Using Singlet Oxygen to Synthesize Natural Products and Drugs

Ghogare, Ashwini A.; Greer, Alexander

doi:10.1021/acs.chemrev.5b00726

Cited by 579 publications

(493 citation statements)

References 372 publications

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“…Photosensitizers generating 1 O 2 have been explored and exploited in the fields of organic synthesis, medical photodynamic therapy and others, but not yet in the field of chemical sensors5354. The proposed analogy between the photo-catalytic and enzymatic detection schemes, Fig.…”

Section: Discussionmentioning

confidence: 99%

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Singlet oxygen-based electrosensing by molecular photosensitizers

et al. 2017

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Enzyme-based electrochemical biosensors are an inspiration for the development of (bio)analytical techniques. However, the instability and reproducibility of the reactivity of enzymes, combined with the need for chemical reagents for sensing remain challenges for the construction of useful devices. Here we present a sensing strategy inspired by the advantages of enzymes and photoelectrochemical sensing, namely the integration of aerobic photocatalysis and electrochemical analysis. The photosensitizer, a bioinspired perfluorinated Zn phthalocyanine, generates singlet-oxygen from air under visible light illumination and oxidizes analytes, yielding electrochemically-detectable products while resisting the oxidizing species it produces. Compared with enzymatic detection methods, the proposed strategy uses air instead of internally added reactive reagents, features intrinsic baseline correction via on/off light switching and shows C-F bonds-type enhanced stability. It also affords selectivity imparted by the catalytic process and nano-level detection, such as 20 nM amoxicillin in μl sample volumes.

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Section: Discussionmentioning

confidence: 99%

“…The high reactivity of 1 O 2 and its ROS daughters, however, limits the use of photocatalytic materials due to photosensitizers degradation and thus low turnover numbers54. This is not surprising considering that C–H bonds containing photosensitizers are being attacked by the 1 O 2 and ROS they produce.…”

Section: Discussionmentioning

confidence: 99%

Singlet oxygen-based electrosensing by molecular photosensitizers

et al. 2017

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“…This is a consequence of the molecule now having a singlet character, which makes it possible for it to interact more efficiently with most chemical compounds [2], [36], [38], [39], [40]. Most commonly, 1 O 2 reacts with other compounds by producing endoperoxides in the first place.…”

Section: Singlet Oxygenmentioning

confidence: 99%

“…This is possible because certain highly exothermic reactions make enough free energy available to efficiently excite 3 O 2 [35], [36], [40]. The reaction produces some excited state product, that collides with 3 O 2 and transfers the excitation energy, after which 1 O 2 is obtained.…”

Section: Singlet Oxygenmentioning

confidence: 99%

Direct 1O2 optical excitation: A tool for redox biology

Blázquez‐Castro

2017

Redox Biology

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Molecular oxygen (O2) displays very interesting properties. Its first excited state, commonly known as singlet oxygen (1O2), is one of the so-called Reactive Oxygen Species (ROS). It has been implicated in many redox processes in biological systems. For many decades its role has been that of a deleterious chemical species, although very positive clinical applications in the Photodynamic Therapy of cancer (PDT) have been reported. More recently, many ROS, and also 1O2, are in the spotlight because of their role in physiological signaling, like cell proliferation or tissue regeneration. However, there are methodological shortcomings to properly assess the role of 1O2 in redox biology with classical generation procedures. In this review the direct optical excitation of O2 to produce 1O2 will be introduced, in order to present its main advantages and drawbacks for biological studies. This photonic approach can provide with many interesting possibilities to understand and put to use ROS in redox signaling and in the biomedical field.

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“…This C 2 -symmetric compound was then subjected to singlet oxygen ( 1 O 2 ), inducing a [4+2] cycloaddition reaction, 65 and after exposure to DBU, a Kornblum-DeLaMare fragmentation ensued. Following Dess-Martin periodinane (DMP) oxidation, enone 41 was obtained.…”

Section: Syntheses From the 21st Centurymentioning

confidence: 99%

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

et al. 2017

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The pool of abundant chiral terpene building blocks (i.e. “chiral pool terpenes”) has long served as a starting point for the chemical synthesis of complex natural products, including many terpenes themselves. As inexpensive and versatile starting materials, such compounds continue to influence modern synthetic chemistry. This review highlights 21st century terpene total syntheses which themselves use small, terpene-derived materials as building blocks. An outlook to the future of research in this area is highlighted as well.

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Using Singlet Oxygen to Synthesize Natural Products and Drugs

Cited by 579 publications

References 372 publications

Singlet oxygen-based electrosensing by molecular photosensitizers

Singlet oxygen-based electrosensing by molecular photosensitizers

Direct 1O2 optical excitation: A tool for redox biology

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

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