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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

O2-dependent CO-release reactivity of a) quercetin and b) 3-hydroxyflavone (3-HflH); C) O2-independent, UV-light-induced isomerization of 3-HflH.
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sch01: O2-dependent CO-release reactivity of a) quercetin and b) 3-hydroxyflavone (3-HflH); C) O2-independent, UV-light-induced isomerization of 3-HflH.

Mentions: Naturally occurring 3-HflH derivatives, such as quercetin (Scheme 1 a), are known to undergo O2-dependent, enzyme-catalyzed degradation to produce CO in bacteria and fungi.10 In the absence of enzyme, quercetin is known to undergo various types of oxidative reactions, including UV-light-induced reactions, which can result in CO release.11 It is known that unsubstituted 3-HflH will undergo incorporation of both atoms of O2 and expulsion of CO in the presence of a photosensitizer, or via direct illumination using UV light (Scheme 1 b).12 These reactions are proposed to proceed from the normal and tautomeric excited-state forms of 3-HlfH, respectively. We have re-examined the photoinduced (λ=300 nm) reactivity of 3-HflH under O2 and found that while a near-quantitative amount of CO is generated (0.95 equiv), multiple organic products are detected by gas chromatography–mass spectrometry (GC–MS). Finally, 3-HflH is also known to undergo UV-light-induced rearrangement resulting in CO release under anaerobic conditions (Scheme 1 C).13 These combined results indicate that 3-HflH derivatives have multiple reaction pathways by which light-induced CO release can occur.


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)

O2-dependent CO-release reactivity of a) quercetin and b) 3-hydroxyflavone (3-HflH); C) O2-independent, UV-light-induced isomerization of 3-HflH.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

sch01: O2-dependent CO-release reactivity of a) quercetin and b) 3-hydroxyflavone (3-HflH); C) O2-independent, UV-light-induced isomerization of 3-HflH.
Mentions: Naturally occurring 3-HflH derivatives, such as quercetin (Scheme 1 a), are known to undergo O2-dependent, enzyme-catalyzed degradation to produce CO in bacteria and fungi.10 In the absence of enzyme, quercetin is known to undergo various types of oxidative reactions, including UV-light-induced reactions, which can result in CO release.11 It is known that unsubstituted 3-HflH will undergo incorporation of both atoms of O2 and expulsion of CO in the presence of a photosensitizer, or via direct illumination using UV light (Scheme 1 b).12 These reactions are proposed to proceed from the normal and tautomeric excited-state forms of 3-HlfH, respectively. We have re-examined the photoinduced (λ=300 nm) reactivity of 3-HflH under O2 and found that while a near-quantitative amount of CO is generated (0.95 equiv), multiple organic products are detected by gas chromatography–mass spectrometry (GC–MS). Finally, 3-HflH is also known to undergo UV-light-induced rearrangement resulting in CO release under anaerobic conditions (Scheme 1 C).13 These combined results indicate that 3-HflH derivatives have multiple reaction pathways by which light-induced CO release can occur.

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