Tuba ÖZDEMİR ÖGE, Adnan SAĞLAM, Firdevs Banu ÖZDEMİR, Ali Ünsal KESKİNER, Mecit ÖGE

Pioglitazon Molekülünün Spektroskopik Özelliklerinin FT-IR, Raman, UV-Vis ve NMR Yöntemleri ile Teorik ve Deneysel Olarak İncelenmesi

Bu çalışmada pioglitazon molekülünün geometrik yapıları, bağ uzunlukları, bağ açıları, titreşim frekansları, dipol momentleri, proton ve karbon-13 NMR izotropik kimyasal kaymaları, UV-Vis. Parametreleri ile HOMO ve LUMO enerjileri Gaussian09 programı ve DFT/B3LYP yöntemi kullanılarak 6-311G++(2d,2p) temel setinde incelenmiştir. Teorik titreşim modlarının potansiyel enerji dağılımı (PED) üzerinden belirlenmesi VEDA 4 yazılımı ile gerçekleştirilmiştir. Pioglitazon molekülünün spektroskopik karakterizasyonu FT-IR, Lazer-Raman ve NMR kimyasal kayma ve UV-vis deneysel yöntemleri ile gerçekleştirilmiştir. Teorik olarak elde edilen geometrik parametreler, titreşimsel dalgaboyları ve NMR kimyasal kayma değerleri de aynı zamanda deneysel sonuçlarla karşılaştırılmıştır.

Anahtar Kelimeler:

Pioglitazon, FTIR, Lazer-Raman, Proton ve Carbon-13 NMR, DFT/B3LYP

Spectroscopic and Theoretical Investigation of Pioglitazone with FT-IR, Raman, UV-Vis. and NMR

Geometric structures, bond lengths, bond angles, vibrational frequencies, dipole moments, proton and carbon-13 NMR isotropic chemical shifts, UV-Vis. Parameters, HOMO and LUMO energies of pioglitazone molecules were studied using Gaussian09 program with DFT/B3LYP method at the 6-311G++(2d,2p) basis set. The assignments of theoretical vibrational modes were obtained using VEDA 4 software in terms of potential energy distribution (PED). The spectroscopic characterizations of pioglitazone molecule were performed using FT-IR, Laser-Raman, and NMR chemical shift and UV-vis. experimental methods. Theoretically obtained geometric parameters, vibrational wavenumbers and NMR chemical shifts will also be compared with the experimental results.

Keywords:

Pioglitazone, FTIR, Laser-Raman, Proton and Carbon-13 NMR chemical shifts, DFT/B3LYP,

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Adhikari, L., Jagadev, S., Sahoo, S., Murthy, P., Mishra, U.S., 2012. “Development and Validation of UV-Visible Spectrophotometric Method for Simultaneous Determination of Pioglitazone Hydrochloride, Metformin Hydrochloride and Glipizide in its Bulk and Pharmaceutical Dosage Form (Tablet)”, International Journal of ChemTech Research. Vol.4, No.2 625-630.
Alexandar, S., Diwedi, R., Chandrasekar, M., 2010. “A RP-HPLC method for simultaneous estimation of metformin and pioglitazone in pharmaceutical formulation”, Res. J. Pharm. Biol. Chem. Sci. 1 (4) 858–866.
Al-Majed, A., Bakheit, A.H.H., Abdel Aziz, H.A., Alharbi, H., Al-Jenoobi, F.I., 2016. “Profiles of Drug Substances, Excipients, and Related Methodology”, Volume 41, Elsevier Inc. ISSN 1871-5125.
Appana Chowdary K., Navya Lakshmi Raju Suravarapu., Swathi Meddala., 2015. “Formulation and Characterization of Pioglitazone Hydrochloride Nanoparticles”, World Journal of Pharmacy and Pharmaceutical Sciences. Volume 4, Issue 04, 1638-1648.
Attia, A. K., Ibrahim, M. M., El-Ries, M. Abdel-Nabi., 2013. “Thermal Analysis of Some Antidiabetic Pharmaceutical Compounds”, Advanced Pharmaceutical Bulletin, 3 (2), 419-424.
AIST, (2017). National Institute of Advanced Industrial Science and Technology Spectral Database for Organic Compounds, SDBS. http://sdbs.db.aist.go.jp/sdbs/cgibin/cre_index.cgi, (Accessed on 02 February 2018).
Becke, A. D., 1993. “Density‐functional thermochemistry. III. The role of exact Exchange”, J. Chem. Phys., 98, 5648.
Chebbi H, Chebbi M, Guesmi A, Arfaoui Y., 2016. “Crystal Structure Determination, and DFT Calculations of Dichlorobis (Dimethylsulfoxide-O)Copper(II)”, Journal of Structural Chemistry, 57 (6) 1104-1110.
Dubey, S., Kashyap, P., Pandey, A., Thakur, D., 2013. “A Validated Method Development For Estimation of Pioglitazone By First Order Derivative Spectroscopy”, International Journal of PharmTech Research. Vol.5, No.4 1451-1455.
Frish, A., Nielsen, A. B., Holder, A. J., 2001. “Gauss View User Manual”, Gaussian Inc., Pittsburg, PA.
Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A. et al. 2009. Gaussian 09, Revision, A.1, Gaussian Inc., Wallingford CT.
Fukui, K., 1982. “Role of frontier orbitals in chemical reactions”, Science 218 747-754.
Gadape, H. H., Parikh, K. S., 2011. “Quantitative Determination and Validation of Pioglitazone in Pharmaceutical using Quantitative Nuclear Magnetic Resonance Spectroscopy”, J. Chem. Pharm. Res., 3(1): 649-664.
Gaussian website, Visualizing Molecules&Reactions with Gaussview 5. http://www.gaussian.com/g_prod/gv5.htm (Son erişim tarihi: 10.08.2016).
Gowrav M.P., Shivakumar H.G., Vishal Gupta N., 2014. “Design and evaluation of pH sensitive multi-particulate systems for chronotherapeutic delivery of pioglitazone hydrochloride”, World J Pharm Sci, 2(12): 1813-1821.
Gökce H., Bahçeli S. 2013. “Analysis of molecular structure, spectroscopic properties (FT-IR, micro-Raman and UV–vis) and quantum chemical calculations of free and ligand 2-thiopheneglyoxylic acid in metal halides (Cd, Co, Cu, Ni and Zn)”, Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 116, 242-250.
Jamr’oz, M.H., 2004. “Vibrational Energy Distribution Analysis”, VEDA4.
Kulkarni, A.P., Mohd, S., Zaheer, Z., Dehghan, M.H., 2012. “Spectroscopic Estimation of Pioglitazone Hydrochloride”. Global Journal of Medical Research Volume XII Issue II 57-61.
Lee, C., Yang, W., Parr, R. G., 1988. “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”, Phys. Rev. B., 37, 785.
Moffat, A.C., Osselton, M.D., Widdop, B., 2011. “Clarke’s Analysis of Drugs and Poisons”, Vol. 3, Pharmaceutical Press, London.
O’Neil, M.J., 2013. “The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals”, Merck and Co, Whitehouse Station, NJ.
O'boyle, M., Tenderholt, A.L., Langner, K.M., 2008. “cclib: a library for package-independent computational chemistry algorithms”, J. Comput. Chem. 29 839-845.
Patil, S., Dwivedi, S., Bagade, S., 2011. “Development of Spectrophotometric Method for the Estimation of Pioglitazone HCL from Two Different Marketed Brands”, American Journal of Pharmtech Research. Volume 1, Issue 4 264-275.
Pioglitazone, Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/Pioglitazone#section=Synonyms Son erişim tarihi: 16.03.2021.
Soni, H., 2014. “Martindale: the complete drug reference”, Emerg. Nurse, 22 (5) 12.
Sujana, K., Abdulu, K., Bala Souri, O. Archana, B., Sindu, M., Swathi Rani, G., 2011. “Difference Spectrophotometric Methods for Pioglitazone Hydrochloride and Metformin Hydrochloride”, J. Pharm. Sci. & Res. Vol. 3(4) 1122-1126.
Shrivastaval, P., Basniwala, P.K., Jainz, D., 2008. “Alkaline hydrolysis of pioglitazone hydrochloride by RP-HPLC: stress stability study”, Acta Pharm. Sci. 50 41–46.
Satheeshkumar, N., Shantikumar, S., Srinivas, R., 2014. “Pioglitazone: A review of analytical methods”, Journal of Pharmaceutical Analysis. 4(5) 295-302.
Sundaraganesan N., Joshua B.D., Settu K. 2007. “Vibrational spectra and assignments of 5-amino-2-chlorobenzoic acid by ab initio Hartree-Fock and density functional methods”, Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 66 (2), 381-388.
Ulu, S. T., Elmalı, F.T., 2009. “UV-Second Derivative Spectrophotometric and Colorimetric Methods for the Determination, Validation and Thermogravimetric Analysis of New Oral Antidiabetic Pioglitazone in Pure and Pharmaceutical Preparations”, Analytical Letters. 42 2254-2270.
Yathirajan, Hemmige S., Nagaraj, B., Nagaraja, P., Bolte, M., 2005. “Pioglitazone hydrochloride”, Acta Cryst. E61, 154-155.

Erzincan Üniversitesi Fen Bilimleri Enstitüsü Dergisi-Cover

ISSN: 1307-9085
Yayın Aralığı: Yılda 3 Sayı
Başlangıç: 2008
Yayıncı: Erzincan Binali Yıldırım Üniversitesi, Fen Bilimleri Enstitüsü

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