Spectrophotofluorometric Studies of Some Aromatic Aldehydes and Their Acetals.

Regioselective reductive openings of mixed phenolic-benzylic acetals, using BH3.NMe3-AlCl3, was investigated, and a mechanism where the outcome is directed by the electrostatic potential of the two oxygen atoms is presented. The regioselective acetal opening was used in the synthesis of a fluorescently labeled analogue to antiproliferative xylosides. The fluorescently labeled xyloside was tested for uptake, antiproliferative activity, and glycosaminoglycan priming in different cell lines. The xyloside was taken up by all cell lines but did not initiate glycosaminoglycan biosynthesis.

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“…Absorbance and Fluorescence. Compound 2 (1.18 mg) was dissolved on DMSO (0.100 mL), and 0.010 mL of this solution was added to 2.00 mL MeCN …”

Section: Methodsmentioning

confidence: 99%

Regioselective Reductive Openings of Acetals; Mechanistic Details and Synthesis of Fluorescently Labeled Compounds

Johnsson

Mani²,

Cheng³

et al. 2006

J. Org. Chem.

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“…With few exceptions, aromatic aldehydes are known to be either weakly fluorescent or non-fluorescent in aqueous media, 13 whereas the corresponding carboxylates are in many cases strongly fluorescent. 5,8 Spectral properties of the aromatic aldehydes of naphthalenes, phenanthrenes and anthracenes and their oxidation products, investigated in this work, are summarized in Table 4.…”

Section: Fluorescence Properties Of Aromatic Aldehydes and Correspond...mentioning

confidence: 99%

“…The fluorescence of aromatic aldehydes is known to be strongly solvent dependent, 13 virtually disappearing in nonhydroxylic media. This is of importance in assays of proteinrich samples, where non-polar aldehydes tend to associate with proteins, but in most cases this association did not affect the fluorescence background.…”

Section: Fluorescence Properties Of Aromatic Aldehydes and Correspond...mentioning

confidence: 99%

Aromatic aldehydes as fluorogenic indicators for human aldehyde dehydrogenases and oxidases: substrate and isozyme specificity

Wroczyński

Wierzchowski²

2000

Analyst

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Substrate properties of a number of potentially fluorogenic aromatic aldehydes of naphthalenes, phenanthrenes and anthracenes and of some coumarin aldehydes towards various forms of the human and rat aldehyde oxidase and dehydrogenase were examined using absorption and emission spectroscopy. It was demonstrated that recombinant human class 1 aldehyde dehydrogenase (ALDH-1) readily oxidizes naphthalene (except for those ortho-substituted), phenanthrene and coumarin aldehydes, whereas the class 3 enzyme (ALDH-3) from human saliva is active only towards 2-naphthaldehyde derivatives. The observed reaction rates in both cases are comparable to those of the best known substrates, and the Km values are typically in the sub-micromolar range. Aldehyde oxidases (AlOx), which are present in mammalian liver, reveal much broader substrate specificity, oxidizing nearly all the compounds examined, including those of the anthracene series, with maximum activity in the micromolar range of substrate concentration. In rat liver, nearly all AlOx activity was located in the cytosolic fraction.

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“…) can be oxidized to the bimolecdar base pseudomorphine (11) by reaction with potassium ferricyanide in aqueous solution (1). The structure of this derivative was shown to be 2,2'-bimorphine on the basis of spectral and chemical studies (2).…”

Section: Morphine (Imentioning

confidence: 99%

Fluorescence Properties of Pseudomorphine and Congeners: Structure–Activity Relationships

Darwin

Cone

1980

Journal of Pharmaceutical Sciences

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Spectrophotofluorometric Studies of Some Aromatic Aldehydes and Their Acetals.

Cited by 24 publications

References 3 publications

Regioselective Reductive Openings of Acetals; Mechanistic Details and Synthesis of Fluorescently Labeled Compounds

Regioselective Reductive Openings of Acetals; Mechanistic Details and Synthesis of Fluorescently Labeled Compounds

Aromatic aldehydes as fluorogenic indicators for human aldehyde dehydrogenases and oxidases: substrate and isozyme specificity

Fluorescence Properties of Pseudomorphine and Congeners: Structure–Activity Relationships

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