Some old 2-(4-(Aryl)- thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-tethanoisoindole-1,3(2H)-dione derivatives: Synthesis, inhibition effects and molecular docking studies on Aldose reductase and α-Glycosidase

Parham Taslımı; Yeliz Demir; Hatice Esra Duran; Ümit Muhammet Koçyiğit; Burak Tüzün; Osman Nuri Aslan; Mustafa Ceylan; İlhami Gülçin

doi:10.17776/csj.897800

TR EN

Abstract

Basit kromatik teknikler kullanılarak Aldoz redüktaz AR, koyun karaciğerinden elde edildi. Ek olarak, Saccharomyces cerevisiae'den elde edilen a-glikosidaz enzim olarak kullanıldı. Bileşikler ve enzimler arasındaki etkileşimler belirlendi. Moleküllerin biyolojik aktivite değerlerini enzimlerle karşılaştırmak için kullanılan moleküler yerleştirme yöntemi. Bu çalışmada, sentetik izoindol ikame tiyazol türevlerinin (3a-f) aldoz redüktaz ve α-glikozidaz enzimleri üzerindeki inhibisyon etkisi incelenmiştir. Tiyazol serisinde, bileşik 3b (Ki: 9.70 ± 4.72 M), AR'ye karşı maksimum bir inhibitör etki gösterirken, bileşik 3f (Ki: 44.40 ± 17.18 M), AR'ye karşı en düşük bir inhibitör etki gösterdi. Α-glikozidaza karşı Ki değerleri 24.54 ± 6.92–44.25 ± 10.34 M aralığında olan güçlü inhibisyon profilleri araştırıldı. Teorik sonuçlar deneysel sonuçlarla uyumlu bulundu. Antidiyabetik maddeler olarak hareket eden bu bileşikler, AR ve a-glikosidaz enzimlerinin seçici inhibitörü olma potansiyeline sahiptir. Çalışılan moleküllerin Aldoz redüktaz ve α-glikosidaz enzimlerine karşı biyolojik aktiviteleri moleküler yerleştirme yöntemi ile karşılaştırılacaktır. Moleküllerin ADME analizi (Absorpsiyon, dağılım, metabolizma, atılım ve toksisite) yapılacaktır.

Keywords

Asimetrik sentez, kiral organik katalizörler, enzim inhibisyonu, aldoz redüktaz, α-Glikosidaz, moleküler yerleştirme

Project Number

RGD-020

Some old 2-(4-(Aryl)- thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-tethanoisoindole-1,3(2H)-dione derivatives: Synthesis, inhibition effects and molecular docking studies on Aldose reductase and α-Glycosidase

Abstract

Utilizing the simple chromatic techniques, Aldose reductase (AR) was derived from sheep liver. In addition, α-glycosidase from Saccharomyces cerevisiae was used as the enzyme. It was determined the interactions between compounds and the enzymes. Molecular docking method used to compare biological activity values of molecules against enzymes.
In the current study, the inhibition effect of synthetic isoindol-substitute thiazole derivatives (3a-f) on AR, and α-glycosidase enzymes was studied. In the thiazole series, compound 3b (Ki: 9.70±4.72 M) showed a maximum inhibitory impact towards AR while compound 3f (Ki: 44.40±17.18 M) showed a lowest inhibitory impact towards AR. It was investigated potent inhibition profiles with Ki values in the range of 24.54±6.92–44.25±10.34 M against α-glycosidase. Theoretical results were found consistent with experimental results.
Acting as antidiabetic agents, these compounds have the potential to be the selective inhibitor of α-glycosidase and AR enzymes. The biological activities of the studied molecules against AR and α-glycosidase enzymes will be compared with molecular docking method. ADME analysis of the molecules will be done.

Keywords

Asymmetric synthesis, Enzyme inhibition, Aldose reductase, α-Glycosidase, Molecular docking

Supporting Institution

Sivas Cumhuriyet University

Project Number

RGD-020

Thanks

This work is supported by the Scientific Research Project Fund of Sivas Cumhuriyet University under the project number RGD-020. This research was made possible by TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).

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Details

Primary Language

English

Subjects

Structural Biology

Journal Section

Research Article

Authors

Parham Taslımı
0000-0002-3171-0633
Türkiye

Yeliz Demir
Türkiye

Hatice Esra Duran
Türkiye

Ümit Muhammet Koçyiğit
Türkiye

Burak Tüzün ^*
0000-0002-0420-2043
Türkiye

Osman Nuri Aslan
0000-0002-1330-6194
Türkiye

Mustafa Ceylan
Türkiye

İlhami Gülçin
0000-0001-5993-1668
Türkiye

Publication Date

September 24, 2021

Submission Date

March 16, 2021

Acceptance Date

September 20, 2021

Published in Issue

Year 2021 Volume: 42 Number: 3

DOI

https://doi.org/10.17776/csj.897800

IZ

https://izlik.org/JA57NL55JK

APA

Taslımı, P., Demir, Y., Duran, H. E., Koçyiğit, Ü. M., Tüzün, B., Aslan, O. N., Ceylan, M., & Gülçin, İ. (2021). Some old 2-(4-(Aryl)- thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-tethanoisoindole-1,3(2H)-dione derivatives: Synthesis, inhibition effects and molecular docking studies on Aldose reductase and α-Glycosidase. Cumhuriyet Science Journal, 42(3), 553-564. https://doi.org/10.17776/csj.897800

AMA

1.Taslımı P, Demir Y, Duran HE, et al. Some old 2-(4-(Aryl)- thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-tethanoisoindole-1,3(2H)-dione derivatives: Synthesis, inhibition effects and molecular docking studies on Aldose reductase and α-Glycosidase. CSJ. 2021;42(3):553-564. doi:10.17776/csj.897800

Chicago

Taslımı, Parham, Yeliz Demir, Hatice Esra Duran, et al. 2021. “Some Old 2-(4-(Aryl)- Thiazole-2-Yl)-3a,4,7,7a-Tetrahydro-1H-4,7-Tethanoisoindole-1,3(2H)-Dione Derivatives: Synthesis, Inhibition Effects and Molecular Docking Studies on Aldose Reductase and α-Glycosidase”. Cumhuriyet Science Journal 42 (3): 553-64. https://doi.org/10.17776/csj.897800.

EndNote

Taslımı P, Demir Y, Duran HE, Koçyiğit ÜM, Tüzün B, Aslan ON, Ceylan M, Gülçin İ (September 1, 2021) Some old 2-(4-(Aryl)- thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-tethanoisoindole-1,3(2H)-dione derivatives: Synthesis, inhibition effects and molecular docking studies on Aldose reductase and α-Glycosidase. Cumhuriyet Science Journal 42 3 553–564.

IEEE

[1]P. Taslımı et al., “Some old 2-(4-(Aryl)- thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-tethanoisoindole-1,3(2H)-dione derivatives: Synthesis, inhibition effects and molecular docking studies on Aldose reductase and α-Glycosidase”, CSJ, vol. 42, no. 3, pp. 553–564, Sept. 2021, doi: 10.17776/csj.897800.

ISNAD

Taslımı, Parham - Demir, Yeliz - Duran, Hatice Esra - Koçyiğit, Ümit Muhammet - Tüzün, Burak - Aslan, Osman Nuri - Ceylan, Mustafa - Gülçin, İlhami. “Some Old 2-(4-(Aryl)- Thiazole-2-Yl)-3a,4,7,7a-Tetrahydro-1H-4,7-Tethanoisoindole-1,3(2H)-Dione Derivatives: Synthesis, Inhibition Effects and Molecular Docking Studies on Aldose Reductase and α-Glycosidase”. Cumhuriyet Science Journal 42/3 (September 1, 2021): 553-564. https://doi.org/10.17776/csj.897800.

JAMA

1.Taslımı P, Demir Y, Duran HE, Koçyiğit ÜM, Tüzün B, Aslan ON, Ceylan M, Gülçin İ. Some old 2-(4-(Aryl)- thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-tethanoisoindole-1,3(2H)-dione derivatives: Synthesis, inhibition effects and molecular docking studies on Aldose reductase and α-Glycosidase. CSJ. 2021;42:553–564.

MLA

Taslımı, Parham, et al. “Some Old 2-(4-(Aryl)- Thiazole-2-Yl)-3a,4,7,7a-Tetrahydro-1H-4,7-Tethanoisoindole-1,3(2H)-Dione Derivatives: Synthesis, Inhibition Effects and Molecular Docking Studies on Aldose Reductase and α-Glycosidase”. Cumhuriyet Science Journal, vol. 42, no. 3, Sept. 2021, pp. 553-64, doi:10.17776/csj.897800.

Vancouver

1.Parham Taslımı, Yeliz Demir, Hatice Esra Duran, Ümit Muhammet Koçyiğit, Burak Tüzün, Osman Nuri Aslan, Mustafa Ceylan, İlhami Gülçin. Some old 2-(4-(Aryl)- thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-tethanoisoindole-1,3(2H)-dione derivatives: Synthesis, inhibition effects and molecular docking studies on Aldose reductase and α-Glycosidase. CSJ. 2021 Sep. 1;42(3):553-64. doi:10.17776/csj.897800

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