Hydroxamic Acid as a Potent Metal-Binding Group for Inhibiting Tyrosinase

Choi, Joonhyeok; Neupane, Trilok; Baral, Rishiram; Jee, Jun-Goo

doi:10.3390/antiox11020280

Cited by 8 publications

(2 citation statements)

References 69 publications

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“…There are several phase trials for three drugs (dasatinib, navitoclax, vorinostat) listed by Adamic-Adar-2 ( Table 7 ), four drugs (vorinostat, navitoclax, dinaciclib, MK-1775) listed by PageRank-2 ( Table 8 ) and all the drugs (paclitaxel, imexon, sulforaphane, vorinostat) predicted by neighborhood scoring ( Table 9 ) for the treatment of melanoma. Some of these predictions suggested by the new DR method have been used in several studies and clinical trials in the search for new treatment alternatives for melanoma(these include: vorinostat: NCT00121225 ( Haas et al, 2014 ; Choi et al, 2022 ; Wang et al, 2018 ; Nihal, Roelke & Wood, 2010 ); MK-1775: ( Margue et al, 2019 ); imexon: NCT00327600 ( Weber et al, 2010 ); paclitaxel: NCT01107665 ( Fruehauf et al, 2018 ).…”

Section: Resultsmentioning

confidence: 99%

Network neighborhood operates as a drug repositioning method for cancer treatment

Cüvitoğlu

Işık

2023

PeerJ

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Computational drug repositioning approaches are important, as they cost less compared to the traditional drug development processes. This study proposes a novel network-based drug repositioning approach, which computes similarities between disease-causing genes and drug-affected genes in a network topology to suggest candidate drugs with highest similarity scores. This new method aims to identify better treatment options by integrating systems biology approaches. It uses a protein-protein interaction network that is the main topology to compute a similarity score between candidate drugs and disease-causing genes. The disease-causing genes were mapped on this network structure. Transcriptome profiles of drug candidates were taken from the LINCS project and mapped individually on the network structure. The similarity of these two networks was calculated by different network neighborhood metrics, including Adamic-Adar, PageRank and neighborhood scoring. The proposed approach identifies the best candidates by choosing the drugs with significant similarity scores. The method was experimented on melanoma, colorectal, and prostate cancers. Several candidate drugs were predicted by applying AUC values of 0.6 or higher. Some of the predictions were approved by clinical phase trials or other in-vivo studies found in literature. The proposed drug repositioning approach would suggest better treatment options with integration of functional information between genes and transcriptome level effects of drug perturbations and diseases.

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Section: Resultsmentioning

confidence: 99%

Network neighborhood operates as a drug repositioning method for cancer treatment

Cüvitoğlu

Işık

2023

PeerJ

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“…Inhibition of tyrosinase has major roles and applications, e.g., in biomedicine, to contrast skin pigmentation disorders like melasma [ 14 , 15 , 16 , 17 ] and in food safety, to prevent enzymatic food oxidative spoilage on storage [ 16 , 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Potent Antioxidant and Anti-Tyrosinase Activity of Butein and Homobutein Probed by Molecular Kinetic and Mechanistic Studies

Pan,

Giovanardi,

Sagynova

et al. 2023

Antioxidants

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Butein (BU) and homobutein (HB) are bioactive polyhydroxylated chalcones widespread in dietary plants, whose antioxidant properties require mechanistic definition. They were investigated by inhibited autoxidation kinetic studies of methyl linoleate in Triton™ X-100 micelles at pH 7.4, 37 °C. Butein had kinh = (3.0 ± 0.9) × 104 M−1s−1 showing a chain-breaking mechanism with higher antioxidant activity than reference α-tocopherol (kinh = (2.2 ± 0.6) × 104 M−1s−1), particularly concerning the stoichiometry or peroxyl radical trapping n = 3.7 ± 1.1 vs. 2.0 for tocopherol. Homobutein had kinh = (2.8 ± 0.9) × 103 M−1s−1, pairing the relative BDEOH measured by radical equilibration EPR as 78.4 ± 0.2 kcal/mol for BU and estimated as 82.6 kcal/mol for HB. The inhibition of mushroom tyrosinase (mTYR) by HB and BU was also investigated. BU gives a reversible uncompetitive inhibition of monophenolase reaction with KI′ = 9.95 ± 2.69 µM and mixed-type diphenolase inhibition with KI = 3.30 ± 0.75 µM and KI′ = 18.75 ± 5.15 µM, while HB was nearly competitive toward both mono- and diphenolase with respective KI of 2.76 ± 0.70 µM and 2.50 ± 1.56 µM. IC50 values (monophenolase/diphenolase at 1 mM substrate) were 10.88 ± 2.19 µM/15.20 ± 1.25 µM, 14.78 ± 1.05 µM/12.36 ± 2.00 µM, and 33.14 ± 5.03 µM/18.27 ± 3.42 µM, respectively, for BU, HB, and reference kojic acid. Molecular docking studies confirmed the mechanism. Results indicate very potent antioxidant activity for BU and potent anti-tyrosinase activity for both chalcones, which is discussed in relation to bioactivity toward protection from skin disorders and food oxidative spoilage.

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