Monophasic coamorphous sulpiride: a leap in physicochemical attributes and dual inhibition of GlyT1 and P-glycoprotein, supported by experimental and computational insights

References

• Abdullahi, M., Uzairu, A., Shallangwa, G. A., Mamza, P. A., Ibrahim, M. T., Ahmad, I., & Patel, H. (2023). Structure-based drug design, molecular dynamics simulation, ADMET, and quantum chemical studies of some thiazolinones targeting influenza neuraminidase. Journal of Biomolecular Structure & Dynamics, 41(23), 13829–13843. https://doi.org/10.1080/07391102.2023.2208225
   PubMed Web of Science ®Google Scholar
• Al-Otaibi, J. S., Mary, Y. S., Armaković, S., & Thomas, R. (2020). Hybrid and bioactive cocrystals of pyrazinamide with hydroxybenzoic acids: Detailed study of structure, spectroscopic characteristics, other potential applications and noncovalent interactions using SAPT. Journal of Molecular Structure, 1202, 127316. https://doi.org/10.1016/j.molstruc.2019.127316
   Web of Science ®Google Scholar
• Andronis, V., Yoshioka, M., & Zografi, G. (1997). Effects of sorbed water on the crystallization of indomethacin from the amorphous state. Journal of Pharmaceutical Sciences, 86(3), 346–351. https://doi.org/10.1021/js9602711
   PubMed Web of Science ®Google Scholar
• Arulraj, R. A., Gajjela, R., Chauthe, S. K., Bagadi, M., & Mathur, A. J. C. (2022). Correction to: High-throughput GC-FID method for the determination of residual solvents in early-phase drug discovery samples. Chromatographia, 85(6), 497–506. https://doi.org/10.1007/s10337-022-04157-9
   Web of Science ®Google Scholar
• Ayoub, A. M., Ibrahim, M. M., Abdallah, M. H., & Mahdy, M. A. (2016). Sulpiride microemulsions as antipsychotic nasal drug delivery systems: In-vitro and pharmacodynamic study. Journal of Drug Delivery Science and Technology, 36, 10–22. https://doi.org/10.1016/j.jddst.2016.09.002
   Web of Science ®Google Scholar
• Baird, J. A., & Taylor, L. S. (2012). Evaluation of amorphous solid dispersion properties using thermal analysis techniques. Advanced Drug Delivery Reviews, 64(5), 396–421. https://doi.org/10.1016/j.addr.2011.07.009
   PubMed Web of Science ®Google Scholar
• Baluom, M. Friedman, M.,& Rubinstein, A (2001). Improved intestinal absorption of sulpiride in rats with synchronized oral delivery systems. Journal of Controlled Release, 70(1-2), 139–147. https://doi.org/10.1016/S0168-3659(00)00337-0.
   PubMed Web of Science ®Google Scholar
• Banerjee, P., Chandra, A., Mohammad, T., Singh, N., Hassan, M. I., & Qamar, I. (2023). Identification of high-affinity pyridoxal kinase inhibitors targeting cancer therapy: An integrated docking and molecular dynamics simulation approach. Journal of Biomolecular Structure & Dynamics, 42 (1), 1–18. https://doi.org/10.1080/07391102.2023.2246580
   PubMedGoogle Scholar
• Bharti, S., Rani, N., Krishnamurthy, B., & Arya, D. S. (2014). Preclinical evidence for the pharmacological actions of naringin: A review. Planta Medica, 80(6), 437–451. https://doi.org/10.1055/s-0034-1368351
   PubMed Web of Science ®Google Scholar
• Bochevarov, A. D., Harder, E., Hughes, T. F., Greenwood, J. R., Braden, D. A., Philipp, D. M., Rinaldo, D., Halls, M. D., Zhang, J., & Friesner, R. A. (2013). Jaguar: A high-performance quantum chemistry software program with strengths in life and materials sciences. International Journal of Quantum Chemistry, 113(18), 2110–2142. https://doi.org/10.1002/qua.24481
   Web of Science ®Google Scholar
• Castner, S. A., Murthy, N. V., Ridler, K., Herdon, H., Roberts, B. M., Weinzimmer, D. P., Huang, Y., Zheng, M. Q., Rabiner, E. A., Gunn, R. N., Carson, R. E., Williams, G. V., & Laruelle, M. (2014). Relationship between glycine transporter 1 inhibition as measured with positron emission tomography and changes in cognitive performances in nonhuman primates. Neuropsychopharmacology, 39(12), 2742–2749. https://doi.org/10.1038/npp.2014.4
   PubMed Web of Science ®Google Scholar
• Castro-Alvarez, A., Costa, A., & Vilarrasa, J. (2017). The performance of several docking programs at reproducing protein–macrolide-like crystal structures. Molecules (Basel, Switzerland), 22(1), 136. https://doi.org/10.3390/molecules22010136
   PubMed Web of Science ®Google Scholar
• Cavia-Saiz, M., Busto, M. D., Pilar-Izquierdo, M. C., Ortega, N., Perez-Mateos, M., & Muñiz, P. (2010). Antioxidant properties, radical scavenging activity and biomolecule protection capacity of flavonoid naringenin and its glycoside naringin: A comparative study. Journal of the Science of Food and Agriculture, 90(7), 1238–1244. https://doi.org/10.1002/jsfa.3959
   PubMed Web of Science ®Google Scholar
• Celiz, G., Suarez, S. A., Arias, A., Molina, J., Brondino, C. D., & Doctorovich, F. (2019). Synthesis, structural elucidation and antiradical activity of a copper (II) naringenin complex. Biometals: An International Journal on the Role of Metal Ions in Biology, Biochemistry, and Medicine, 32(4), 595–610. https://doi.org/10.1007/s10534-019-00187-3
   PubMed Web of Science ®Google Scholar
• Chieng, N., Rehder, S., Saville, D., Rades, T., & Aaltonen, J. (2009). Quantitative solid-state analysis of three solid forms of ranitidine hydrochloride in ternary mixtures using Raman spectroscopy and X-ray powder diffraction. Journal of Pharmaceutical and Biomedical Analysis, 49(1), 18–25. https://doi.org/10.1016/j.jpba.2008.09.054
   PubMed Web of Science ®Google Scholar
• Chintha, N., Jupudi, S., Palathoti, N., Bharathi J, J., & Justin, A. (2023). In-silico docking and molecular dynamic introspective study of multiple targets of AChE with Rivastigmine and NMDA receptors with Riluzole for Alzheimer’s disease. Journal of Biomolecular Structure & Dynamics, 41(22), 12620–12631. https://doi.org/10.1080/07391102.2023.2167119
   PubMedGoogle Scholar
• Chitneni, M., Peh, K. K., Darwis, D., Abdulkarim, M., Abdullah, G. Z., & Qureshi, M. J. (2011). Intestinal permeability studies of sulpiride incorporated into self-microemulsifying drug delivery system (SMEDDS). Pakistan Journal of Pharmaceutical Sciences, 24(2), 113–121. PMID:21454158
   PubMed Web of Science ®Google Scholar
• Clark, J. J., Benson, M. L., Smith, R. D., & Carlson, H. A. (2019). Inherent versus induced protein flexibility: Comparisons within and between apo and holo structures. PLoS Computational Biology, 15(1), e1006705. https://doi.org/10.1371/journal.pcbi.1006705
   PubMed Web of Science ®Google Scholar
• Dasmahapatra, U., Kumar, C. K., Das, S., Subramanian, P. T., Murali, P., Isaac, A. E., Ramanathan, K., Mm, B., & Chanda, K. (2022). In-silico molecular modelling, MM/GBSA binding free energy and molecular dynamics simulation study of novel pyrido fused imidazo[4,5-c]quinolines as potential anti-tumor agents. Frontiers in Chemistry, 10, 991369. https://doi.org/10.3389/fchem.2022.991369
   PubMed Web of Science ®Google Scholar
• De Oliveira, M. V. D., Bittencourt Fernandes, G. M., Da Costa, K. S., Vakal, S., & Lima, A. H. (2022). Virtual screening of natural products against 5-enolpyruvylshikimate-3-phosphate synthase using the Anagreen herbicide-like natural compound library. RSC Advances, 12(29), 18834–18847. https://doi.org/10.1039/d2ra02645g
   PubMed Web of Science ®Google Scholar
• De Vivo, M., Masetti, M., Bottegoni, G., & Cavalli, A. (2016). Role of molecular dynamics and related methods in drug discovery. Journal of Medicinal Chemistry, 59(9), 4035–4061. https://doi.org/10.1021/acs.jmedchem.5b01684
   PubMed Web of Science ®Google Scholar
• Dengale, S. J., Grohganz, H., Rades, T., & Löbmann, K. (2016). Recent advances in co-amorphous drug formulations. Advanced Drug Delivery Reviews, 100, 116–125. https://doi.org/10.1016/j.addr.2015.12.009
   PubMed Web of Science ®Google Scholar
• Dengale, S. J., Ranjan, O. P., Hussen, S. S., Krishna, B., Musmade, P. B., Shenoy, G. G., & Bhat, K. (2014). Preparation and characterization of co-amorphous Ritonavir–Indomethacin systems by solvent evaporation technique: Improved dissolution behavior and physical stability without evidence of intermolecular interactions. European Journal of Pharmaceutical Sciences, 62, 57–64. https://doi.org/10.1016/j.ejps.2014.05.015
   PubMed Web of Science ®Google Scholar
• DiLabio, G. A., Koleini, M., & Torres, E. (2013). Extension of the B3LYP–dispersion-correcting potential approach to the accurate treatment of both inter- and intra-molecular interactions. Theoretical Chemistry Accounts, 132(10), 1389. https://doi.org/10.1007/s00214-013-1389-x
   Web of Science ®Google Scholar
• El Fadili, M., Er-Rajy, M., Ali Eltayb, W., Kara, M., Assouguem, A., Saleh, A., Al Kamaly, O., Zarougui, S., & Elhallaoui, M. (2023). In-silico screening based on molecular simulations of 3,4-disubstituted pyrrolidine sulfonamides as selective and competitive GlyT1 inhibitors. Arabian Journal of Chemistry, 16(10), 105105. https://doi.org/10.1016/j.arabjc.2023.105105
   Web of Science ®Google Scholar
• El Fadili, M., Er-Rajy, M., Kara, M., Assouguem, A., Belhassan, A., Alotaibi, A., Mrabti, N. N., Fidan, H., Ullah, R., Ercisli, S., Zarougui, S., & Elhallaoui, M. (2022). QSAR, ADMET In silico pharmacokinetics, molecular docking and molecular dynamics studies of novel bicyclo (aryl methyl) benzamides as potent GlyT1 inhibitors for the treatment of schizophrenia. Pharmaceuticals (Basel, Switzerland), 15(6), 670. https://doi.org/10.3390/ph15060670
   PubMedGoogle Scholar
• Elangovan, N. D., Dhanabalan, A. K., Gunasekaran, K., Kandimalla, R., & Sankarganesh, D. (2021). Screening of potential drug for Alzheimer’s disease: A computational study with GSK-3 β inhibition through virtual screening, docking, and molecular dynamics simulation. Journal of Biomolecular Structure & Dynamics, 39(18), 7065–7079. https://doi.org/10.1080/07391102.2020.1805362
   PubMed Web of Science ®Google Scholar
• El Fadili, M., Er-Rajy, M., Imtara, H., Noman, O. M., Mothana, R. A., Abdullah, S., Zerougui, S., & Elhallaoui, M. (2023). QSAR, ADME-Tox, molecular docking and molecular dynamics simulations of novel selective glycine transporter type 1 inhibitors with memory enhancing properties. Heliyon, 9(2), e13706. https://doi.org/10.1016/j.heliyon.2023.e13706
   PubMed Web of Science ®Google Scholar
• Fael, H. D., & Levent, A. (2021). Indomethacin co-amorphous drug-drug systems with improved solubility, supersaturation, dissolution rate and physical stability. International Journal of Pharmaceutics, 600, 120448. https://doi.org/10.1016/j.ijpharm.2021.120448
   PubMed Web of Science ®Google Scholar
• Fang, X., Hu, Y., Huang, Z., Han, L., Li, B., Lu, S., & Cao, Y. (2022). Exploring the formation mechanism of coamorphous andrographolide-oxymatrine based on molecular dynamics and spectroscopy. Journal of Pharmaceutical Sciences, 111(7), 2056–2071. https://doi.org/10.1016/j.xphs.2022.02.003
   PubMed Web of Science ®Google Scholar
• Fawcett, R. W. (1973). A radial distribution function analysis of an amorphous calcium phosphate with calcium to phosphorus molar ratio of 1.42. Calcified Tissue Research, 13(4), 319–325. https://doi.org/10.1007/bf02015422
   PubMedGoogle Scholar
• Feng, J., Chen, X., Lu, S., Li, W., Yang, D., Su, W., Wang, X., & Shen, J. (2018). Naringin attenuates cerebral ischemia-reperfusion injury through inhibiting peroxynitrite-mediated mitophagy activation. Molecular Neurobiology, 55(12), 9029–9042. https://doi.org/10.1007/s12035-018-1027-7
   PubMed Web of Science ®Google Scholar
• Firdhouse, M. J., & Lalitha, P. (2015). Maestro 9.4 as a tool in the structure based screening of glycoalkaloids and related compounds, targeting aldose reductase. Trends in Bioinformatics, 8(1), 26–36. https://doi.org/10.3923/tb.2015.26.36
   Google Scholar
• Garg, A. ,Bhalala, K., Tomar, D. S., & Wahajuddin. (2017). In-situ single pass intestinal permeability andpharmacokinetic study of developed Lumefantrine loaded solid lipid nanoparticles. International Journal of Pharmaceutics, 516(1-2), 120–130. https://doi.org/10.1016/j.ijpharm.2016.10.064.
   PubMed Web of Science ®Google Scholar
• Gollavilli, H., Hegde, A. R., Managuli, R. S., Bhaskar, K. V., Dengale, S. J., Reddy, M. S., Kalthur, G., & Mutalik, S. (2020). Naringin nano-ethosomal novel sunscreen creams: Development and performance evaluation. Colloids and Surfaces B, Biointerfaces, 193, 111122. https://doi.org/10.1016/j.colsurfb.2020.111122
   PubMed Web of Science ®Google Scholar
• Han, J., Wei, Y., Lu, Y., Wang, R., Zhang, J., Gao, Y., & Qian, S. (2020). Co-amorphous systems for the delivery of poorly water-soluble drugs: Recent advances and an update. Expert Opinion on Drug Delivery, 17(10), 1411–1435. https://doi.org/10.1080/17425247.2020.1796631
   PubMed Web of Science ®Google Scholar
• Han, Y., Pan, Y., Lv, J., Guo, W., & Wang, J. (2016). Powder grinding preparation of co-amorphous β-azelnidipine and maleic acid combination: Molecular interactions and physicochemical properties. Powder Technology, 291, 110–120. https://doi.org/10.1016/j.powtec.2015.11.068
   Web of Science ®Google Scholar
• Hao, H., Zhang, Y., Hu, X., Guo, W., Yang, C., & Wang, J. (2023). Cocrystallization of 5-fluorouracil with gallic acid: A novel 5-fluorouracil cocrystal displaying synergistic anti-tumor activity both in oral and intraperitoneal injection administration. European Journal of Pharmaceutics and Biopharmaceutics, 187, 12–23. https://doi.org/10.1016/j.ejpb.2023.04.001
   PubMed Web of Science ®Google Scholar
• Harvey, R. J., & Yee, B. K. (2013). Glycine transporters as novel therapeutic targets in schizophrenia, alcohol dependence and pain. Nature Reviews Drug Discovery, 12(11), 866–885. https://doi.org/10.1038/nrd3893
   PubMed Web of Science ®Google Scholar
• Hosen, S. Z., Dash, R., Khatun, M., Akter, R., Bhuiyan, M. H. R., Karim, M. R., Mouri, N. J., Ahamed, F., Islam, K. S., & Afrin, S. (2017). In silico ADME/T and 3D QSAR analysis of KDR inhibitors. Journal of Applied Pharmaceutical Science, 7(1), 120–128. https://doi.org/10.7324/JAPS.2017.70116
   Google Scholar
• Hu, D., Chen, X., Li, D., Zhang, H., Duan, Y., & Huang, Y. (2023). Tranilast-matrine co-amorphous system: Strong intermolecular interactions, improved solubility, and physiochemical stability. International Journal of Pharmaceutics, 635, 122707. https://doi.org/10.1016/j.ijpharm.2023.122707
   PubMed Web of Science ®Google Scholar
• Ibrahim, W. M., AlOmrani, A. H., & Yassin, A. E. B. (2014). Novel sulpiride-loaded solid lipid nanoparticles with enhanced intestinal permeability. International Journal of Nanomedicine, 9, 129–144. https://doi.org/10.2147/IJN.S54413
   PubMed Web of Science ®Google Scholar
• Impurities: Guideline for Residual Solvents Q3C(R8). (2021). Ich harmonised guideline. https://www.ema.europa.eu/documents/regulatory-procedural-guideline/ich-guideline-q3c-r8-impurities-guideline-residual-solvents-step-5_en.pdf
   Google Scholar
• Javitt, D. C. (2012). Glycine transport inhibitors in the treatment of schizophrenia. Novel antischizophrenia treatments (pp. 367–399). https://doi.org/10.1007/978-3-642-25758-2_12
   Google Scholar
• Kagami, L. P., das Neves, G. M., Timmers, L. F. S. M., Caceres, R. A., & Eifler-Lima, V. L. (2020). Geo-Measures: A PyMOL plugin for protein structure ensembles analysis. Computational Biology and Chemistry, 87, 107322. https://doi.org/10.1016/j.compbiolchem.2020.107322
   PubMed Web of Science ®Google Scholar
• Kalam, M. A., Alshamsan, A., Alkholief, M., Alsarra, I. A., Ali, R., Haq, N., Anwer, M. K., & Shakeel, F. (2020). Solubility measurement and various solubility parameters of glipizide in different neat solvents. ACS Omega, 5(3), 1708–1716. https://doi.org/10.1021/acsomega.9b04004
   PubMed Web of Science ®Google Scholar
• Kasten, G., Löbmann, K., Grohganz, H., & Rades, T. (2019). Co-former selection for co-amorphous drug-amino acid formulations. International Journal of Pharmaceutics, 557, 366–373. https://doi.org/10.1016/j.ijpharm.2018.12.036
   PubMed Web of Science ®Google Scholar
• Kecel-Gunduz, S., Budama-Kilinc, Y., Cakir-Koc, R., Zorlu, T., Bicak, B., Kokcu, Y., Kaya, Z., Ozel, A. E., & Akyuz, S. (2020). In silico analysis of sulpiride, synthesis, characterization and in vitro studies of its nanoparticle for the treatment of schizophrenia. Current Computer-Aided Drug Design, 16(2), 104–121. https://doi.org/10.2174/1573409915666190627125643
   PubMed Web of Science ®Google Scholar
• Kim, D. S., Choi, J. S., Kim, D. W., Kim, K. S., Seo, Y. G., Cho, K. H., Kim, J. O., Yong, C. S., Youn, Y. S., Lim, S. J., Jin, S. G., & Choi, H. G. (2016). Comparison of solvent wetted and kneaded l-sulpiride loaded solid dispersions: Powder characterization and in vivo evaluation. International Journal of Pharmaceutics, 511(1), 351–358. https://doi.org/10.1016/j.ijpharm.2016.07.006
   PubMed Web of Science ®Google Scholar
• Kim, D. S., Kim, D. W., Kim, K. S., Choi, J. S., Seo, Y. G., Youn, Y. S., Oh, K. T., Yong, C. S., Kim, J. O., Jin, S. G., & Choi, H. G. (2016). Development of a novel l-sulpiride-loaded quaternary microcapsule: Effect of TPGS as an absorption enhancer on physicochemical characterization and oral bioavailability. Colloids and Surfaces B, Biointerfaces, 147, 250–257. https://doi.org/10.1016/j.colsurfb.2016.08.010
   PubMed Web of Science ®Google Scholar
• Kirubakaran, P., Karthikeyan, M., Singh, K. D., Nagamani, S., & Premkumar, K. (2013). In silico structural and functional analysis of the human TOPK protein by structure modeling and molecular dynamics studies. Journal of Molecular Modeling, 19(1), 407–419. https://doi.org/10.1007/s00894-012-1566-1
   PubMed Web of Science ®Google Scholar
• Kohri, N., Naasani, I., Iseki, K., & Miyazaki, K. (1996). Improving the oral bioavailability of sulpiride by a gastric-retained form in rabbits. The Journal of Pharmacy and Pharmacology, 48(4), 371–374. https://doi.org/10.1111/j.2042-7158.1996.tb05935.x
   PubMed Web of Science ®Google Scholar
• Ks, N. S., Dengale, S. J., Mutalik, S., & Bhat, K. (2022). Raloxifene HCl–quercetin co-amorphous system: Preparation, characterization, and investigation of its behavior in phosphate buffer. Drug development industrial pharmacy (just-accepted) (pp. 1–34). https://doi.org/10.1080/03639045.2022.2104308
   Google Scholar
• Kumar, N., James, R., Sinha, S., Kinra, M., Anuranjana, P., & Nandakumar, K. (2021). Naringin exhibited Anti-Parkinsonian like effect against haloperidol-induced catalepsy in mice. Research Journal of Pharmacy and Technology, 14(2), 662–666. https://doi.org/10.5958/0974-360X.2021.00118.9
   Google Scholar
• Kumari, P., Sharma, B., & Som, A. (2023). (2-Cyclohexyl-1-methylpropyl) cyclohexane isolated from garlic extract exhibits antidepressant-like activity: Extraction, docking, drug-like properties, molecular dynamics simulations and MM/GBSA studies. Journal of Biomolecular Structure & Dynamics, 41(7), 1–13. https://doi.org/10.1080/07391102.2023.2202250
   Google Scholar
• Lai, E. C. C., Hsieh, C. Y., Kao Yang, Y. H., & Lin, S. J. (2014). Detecting potential adverse reactions of sulpiride in schizophrenic patients by prescription sequence symmetry analysis. PLoS One, 9(2), e89795. https://doi.org/10.1371/journal.pone.0089795
   PubMed Web of Science ®Google Scholar
• Lai, M., Zhang, X., & Fang, F. (2017). Crystal orientation effect on the subsurface deformation of monocrystalline germanium in nanometric cutting. Nanoscale Research Letters, 12(1), 296. https://doi.org/10.1186/s11671-017-2047-3
   PubMedGoogle Scholar
• Laitinen, R., Löbmann, K., Strachan, C. J., Grohganz, H., & Rades, T. (2013). Emerging trends in the stabilization of amorphous drugs. International Journal of Pharmaceutics, 453(1), 65–79. https://doi.org/10.1016/j.ijpharm.2012.04.066
   PubMed Web of Science ®Google Scholar
• Łątka, K., & Bajda, M. (2022). Analysis of binding determinants for different classes of competitive and noncompetitive inhibitors of glycine transporters. International Journal of Molecular Sciences, 23(14), 8050. https://doi.org/10.3390/ijms23148050
   PubMed Web of Science ®Google Scholar
• Li, B., Hu, Y., Guo, Y., Xu, R., Fang, X., Xiao, X., Jiang, C., & Lu, S. (2021). Coamorphous system of Florfenicol-Oxymatrine for improving the solubility and dissolution rate of Florfenicol: Preparation, characterization and molecular dynamics simulation. Journal of Pharmaceutical Sciences, 110(6), 2544–2554. https://doi.org/10.1016/j.xphs.2021.02.005
   PubMed Web of Science ®Google Scholar
• Li, B., Wang, Y., Feng, Y., Yuan, D., Xu, R., Jiang, C., Xiao, X., & Lu, S. (2022). Design and molecular insights of drug-active metabolite based co-amorphous formulation: A case study of toltrazuril-ponazuril co-amorphous. International Journal of Pharmaceutics, 615, 121475. https://doi.org/10.1016/j.ijpharm.2022.121475
   PubMed Web of Science ®Google Scholar
• Liu, W., Pan, H., Zhang, C., Zhao, L., Zhao, R., Zhu, Y., & Pan, W. (2016). Developments in methods for measuring the intestinal absorption of nanoparticle-bound drugs. International Journal of Molecular Sciences, 17(7), 1171. https://doi.org/10.3390/ijms17071171
   PubMed Web of Science ®Google Scholar
• Löbmann, K., Grohganz, H., Laitinen, R., Strachan, C., & Rades, T. (2013). Amino acids as co-amorphous stabilizers for poorly water soluble drugs–Part 1: Preparation, stability and dissolution enhancement. European Journal of Pharmaceutics and Biopharmaceutics, 85(3 Pt B), 873–881. https://doi.org/10.1016/j.ejpb.2013.03.014
   PubMed Web of Science ®Google Scholar
• Lokhande, K. B., Doiphode, S., Vyas, R., & Swamy, K. V. (2021). Molecular docking and simulation studies on SARS-CoV-2 Mpro reveals Mitoxantrone, Leucovorin, Birinapant, and Dynasore as potent drugs against COVID-19. Journal of Biomolecular Structure & Dynamics, 39(18), 7294–7305. https://doi.org/10.1080/07391102.2020.1805019
   PubMed Web of Science ®Google Scholar
• Lu, L. (2015). Can B3LYP be improved by optimization of the proportions of exchange and correlation functionals? International Journal of Quantum Chemistry, 115(8), 502–509. https://doi.org/10.1002/qua.24876
   Web of Science ®Google Scholar
• M’bitsi-Ibouily, G., Marimuthu, T., Kumar, P., Choonara, Y., Toit, L., Pradeep, P., Modi, G., & Pillay, V. (2019). Synthesis, characterisation and in vitro permeation, dissolution and cytotoxic evaluation of ruthenium(II)-liganded sulpiride and amino alcohol. Scientific Reports, 9(1), 4146. https://doi.org/10.1038/s41598-019-40538-1
   PubMedGoogle Scholar
• Malgarim Cordenonsi, L., Sponchiado, R., Campanharo, S. C., Garcia, C., Raffin, R., & Schapoval, E. (2017). Study of flavonoids present in pomelo (Citrus Maxima) BY DSC, UV-VIS, IR, 1H and 13C NMR and MS. Drug Analytical Research, 1(1), 31–37. https://doi.org/10.22456/2527-2616.74097
   Google Scholar
• Mizoguchi, R., Waraya, H., & Hirakura, Y. (2019). Application of co-amorphous technology for improving the physicochemical properties of amorphous formulations. Molecular Pharmaceutics, 16(5), 2142–2152. https://doi.org/10.1021/acs.molpharmaceut.9b00105
   PubMed Web of Science ®Google Scholar
• Mohamed, G. G., & Soliman, M. H. (2010). Synthesis, spectroscopic and thermal characterization of sulpiride complexes of iron, manganese, copper, cobalt, nickel, and zinc salts. Antibacterial and antifungal activity. Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy, 76(3–4), 341–347. https://doi.org/10.1016/j.saa.2010.03.016
   PubMed Web of Science ®Google Scholar
• Moinuddin, S. M., Ruan, S., Huang, Y., Gao, Q., Shi, Q., Cai, B., & Cai, T. (2017). Facile formation of co-amorphous atenolol and hydrochlorothiazide mixtures via cryogenic-milling: Enhanced physical stability, dissolution and pharmacokinetic profile. International Journal of Pharmaceutics, 532(1), 393–400. https://doi.org/10.1016/j.ijpharm.2017.09.020
   PubMed Web of Science ®Google Scholar
• Nagamani, S., Muthusamy, K., Kirubakaran, P., Singh, K. D., & Krishnasamy, G. (2012). Theoretical studies on benzimidazole derivatives as E. coli biotin carboxylase inhibitors. Medicinal Chemistry Research, 21(9), 2169–2180. https://doi.org/10.1007/s00044-011-9738-6
   Web of Science ®Google Scholar
• Naik, B., Mattaparthi, V. S. K., Gupta, N., Ojha, R., Das, P., Singh, S., Prajapati, V. K., & Prusty, D. (2022). Chemical system biology approach to identify multi-targeting FDA inhibitors for treating COVID-19 and associated health complications. Journal of Biomolecular Structure & Dynamics, 40(19), 9543–9567. https://doi.org/10.1080/07391102.2021.1931451
   PubMed Web of Science ®Google Scholar
• Otte, A., Zhang, Y., Carvajal, M. T., & Pinal, R. (2012). Milling induces disorder in crystalline griseofulvin and order in its amorphous counterpart. CrystEngComm, 14(7), 2560–2570. https://doi.org/10.1039/c2ce06365d
   Web of Science ®Google Scholar
• Panda, S. P., Roy, P., Soren, D., Ranjan Sahoo, D., Dehury, B., Rout, A. K., Behera, B. K., & Das, B. K. (2023). Structural insights of Labeo catla (catla) myxovirus resistance protein,GTP binding recognition and constitutive expression induced with Poly I:C. Journal of Biomolecular Structure & Dynamics, 42 (1), 1–15. https://doi.org/10.1080/07391102.2023.2213345
   PubMedGoogle Scholar
• Pandey, R. K., Kumbhar, B. V., Srivastava, S., Malik, R., Sundar, S., Kunwar, A., & Prajapati, V. K. (2017). Febrifugine analogues as Leishmania donovani trypanothione reductase inhibitors: Binding energy analysis assisted by molecular docking, ADMET and molecular dynamics simulation. Journal of Biomolecular Structure & Dynamics, 35(1), 141–158. https://doi.org/10.1080/07391102.2015.1135298
   PubMed Web of Science ®Google Scholar
• Pandi, P., Bulusu, R., Kommineni, N., Khan, W., & Singh, M. (2020). Amorphous solid dispersions: An update for preparation, characterization, mechanism on bioavailability, stability, regulatory considerations and marketed products. International Journal of Pharmaceutics, 586, 119560. https://doi.org/10.1016/j.ijpharm.2020.119560
   PubMed Web of Science ®Google Scholar
• Pang, W., Lv, J., Du, S., Wang, J., Wang, J., & Zeng, Y. (2017). Preparation of curcumin-piperazine coamorphous phase and fluorescence spectroscopic and density functional theory simulation studies on the interaction with bovine serum albumin. Molecular Pharmaceutics, 14(9), 3013–3024. https://doi.org/10.1021/acs.molpharmaceut.7b00217
   PubMed Web of Science ®Google Scholar
• Panwar, U., & Singh, S. K. (2021). Atom-based 3D-QSAR, molecular docking, DFT, and simulation studies of acylhydrazone, hydrazine, and diazene derivatives as IN-LEDGF/p75 inhibitors. Structural Chemistry, 32(1), 337–352. https://doi.org/10.1007/s11224-020-01628-3
   Web of Science ®Google Scholar
• Pardhi, E., Tomar, D. S., Khemchandani, R., Samanthula, G., Singh, P. K., & Mehra, N. K. (2023). Design, development and characterization of the Apremilast and Indomethacin coamorphous system. Journal of Molecular Structure, 1299, 137045. https://doi.org/10.1016/j.molstruc.2023.137045
   Web of Science ®Google Scholar
• PerkinElmer Informatics 2020, ChemDraw 20.0. https://perkinelmerinformatics.com
   Google Scholar
• Pešić, N., Dapčević, A., Ivković, B., Kachrimanis, K., Mitrić, M., Ibrić, S., & Medarević, D. (2021). Potential application of low molecular weight excipients for amorphization and dissolution enhancement of carvedilol. International Journal of Pharmaceutics, 608, 121033. https://doi.org/10.1016/j.ijpharm.2021.121033
   PubMed Web of Science ®Google Scholar
• Pinheiro Barros, M. C., Sousa Lima, M. A., Braz-Filho, R., & Rocha Silveira, E. (2003). 1H and 13C NMR assignments of abietane diterpenes from Aegiphila lhotzkyana. Magnetic Resonance in Chemistry, 41(9), 731–734. https://doi.org/10.1002/mrc.1236
   Web of Science ®Google Scholar
• R Sá, M., Sarraguça, J. M. G., de Sousa, F. F., Sarraguça, M. S. C., Lopes, J. A., Lima, A. D. D S. G., Lage, M. R., & Ribeiro, P. R. S. (2022). Structural, thermal, vibrational, solubility and DFT studies of a tolbutamide co-amorphous drug delivery system for treatment of diabetes. International Journal of Pharmaceutics, 615, 121500. https://doi.org/10.1016/j.ijpharm.2022.121500
   PubMed Web of Science ®Google Scholar
• Raghunathan, S., El Hage, K., Desmond, J. L., Zhang, L., & Meuwly, M. (2018). The role of water in the stability of wild-type and mutant insulin dimers. The Journal of Physical Chemistry B, 122(28), 7038–7048. https://doi.org/10.1021/acs.jpcb.8b04448
   PubMed Web of Science ®Google Scholar
• Rahmani, R., Boukabcha, N., Chouaih, A., Hamzaoui, F., & Goumri-Said, S. (2018). On the molecular structure, vibrational spectra, HOMO-LUMO, molecular electrostatic potential, UV–Vis, first order hyperpolarizability, and thermodynamic investigations of 3-(4-chlorophenyl)-1-(1yridine-3-yl) prop-2-en-1-one by quantum chemistry calculations. Journal of Molecular Structure, 1155, 484–495. https://doi.org/10.1016/j.molstruc.2017.11.033
   Web of Science ®Google Scholar
• Rosenbrock, H., Desch, M., & Wunderlich, G. (2023). Development of the novel GlyT1 inhibitor, iclepertin (BI 425809), for the treatment of cognitive impairment associated with schizophrenia. European Archives of Psychiatry and Clinical Neuroscience, 273(7), 1557–1566. https://doi.org/10.1007/s00406-023-01576-z
   PubMedGoogle Scholar
• Russo, M. G., Baldoni, H. A., Dávila, Y. A., Brusau, E. V., Ellena, J. A., & Narda, G. E. (2018). Rational design of a famotidine–ibuprofen coamorphous system: An experimental and theoretical study. The Journal of Physical Chemistry. B, 122(37), 8772–8782. https://doi.org/10.1021/acs.jpcb.8b06105
   PubMed Web of Science ®Google Scholar
• Salam, N. K., Nuti, R., & Sherman, W. (2009). Novel method for generating structure-based pharmacophores using energetic analysis. Journal of Chemical Information and Modeling, 49(10), 2356–2368. https://doi.org/10.1021/ci900212v
   PubMed Web of Science ®Google Scholar
• Shahsavar, A., Stohler, P., Bourenkov, G., Zimmermann, I., Siegrist, M., Guba, W., Pinard, E., Sinning, S., Seeger, M. A., Schneider, T. R., Dawson, R. J. P., & Nissen, P. (2021). Structural insights into the inhibition of glycine reuptake. Nature, 591(7851), 677–681. https://doi.org/10.1038/s41586-021-03274-z
   PubMed Web of Science ®Google Scholar
• Shi, Q., Moinuddin, S. M., & Cai, T. (2019). Advances in coamorphous drug delivery systems. Acta Pharmaceutica Sinica B, 9(1), 19–35. https://doi.org/10.1016/j.apsb.2018.08.002
   PubMed Web of Science ®Google Scholar
• Shirasaka, Y., Li, Y., Shibue, Y., Kuraoka, E., Spahn-Langguth, H., Kato, Y., Langguth, P., & Tamai, I. (2009). Concentration-dependent effect of naringin on intestinal absorption of β1-adrenoceptor antagonist talinolol mediated by P-glycoprotein and organic anion transporting polypeptide (Oatp). Pharmaceutical Research, 26(3), 560–567. https://doi.org/10.1007/s11095-008-9771-4
   PubMed Web of Science ®Google Scholar
• Shukr, M. H., & Ahmed Farid, O. A. (2018). Amisulpride–CD-loaded liposomes: Optimization and in vivo evaluation. AAPS PharmSciTech, 19(6), 2658–2671. https://doi.org/10.1208/s12249-018-1079-z
   PubMed Web of Science ®Google Scholar
• Simoben, C., Robaa, D., Chakrabarti, A., Schmidtkunz, K., Marek, M., Lancelot, J., Kannan, S., Melesina, J., Shaik, T., Pierce, R., Romier, C., Jung, M., & Sippl, W. (2018). A novel class of Schistosoma mansoni histone deacetylase 8 (HDAC8) inhibitors identified by structure-based virtual screening and in vitro testing. Molecules (Basel, Switzerland), 23(3), 566. https://doi.org/10.3390/molecules23030566
   PubMed Web of Science ®Google Scholar
• Singh, K. D., Kirubakaran, P., Nagarajan, S., Sakkiah, S., Muthusamy, K., Velmurgan, D., & Jeyakanthan, J. (2012). Homology modeling, molecular dynamics, e-pharmacophore mapping and docking study of Chikungunya virus nsP2 protease. Journal of Molecular Modeling, 18(1), 39–51. https://doi.org/10.1007/s00894-011-1018-3
   PubMed Web of Science ®Google Scholar
• Skotnicki, M., Jadach, B., Skotnicka, A., Milanowski, B., Tajber, L., Pyda, M., & Kujawski, J. (2021). Physicochemical characterization of a co-amorphous atorvastatin-irbesartan system with a potential application in fixed-dose combination therapy. Pharmaceutics, 13(1), 118. https://doi.org/10.3390/pharmaceutics13010118
   PubMed Web of Science ®Google Scholar
• Srolovitz, D., Egami, T., & Vitek, V. (1981). Radial distribution function and structural relaxation in amorphous solids. Physical Review B, 24(12), 6936–6944. https://doi.org/10.1103/PhysRevB.24.6936
   Web of Science ®Google Scholar
• Surampalli, G. Nanjwade, B. K., & Patil, P.(2013). Drug Development and Industrial Pharmacy. Drug Development and Industrial Pharmacy, 1, 170–176. https://doi.org/10.3109/03639045.2013.850716
   Google Scholar
• Teja, A., Musmade, P. B., Khade, A. B., & Dengale, S. J. (2015). Simultaneous improvement of solubility and permeability by fabricating binary glassy materials of Talinolol with Naringin: Solid state characterization, in-vivo in-situ evaluation. European Journal of Pharmaceutical Sciences, 78, 234–244. https://doi.org/10.1016/j.ejps.2015.08.002
   PubMed Web of Science ®Google Scholar
• Terban, M. W., & Billinge, S. J. (2021). Structural analysis of molecular materials using the pair distribution function. Chemical Reviews, 122(1), 1208–1272. https://doi.org/10.1021/acs.chemrev.1c00237
   PubMed Web of Science ®Google Scholar
• Tiwari, S., Arya, N., Mishra, S. K., & Suryaprakash, N. (2021). Competing HB acceptors: An extensive NMR investigations corroborated by single crystal XRD and DFT calculations. RSC Advances, 11(25), 15195–15202. https://doi.org/10.1039/d1ra02538d
   PubMed Web of Science ®Google Scholar
• Tomar, D., Singh, P. K., Hoque, S., Modani, S., Sriram, A., Kumar, R., Madan, J., Khatri, D., & Dua, K. (2022). Amorphous systems for delivery of nutraceuticals: Challenges opportunities. Critical Reviews in Food Science and Nutrition, 62(5), 1204–1221. https://doi.org/10.1080/10408398.2020.1836607
   PubMed Web of Science ®Google Scholar
• Uppala, S., Vullendula, S. K. A., Yarlagadda, D. L., & Dengale, S. J. (2022). Exploring the utility of co-amorphous materials to concurrently improve the solubility and permeability of Fexofenadine. Journal of Drug Delivery Science and Technology, 72, 103431. https://doi.org/10.1016/j.jddst.2022.103431
   Web of Science ®Google Scholar
• Vullendula, S. K. A., Nair, A. R., Yarlagadda, D. L., Navya Sree, K. S., Bhat, K., & Dengale, S. J. (2022). Polymeric solid dispersion Vs co-amorphous technology: A critical comparison. Journal of Drug Delivery Science and Technology, 78, 103980. https://doi.org/10.1016/j.jddst.2022.103980
   Web of Science ®Google Scholar
• Wang, E., Sun, H., Wang, J., Wang, Z., Liu, H., Zhang, J. Z. H., & Hou, T. (2019). End-point binding free energy calculation with MM/PBSA and MM/GBSA: Strategies and applications in drug design. Chemical Reviews, 119(16), 9478–9508. https://doi.org/10.1021/acs.chemrev.9b00055
   PubMed Web of Science ®Google Scholar
• Wang, W., Li, X., Wang, Q., Zhu, X., Zhang, Q., & Du, L. (2018). The acidic pH-induced structural changes in apo-CP43 by spectral methodologies and molecular dynamics simulations. Journal of Molecular Structure, 1152, 177–188. https://doi.org/10.1016/j.molstruc.2017.09.082
   Web of Science ®Google Scholar
• Warren, H. R., & Hejmadi, M. (2016). Effect of hypoxia on chemosensitivity to 5-fluorouracil in SH-SY5Y neuroblastoma cells. Bioscience Horizons, 9, hzw005. https://doi.org/10.1093/biohorizons/hzw005
   Google Scholar
• Wei, Y., Zhou, S., Hao, T., Zhang, J., Gao, Y., & Qian, S. (2019). Further enhanced dissolution and oral bioavailability of docetaxel by coamorphization with a natural P-gp inhibitor myricetin. European Journal of Pharmaceutical Sciences, 129, 21–30. https://doi.org/10.1016/j.ejps.2018.12.016
   PubMed Web of Science ®Google Scholar
• Xu, Y., Shrestha, N., Préat, V., & Beloqui, A. (2021). An overview of in vitro, ex vivo and in vivo models for studying the transport of drugs across intestinal barriers. Advanced Drug Delivery Reviews, 175, 113795. https://doi.org/10.1016/j.addr.2021.05.005
   PubMed Web of Science ®Google Scholar
• Yang, C., Di, P., Fu, J., Xiong, H., Jing, Q., Ren, G., Tang, Y., Zheng, W., Liu, G., & Ren, F. (2017). Improving the physicochemical properties of bicalutamide by complex formation with bovine serum albumin. European Journal of Pharmaceutical Sciences, 106, 381–392. https://doi.org/10.1016/j.ejps.2017.05.059
   PubMed Web of Science ®Google Scholar
• Yang, Y., Tang, W., Liu, S., Han, D., Liu, Y., & Gong, J. (2017). Solubility of benzoin in three binary solvent mixtures and investigation of intermolecular interactions by molecular dynamic simulation. Journal of Molecular Liquids, 243, 472–483. https://doi.org/10.1016/j.molliq.2017.07.125
   Web of Science ®Google Scholar
• Yarlagadda, D. L., Sai Krishna Anand, V., Nair, A. R., Navya Sree, K. N., Dengale, S. J., & Bhat, K. (2021a). Considerations for the selection of co-formers in the preparation of co-amorphous formulations. International Journal of Pharmaceutics, 602, 120649. https://doi.org/10.1016/j.ijpharm.2021.120649
   PubMed Web of Science ®Google Scholar
• Yarlagadda, D. L., Sai Krishna Anand, V., Nair, A. R., Navya Sree, K. S., Dengale, S. J., & Bhat, K. (2021b). Considerations for the selection of co-formers in the preparation of co-amorphous formulations .  International Journal of Pharmaceutics, 602, 120649. https://doi.org/10.1016/j.ijpharm.2021.120649
   PubMed Web of Science ®Google Scholar
• Yoda, O., Kuriyama, I., & Odajima, A. (1978). RDF analysis for the degree of interchain ordering in amorphous solid polyethylene. Journal of Applied Physics, 49(11), 5468–5472. https://doi.org/10.1063/1.324516
   Web of Science ®Google Scholar
• Zhang, X., Perez-Sanchez, H., & Lightstone, F. C. (2017). A comprehensive docking and MM/GBSA rescoring study of ligand recognition upon binding antithrombin. Current Topics in Medicinal Chemistry, 17(14), 1631–1639. https://doi.org/10.2174/1568026616666161117112604
   PubMed Web of Science ®Google Scholar
• Zhang, Y., Huo, M., Zhou, J., Zou, A., Li, W., Yao, C., & Xie, S. (2010). DDSolver: An add-in program for modeling and comparison of drug dissolution profiles. The AAPS Journal, 12(3), 263–271. https://doi.org/10.1208/s12248-010-9185-1
   PubMed Web of Science ®Google Scholar
• Zhu, S., Gao, H., Babu, S., & Garad, S. (2018). Co-amorphous formation of high-dose zwitterionic compounds with amino acids to improve solubility and enable parenteral delivery. Molecular Pharmaceutics, 15(1), 97–107. https://doi.org/10.1021/acs.molpharmaceut.7b00738
   PubMed Web of Science ®Google Scholar
• Zochedh, A., Priya, M., Chakaravarthy, C., Sultan, A. B., & Kathiresan, T. (2023). Experimental and computational evaluation of syringic acid – structural, spectroscopic, biological activity and docking simulation. Polycyclic Aromatic Compounds, 43(7), 6516–6548. https://doi.org/10.1080/10406638.2022.2118332
   Web of Science ®Google Scholar