The Dithiolate-Bridged Diiron Hexacarbonyl Complex Na2[(μ-SCH2CH2COO)Fe(CO)3]2 as a Water-Soluble PhotoCORM

Poh, Hwa Tiong; Sim, Bai Ting; Chwee, Tsz Sian; Leong, Weng Kee; Fan, Wai Yip

doi:10.1021/om401013a

Cited by 38 publications

(22 citation statements)

References 34 publications

(37 reference statements)

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“…The optical spectral changes that occur during 365 nm irradiation of -pdt-[Fe(CO) 3 ] 2 in acetonitrile are shown in Figure 4. A nearly identical UV-vis spectrum was reported for a water soluble derivative recently synthesized by Fan et al [48] that contains an open structure, as opposed to the more basket-like apex of -pdt-[Fe(CO) 3 ] 2 . For -pdt-[Fe(CO) 3 ] 2 , FTIR headspace analysis, the myoglobin assay, and GC-TCD, as well as detection of CO by its coordination to a rhodium binuclear complex (described below) were used to confirm CO release.…”

Section: Iron Based Photocormssupporting

confidence: 68%

“…A small number of PhotoCORMs based on iron have been reported, and two of these were discussed in recent reviews [19,[45][46][47]. Iron-iron hydrogenase model compounds photochemically generate CO when irradiated with 365 nm light [48,49]. These molecules contain two irons and up to six CO groups that can be liberated photochemically.…”

Section: Iron Based Photocormsmentioning

confidence: 99%

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The chemistry, biology and design of photochemical CO releasing molecules and the efforts to detect CO for biological applications

Marhenke

Trevino

Works

2016

Coordination Chemistry Reviews

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Several beneficial biological effects of carbon monoxide (CO) have been identified. CO contributes to vascular tone, is anti-inflammatory and antiapoptotic, and protects tissue against hypoxia. In response, a number of novel COreleasing systems, mostly transition-metal carbonyl compounds, have been reported. Recent research in the area of photochemical CO-releasing molecules (PhotoCORMs) is reviewed. The photophysical and chemical properties of these PhotoCORMs are described, along with studies of biological activity in some cases. Spectral data and quantum yields, when available, are compared. In addition, various methods for the detection and quantification of CO are discussed.

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Section: Iron Based Photocormssupporting

confidence: 68%

Section: Iron Based Photocormsmentioning

confidence: 99%

The chemistry, biology and design of photochemical CO releasing molecules and the efforts to detect CO for biological applications

Marhenke

Trevino

Works

2016

Coordination Chemistry Reviews

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“…65,67,75,80 Whilst these studies show that the compounds tests are not toxic, the potential of photoCORMs in active toxicity toward cancer cells has also been considered. 46,74 The latter studies focus on the possible 'turn on' of activity when irradiated.…”

Section: Biological Testingmentioning

confidence: 99%

PhotoCORMs: CO release moves into the visible

Wright

2016

Dalton Trans.

114

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The potential of carbon monoxide to act as a therapeutic agent is now well-established. Controlled delivery of CO is best achieved using 'CORMs': molecules which release known amounts of carbon monoxide in response to a stimulus. Metal carbonyl complexes will release CO if irradiated with ultraviolet light, but it is only in the past five years that development of true 'photoCORMs' has been explored. Recent exciting developments in this area now show that design of photoCORMs operating well into the visible region is achievable. In this Perspective, we examine the growth of photoCORMs from their origins in the photophysics of metal carbonyls to the latest visible-light agents.

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“…20 Further illustrating the robustness of these compounds, Fe 2 ( μ -SMe) 2 (CO) 6 is prepared at 120–30 °C and 65 atm of CO (see Section 2.2.1). Most derivatives are soluble in organic solvents, although water solubility can be achieved 21 through the use of hydrophilic substituents, e.g., the tetraol Fe 2 [ μ -SCH 2 CH(OH)CH 2 OH] 2 (CO) 6 22 and the sodium sulfonate Fe 2 [ μ -S 2 C 2 H 3 (CH 2 SO 3 Na)](CO) 6 . 23 Because of their convenient stability and solubility, Fe 2 ( μ -SR) 2 (CO) 6 complexes are usually purified by chromatography, as illustrated by separation of two isomers of Fe 2 ( μ -SMe) 2 (CO) 6 .…”

Section: Introductionmentioning

confidence: 99%

“…24 Although these compounds are probably toxic, they have been considered in the pharmaceutical context. 21 …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Diiron(I) Dithiolato Carbonyl Complexes

2016

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Virtually all organosulfur compounds react with Fe(0) carbonyls to give the title complexes. These reactions are reviewed in light of major advances over the past few decades, spurred by interest in Fe2(μ-SR)2(CO)x centers at the active sites of the [FeFe]-hydrogenase enzymes. The most useful synthetic route to Fe2(μ-SR)2(CO)6 involves the reaction of thiols with Fe2(CO)9 and Fe3(CO)12. Such reactions can proceed via mono-, di-, and triiron intermediates. The reactivity of Fe(0) carbonyls toward thiols is highly chemoselective, and the resulting dithiolato complexes are fairly rugged. Thus, many complexes tolerate further synthetic elaboration directed at the organic substituents. A second major route involves alkylation of Fe2(μ-S2)(CO)6, Fe2(μ-SH)2(CO)6, and Li2Fe2(μ-S)2(CO)6. This approach is especially useful for azadithiolates Fe2[(μ-SCH2)2NR](CO)6. Elaborate complexes arise via addition of the FeSH group to electrophilic alkenes, alkynes, and carbonyls. Although the first example of Fe2(μ-SR)2(CO)6 was prepared from ferrous reagents, ferrous compounds are infrequently used, although the Fe(II)(SR)2 + Fe(0) condensation reaction is promising. Almost invariably low-yielding, the reaction of Fe3(CO)12, S8, and a variety of unsaturated substrates results in C–H activation, affording otherwise inaccessible derivatives. Thiones and related C═S-containing reagents are highly reactive toward Fe(0), often giving complexes derived from substituted methanedithiolates and C–H activation.

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The Dithiolate-Bridged Diiron Hexacarbonyl Complex Na₂[(μ-SCH₂CH₂COO)Fe(CO)₃]₂ as a Water-Soluble PhotoCORM

Abstract: The dithiolate-bridged diiron hexacarbonyl complex Na2[(μ-SCH2CH2COO)Fe(CO)3]2 as a water-soluble photoCORM

Cited by 38 publications

References 34 publications

The chemistry, biology and design of photochemical CO releasing molecules and the efforts to detect CO for biological applications

The chemistry, biology and design of photochemical CO releasing molecules and the efforts to detect CO for biological applications

PhotoCORMs: CO release moves into the visible

Synthesis of Diiron(I) Dithiolato Carbonyl Complexes

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