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1 Volume 119 No , ISSN: (on-line version) url: ijpam.eu MOLECULAR MODELING STUDIES OF 2,6-BIS(4-CHLOROPHENYL)-1-(2,2- DICHLOROACETYL)-3,3-DIMETHYLPIPERIDIN-4-ONE AGAINST HUMAN DIPEPTIDYL PEPTIDASE IV AS PROTEIN TARGET Dr. P.Sugumar 1, Dr.R.Krithiga 2 Associate Professor 1 2 Department of Physics, BIST, BIHER, Bharath University, Chennai. sugumar.phy@bharathuniv.ac.in Abstract: Piperidines are the important group of heterocyclic compounds in the field of medicinal chemistry due to their biological activities like anticancer, analgesic, anti-inflammatory, antimicrobial activity, etc. The design and synthesis of conformationally anchored molecules of piperidines is an important approach towards improving potency and selectivity. In view of this biological importance, crystal structure determination and molecular docking studies for the two piperidine derivatives has been carried out. The single crystal X- ray diffraction data for all the compounds were collected using BRUKER AXS KAPPA APEX-II area-detector diffractometer and the docking study was carried using GLIDE program of Schrödinger package, Induced Fit Docking algorithms were used for our docking studies. The structure of the compounds was solved using direct method and refined using full matrix least-squares procedure. Molecular docking studies show that these piperidine derivatives bind well in the active site pocket of the target protein and interact with the active site of the amino acid residues. X-ray Crystallography: Data Collection & Refinement Data collection was colleted using APEX2, the cell refinement and data reduction was used by SAINT (Bruker, 2008)[1-5]. The structure was solved and refined by using SHELXS97 (Sheldrick, 2008). The molecular graphics works were carried out using ORTEP-3 (Farrugia, 1977
2 1997) and the software used to prepare material for publication SHELXL97 and PLATON (Spek, 2009)[6-12]. Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances[13-19], angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement Details: Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F2 > σ(f2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F[20-25], and R- factors based on ALL data will be even larger. H atoms were positioned geometrically (C H= Å) and allowed to ride on their parent atoms,with Uiso(H) = 1.5 Ueq (C) for methyl H 1.2 Ueq (C) for other H atoms. Molecular Docking Introduction about ligand: Piperidines are the important group of heterocyclic compounds in the field of medicinal chemistry due to their biological activities like anticancer[26-29], analgesic, anti-inflammatory, antimicrobial activity, etc. The design and synthesis of conformationally anchored molecules of piperidines is an important approach towards improving potency and selectivity. In view of this 1978
3 biological importance, crystal structure determination and molecular docking studies for the two piperidine derivatives has been carried out. Introduction about protein: Type 2 diabetes is a rapidly growing disease that affects millions of people worldwide. Dipeptidyl peptidase IV (DPP4) inhibitors are emerging as a new class of therapeutic agents for the treatment of type 2 diabetes[30-35]. DPP-IV is a member of a family of serine peptidases and is a key regulator of incretin hormones. The efficacy of DPP-IV inhibitors is mediated primarily via stabilization of the incretin hormones Glucagon-like Peptide 1 (GLP-1) and glucosedependent insulinotropic polypeptide, which have clearly established roles in glucose-dependent insulin secretion. Compared to other existing antidiabetic agents, DPP4 inhibitors have the advantage of not causing hypoglycemic episodes; not causing body-weight gain; and potentially altering disease progression by restoring â-cell function of the pancreas. Dipeptidyl peptidase-4 (DPP4) as target protein DPP4 is the CD26 T-cell-activating antigen, which is widely distributed in human organs and tissues. Tissues, which strongly express DPP4, include the exocrine pancreas, sweat glands, salivary and mammary glands, thymus, lymph nodes[36-40], biliary tract, kidney, liver, placenta, uterus, prostate, skin and capillary bed of the gut mucose where most glucagon-like peptide 1 (GLP-1) is inactivated locally (White, 2008). DPP4 is attached to the plasma membrane of the endothelia of almost all organs in the body. It is also present in body fluids, such as blood plasma and cerebrospinal fluid, in a soluble form (Thornberry & Weber, 2007). Activity of DPP4 inhibitors prolong the duration of GLP-1 and gastric inhibitory polypeptide (GIP) activity, thereby lowering the blood glucose level. During a meal, the incretins GLP-1 and glucose-dependent GIP are released from the small intestine into the vasculature 1979
4 (Sebokova et al., 2006). GLP-1 has many roles in the human body; it stimulates insulin biosynthesis, inhibits glucagon secretion, slows gastric emptying, reduces appetite and stimulates regeneration of islet β-cells (Veken et al., 2007)[41-45]. The enzyme responsible for the metabolism is DPP4. Material & Methods: The docking study was carried using GLIDE program of Schrödinger package, Induced Fit Docking algorithms were used for our docking studies. The structure of the compounds was solved using direct method and refined using full matrix least-squares procedure. Molecular docking studies show that these piperidine derivatives bind well in the active site pocket of the target protein and interact with the active site of the amino acid residues. All computational work was performed on Linux Fedora 7.0 workstation using the molecular modeling software Schrödinger. The three dimensional structure of the target protein was taken from the Protein Data Bank (PDB ID: IJ4H). The side chains were built using the builder option in Schrödinger package. 1980
5 The synthesized piperidine compound bind with active site of the targeted protein molecule residues Result & Discussion: DPP4 inhibitors exert their beneficial effects by increasing the levels of active Glucagon like Peptide-1 (GLP-1) and Glucose-dependent Insulinotropic Peptide (GIP).. The oxygen atom, in the ligands makes a hydrogen bond interaction with oxygen of Tyr 547 and Tyr 666. All compounds bear an OH group, which helps in better interactions with the target and stands for their mechanism of inhibition. References: 1. Ramamoorthy, R., Kanagasabai, V., Kausalya, R., Impact of celebrities' image on brand,, V-116, I-18 Special Issue, PP , Ramamoorthy, R., Kanagasabai, V., Vignesh, M., Quality assurance in operation theatre withreference to fortis malar hospital, International Journal of Pure and Applied Mathematics, V-116, I-14, PP-87-93, Ramya, N., Arthy, J., Honey comb graphs and its energy, International Journal of Pure and Applied Mathematics, V-116, I-18, PP-83-86, Ramya, N., Jagadeeswari, P., Proper coloring of regular graphs, International Journal of Pure and Applied Mathematics, V-116, I-16, PP , Ramya, N., Karunagaran, K., Proper, star and acyclic coloring of some graphs,, V-116, I-16, PP , Ramya, N., Muthukumar, M., On coloring of 4-regular graphs, International Journal of Pure and Applied Mathematics, V-116, I-16, PP , Ramya, N., Muthukumar, M., On star and acyclic coloring of graphs, International Journal of Pure and Applied Mathematics, V-116, I-16, PP , Ramya, N., Pavi, J., Coloring of book and gear graphs, International Journal of Pure and Applied Mathematics, V-116, I-17, PP ,
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7 24. Saritha, B., Chockalingam, M.P., Photodradation of malachite green DYE using TIO<inf>2</inf>/activated carbon composite, International Journal of Civil Engineering and Technology, V-8, I-8, PP , Saritha, B., Chockalingam, M.P., Synthesis of photocatalytic composite Fe-C/TiO2 for degradation of malachite green dye from aqueous medium, International Journal of Pure and Applied Mathematics, V-116, I-13, PP , Saritha, B., Chockalingam, M.P., Removal of heavy X`X`l from aqueous medium using modified natural adsorbent, International Journal of Pure and Applied Mathematics, V-116, I-13, PP , Saritha, B., Chockalingam, M.P., Degradation of malachite green dye using a semiconductor composite,, V- 116, I-13, PP , Sartiha, B., Chockalingam, M.P., Photocatalytic decolourisationoftextileindustrywastewaterby TiO2, International Journal of Pure and Applied Mathematics, V-116, I-18, PP , Sartiha, B., Chockalingam, M.P., Study on photocatalytic degradation of Crystal Violet dye using a semiconductor, International Journal of Pure and Applied Mathematics, V-116, I-18, PP , Shanthi, E., Nalini, C., Rama, A., The effect of highly-available epistemologies on hardware and architecture, International Journal of Pharmacy and Technology, V-8, I- 3, PP , Shanthi, E., Nalini, C., Rama, A., Drith: Autonomous,random communication, International Journal of Pharmacy and Technology, V-8, I-3, PP , Shanthi, E., Nalini, C., Rama, A., A case for replication, International Journal of Pharmacy and Technology, V-8, I-3, PP , Shanthi, E., Nalini, C., Rama, A., Elve: A methodology for the emulation of robots, International Journal of Pharmacy and Technology, V-8, I-3, PP , Shanthi, E., Nalini, C., Rama, A., Autonomous epistemologies for mesh networks, International Journal of Pharmacy and Technology, V-8, I-3, PP , Sharavanan, R., Golden Renjith, R.J., Design and analysis of fuel flow in bend pipes,, V-116, I-15, PP , Sharavanan, R., Jose Ananth Vino, V., Emission analysis of C.I engine run by diesel,sunflower oil,2 ethyl hexyl nitrate blends, International Journal of Pure and Applied Mathematics, V-116, I-14, PP , Sharavanan, R., Sabarish, R., Design of built-in hydraulic jack for light motor vehicles,, V-116, I-17 Special Issue, PP , Sharavanan, R., Sabarish, R., Design and fabrication of aqua silencer using charcoal and lime stone,, V-116, I-14, PP ,
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9 1985
10 1986
Dr. P.Sugumar 1, Dr.N.Selvi 2 Associate Professor 1 2 Department of Physics, BIST, BIHER, Bharath University, Chennai.
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