Green fluorescent protein chromophore derivatives as a new class of aldose reductase inhibitors

Saito, Ryota; Hoshi, Maiko; Ishikawa, Chikako; Komatsu, Toshiya

doi:10.1016/j.ejmech.2016.10.016

Cited by 13 publications

(15 citation statements)

References 62 publications

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“…A possible criticism is that the GOLD analysis should consider "flexible" dockings using the software's Side Chain Flexibility function, but we previously demonstrated that the better method for predicting an appropriate protein structure that accounts for experimental results is assessment of the docking score-pIC 50 correlation. 38) Docking positions for 1a-c and 2a-c with 4IGS demonstrated that 2a, which exhibited the lowest inhibitory activity of the examined botryllazine A derivatives, was predicted to assume a different position relative to the other derivatives (Fig. 4).…”

Section: Resultsmentioning

confidence: 99%

“…33,34) The ChemPLP scoring function 35) was used to predict docking poses for each of the six specificity pocket states, and these were then rescored using the Astex Statistical Potential (ASP) 36) scoring function, validated for protein-ligand specific hydrogen bond scoring. 37) The combination of these scores was used to determine the optimal pose of each ligand (i.e., for which both scoring functions yielded positive, high scores) ( Table 4).…”

Section: Resultsmentioning

confidence: 99%

“…According to our previous pharmacophore modeling analysis of 4IGS, a lipophilic interaction with Trp219 is an important feature conferring additional inhibitory activity. 38) Indeed, the quinolin-3-yl residue of compound 1c, the most potent among 1a-c, forms a π-π interaction with the indole ring of Trp219. The naphthalen-2-yl group of 1b also occurs in proximity to Trp219, and the same trend is observed for 2b and 2c.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Aldose Reductase Inhibitory Activity of Botryllazine A Derivatives

Saito

Ishibashi

Noumi

et al. 2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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Aldose reductase (AR) is associated with the onset of diabetic complications. Botryllazine A and its analogues were synthesized and evaluated for human AR inhibitory activity. Analogues possessing aromatic bicyclic systems at the C5 position of the central pyrazine ring exhibited superior AR inhibiting activity relative to the parent botryllazine A. In addition, the benzoyl groups at positions C2 and C3 of the pyrazine ring were dispensable for this improved inhibitory activity. Conversely, a benzoyl group-containing phenolic hydroxyl groups-at either position C2 or C3 of the pyrazine ring was essential for attainment of high inhibitory activity approaching that of sorbinil (a highly effective AR inhibitor).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis and Aldose Reductase Inhibitory Activity of Botryllazine A Derivatives

Saito

Ishibashi

Noumi

et al. 2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The oxazolones shown in Figure were prepared following methods reported in the bibliography . A wide array of substrates was synthesized to cover the maximum number of possibilities, and the orthopalladation of all ligands was attempted.…”

Section: Resultsmentioning

confidence: 99%

“…HRMS and ESI (ESI+) mass spectra were recorded using an MicroToF Q, API‐Q‐ToF ESI with a mass range from 20 to 3000 m/z and mass resolution of 15000 (FWHM). The oxazolones containing the phenyl ring in the 2‐position ( 1a – 1i ), those containing the methyl group in the 2‐position ( 1j – 1o ), and the oxidation reagent PhICl 2 were prepared by reported procedures. Compounds 2l , 2n and 2o were prepared as described previously .…”

Section: Methodsmentioning

confidence: 99%

Functionalized 1,3‐Diaminotruxillic Acids by Pd‐Mediated C–H Activation and [2+2]‐Photocycloaddition of 5(4H)‐Oxazolones

et al. 2019

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The orthopalladation of (Z)-4-arylidene-5(4H)-oxazolones (1a-1o), with electron-withdrawing substituents (Cl, F, CF 3 ) in the 4-arylidene ring has been carried out by C-H bond activation. The process is regioselective and only the ortho C-H bond of the 4-arylidene ring is activated. The orthopalladated complexes (2a-2o) have different structures (mono-, di-and trinuclear), although the dinuclear open-book scaffold, in which the C=C bonds of the arylidene group are in a face-to-face tran- [a] Scheme 4. Different reaction pathways observed in the oxidation of 3d: synthesis of functionalized halogenated cyclobutanes 5d and 6d.

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Strategies in synthetic design and structure–activity relationship studies of novel heterocyclic scaffolds as aldose reductase‐2 inhibitors

Yahya

Haider

Pathak

et al. 2022

Archiv der Pharmazie

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Heterocyclic scaffolds of natural as well as synthetic origin provide almost all categories of drugs exhibiting a wide range of pharmacological activities, such as antibiotics, antidiabetic and anticancer agents, and so on. Under normal homeostasis, aldose reductase 2 (ALR2) regulates vital metabolic functions; however, in pathological conditions like diabetes, ALR2 is unable to function and leads to secondary diabetic complications. ALR2 inhibitors are a novel target for the treatment of retinopathy (cataract) influenced by diabetes. Epalrestat (stat), an ALR2 inhibitor, is the only drug candidate that was approved in the last four decades; the other drugs from the stat class were retracted after clinical trial studies due to untoward iatrogenic effects. The present study summarizes the recent development (2014 and onwards) of this pharmacologically active ALR2 heterocyclic scaffold and illustrates the rationale behind the design, structure-activity relationships, and biological studies performed on these molecules. The aim of the current review is to pave a straight path for medicinal chemists and chemical biologists, and, in general, to the drug discovery scientists to facilitate the synthesis and development of novel ALR2 inhibitors that may serve as lead molecules for the treatment of diseases related to the ALR2 enzyme.diabetic-related complications (cataract), novel heterocyclic scaffolds, structure-activity relationship studies, synthetic aldose reductase 2 inhibitors | INTRODUCTIONDiabetes mellitus (DM) is an autoimmune metabolic disorder mainly characterized by hyperglycemia which occurs due to impairment in normal blood glucose homeostasis. In DM, there is either no secretion of insulin by the islet of pancreatic β cells or diminished response to glucose by secreted insulin in the body. [1] Diabetes is of two types that is, insulin-dependent diabetes mellitus and insulin-independent diabetes mellitus also termed type 1 and type 2 DM, respectively. Pathophysiological conditions that induce DM include autoimmune imbalance, hormonal as well as the sedentary lifestyle of an individual, additionally urbanization, and exposure to harmful chemicals are other causes of disease. [2] Blood glucose homeostasis is regulated by several hormones. However, insulin and glucagon predominantly performed aforesaid functions. [3] Insulin reduces excess blood sugar levels either by inhibiting glucose synthesis by the liver or by increasing peripheral glucose utilization through the liver, skeletal muscles, and adipose tissues.

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Green fluorescent protein chromophore derivatives as a new class of aldose reductase inhibitors

Cited by 13 publications

References 62 publications

Synthesis and Aldose Reductase Inhibitory Activity of Botryllazine A Derivatives

Synthesis and Aldose Reductase Inhibitory Activity of Botryllazine A Derivatives

Functionalized 1,3‐Diaminotruxillic Acids by Pd‐Mediated C–H Activation and [2+2]‐Photocycloaddition of 5(4H)‐Oxazolones

Strategies in synthetic design and structure–activity relationship studies of novel heterocyclic scaffolds as aldose reductase‐2 inhibitors

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