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A Structurally-Tunable 3-Hydroxyflavone Motif for Visible Light-Induced Carbon Monoxide-Releasing Molecules (CORMs).

Anderson SN, Richards JM, Esquer HJ, Benninghoff AD, Arif AM, Berreau LM - ChemistryOpen (2015)

Bottom Line: Molecules that can be used to deliver a controlled amount of carbon monoxide (CO) have the potential to facilitate investigations into the roles of this gaseous molecule in biology and advance therapeutic treatments.This has led to the development of light-induced CO-releasing molecules (photoCORMs).Herein, we report a new biologically-inspired organic photoCORM motif that exhibits several features that are desirable in a next-generation photoCORM.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry & Biochemistry, Utah State University 0300 Old Main Hill, Logan, UT, 84322-0300, USA.

ABSTRACT
Molecules that can be used to deliver a controlled amount of carbon monoxide (CO) have the potential to facilitate investigations into the roles of this gaseous molecule in biology and advance therapeutic treatments. This has led to the development of light-induced CO-releasing molecules (photoCORMs). A goal in this field of research is the development of molecules that exhibit a combination of controlled CO release, favorable biological properties (e.g., low toxicity and trackability in cells), and structural tunability to affect CO release. Herein, we report a new biologically-inspired organic photoCORM motif that exhibits several features that are desirable in a next-generation photoCORM. We show that 3-hydroxyflavone-based compounds are easily synthesized and modified to impart changes in absorption features and quantum yield for CO release, exhibit low toxicity, are trackable in cells, and can exhibit both O2-dependent and -independent CO release reactivity.

No MeSH data available.


Related in: MedlinePlus

Structural motifs of selected previously reported CORMs
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fig01: Structural motifs of selected previously reported CORMs

Mentions: The lack of temporal control of CO release in such systems has led to the use of metal carbonyl complexes that release CO only when triggered.4,5 Examples of such complexes include photoCORMs, which release CO from a metal carbonyl unit upon illumination with UV or visible light.4 Recent advances in the field of metal carbonyl photoCORMs demonstrate that CO release can be tuned to occur upon illumination with low-energy red or near infrared (NIR) light through modification of supporting ligands or through approaches using nanoparticles.4 However, a concern associated with some metal-carbonyl-based photoCORMs are side effects related to the metal-containing photoproducts.6 A limited number of organic photoCORMs (1–3, Figure 1) have also been recently reported.7 However, these molecules also have limitations. For example, 1 and 2 are derived from relatively low-yield, multistep synthetic routes that have not been shown to be amenable to structural modification for the tuning of physical properties or biological targeting. Diels–Alder product 3 can be generated in good yield and subsequently undergoes CO release. However, this compound cannot be isolated and stored.


A Structurally-Tunable 3-Hydroxyflavone Motif for Visible Light-Induced Carbon Monoxide-Releasing Molecules (CORMs).

Anderson SN, Richards JM, Esquer HJ, Benninghoff AD, Arif AM, Berreau LM - ChemistryOpen (2015)

Structural motifs of selected previously reported CORMs
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4608525&req=5

fig01: Structural motifs of selected previously reported CORMs
Mentions: The lack of temporal control of CO release in such systems has led to the use of metal carbonyl complexes that release CO only when triggered.4,5 Examples of such complexes include photoCORMs, which release CO from a metal carbonyl unit upon illumination with UV or visible light.4 Recent advances in the field of metal carbonyl photoCORMs demonstrate that CO release can be tuned to occur upon illumination with low-energy red or near infrared (NIR) light through modification of supporting ligands or through approaches using nanoparticles.4 However, a concern associated with some metal-carbonyl-based photoCORMs are side effects related to the metal-containing photoproducts.6 A limited number of organic photoCORMs (1–3, Figure 1) have also been recently reported.7 However, these molecules also have limitations. For example, 1 and 2 are derived from relatively low-yield, multistep synthetic routes that have not been shown to be amenable to structural modification for the tuning of physical properties or biological targeting. Diels–Alder product 3 can be generated in good yield and subsequently undergoes CO release. However, this compound cannot be isolated and stored.

Bottom Line: Molecules that can be used to deliver a controlled amount of carbon monoxide (CO) have the potential to facilitate investigations into the roles of this gaseous molecule in biology and advance therapeutic treatments.This has led to the development of light-induced CO-releasing molecules (photoCORMs).Herein, we report a new biologically-inspired organic photoCORM motif that exhibits several features that are desirable in a next-generation photoCORM.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry & Biochemistry, Utah State University 0300 Old Main Hill, Logan, UT, 84322-0300, USA.

ABSTRACT
Molecules that can be used to deliver a controlled amount of carbon monoxide (CO) have the potential to facilitate investigations into the roles of this gaseous molecule in biology and advance therapeutic treatments. This has led to the development of light-induced CO-releasing molecules (photoCORMs). A goal in this field of research is the development of molecules that exhibit a combination of controlled CO release, favorable biological properties (e.g., low toxicity and trackability in cells), and structural tunability to affect CO release. Herein, we report a new biologically-inspired organic photoCORM motif that exhibits several features that are desirable in a next-generation photoCORM. We show that 3-hydroxyflavone-based compounds are easily synthesized and modified to impart changes in absorption features and quantum yield for CO release, exhibit low toxicity, are trackable in cells, and can exhibit both O2-dependent and -independent CO release reactivity.

No MeSH data available.


Related in: MedlinePlus