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Amy Oo. In silico and in vitro studies on inclusion complexation of anthraquinone derivatives with beta-cyclodextrin derivatives. Master's Degree(Biochemistry and Molecular Biology). Chulalongkorn University. Office of Academic Resources. : Chulalongkorn University, 2021.
In silico and in vitro studies on inclusion complexation of anthraquinone derivatives with beta-cyclodextrin derivatives
การศึกษาเชิงคอมพิวเตอร์และในหลอดทดลองของการเกิดสารประกอบเชิงซ้อนอินคลูชันของอนุพันธ์แอนทราควิโนนกับอนุพันธ์บีตาไซโคลเดกซ์ทริน
Name: Amy Oo
Abstract:
In this study, we investigated the cytotoxicity of 6 anthraquinones (ventilanone K, emodin, chrysophanol, aurantio-obtusin, 1-O-methyl-2-methyoxychrysophanol, and questin) toward A549 lung cancer cells and emodin (ED) exerted the most potent cytotoxicity with IC50 value of 34.27 ± 1.27 µM. The anti-cancer activity of ED has been well reported but its usage in practical applications has been restricted due to its poor solubility. To address this issue, we performed inclusion complexation of ED with βCD, hydroxypropyl-β-cyclodextrin (HPβCD), 2,6-di-O-methyl-β-cyclodextrin (DMβCD), and sulfobutylether-β-cyclodextrin (SBEβCD) theoretically using molecular dynamics simulations and experimentally using phase solubility study and cytotoxicity screening toward cholangiocarcinoma cell lines (KKU-213A and KKU-213B). The 500-ns MD simulations revealed that ED is able to form inclusion complexes with βCDs in two possible orientations: resorcinol ring insertion (R-form) and m-cresol ring insertion (C-form) mainly driven by van der Waals interaction. The ED in complex with SBEβCD (degree of substitution, DS-7) inclusion complex showed the highest number of atom contacts and the lowest solvent accessibility, in line with the ΔGbind results ranked in the order of ED/SBEβCD (-6.18 ± 1.15 kcal/mol) > ED/HPβCD (-3.81 ± 0.65 kcal/mol) > ED/βCD (0.11 ± 0.51 kcal/mol). Consequently, the inclusion complexes between ED and βCDs (βCD, HPβCD, SBEβCD and DMβCD), were experimentally studied. The phase solubility testing provides AL-type diagrams indicating the 1:1 stoichiometry between ED and βCDs. Altogether, the stability constants of studied complexes can be ranked in the order of ED/DMβCD (1500 M-1) > ED/HPβCD (1000 M-1) > ED/βCD (980 M-1) > SBEβCD with low degree of substitution (880 M-1) at 25оC and the highest water solubility was observed in ED/DMβCD complex with 113.86 ug/mL. Moreover, ED/DMβCD complex shows the most promising inhibition with the IC50 values of 52.78 ± 1.57 and 47.00± 0.58 µM toward KKU-213A and KKU-213B, respectively.
Chulalongkorn University. Office of Academic Resources
Address:
BANGKOK
Email:
cuir@car.chula.ac.th
Name: Thanyada Rungrotmongkol
Role:
advisor
Name: Panupong Mahalapbutr
Role:
co-advisor
Created:
2021
Modified:
2024-01-03
Issued:
2024-01-03
วิทยานิพนธ์/Thesis
application/pdf
eng
DegreeName: Master of Science
Level: Master's Degree
Descipline: Biochemistry and Molecular Biology
Grantor: Chulalongkorn University
©copyrights Chulalongkorn University
RightsAccess:
ใช้เวลา
0.036882 วินาที
Amy Oo
| Title | Contributor | Type |
|---|---|---|
| In silico and in vitro studies on inclusion complexation of anthraquinone derivatives with beta-cyclodextrin derivatives
จุฬาลงกรณ์มหาวิทยาลัย Amy Oo | Thanyada Rungrotmongkol Panupong Mahalapbutr | วิทยานิพนธ์/Thesis |
Thanyada Rungrotmongkol
Panupong Mahalapbutr
| Title | Creator | Type and Date Create |
|---|---|---|
| In silico and in vitro studies on inclusion complexation of anthraquinone derivatives with beta-cyclodextrin derivatives
จุฬาลงกรณ์มหาวิทยาลัย Thanyada Rungrotmongkol;Panupong Mahalapbutr | Amy Oo | วิทยานิพนธ์/Thesis |