Drawing on biology to inspire molecular design: a redox-responsive MRI probe based on Gd(<scp>iii</scp>)-nicotinamide

Harris, Michael; Kolanowski, Jacek L.; O’Neill, Edward; Henoumont, Céline; Laurent, Sophie; Parac‐Vogt, Tatjana N.; New, Elizabeth J.

doi:10.1039/c8cc07092j

Cited by 10 publications

(6 citation statements)

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“…[207] In der Arbeitsgruppe von New wurden Flavine als reversible Redoxschalter biologischen Ursprungs eingesetzt, welche die dynamischen Flüsse von Oxidationsund Reduktionsereignissen in Zellen überwachen kçnnen. [208] Innovative Ansätze mit redoxempfindlichen niedermolekularen Substanzen, gekoppelt an Sensorplattformen, ergaben Nicotinimidium-gekoppelte MRT-Kontrastmittel, [209] ebenso wie Naphthalimid-, [210] subzellulärl okalisierbare [211] und ratiometrische, [212] an fluoreszierende Gerüste gekoppelte Flavinredoxsensoren.…”

Section: Methodsunclassified

Aktivitätsbasierte Sensorik: ein synthetisch‐methodischer Ansatz für die selektive molekulare Bildgebung und darüber hinaus.

2020

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National Laboratory.Ere rlangte 1997 seinen B.S. und M.S. von Caltech und arbeitete bei Prof. Harry Gray.E in Jahr verbrachte er als Fulbright Scholar bei Dr.Jean-Pierre Sauvage und wurde 2002 für eine Arbeit bei Prof. Dan Nocera vom MIT promoviert. Nach einer Zeit als Postdoktorand bei Prof. Steve Lippard (MIT) schloss er sich 2004 der FakultätinB erkeley an. Er befasst sich mit der Untersuchung von Metallen und redoxaktiven Molekülen in Biologie und Energie.

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Section: Methodsunclassified

Aktivitätsbasierte Sensorik: ein synthetisch‐methodischer Ansatz für die selektive molekulare Bildgebung und darüber hinaus.

2020

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“…Inspired by the excellent reversibility of the nicotinamide redox switch, we recently reported GdNR1 (Figure 1b), a Gd complex bearing a nicotinimidium-conjugated DO3A ligand. 30 Reduction of the complex results in a 2.5-fold increase in relaxivity due to a change in hydration state. This is a rare example of a redox-responsive MRI contrast agent bearing a biologically inspired redox-active ligand.…”

Section: ■ Bioinspired Molecular Imaging Tools Redox Cofactorsmentioning

confidence: 99%

Bioinspired Small-Molecule Tools for the Imaging of Redox Biology

Kaur

New

2019

Acc. Chem. Res.

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CONSPECTUSThe availability of electrons to biological systems underpins the mitochondrial electron transport chain (ETC) that powers living cells. It is little wonder, therefore, that the sufficiency of electron supply is critical to cellular health. Considering mitochondrial redox activity alone, a lack of oxygen (hypoxia) leads to impaired production of adenosine triphosphate (ATP), the major energy currency of the cell; whereas excess oxygen (hyperoxia) is associated with elevated production of reactive oxygen species (ROS) from the interaction of oxygen with electrons that have leaked from the ETC. Furthermore, the redox proteome, which describes the reversible and irreversible redox modifications of proteins, controls many aspects of biological structure and function. Indeed, many major diseases, including cancer and diabetes, are now termed "redox diseases", spurring much interest in the measurement and monitoring of redox states and redox-active species within biological systems.

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“…[207] The New group has exploited flavins as bioderived reversible redox switches,w hich can monitor dynamic fluxes of oxida- tion and reduction events in cells. [208] Innovative work using redox-sensitive small molecules coupled to sensor platforms led to nicotinimidium-coupled MRI contrast agents, [209] as well as naphthalimide, [210] subcellular-targetable, [211] and ratiometric [212] fluorescent scaffold-coupled flavin redox sensors.…”

Section: Reviewsmentioning

confidence: 99%

Activity‐Based Sensing: A Synthetic Methods Approach for Selective Molecular Imaging and Beyond

2020

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Kevin J. Bruemmer received his B.S. in Chemistry and Mathematics from Southern Methodist University in 2014, where he worked with Prof. Alexander Lippert on the development of fluorescence and magnetic resonancep robes for reactive nitrogen and sulfur species. He then moved to UC Berkeley to continue work on studying reactive species with Prof. Chris Chang in 2015, where his work as an NSF graduate fellow focuses on developing and applying activitybased sensing methods to study the physiological roles of formaldehyde. Steven W. M. Crossley received his B.Sc. in Chemistry from the University of British Columbia in 2012. After agap year,h e pursued Ph.D. studies as an NSERC postgraduate scholar at The Scripps Research Institute with Prof. Ryan Shenvi to work on first-row transition-metal hydrofunctionalization of alkenes and total synthesist osupport interrogation of GABAA receptor neurobiology.In2 018, he joined the group of Prof. Chris Chang, where he is developing amino acid specific reaction-based probes for cancer therapeutics discovery.

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Drawing on biology to inspire molecular design: a redox-responsive MRI probe based on Gd(iii)-nicotinamide

Abstract: A novel, reversible redox-active MRI probe, GdNR1, has been developed based on the biologically-inspired nicotinimidium redox switch.

Cited by 10 publications

References 40 publications

Aktivitätsbasierte Sensorik: ein synthetisch‐methodischer Ansatz für die selektive molekulare Bildgebung und darüber hinaus.

Aktivitätsbasierte Sensorik: ein synthetisch‐methodischer Ansatz für die selektive molekulare Bildgebung und darüber hinaus.

Bioinspired Small-Molecule Tools for the Imaging of Redox Biology

Activity‐Based Sensing: A Synthetic Methods Approach for Selective Molecular Imaging and Beyond

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