Research Article
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Investigation of Chloride Anion Binding Properties of Glipizide Drug

Year 2023, , 262 - 277, 29.09.2023
https://doi.org/10.54287/gujsa.1281246

Abstract

This study addresses the anion binding property of Glipizide (GLP), an oral antidiabetic a second-generation drug member of the sulphonylurea (SU) family. GLP effectively interacts with Cl- anion according to 1H-NMR spectroscopic titrations of successive tetrabutylammonium chloride (TBACl) in deuterated chloroform (CDCl3) and dimethyl sulfoxide (d6-DMSO). Upon the addition of TBACl, the change in chemical shift was observed for both N-H protons of SU in CDCl3, whereas it causes a difference in the shift of only one of N-H proton in SU in d6-DMSO. In addition, the data obtained from 1H-NMR spectroscopic titrations was analyzed by DynaFit program to calculate the binding constant (Ka) value between GLP and Cl- anion. It was found that GLP binds Cl- anion in CDCl3 with higher affinity (Ka=77.37 M-1, Fitplot for N-Hh proton at δ=6.47 ppm) than in d6-DMSO (Ka=38.53 M-1, Fitplot for N-Hh proton at δ=6.32 ppm).

References

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  • Aguilar-Bryan, L., Nichols, C. G., Wechsler, S. W., Clement IV, J. P., Boyd III, A. E., González, G., Herrera-Sosa, H., Nguy, K., Bryan, J., & Nelson, D. A. (1995). Cloning of the β Cell High-Affinity Sulfonylurea Receptor: a Regulator of Insulin Secretion. Science, 268(5209), 423-426. doi:10.1126/science.7716547
  • Ambadekar, S., & Keni, S. (2018). Fast and Economic Spectrophotometric Method for Metformin and Glipizide in Combination Tablet. International Journal of Advances in Science Engineering and Technology, 6(1), 31-35.
  • Amendola, V., Bergamaschi, G., Boiocchi, M., Fabbrizzi, L., & Milani, M. (2010). The Squaramide versus Urea Contest for Anion Recognition. Chemistry, 16(14), 4368-4380. doi:10.1002/chem.200903190
  • Amendola, V., Fabbrizzi, L., Mosca, L., & Schmidtchen, F.-P. (2011). Urea-, Squaramide-, and Sulfonamide-Based Anion Receptors: A Thermodynamic Study. Chemistry, 17(21), 5972-5981. doi:10.1002/chem.201003411
  • Anwer, R., AlQumaizi, K. I., Haque, S., Somvanshi, P., Ahmad, N., AlOsaimi, S. M., & Fatma, T. (2021). Unravelling the Interaction of Glipizide with Human Serum Albumin Using Various Spectroscopic Techniques and Molecular Dynamics Studies. Journal of Biomolecular Structure and Dynamics, 39(1), 336-347. doi:10.1080/07391102.2019.1711195
  • Bao, X., Wu, X., Berry, S. N., Howe, E. N. W., Chang, Y.-T., & Gale, P. A. (2018). Fluorescent squaramides as anion receptors and transmembrane anion transporters. Chemical Communications, 54(11), 1363-1366. doi:10.1039/C7CC08706C
  • Barišić, D., Cindro, N., Vidović, N., Bregović, N., & Tomišić, V. (2021). Protonation and anion-binding properties of aromatic sulfonylurea derivatives. RSC Advances, 11(39), 23992-24000. doi:10.1039/D1RA04738H
  • Barišić, D., Lešić, F., Tireli Vlašić, M., Užarević, K., Bregović, N., & Tomišić, V. (2022). Anion Binding by receptors containing NH donating groups – What do anions prefer?. Tetrahedron, 120, 132875-132883. doi:10.1016/j.tet.2022.132875
  • Best, L., & Benington, S. (1998). Effects of sulphonylureas on the volume-sensitive anion channel in rat pancreatic β-cells. British Journal of Pharmacology, 125(4), 874-878. doi:10.1038/sj.bjp.0702148
  • Best, L., Davies, S., & Brown, P. D. (2004). Tolbutamide potentiates the volume-regulated anion channel current in rat pancreatic beta cells. Diabetologia, 47(11), 1990-1997. doi:10.1007/s00125-004-1559-4
  • Bondy, C. R., & Loeb, S. J. (2003). Amide based receptors for anions. Coordination Chemistry Reviews, 240(1-2), 77-99. doi:10.1016/S0010-8545(02)00304-1
  • Brogden, R. N., Heel, R. C., Pakes, G. E., Speight, T. M., & Avery, G. S. (1979). Glipizide: A Review of its Pharmacological Properties and Therapeutic Use. Drugs, 18(5), 329-353 doi:10.2165/00003495-197918050-00001
  • Cai, X.-J., Li, Z., & Chen, W.-H. (2018). Synthesis, Anion Recognition and Transmembrane Anion-transport Properties of Squaramides and Their Derivatives. Mini-Reviews in Organic Chemistry, 15(2), 148-156. doi:10.2174/1570193X14666171114115629
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  • Gribble, F. M., & Reimann, F. (2002). Pharmacological modulation of KATP channels. Biochemical Society Transactions, 30(2), 333-339. doi:10.1042/bst0300333
  • Hasanah, A. N., Pessagno, F., Kartasasmita, R. E., Ibrahim, S., & Manesiotis, P. (2015). Tetrabutylammonium methacrylate as a novel receptor for selective extraction of sulphonylurea drugs from biological fluids using molecular imprinting. Journal of Materials Chemistry B, 3(43), 8577-8583. doi:10.1039/C5TB01512J
  • Hosogi, S., Kusuzaki, K., Inui, T., Wang, X., & Marunaka, Y. (2014). Cytosolic chloride ion is a key factor in lysosomal acidification and function of autophagy in human gastric cancer cell. Journal of Cellular and Molecular Medicine, 18(6), 1124-1133. doi:10.1111/jcmm.12257
  • Huggins, M. T., Butler, T., Barber, P., & Hunt, J. (2009). Synthesis and molecular recognition studies of pyrrole sulfonamides. Chemical Communications, (35), 5254-5256. doi:10.1039/B911985J
  • Hussan, K. P. S., Rahoof, K. A. A., Medammal, Z., Thayyil, M. S., & Babu, T. D. (2022). Theoretical insights into the radical scavenging activity of glipizide: DFT and molecular docking studies. Free Radical Research, 56(1), 53-62. doi:10.1080/10715762.2022.2034803
  • Jena, B. R., Swain, S., Babu, S. M., Pradhan, D. P., & Sasikanth, K. (2017). UV spectrophotometric Method Development and Quantitative Estimation of Glipizide in Bulk and Pharmaceutical Dosage Forms. International Journal of Drug Research and Technology, 7(3), 112-122.
  • Kang, S. O., Begum, R. A., & Bowman-James, K. (2006). Amide-Based Ligands for Anion Coordination. Angewandte Chemie International Edition, 45(47), 7882-7894. doi:10.1002/anie.200602006
  • Kinard, T. A., & Satin, L. S. (1995). An ATP-Sensitive Cl- Channel Current That Is Activated by Cell Swelling, cAMP, and Glyburide in Insulin-Secreting Cells. Diabetes, 44(12), 1461-1466. doi:10.2337/diab.44.12.1461
  • Kumawat, L. K., Wynne, C., Cappello, E., Fisher, P., Brennan, L. E., Strofaldi, A., McManus, J. J., Hawes, C. S., Jolliffe, K. A., Gunnlaugsson, T., & Elmes, R. B. P. (2021). Squaramide-Based Self-Associating Amphiphiles for Anion Recognition. ChemPlusChem, 86(8), 1058-1068. doi:10.1002/cplu.202100275
  • Kuzmič, P. (2009). DynaFit-A Software Package for Enzymology. In: M. L. Johnson, & L. Brand (Eds.), Computer Methods Part B (Methods in Enzymology book series, vol. 467), (pp. 247-280). doi:10.1016/S0076-6879(09)67010-5
  • Lebovitz, H. E., & Feinglos, M. N. (1983). Mechanism of Action of the Second-Generation Sulfonylurea Glipizide. The American Journal of Medicine, 75(5), 46-54. doi:10.1016/0002-9343(83)90253-X
  • Li, A.-F., Wang, J.-H., Wang, F., & Jiang, Y.-B. (2010). Anion complexation and sensing using modified urea and thiourea-based receptors. Chemical Society Reviews, 39(10), 3729-3745. doi:10.1039/B926160P
  • Marchetti, L. A., Kumawat, L. K., Mao, N., Stephens, J. C., & Elmes, R. B. P. (2019). The Versatility of Squaramides: From Supramolecular Chemistry to Chemical Biology. Chem, 5(6), 1398-1485. doi:10.1016/j.chempr.2019.02.027
  • Martin, S. L., Saint-Criq, V., Hwang, T.-C., & Csanády, L. (2018). Ion channels as targets to treat cystic fibrosis lung disease. Journal of Cystic Fibrosis, 17(2), S22-S27. doi:10.1016/j.jcf.2017.10.006
  • Mercurio, J. M., Caballero, A., Cookson, J., & Beer, P. D. (2015). A halogen- and hydrogen-bonding [2]catenane for anion recognition and sensing. RSC Advances, 5(12), 9298-9306. doi:10.1039/C4RA15380D
  • Ming, X., Qi, Z.-C., Lian, H.-Z., & Wang, S.-K. (2008). Spectral Data Analyses and Structure Elucidation of Hypoglycemic Drug Glipizide. Instrumentation Science & Technology, 36(5), 503-514. doi:10.1080/10739140802234956
  • Norris, E. (1979). Glipizide, a new second-generation sulfonylurea. In: R. A. Camerini-Davalos, B. Hanover (Eds.), Treatment of EARLY DIABETES (Advances in Experimental Medicine and Biology book series, vol.119), (pp. 427-434). doi:10.1007/978-1-4615-9110-8_62
  • Pahwa, R., Bohra, P., Sharma, P. C., Kumar, V., & Dureja, H. (2010). Glipizide: Some Analytical, Clinical and Therapeutic Vistas. International Journal of Chemical Sciences, 8(1), 59-80.
  • Pessagno, F., Hasanah, A. N., & Manesiotis, P. (2018). Molecularly imprinted 'traps' for sulfonylureas prepared using polymerisable ion pairs. RSC Advances, 8(26), 14212-14220. doi:10.1039/C8RA01135D
  • Picci, G., Kubicki, M., Garau, A., Lippolis, V., Mocci, R., Porcheddu, A., Quesada, R., Ricci, P. C., Scorciapino, M. A., & Caltagirone, C. (2020). Simple squaramide receptors for highly efficient anion binding in aqueous media and transmembrane transport. Chemical Communications, 56(75), 11066-11069. doi:10.1039/D0CC04090H
  • Prakash, O., & Iqbal, S. A. (2015). FTIR, 1H NMR, mass spectral, XRD and thermal characterization studies of NdIII and SmIII complexes of glipizide: An oral antidiabetic drug. Journal of Indian Chemical Society, 92(1), 51-63. doi:10.5281/zenodo.5602962
  • Prasad, N., Issarani, R., & Nagori, B. P. (2013). Ultraviolet Spectrophotometric Method for Determination of Glipizide in Presence of Liposomal/Proliposomal Turbidity. Journal of Spectroscopy, 2013, 836372. doi:10.1155/2013/836372
  • Qi, C., Zhou, Q., Li, B., Yang, Y., Cao, L., Ye, Y., Li, J., Ding, Y., Wang, H., Wang, J., He, X., Zhang, Q., Lan, T., Ka Ho Lee, K., Li, W., Song, X., Zhou, J., Yang, X., & Wang, L. (2014). Glipizide, an antidiabetic drug, suppresses tumor growth and metastasis by inhibiting angiogenesis. Oncotarget, 5(20), 9966-9979. doi:10.18632/oncotarget.2483
  • Ramalingam, V., Domaradzki, M. E., Jang, S., & Muthyala, R. S. (2008). Carbonyl Groups as Molecular Valves to Regulate Chloride Binding to Squaramides. Organic Letters, 10(15), 3315-3318. doi:10.1021/ol801204s
  • Renström, E., Barg, S., Thévenod, F., & Rorsman, P. (2002). Sulfonylurea-Mediated Stimulation of Insulin Exocytosis via an ATP-sensitive K+ Channel-Independent Action. Diabetes, 51(1), S33-S36. doi:10.2337/diabetes.51.2007.S33
  • Rowe, S. M., Miller, S., & Sorscher, E. J. (2005). Cystic Fibrosis. New England Journal of Medicine, 352(19), 1992-2001. doi:10.1056/NEJMra043184
  • Sehlin, J. (1981). Are Cl- Mechanisms in Mouse Pancreatic Islets involved in Insulin Release?. Upsala Journal of Medical Sciences, 86(2), 177-182. doi:10.3109/03009738109179226
  • Shuman, C. R. (1983). Glipizide: An Overview. The American Journal of Medicine, 75(5), 55-59. doi:10.1016/0002-9343(83)90254-1
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Year 2023, , 262 - 277, 29.09.2023
https://doi.org/10.54287/gujsa.1281246

Abstract

References

  • Adhikari, L., Jagadev, S., Sahoo, S., Murthy, P. N., & Mishra, U. S. (2012). Devlopement 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 Chem Tech Research, 4(2), 625-630.
  • Aguilar-Bryan, L., Nichols, C. G., Wechsler, S. W., Clement IV, J. P., Boyd III, A. E., González, G., Herrera-Sosa, H., Nguy, K., Bryan, J., & Nelson, D. A. (1995). Cloning of the β Cell High-Affinity Sulfonylurea Receptor: a Regulator of Insulin Secretion. Science, 268(5209), 423-426. doi:10.1126/science.7716547
  • Ambadekar, S., & Keni, S. (2018). Fast and Economic Spectrophotometric Method for Metformin and Glipizide in Combination Tablet. International Journal of Advances in Science Engineering and Technology, 6(1), 31-35.
  • Amendola, V., Bergamaschi, G., Boiocchi, M., Fabbrizzi, L., & Milani, M. (2010). The Squaramide versus Urea Contest for Anion Recognition. Chemistry, 16(14), 4368-4380. doi:10.1002/chem.200903190
  • Amendola, V., Fabbrizzi, L., Mosca, L., & Schmidtchen, F.-P. (2011). Urea-, Squaramide-, and Sulfonamide-Based Anion Receptors: A Thermodynamic Study. Chemistry, 17(21), 5972-5981. doi:10.1002/chem.201003411
  • Anwer, R., AlQumaizi, K. I., Haque, S., Somvanshi, P., Ahmad, N., AlOsaimi, S. M., & Fatma, T. (2021). Unravelling the Interaction of Glipizide with Human Serum Albumin Using Various Spectroscopic Techniques and Molecular Dynamics Studies. Journal of Biomolecular Structure and Dynamics, 39(1), 336-347. doi:10.1080/07391102.2019.1711195
  • Bao, X., Wu, X., Berry, S. N., Howe, E. N. W., Chang, Y.-T., & Gale, P. A. (2018). Fluorescent squaramides as anion receptors and transmembrane anion transporters. Chemical Communications, 54(11), 1363-1366. doi:10.1039/C7CC08706C
  • Barišić, D., Cindro, N., Vidović, N., Bregović, N., & Tomišić, V. (2021). Protonation and anion-binding properties of aromatic sulfonylurea derivatives. RSC Advances, 11(39), 23992-24000. doi:10.1039/D1RA04738H
  • Barišić, D., Lešić, F., Tireli Vlašić, M., Užarević, K., Bregović, N., & Tomišić, V. (2022). Anion Binding by receptors containing NH donating groups – What do anions prefer?. Tetrahedron, 120, 132875-132883. doi:10.1016/j.tet.2022.132875
  • Best, L., & Benington, S. (1998). Effects of sulphonylureas on the volume-sensitive anion channel in rat pancreatic β-cells. British Journal of Pharmacology, 125(4), 874-878. doi:10.1038/sj.bjp.0702148
  • Best, L., Davies, S., & Brown, P. D. (2004). Tolbutamide potentiates the volume-regulated anion channel current in rat pancreatic beta cells. Diabetologia, 47(11), 1990-1997. doi:10.1007/s00125-004-1559-4
  • Bondy, C. R., & Loeb, S. J. (2003). Amide based receptors for anions. Coordination Chemistry Reviews, 240(1-2), 77-99. doi:10.1016/S0010-8545(02)00304-1
  • Brogden, R. N., Heel, R. C., Pakes, G. E., Speight, T. M., & Avery, G. S. (1979). Glipizide: A Review of its Pharmacological Properties and Therapeutic Use. Drugs, 18(5), 329-353 doi:10.2165/00003495-197918050-00001
  • Cai, X.-J., Li, Z., & Chen, W.-H. (2018). Synthesis, Anion Recognition and Transmembrane Anion-transport Properties of Squaramides and Their Derivatives. Mini-Reviews in Organic Chemistry, 15(2), 148-156. doi:10.2174/1570193X14666171114115629
  • Davis, A. P., Sheppard, D. N., & Smith, B. D. (2007). Development of synthetic membrane transporters for anions. Chemical Society Reviews, 36(2), 348-357. doi:10.1039/B512651G
  • Emami, J., Boushehri, M. S. S., & Varshosaz, J. (2014). Preparation, characterization and optimization of glipizide controlled release nanoparticles. Research in Pharmaceutical Sciences, 9(5), 301-314.
  • Ganesh, K., Nikitha, G., Sireesha, D., & Vasudha, B. (2016). Development and Validation of UV Spectrophotometric Method for Simultaneous Estimation of Metformin and Glipizide in Tablet Dosage Form. International Journal of Applied Pharmaceutical Sciences and Research, 1(2), 56-59. doi:10.21477/ijapsr.v1i2.10176
  • Gribble, F. M., & Reimann, F. (2002). Pharmacological modulation of KATP channels. Biochemical Society Transactions, 30(2), 333-339. doi:10.1042/bst0300333
  • Hasanah, A. N., Pessagno, F., Kartasasmita, R. E., Ibrahim, S., & Manesiotis, P. (2015). Tetrabutylammonium methacrylate as a novel receptor for selective extraction of sulphonylurea drugs from biological fluids using molecular imprinting. Journal of Materials Chemistry B, 3(43), 8577-8583. doi:10.1039/C5TB01512J
  • Hosogi, S., Kusuzaki, K., Inui, T., Wang, X., & Marunaka, Y. (2014). Cytosolic chloride ion is a key factor in lysosomal acidification and function of autophagy in human gastric cancer cell. Journal of Cellular and Molecular Medicine, 18(6), 1124-1133. doi:10.1111/jcmm.12257
  • Huggins, M. T., Butler, T., Barber, P., & Hunt, J. (2009). Synthesis and molecular recognition studies of pyrrole sulfonamides. Chemical Communications, (35), 5254-5256. doi:10.1039/B911985J
  • Hussan, K. P. S., Rahoof, K. A. A., Medammal, Z., Thayyil, M. S., & Babu, T. D. (2022). Theoretical insights into the radical scavenging activity of glipizide: DFT and molecular docking studies. Free Radical Research, 56(1), 53-62. doi:10.1080/10715762.2022.2034803
  • Jena, B. R., Swain, S., Babu, S. M., Pradhan, D. P., & Sasikanth, K. (2017). UV spectrophotometric Method Development and Quantitative Estimation of Glipizide in Bulk and Pharmaceutical Dosage Forms. International Journal of Drug Research and Technology, 7(3), 112-122.
  • Kang, S. O., Begum, R. A., & Bowman-James, K. (2006). Amide-Based Ligands for Anion Coordination. Angewandte Chemie International Edition, 45(47), 7882-7894. doi:10.1002/anie.200602006
  • Kinard, T. A., & Satin, L. S. (1995). An ATP-Sensitive Cl- Channel Current That Is Activated by Cell Swelling, cAMP, and Glyburide in Insulin-Secreting Cells. Diabetes, 44(12), 1461-1466. doi:10.2337/diab.44.12.1461
  • Kumawat, L. K., Wynne, C., Cappello, E., Fisher, P., Brennan, L. E., Strofaldi, A., McManus, J. J., Hawes, C. S., Jolliffe, K. A., Gunnlaugsson, T., & Elmes, R. B. P. (2021). Squaramide-Based Self-Associating Amphiphiles for Anion Recognition. ChemPlusChem, 86(8), 1058-1068. doi:10.1002/cplu.202100275
  • Kuzmič, P. (2009). DynaFit-A Software Package for Enzymology. In: M. L. Johnson, & L. Brand (Eds.), Computer Methods Part B (Methods in Enzymology book series, vol. 467), (pp. 247-280). doi:10.1016/S0076-6879(09)67010-5
  • Lebovitz, H. E., & Feinglos, M. N. (1983). Mechanism of Action of the Second-Generation Sulfonylurea Glipizide. The American Journal of Medicine, 75(5), 46-54. doi:10.1016/0002-9343(83)90253-X
  • Li, A.-F., Wang, J.-H., Wang, F., & Jiang, Y.-B. (2010). Anion complexation and sensing using modified urea and thiourea-based receptors. Chemical Society Reviews, 39(10), 3729-3745. doi:10.1039/B926160P
  • Marchetti, L. A., Kumawat, L. K., Mao, N., Stephens, J. C., & Elmes, R. B. P. (2019). The Versatility of Squaramides: From Supramolecular Chemistry to Chemical Biology. Chem, 5(6), 1398-1485. doi:10.1016/j.chempr.2019.02.027
  • Martin, S. L., Saint-Criq, V., Hwang, T.-C., & Csanády, L. (2018). Ion channels as targets to treat cystic fibrosis lung disease. Journal of Cystic Fibrosis, 17(2), S22-S27. doi:10.1016/j.jcf.2017.10.006
  • Mercurio, J. M., Caballero, A., Cookson, J., & Beer, P. D. (2015). A halogen- and hydrogen-bonding [2]catenane for anion recognition and sensing. RSC Advances, 5(12), 9298-9306. doi:10.1039/C4RA15380D
  • Ming, X., Qi, Z.-C., Lian, H.-Z., & Wang, S.-K. (2008). Spectral Data Analyses and Structure Elucidation of Hypoglycemic Drug Glipizide. Instrumentation Science & Technology, 36(5), 503-514. doi:10.1080/10739140802234956
  • Norris, E. (1979). Glipizide, a new second-generation sulfonylurea. In: R. A. Camerini-Davalos, B. Hanover (Eds.), Treatment of EARLY DIABETES (Advances in Experimental Medicine and Biology book series, vol.119), (pp. 427-434). doi:10.1007/978-1-4615-9110-8_62
  • Pahwa, R., Bohra, P., Sharma, P. C., Kumar, V., & Dureja, H. (2010). Glipizide: Some Analytical, Clinical and Therapeutic Vistas. International Journal of Chemical Sciences, 8(1), 59-80.
  • Pessagno, F., Hasanah, A. N., & Manesiotis, P. (2018). Molecularly imprinted 'traps' for sulfonylureas prepared using polymerisable ion pairs. RSC Advances, 8(26), 14212-14220. doi:10.1039/C8RA01135D
  • Picci, G., Kubicki, M., Garau, A., Lippolis, V., Mocci, R., Porcheddu, A., Quesada, R., Ricci, P. C., Scorciapino, M. A., & Caltagirone, C. (2020). Simple squaramide receptors for highly efficient anion binding in aqueous media and transmembrane transport. Chemical Communications, 56(75), 11066-11069. doi:10.1039/D0CC04090H
  • Prakash, O., & Iqbal, S. A. (2015). FTIR, 1H NMR, mass spectral, XRD and thermal characterization studies of NdIII and SmIII complexes of glipizide: An oral antidiabetic drug. Journal of Indian Chemical Society, 92(1), 51-63. doi:10.5281/zenodo.5602962
  • Prasad, N., Issarani, R., & Nagori, B. P. (2013). Ultraviolet Spectrophotometric Method for Determination of Glipizide in Presence of Liposomal/Proliposomal Turbidity. Journal of Spectroscopy, 2013, 836372. doi:10.1155/2013/836372
  • Qi, C., Zhou, Q., Li, B., Yang, Y., Cao, L., Ye, Y., Li, J., Ding, Y., Wang, H., Wang, J., He, X., Zhang, Q., Lan, T., Ka Ho Lee, K., Li, W., Song, X., Zhou, J., Yang, X., & Wang, L. (2014). Glipizide, an antidiabetic drug, suppresses tumor growth and metastasis by inhibiting angiogenesis. Oncotarget, 5(20), 9966-9979. doi:10.18632/oncotarget.2483
  • Ramalingam, V., Domaradzki, M. E., Jang, S., & Muthyala, R. S. (2008). Carbonyl Groups as Molecular Valves to Regulate Chloride Binding to Squaramides. Organic Letters, 10(15), 3315-3318. doi:10.1021/ol801204s
  • Renström, E., Barg, S., Thévenod, F., & Rorsman, P. (2002). Sulfonylurea-Mediated Stimulation of Insulin Exocytosis via an ATP-sensitive K+ Channel-Independent Action. Diabetes, 51(1), S33-S36. doi:10.2337/diabetes.51.2007.S33
  • Rowe, S. M., Miller, S., & Sorscher, E. J. (2005). Cystic Fibrosis. New England Journal of Medicine, 352(19), 1992-2001. doi:10.1056/NEJMra043184
  • Sehlin, J. (1981). Are Cl- Mechanisms in Mouse Pancreatic Islets involved in Insulin Release?. Upsala Journal of Medical Sciences, 86(2), 177-182. doi:10.3109/03009738109179226
  • Shuman, C. R. (1983). Glipizide: An Overview. The American Journal of Medicine, 75(5), 55-59. doi:10.1016/0002-9343(83)90254-1
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There are 49 citations in total.

Details

Primary Language English
Subjects Organic Chemistry (Other)
Journal Section Chemistry
Authors

Serap Mert 0000-0001-5939-5295

Early Pub Date August 22, 2023
Publication Date September 29, 2023
Submission Date April 11, 2023
Published in Issue Year 2023

Cite

APA Mert, S. (2023). Investigation of Chloride Anion Binding Properties of Glipizide Drug. Gazi University Journal of Science Part A: Engineering and Innovation, 10(3), 262-277. https://doi.org/10.54287/gujsa.1281246