Marie; Skala, Luke P.; Plank, Taylor N. Journal of the American Chemical Society, Vol. 136, Issue 36 https://doi.org/10.1021/ja507506c	journal	August 2014
Gelation-driven component selection in the generation of constitutional dynamic hydrogels based on guanine-quartet formation Sreenivasachary, N.; Lehn, J. -M. Proceedings of the National Academy of Sciences, Vol. 102, Issue 17 https://doi.org/10.1073/pnas.0501663102	journal	April 2005
Multifunctional Fe(III)‐Binding Polyethers from Hydroxamic Acid‐Based Epoxide Monomers Johann, Tobias; Kemmer‐Jonas, Ulrike; Barent, Ramona D. Macromolecular Rapid Communications https://doi.org/10.1002/marc.201900282	journal	July 2019
Photo Gel-Sol/Sol-Gel Transition and Its Patterning of a Supramolecular Hydrogel as Stimuli-Responsive Biomaterials Matsumoto, Shinji; Yamaguchi, Satoshi; Ueno, Shiori Chemistry - A European Journal, Vol. 14, Issue 13 https://doi.org/10.1002/chem.200701904	journal	March 2008
Engineering Bisquinolinium/Thiazole Orange Conjugates for Fluorescent Sensing of G-Quadruplex DNA Yang, Peng; De Cian, Anne; Teulade-Fichou, Marie-Paule Angewandte Chemie International Edition, Vol. 48, Issue 12 https://doi.org/10.1002/anie.200805613	journal	March 2009
Efficient Self-Assembly in Water of Long Noncovalent Polymers by Nucleobase Analogues Cafferty, Brian J.; Gállego, Isaac; Chen, Michael C. Journal of the American Chemical Society, Vol. 135, Issue 7 https://doi.org/10.1021/ja312155v	journal	February 2013
Oxidation-Induced Degradable Nanogels for Iron Chelation Liu, Zhi; Wang, Yan; Purro, Max Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep20923	journal	February 2016
Self-Assembly of Enzyme-Like Nanofibrous G-Molecular Hydrogel for Printed Flexible Electrochemical Sensors Zhong, Ruibo; Tang, Qian; Wang, Shaopeng Advanced Materials, Vol. 30, Issue 12 https://doi.org/10.1002/adma.201706887	journal	February 2018
Acid dissociation constants (Ka) and their temperature dependencies (.DELTA.Ha, .DELTA.Sa) for a series of carbon- and nitrogen-substituted hydroxamic acids in aqueous solution Monzyk, Bruce; Crumbliss, Alvin L. The Journal of Organic Chemistry, Vol. 45, Issue 23 https://doi.org/10.1021/jo01311a024	journal	November 1980
Elucidation of the Fe(III) Gallate Structure in Historical Iron Gall Ink Ponce, Aldo; Brostoff, Lynn B.; Gibbons, Sarah K. Analytical Chemistry, Vol. 88, Issue 10 https://doi.org/10.1021/acs.analchem.6b00088	journal	April 2016
Spatially resolved multicomponent gels Draper, Emily R.; Eden, Edward G. B.; McDonald, Tom O. Nature Chemistry, Vol. 7, Issue 10 https://doi.org/10.1038/nchem.2347	journal	September 2015
G ₄ -quartet hydrogels from 5′-hydrazino-guanosine for the non-covalent and covalent remediation of contaminants from water Xiao, Songjun; Davis, Jeffery T. Faraday Discussions, Vol. 209 https://doi.org/10.1039/C8FD00038G	journal	January 2018
Supramolecular gels made from nucleobase, nucleoside and nucleotide analogs Peters, Gretchen Marie; Davis, Jeffery T. Chemical Society Reviews, Vol. 45, Issue 11 https://doi.org/10.1039/C6CS00183A	journal	January 2016
Supramolecular materials Amabilino, David B.; Smith, David K.; Steed, Jonathan W. Chemical Society Reviews, Vol. 46, Issue 9 https://doi.org/10.1039/C7CS00163K	journal	January 2017
Amplification and Transcription of the Dynamic Supramolecular Chirality of the Guanine Quadruplex Arnal-Hérault, Carole; Banu, Andreea; Barboiu, Mihail Angewandte Chemie International Edition, Vol. 46, Issue 23 https://doi.org/10.1002/anie.200700787	journal	June 2007
Low-Molecular-Weight Gels: The State of the Art Draper, Emily R.; Adams, Dave J. Chem, Vol. 3, Issue 3 https://doi.org/10.1016/j.chempr.2017.07.012	journal	September 2017
Spatial Structuring of a Supramolecular Hydrogel by using a Visible-Light Triggered Catalyst Maity, Chandan; Hendriksen, Wouter E.; van Esch, Jan H. Angewandte Chemie, Vol. 127, Issue 3 https://doi.org/10.1002/ange.201409198	journal	November 2014
Arylboronate esters mediated self-healable and biocompatible dynamic G-quadruplex hydrogels as promising 3D-bioinks Biswas, Ankan; Malferrari, Sara; Kalaskar, Deepak M. Chemical Communications, Vol. 54, Issue 14 https://doi.org/10.1039/C7CC09051J	journal	January 2018
Occurrence of hydroxamate siderophore iron chelators in soils Powell, P. E.; Cline, G. R.; Reid, C. P. P. Nature, Vol. 287, Issue 5785 https://doi.org/10.1038/287833a0	journal	October 1980
Iron Chelation Equilibria, Redox, and Siderophore Activity of a Saccharide Platform Ferrichrome Analogue Dhungana, Suraj; Harrington, James M.; Gebhardt, Peter Inorganic Chemistry, Vol. 46, Issue 20 https://doi.org/10.1021/ic070158l	journal	October 2007
Softening and Shape Morphing of Stiff Tough Hydrogels by Localized Unlocking of the Trivalent Ionically Cross-Linked Centers Wang, Jiahui; Li, Tianzhen; Chen, Fan Macromolecular Rapid Communications, Vol. 39, Issue 12 https://doi.org/10.1002/marc.201800143	journal	May 2018
Spatial Structuring of a Supramolecular Hydrogel by using a Visible-Light Triggered Catalyst Maity, Chandan; Hendriksen, Wouter E.; van Esch, Jan H. Angewandte Chemie International Edition, Vol. 54, Issue 3 https://doi.org/10.1002/anie.201409198	journal	November 2014
A pH-responsive supramolecular polymer gel as an enteric elastomer for use in gastric devices Zhang, Shiyi; Bellinger, Andrew M.; Glettig, Dean L. Nature Materials, Vol. 14, Issue 10 https://doi.org/10.1038/nmat4355	journal	July 2015
Siderophore electrochemistry: relation to intracellular iron release mechanism. Cooper, S. R.; McArdle, J. V.; Raymond, K. N. Proceedings of the National Academy of Sciences, Vol. 75, Issue 8 https://doi.org/10.1073/pnas.75.8.3551	journal	August 1978
Hydroxamic Acid-Containing Hydrogels for Nonabsorbed Iron Chelation Therapy: Synthesis, Characterization, and Biological Evaluation Polomoscanik, Steven C.; Cannon, C. Pat; Neenan, Thomas X. Biomacromolecules, Vol. 6, Issue 6 https://doi.org/10.1021/bm050036p	journal	November 2005
Supramolecular Photoactivatable Anticancer Hydrogels Venkatesh, V.; Mishra, Narendra Kumar; Romero-Canelón, Isolda Journal of the American Chemical Society, Vol. 139, Issue 16 https://doi.org/10.1021/jacs.7b00186	journal	April 2017
A G ₄ ·K ⁺ hydrogel made from 5′-hydrazinoguanosine for remediation of α,β-unsaturated carbonyls Xiao, Songjun; Davis, Jeffery T. Chemical Communications, Vol. 54, Issue 80 https://doi.org/10.1039/C8CC07228K	journal	January 2018
Engineering Bisquinolinium/Thiazole Orange Conjugates for Fluorescent Sensing of G-Quadruplex DNA Yang, Peng; De Cian, Anne; Teulade-Fichou, Marie-Paule Angewandte Chemie, Vol. 121, Issue 12 https://doi.org/10.1002/ange.200805613	journal	March 2009
Investigation of Guanosine-Quartet Assemblies by Vibrational and Electronic Circular Dichroism Spectroscopy, a Novel Approach for Studying Supramolecular Entities Setnička, Vladimír; Urbanová, Marie; Volka, Karel Chemistry - A European Journal, Vol. 12, Issue 34 https://doi.org/10.1002/chem.200500973	journal	November 2006
Acidity of hydroxamic acids: an ab initio and semiempirical study Ventura, Oscar N.; Rama, Jose B.; Turi, Laszlo Journal of the American Chemical Society, Vol. 115, Issue 13 https://doi.org/10.1021/ja00066a047	journal	June 1993
Controlled Fabrication of Micropatterned Supramolecular Gels by Directed Self-Assembly of Small Molecular Gelators Wang, Yiming; Oldenhof, Sander; Versluis, Frank Small, Vol. 15, Issue 8 https://doi.org/10.1002/smll.201804154	journal	January 2019
A family of simple benzene 1,3,5-tricarboxamide (BTA) aromatic carboxylic acid hydrogels Howe, Richard C. T.; Smalley, Adam P.; Guttenplan, Alexander P. M. Chem. Commun., Vol. 49, Issue 39 https://doi.org/10.1039/C2CC37428E	journal	January 2013
Ligands playing musical chairs with G-quadruplex DNA: A rapid and simple displacement assay for identifying selective G-quadruplex binders Monchaud, D.; Allain, C.; Bertrand, H. Biochimie, Vol. 90, Issue 8 https://doi.org/10.1016/j.biochi.2008.02.019	journal	August 2008
Coordination chemistry of microbial iron transport compounds. 15. Electrochemistry and magnetic susceptibility of iron(III)-hydroxamate and -thiohydroxamate complexes Abu-Dari, Kamal; Cooper, Stephen R.; Raymond, Kenneth N. Inorganic Chemistry, Vol. 17, Issue 12 https://doi.org/10.1021/ic50190a019	journal	December 1978
Reversible Redox-Responsive Assembly/Disassembly of Nanoparticles Mediated by Metal Complex Formation Bannwarth, Markus B.; Weidner, Thomas; Eidmann, Evelyn Chemistry of Materials, Vol. 26, Issue 3 https://doi.org/10.1021/cm4040769	journal	January 2014
Thiazole Orange-Induced c-di-GMP Quadruplex Formation Facilitates a Simple Fluorescent Detection of This Ubiquitous Biofilm Regulating Molecule Nakayama, Shizuka; Kelsey, Ilana; Wang, Jingxin Journal of the American Chemical Society, Vol. 133, Issue 13 https://doi.org/10.1021/ja1091062	journal	April 2011
Advancing Metal–Phenolic Networks for Visual Information Storage Dai, Qiong; Yu, Qun; Tian, Yuan ACS Applied Materials & Interfaces, Vol. 11, Issue 32 https://doi.org/10.1021/acsami.9b09830	journal	July 2019
G-Quartet hydrogels for effective cell growth applications Rotaru, Alexandru; Pricope, Gabriela; Plank, Taylor N. Chemical Communications, Vol. 53, Issue 94 https://doi.org/10.1039/C7CC07806D	journal	January 2017
Supramolecular Hydrogel Inspired from DNA Structures Mimics Peroxidase Activity Bhattacharyya, Tanima; Kumar, Y. Pavan; Dash, Jyotirmayee ACS Biomaterials Science & Engineering, Vol. 3, Issue 10 https://doi.org/10.1021/acsbiomaterials.7b00563	journal	September 2017
Toward potential supramolecular tissue engineering scaffolds based on guanosine derivatives Buerkle, Lauren E.; von Recum, Horst A.; Rowan, Stuart J. Chem. Sci., Vol. 3, Issue 2 https://doi.org/10.1039/C1SC00729G	journal	January 2012
Traversing the coordination chemistry and chemical biology of hydroxamic acids Codd, Rachel Coordination Chemistry Reviews, Vol. 252, Issue 12-14 https://doi.org/10.1016/j.ccr.2007.08.001	journal	July 2008
A Molecular Chaperone for G4-Quartet Hydrogels Peters, Gretchen Marie; Skala, Luke P.; Davis, Jeffery T. Journal of the American Chemical Society, Vol. 138, Issue 1 https://doi.org/10.1021/jacs.5b08769	journal	December 2015
Versatile supramolecular pH-tolerant hydrogels which demonstrate pH-dependent selective adsorption of dyes from aqueous solution Okesola, Babatunde O.; Smith, David K. Chemical Communications, Vol. 49, Issue 95 https://doi.org/10.1039/c3cc45969a	journal	January 2013

Similar Records

Drawing with Iron on a Gel Containing a Supramolecular Siderophore

Journal Article · 2019 · Angewandte Chemie (International Edition) · OSTI ID:1800949

Xiao, Songjun; Paukstelis, Paul J.; Ash, Richard D.; +2 more

Plant mechanisms of siderophore-iron utilization

Thesis/Dissertation · 1986 · OSTI ID:6717584

Crowley, D E

Characterization of iron uptake from hydroxamate siderophores by Chlorella vulgaris

Thesis/Dissertation · 1985 · OSTI ID:6067449

Allnutt, F C.T.

Title: Drawing with Iron on a Gel Containing a Supramolecular Siderophore

Citation Formats

References (47)

Similar Records

Related Subjects