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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

A) Representation of the molecular structure of 4 as determined by X-ray crystallography; B) side-on structural view.
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fig02: A) Representation of the molecular structure of 4 as determined by X-ray crystallography; B) side-on structural view.

Mentions: We hypothesized that the 3-HflH structural motif could be tuned to undergo visible-light-induced CO release. With this strategy in mind, 4 was designed and prepared using Alger–Flynn–Oyamada methodology (Scheme 2).14 X-ray-quality crystals of 4 were obtained via slow evaporation of a dichloromethane solution. Compound 4 was additionally characterized by elemental analysis, spectroscopic methods, and mass spectrometry (see Figures S1–S5 in the Supporting Information). Compound 4 is readily soluble in organic solvents and is also soluble in aqueous DMSO at concentrations suitable for spectroscopic measurements (H2O/DMSO, 1:1) and biological experiments (1 % DMSO). Compound 4 crystallizes in the monoclinic space group C2/c.15 A representation of the molecular structure of 4 is shown in Figure 2. In the solid state, the 3-hydroxy-4-pyrone units from two molecules form centrosymmetric hydrogen-bonded dimers with two identical intermolecular O−H⋅⋅⋅O hydrogen bonds (O⋅⋅⋅O: 2.69 Å and 145.3°).16 The naphthyl-fused 3-hydroxy-4-pyrone ring structure is nearly planar, and the phenyl appendage twists only slightly out of this plane. This overall structure favors conjugation of the two electronic systems. Compound 4 has bond lengths and angles very similar to those of 3-HflH.16


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)

A) Representation of the molecular structure of 4 as determined by X-ray crystallography; B) side-on structural view.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig02: A) Representation of the molecular structure of 4 as determined by X-ray crystallography; B) side-on structural view.
Mentions: We hypothesized that the 3-HflH structural motif could be tuned to undergo visible-light-induced CO release. With this strategy in mind, 4 was designed and prepared using Alger–Flynn–Oyamada methodology (Scheme 2).14 X-ray-quality crystals of 4 were obtained via slow evaporation of a dichloromethane solution. Compound 4 was additionally characterized by elemental analysis, spectroscopic methods, and mass spectrometry (see Figures S1–S5 in the Supporting Information). Compound 4 is readily soluble in organic solvents and is also soluble in aqueous DMSO at concentrations suitable for spectroscopic measurements (H2O/DMSO, 1:1) and biological experiments (1 % DMSO). Compound 4 crystallizes in the monoclinic space group C2/c.15 A representation of the molecular structure of 4 is shown in Figure 2. In the solid state, the 3-hydroxy-4-pyrone units from two molecules form centrosymmetric hydrogen-bonded dimers with two identical intermolecular O−H⋅⋅⋅O hydrogen bonds (O⋅⋅⋅O: 2.69 Å and 145.3°).16 The naphthyl-fused 3-hydroxy-4-pyrone ring structure is nearly planar, and the phenyl appendage twists only slightly out of this plane. This overall structure favors conjugation of the two electronic systems. Compound 4 has bond lengths and angles very similar to those of 3-HflH.16

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