CuproCleav-1, a first generation photocage for Cu+

Mbatia, Hannah W.; Bandara, H. M. Dhammika; Burdette, Shawn C.

doi:10.1039/c2cc31281f

Cited by 25 publications

(20 citation statements)

References 37 publications

(42 reference statements)

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“…The o ‐nitrobenzyl system undergoes a photoreaction, yielding the release of the metal ion. Similar irreversible metal ion release has been shown for other o ‐nitrobenzyl caged compounds or by using light as a stimulus in conjugation with photosensitized singlet‐oxygen formation …”

Section: Chemical Communication Through Release Of Metal Cationssupporting

confidence: 69%

“…[11,39] The Zn 2 + source consisted of ac oordination complex with ap hotocleavable ligand system (15). The o-nitrobenzyl system undergoes ap hotoreaction,y ieldingt he releaseo ft he metal ion.S imilar irreversible metal ion release has been shown for other o-nitrobenzyl caged compounds [40,41] or by using light as as timulus in conjugation with photosensitized singletoxygenf ormation. [42] Notably,t he light-induced release of metal ions can be performed with reversibly operating systems.…”

Section: Chemical Communication Through Release Of Metal Cationsmentioning

confidence: 89%

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Chemical Communication between Molecules

Remón

Pischel

2017

ChemPhysChem

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In this Minireview conceptual approaches towards the communication between (supra)molecular species are illustrated. The reviewed mechanisms include photophysical communication through energy transfer and communication mediated by chemical species that are released from precursors upon application of an external stimulus. The focus is on the stimulation by (reversible) photoreactions. Special attention has been given to supramolecular systems that illustrate the idea of chemical communication and information transfer in a very descriptive manner.

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Section: Chemical Communication Through Release Of Metal Cationssupporting

confidence: 69%

Section: Chemical Communication Through Release Of Metal Cationsmentioning

confidence: 89%

Chemical Communication between Molecules

Remón

Pischel

2017

ChemPhysChem

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“…14 The present review covers recent developments in the field, focusing on the scope, limitations, and applications of PPGs, which are used to release organic molecules. Photoactivation of small inorganic species and ions, such as NO, 15 CO, 16 Ca 2+ , 9h,17 Zn 2+ , 18 Cd 2+ , 19 or Cu + , 20 is not covered. Simplified basic structures of the photoremovable protecting groups discussed in this review are listed in Table 1 (the leaving groups are shown in red).…”

Section: Introductionmentioning

confidence: 99%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

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“…[11] Alternatively, photolytically breaking a carbon-heteroatom bond provides compounds that release metal ions through the reduction of chelate effects. The Cleav class of photocaged complexes can effectively buffer and release Ca 2+ , [13] Cu 2+/1+ , [14,15] or Zn 2+ depending on the ligand design. [16,17] Photocages based on oNB remain the dominant technology to study signal transduction mediated by biomolecules despite limitations like slow analyte-release kinetics, the requirement of UV light for photolysis and the formation of potentially toxic nitroso photoproducts.…”

mentioning

confidence: 99%

A Zinc(II) Photocage Based on a Decarboxylation Metal Ion Release Mechanism for Investigating Homeostasis and Biological Signaling

et al. 2015

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Metal ion signaling in biology has been studied extensively with ortho-nitrobenzyl photocages; however, the low quantum yields and other optical properties are not ideal for these applications. We describe the synthesis and characterization of NTAdeCage, the first member in a new class of Zn 2+ photocages that utilizes a light-driven decarboxylation reaction in the metal ion release mechanism. NTAdeCage binds Zn 2+ with sub-pM affinity using a modified nitrilotriacetate chelator and exhibits an almost 6 order of magnitude decrease in metal binding affinity upon uncaging. In contrast to other metal ion photocages, NTAdeCage and the corresponding Zn 2+ complex undergo efficient photolysis with quantum yields approaching 30%. The ability of NTAdeCage to mediate the uptake of 65 Zn 2+ by Xenopus laevis oocytes expressing hZIP4 demonstrates the viability of this photocaging strategy to execute biological assays. Keywords cage compounds; coordination compounds; photolysis; X-ray diffraction; zinc The importance of Zn 2+ beyond structural and catalytic functions in proteins has become increasingly apparent. [1] Zinc and iron regulated proteins (ZIPs) increase cytosolic Zn 2+ concentrations; in contrast, zinc transporter (ZnT) proteins decrease cytosolic Zn 2+ . [2,3] Elucidating the function of free or loosely bound Zn 2+ in the cytosol as well as in intracellular compartments remains important; however, the ability to modulate Zn 2+ levels in vivo in a time-resolved manner remains elusive. [4] Free Zn 2+ has been implicated in various signaling pathways, [1] and recently fertilization of oocytes has been shown to trigger "zinc sparks" that serve to initiate meiosis at the beginning stages of embryotic development. [5] The development of new methodologies to simulate fluctuations in Zn 2+ concentrations in a spatiotemporal manner would facilitate the understanding of complex signaling processes.Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/anie.201505778. HHS Public Access Author Manuscript Author ManuscriptAuthor Manuscript Author ManuscriptThe photochemistry of ortho-nitrobenzyl (oNB) chromophores initially was recognized as a means to deliver Ca 2+ in a controlled manner to biological receptors using light. [6] We subsequently adapted two Ca 2+ -releasing strategies to develop photocaged complexes for biologically relevant metal ions such as Zn 2+ , Cu + and Fe 3+ . [7,8] In the Cast photocages, decreased electron density on a coordinated aniline nitrogen atom following photolysis lowers chelator binding affinity. [9][10][11] While this strategy can adequately buffer Ca 2+ at typical intracellular resting levels (ca. 100 nM) and simulate biologically relevant concentration increases, [6,12] the reliance on weakly coordinating aniline-based ligands precludes use with Zn 2+ , which experiences tighter intracellular homeostasis. [11] Alternatively, photolytically breaking a carbon-heteroatom bond provides compounds that release metal ions through the reduction ...

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CuproCleav-1, a first generation photocage for Cu+

Cited by 25 publications

References 37 publications

Chemical Communication between Molecules

Chemical Communication between Molecules

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

A Zinc(II) Photocage Based on a Decarboxylation Metal Ion Release Mechanism for Investigating Homeostasis and Biological Signaling

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