In Silico Investigation of Some Glucose-Aspirin as COX Inhibitor

Abstract

Monosaccharide derived glucose-aspirin (GA) can be prepared by conjugation between glucose and aspirin (ASA). The GA is reported to show higher analgesic and anti-inflammatory properties than ASA itself. In this perspective, six GAs which are composed of β-D-glucopyranose, ASA and acetyl groups are considered for the present investigations. The glucose unit in these GAs possesses regular chair conformation with slightly lower dipole moments. Molecular orbitals indicated a higher HOMO-LUMO gap of the molecules. All GAs showed more prone to electrophilic interactions than aspirin. Overall, glucose-aspirin esters are found to have better non-steroidal anti-inflammatory properties than the original aspirin. These GAs are better inhibitors of cyclooxygenase-2 (COX2, 5f19) compared to cyclooxygenase-1 (COX1, 6y3c) indicating that these GAs are potential drug candidates for COX2 related inflammation. Additionally, aspirinyl group at C-6 or C-3 position of the glucopyranose unit is found more suitable for anti-inflammatory activities as compared to C-4 position.

Keywords

• Anti-inflammatory drug
• Cyclooxygenase (COX)
• Aspirin
• Molecular docking,
• Sugar esters