Hydrogen Peroxide Triggered Prochelator Activation, Subsequent Metal Chelation, and Attenuation of the Fenton Reaction

Wei, Yibin; Guo, Maolin

doi:10.1002/anie.200604859

Cited by 50 publications

(30 citation statements)

References 20 publications

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“…We have also defined the physiology of H 2 O 2 signalling for growth, migration, differentiation and phagocytic responses in a variety of cancer cell 22 , immune cell 19 and primary neuron models 17 . Finally, the boronate switch has also been used to prepare H 2 O 2 -responsive prochelators 29,30 , pro-drugs 31,32 , polymers 33,34 and mass spectrometry probes 35 . As with the diamino switch for NO detection, the H 2 O 2 -sensitive boronate cage provides a second general example that illustrates the potential power of a single robust chemical reaction to improve our biological knowledge.…”

Section: Organic Reaction-based Approachesmentioning

confidence: 99%

Reaction-based small-molecule fluorescent probes for chemoselective bioimaging

2012

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The dynamic chemical diversity of elements, ions and molecules that form the basis of life offers both a challenge and an opportunity for study. Small-molecule fluorescent probes can make use of selective, bioorthogonal chemistries to report on specific analytes in cells and in more complex biological specimens. These probes offer powerful reagents to interrogate the physiology and pathology of reactive chemical species in their native environments with minimal perturbation to living systems. This Review presents a survey of tools and tactics for using such probes to detect biologically important chemical analytes. We highlight design criteria for effective chemical tools for use in biological applications as well as gaps for future exploration.

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Section: Organic Reaction-based Approachesmentioning

confidence: 99%

Reaction-based small-molecule fluorescent probes for chemoselective bioimaging

2012

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“…2L), BSIH (pinacol ester form of SIH-B) (Fig. 2M), and a few other derivatives have been developed recently [56–58] using tridentate chelator salicylaldehyde isocotinoyl hydrazone ( SIH ) (Fig. 2K) as their parent molecule.…”

Section: Synthetic Iron Chelating Compounds As Potential Drugs Trementioning

confidence: 99%

Iron Chelators as Potential Therapeutic Agents for Parkinsons Disease

Perez¹,

Tong²,

Guo³

2008

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Parkinson's disease (PD) is a neurological disorder characterized by the progressive impairment of motor skills in patients. Growing evidence suggests that abnormal redox-active metal accumulation, caused by dysregulation, plays a central role in the neuropathology of PD. Redox-active metals (e.g. Fe and Cu) catalyze essential reactions for brain function. However, these metals can also participate in the generation of highly toxic free radicals that can cause oxidative damage to cells and ultimately lead to the death of dopamine-containing neurons. The emergence of redox-active metals as key players in the pathogenesis of PD strongly suggests that metal-chelators could be beneficial in the treatment of this condition. This mini-review summarizes major recent developments on natural, synthetic iron chelating compounds and hydrogen peroxide-triggered prochelators as potential candidates for PD treatment.

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“…44 Shortly afterwards, 2-boronobenzaldehyde isonicotinoyl hydrazone 35 was also reported. 45 In this molecule the phenol oxygen of SIH, is replaced by a boronic acid group in the prochelator.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…To create ROSsensitive prochelators, self-immolative boronic esters (i.e. 43) and sulfonate esters(44,45) have been used as protecting groups. The sulfonate esters are cleaved by H 2 O 2 only when the metal-binding site contains an N-oxide donor atom (44).…”

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confidence: 99%