Limits...
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

Photoinduced CO-release reactivity of 4.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4608525&req=5

sch03: Photoinduced CO-release reactivity of 4.

Mentions: Solutions of 4 in acetonitrile, 1:1 aqueous DMSO, or cell culture media (RPMI-1640; pH 7.4) are stable in the presence of ambient O2 for >2 weeks when protected from light. Exposure of an aerobic acetonitrile solution of 4 to visible light (419 nm) results in quantitative CO release (0.96(2) equiv) as determined by GC headspace analysis and the formation of 3-(benzoyloxy)-2-naphthoic acid (5, Scheme 3; see also Figures S6–S8 in the Supporting Information). This organic product is pale yellow in color and does not exhibit any emission features in the visible region (Figure S9 in the Supporting Information). The quantum yield for the CO-release reaction of 4 is 0.007(3). The same reaction occurs in methanol (Figure S10 in the Supporting Information) and 1:1 aqueous DMSO as determined by 1H NMR and GC head space gas analysis. Control reactions indicate that both O2 and visible light are needed for the CO release reaction of 4. An 18O2-labeling experiment demonstrates that both oxygen atoms from O2 are incorporated into the organic photoproduct.


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)

Photoinduced CO-release reactivity of 4.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

sch03: Photoinduced CO-release reactivity of 4.
Mentions: Solutions of 4 in acetonitrile, 1:1 aqueous DMSO, or cell culture media (RPMI-1640; pH 7.4) are stable in the presence of ambient O2 for >2 weeks when protected from light. Exposure of an aerobic acetonitrile solution of 4 to visible light (419 nm) results in quantitative CO release (0.96(2) equiv) as determined by GC headspace analysis and the formation of 3-(benzoyloxy)-2-naphthoic acid (5, Scheme 3; see also Figures S6–S8 in the Supporting Information). This organic product is pale yellow in color and does not exhibit any emission features in the visible region (Figure S9 in the Supporting Information). The quantum yield for the CO-release reaction of 4 is 0.007(3). The same reaction occurs in methanol (Figure S10 in the Supporting Information) and 1:1 aqueous DMSO as determined by 1H NMR and GC head space gas analysis. Control reactions indicate that both O2 and visible light are needed for the CO release reaction of 4. An 18O2-labeling experiment demonstrates that both oxygen atoms from O2 are incorporated into the organic photoproduct.

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