Synthesis of 4-methyl-thio-phenyl-propylamine and the evaluation of its interaction with different amine oxidases

Gallardo-Godoy, Alejandra; Hernàndez, Mar; Sanz, Elisenda; Unzeta, Mercedes

doi:10.1016/j.bmc.2003.10.007

Cited by 6 publications

(6 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, its synthesis was reproduced using the protocol described in [ 58 ]. This was also the case for 3-(4-Methylthiophenyl)-propylamine, characterized by the group of Unzeta as a good SSAO substrate [ 51 ], in-house synthetized and elsewhere named as MTPpropylamine. In this comparative study, was also included 1,12-diaminododecane (DIADO), previously reported to be a good substrate for the human SSAO/VAP-1 by Bonaiuto and coworkers [ 49 ], and which was a kindly gift from Maria Luisa Di Paolo (Univ.…”

Section: Methodsmentioning

confidence: 89%

“…Among them was the 1,12-diaminododecane (DIADO), which has been described as a good substrate for SSAO by the group of Di Paolo [ 49 ], but which is also an inhibitor of various polyamine oxidases [ 50 ]. Another poor activator of hydrogen peroxide production in hAT was the 3-(4-Methylthiophenyl)-propylamine (MTPpropylamine), initially characterized by the group of Unzeta [ 51 ] as a SSAO substrate.…”

Section: Resultsmentioning

confidence: 99%

“…A mediation by AR inhibition or activation was therefore discarded. Nevertheless, the present study could not decipher the mechanisms involved in the strong antilipolytic effect of MTPpropylamine, which alongside its SSAO substrate property, also shares MAO-B substrate and MAO-A inhibitor abilities [ 51 ]. In the case of benzylamine and phenylbutylamine, the antilipolytic action was not only a consequence of oxidation by SSAO, since a residual antilipolytic effect was detectable in the presence of semicarbazide.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Effects of Chemical Structures Interacting with Amine Oxidases on Glucose, Lipid and Hydrogen Peroxide Handling by Human Adipocytes

et al. 2022

View full text Add to dashboard Cite

Benzylamine is a natural molecule present in food and edible plants, capable of activating hexose uptake and inhibiting lipolysis in human fat cells. These effects are dependent on its oxidation by amine oxidases present in adipocytes, and on the subsequent hydrogen peroxide production, known to exhibit insulin-like actions. Virtually, other substrates interacting with such hydrogen peroxide-releasing enzymes potentially can modulate lipid accumulation in adipose tissue. Inhibition of such enzymes has also been reported to influence lipid deposition. We have therefore studied in human adipocytes the lipolytic and lipogenic activities of pharmacological entities designed to interact with amine oxidases highly expressed in this cell type: the semicarbazide-sensitive amine oxidase (SSAO also known as PrAO or VAP-1) and the monoamine oxidases (MAO). The results showed that SZV-2016 and SZV-2017 behaved as better substrates than benzylamine, releasing hydrogen peroxide once oxidized, and reproduced or even exceeded its insulin-like metabolic effects in fat cells. Additionally, several novel SSAO inhibitors, such as SZV-2007 and SZV-1398, have been evidenced and shown to inhibit benzylamine metabolic actions. Taken as a whole, our findings reinforce the list of molecules that influence the regulation of triacylglycerol assembly/breakdown, at least in vitro in human adipocytes. The novel compounds deserve deeper investigation of their mechanisms of interaction with SSAO or MAO, and constitute potential candidates for therapeutic use in obesity and diabetes.

show abstract

Section: Methodsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Effects of Chemical Structures Interacting with Amine Oxidases on Glucose, Lipid and Hydrogen Peroxide Handling by Human Adipocytes

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Unzeta and co‐workers studied the effect of rearranging the carbon chain between the phenyl ring and the NH 2 group in 4‐methylthioamphetamine (4‐MTA) to (4‐methylthiophenyl)propylamine on substrate oxidation 61. 4‐MTA is a highly potent and reversible MAO A inhibitor, a less potent inhibitor of SSAO, and a weak inhibitor of MAO B.…”

Section: Introductionmentioning

confidence: 99%

“…The authors proposed that differences in substrate recognition between SSAO and MAO B are because (4‐methylthiophenyl)propylamine probably fits into the cavity of SSAO much better than MAO B. They based their observation on crystallographic data, which indicated that entry of the ligand was restricted and the carbon chain could not fully interact with the FAD cofactor in the active site 61…”

Section: Introductionmentioning

confidence: 99%

Structure–Activity Relationships of SSAO/VAP‐1 Arylalkylamine‐Based Substrates

et al. 2009

View full text Add to dashboard Cite

Semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 (SSAO/VAP-1) substrates show insulin-mimetic effects and are therefore potentially valuable molecules for the treatment of diabetes mellitus. Herein we review several structural and electronic aspects of SSAO arylalkylamine-based substrates. Two main modifications directly affect amine oxidase (AO) activity: 1) variation in ring substitution modulates the biological activity of the arylalkylamine ligand by converting a substrate into a substrate-like inhibitor, and 2) variation in the number of methylene units between the aromatic ring and the ammonium groups of the arylalkylamine substrates dramatically alters the oxidation rate between species. Furthermore, we review relevant information about mammalian SSAO/VAP-1 substrate selectivity and specificity over monoamine oxidases (MAOs).

show abstract

HPLC-UV assays for evaluation of inhibitors of mono and diamine oxidases using novel phenyltetrazolylalkanamine substrates

Mergemeier

Lehr

2018

Analytical Biochemistry

View full text Add to dashboard Cite

Synthesis of 4-methyl-thio-phenyl-propylamine and the evaluation of its interaction with different amine oxidases

Cited by 6 publications

References 27 publications

Effects of Chemical Structures Interacting with Amine Oxidases on Glucose, Lipid and Hydrogen Peroxide Handling by Human Adipocytes

Effects of Chemical Structures Interacting with Amine Oxidases on Glucose, Lipid and Hydrogen Peroxide Handling by Human Adipocytes

Structure–Activity Relationships of SSAO/VAP‐1 Arylalkylamine‐Based Substrates

HPLC-UV assays for evaluation of inhibitors of mono and diamine oxidases using novel phenyltetrazolylalkanamine substrates

Contact Info

Product

Resources

About