Enzymatic oxidation of diphenylmethylphosphine and 3-dimethylaminopropyldiphenylphosphine by rat liver microsomes

Wiley, Robert A.; Sternson, Larry A.; Sasame, Henry A.; Gillette, James R.

doi:10.1016/0006-2952(72)90088-3

Cited by 21 publications

(8 citation statements)

References 8 publications

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“…Moreover, pathways of metabolic clearance will be important to characterize in the design of optimal bioorthogonal reagents. Literature precedents suggest that phosphines (12) and terminal alkynes (38) can be metabolized in the liver by cytochrome P450 enzymes. Internal alkynes also may be oxidized by P450 enzymes, though their routes of metabolism are less well characterized (39).…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Copper-free click chemistry in living animals

Chang

Prescher²,

Sletten³

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

581

506

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Chemical reactions that enable selective biomolecule labeling in living organisms offer a means to probe biological processes in vivo. Very few reactions possess the requisite bioorthogonality, and, among these, only the Staudinger ligation between azides and triarylphosphines has been employed for direct covalent modification of biomolecules with probes in the mouse, an important model organism for studies of human disease. Here we explore an alternative bioorthogonal reaction, the 1,3-dipolar cycloaddition of azides and cyclooctynes, also known as “Cu-free click chemistry,” for labeling biomolecules in live mice. Mice were administered peracetylated N-azidoacetylmannosamine (Ac4ManNAz) to metabolically label cell-surface sialic acids with azides. After subsequent injection with cyclooctyne reagents, glycoconjugate labeling was observed on isolated splenocytes and in a variety of tissues including the intestines, heart, and liver, with no apparent toxicity. The cyclooctynes tested displayed various labeling efficiencies that likely reflect the combined influence of intrinsic reactivity and bioavailability. These studies establish Cu-free click chemistry as a bioorthogonal reaction that can be executed in the physiologically relevant context of a mouse.

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Section: Resultsmentioning

confidence: 99%

“…They are susceptible to oxidation by molecular oxygen, for example, which limits their shelf-life and may also provide a pathway for rapid liver metabolism (12). Moreover, the Staudinger ligation has a relatively sluggish reaction rate, compromising its ability to monitor rapid biological processes in vivo (9).…”

mentioning

confidence: 99%

Copper-free click chemistry in living animals

Chang

Prescher²,

Sletten³

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

581

506

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show abstract

“…42 Several examples of sulfur oxidation by cytochrome P-450 are known,1 and oxygenation of trivalent phosphorus has also been reported. 43 While the literature attributes many N-oxygenations to cytochrome P-450, the only cases where strong evidence exists for the role of this enzyme involve the substrates 2-(acetylamino)fluorene,44 2-aminofluorene,4B azoprocarbazine,20 phentermine,46 and certain tryptophan pyrolysis products. 47 A number of chemical studies have implicated hypervalent states of halogens in oxidation-dependent solvolysis and elimination reactions.…”

Section: Heteroatom Oxygenationmentioning

confidence: 99%

Chemical mechanisms of catalysis by cytochromes P-450: a unified view

Guengerich¹,

Macdonald²

1984

Acc. Chem. Res.

501

171

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“…While bio-orthogonally crosslinked gels elicit minimal inflammation in vivo, [28, 29, 52, 53, 62] systemic effects of the degradation products of such materials should also be investigated. Previous reports indicate that phosphines used in Staudinger ligation [188] and alkynes used in 1,3-dipolar cycloadditions [189] may be metabolized by cytochrome P450 enzymes. The triazoles formed from 1,3-dipolar cycloadditions may also interact with cytochrome P450, as triazole derivatives have been reported as potential P450 inhibitors.…”

Section: Discussionmentioning

confidence: 99%

Bioorthogonal Strategies for Engineering Extracellular Matrices

Madl

Heilshorn

2018

Adv Funct Materials

100

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Hydrogels are commonly used as engineered extracellular matrix (ECM) mimics in applications ranging from tissue engineering to in vitro disease models. Ideal mechanisms used to crosslink ECM-mimicking hydrogels do not interfere with the biology of the system. However, most common hydrogel crosslinking chemistries exhibit some form of cross-reactivity. The field of bio-orthogonal chemistry has arisen to address the need for highly specific and robust reactions in biological contexts. Accordingly, bio-orthogonal crosslinking strategies have been incorporated into hydrogel design, allowing for gentle and efficient encapsulation of cells in various hydrogel materials. Furthermore, the selective nature of bio-orthogonal chemistries can permit dynamic modification of hydrogel materials in the presence of live cells and other biomolecules to alter matrix mechanical properties and biochemistry on demand. In this review, we provide an overview of bio-orthogonal strategies used to prepare cell-encapsulating hydrogels and highlight the potential applications of bio-orthogonal chemistries in the design of dynamic engineered ECMs.

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Enzymatic oxidation of diphenylmethylphosphine and 3-dimethylaminopropyldiphenylphosphine by rat liver microsomes

Cited by 21 publications

References 8 publications

Copper-free click chemistry in living animals

Copper-free click chemistry in living animals

Chemical mechanisms of catalysis by cytochromes P-450: a unified view

Bioorthogonal Strategies for Engineering Extracellular Matrices

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