Transformation of microstructure and phase of disodium guanosine 5'-monophosphate: Thermodynamic perspectives

doi:10.1016/j.cjche.2018.06.003

Chin.J.Chem.Eng. ›› 2018, Vol. 26 ›› Issue (10): 2112-2120.DOI: 10.1016/j.cjche.2018.06.003

• Chemical Engineering Thermodynamics • Previous Articles Next Articles

Transformation of microstructure and phase of disodium guanosine 5'-monophosphate: Thermodynamic perspectives

Qiao Chen^1,2, Fengxia Zou^2,3, Pengpeng Yang^1,2, Jingwei Zhou^1,2, Jinglan Wu^1,2, Wei Zhuang^1,2, Hanjie Ying^1,2

1 State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2 College of Biotechnology and Pharmaceutical Engineering, National Engineering Research Center for Biotechnology, Nanjing Tech University, Nanjing 210009, China;
3 College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China

Received:2018-02-26 Revised:2018-05-14 Online:2018-11-14 Published:2018-10-28
Contact: Wei Zhuang,E-mail addresses:weizhuang@njtech.edu.cn;Hanjie Ying,E-mail addresses:yinghanjie@njtech.edu.cn
Supported by:
Supported by the Program for Changjiang Scholars and Innovative Research Team in University (IRT_14R28), the National Basic Research Program of China (2013CB733602), the Major Research Plan of the National Natural Science Foundation of China (21390204), the National Natural Science Foundation of China (21636003, 21506090), Open Fund by Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals (JSBGFC14005), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

Transformation of microstructure and phase of disodium guanosine 5'-monophosphate: Thermodynamic perspectives

Qiao Chen^1,2, Fengxia Zou^2,3, Pengpeng Yang^1,2, Jingwei Zhou^1,2, Jinglan Wu^1,2, Wei Zhuang^1,2, Hanjie Ying^1,2

1 State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2 College of Biotechnology and Pharmaceutical Engineering, National Engineering Research Center for Biotechnology, Nanjing Tech University, Nanjing 210009, China;
3 College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China

通讯作者: Wei Zhuang,E-mail addresses:weizhuang@njtech.edu.cn;Hanjie Ying,E-mail addresses:yinghanjie@njtech.edu.cn
基金资助:
Supported by the Program for Changjiang Scholars and Innovative Research Team in University (IRT_14R28), the National Basic Research Program of China (2013CB733602), the Major Research Plan of the National Natural Science Foundation of China (21390204), the National Natural Science Foundation of China (21636003, 21506090), Open Fund by Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals (JSBGFC14005), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

Abstract

Abstract: Microstructure and phase transformation of disodium guanosine 5'-monophosphate (5'-GMPNa₂) are extremely important for controlling the process and understanding the mechanism of crystallization. In this work, the thermodynamic properties of polymorphous 5'-GMPNa₂ especially the solubility were studied, the solubility results show that 5'-GMPNa₂ is more soluble in ethanol-water (E-W) than in isopropanol-water (I-W). The amorphous form of 5'-GMPNa₂ is more soluble than the crystalline form at the same mole fraction and temperature. Meanwhile, the crystalline forms and morphologies of the residual solids were characterized by PXRD and SEM. The results indicate that solid forms of 5'-GMPNa₂ transformed spontaneously from amorphous to crystalline when the ethanol proportion is ≥ 20%. In addition, increasing the pH facilitates the dissolution of 5'-GMPNa₂ and helps to maintain the crystalline form. The associated Gibbs free energy values were calculated to verify the trend of transformation from amorphous to crystalline 5'-GMPNa₂. These results should help to guide the industrial crystallization process and to obtain the crystalline form of 5'-GMPNa₂.

Key words: Solid form transformation, Thermodynamics, Disodium guanosine 5'-monophosphate, Solubility, Crystallization, Intermolecular force

摘要： Microstructure and phase transformation of disodium guanosine 5'-monophosphate (5'-GMPNa₂) are extremely important for controlling the process and understanding the mechanism of crystallization. In this work, the thermodynamic properties of polymorphous 5'-GMPNa₂ especially the solubility were studied, the solubility results show that 5'-GMPNa₂ is more soluble in ethanol-water (E-W) than in isopropanol-water (I-W). The amorphous form of 5'-GMPNa₂ is more soluble than the crystalline form at the same mole fraction and temperature. Meanwhile, the crystalline forms and morphologies of the residual solids were characterized by PXRD and SEM. The results indicate that solid forms of 5'-GMPNa₂ transformed spontaneously from amorphous to crystalline when the ethanol proportion is ≥ 20%. In addition, increasing the pH facilitates the dissolution of 5'-GMPNa₂ and helps to maintain the crystalline form. The associated Gibbs free energy values were calculated to verify the trend of transformation from amorphous to crystalline 5'-GMPNa₂. These results should help to guide the industrial crystallization process and to obtain the crystalline form of 5'-GMPNa₂.

关键词: Solid form transformation, Thermodynamics, Disodium guanosine 5'-monophosphate, Solubility, Crystallization, Intermolecular force

Qiao Chen, Fengxia Zou, Pengpeng Yang, Jingwei Zhou, Jinglan Wu, Wei Zhuang, Hanjie Ying. Transformation of microstructure and phase of disodium guanosine 5'-monophosphate: Thermodynamic perspectives[J]. Chin.J.Chem.Eng., 2018, 26(10): 2112-2120.

References

[1] B.C. Hancock, M. Parks, What is the true solubility advantage for amorphous pharmaceuticals? Pharm. Res. 17(2000) 397-404.

[2] D. Mangin, F. Puel, S. Veesler, Polymorphism in processes of crystallization in solution:A practical review, Org. Process. Res. Dev. 13(2009) 1241-1253.

[3] T. Henriet, I. Gana, C. Ghaddar, M. Barrio, Y. Cartigny, N. Yagoubi, B. Do, J.-L. Tamarit, I.B. Rietveld, Solid state stability and solubility of triethylenetetramine dihydrochloride, Int. J. Pharm. 511(2016) 312-321.

[4] H. Al-Obaidi, M. Majumder, F. Bari, Amorphous and crystalline particulates:Challenges and perspectives in drug delivery, Curr. Pharm. Des. 23(2017) 350-361.

[5] A. Burger, R. Ramberger, On the polymorphism of pharmaceuticals and other molecular crystals. I, Microchim. Acta 72(1979) 259-271.

[6] L. Derdour, S. Pack, D. Skliar, C. Lai, S. Kiang, Crystallization from solutions containing multiple conformers:A new modeling approach for solubility and supersaturation, Chem. Eng. Sci. 66(2011) 88-102.

[7] J. Caplette, T. Frigo, M. Jozwiakowski, H. Shea, M. Mirmehrabi, P. Müller, Characterization of new crystalline forms of hydroxyprogesterone caproate, Int. J. Pharm. 527(2017) 42-51.

[8] A.R. Pallipurath, F. Civati, J. Sibik, C. Crowley, J.A. Zeitler, P. McArdle, A. Erxleben, A comprehensive spectroscopic study of the polymorphs of diflunisal and their phase transformations, Int. J. Pharm. 528(2017) 312-321.

[9] X. Xiong, K. Xu, S. Li, P. Tang, Y. Xiao, H. Li, Solid-state amorphization of rebamipide and investigation on solubility and stability of the amorphous form, Drug Dev. Ind. Pharm. 43(2017) 283-292.

[10] G. He, X. Chen, Y. Yin, W. Cai, W. Ke, Y. Kong, H. Zheng, Preparation and antibacterial properties of O-carboxymethyl chitosan/lincomycin hydrogels, J. Biomater. Sci. Polym. Ed. 27(2016) 370-384.

[11] A. Maher, D.M. Croker, Å.C. Rasmuson, B.K. Hodnett, Solution mediated polymorphic transformation:form Ⅱ to form Ⅲ piracetam in ethanol, Cryst. Growth Des. 12(2012) 6151-6157.

[12] S.A. Kulkarni, E. McGarrity, H. Meekes, J.H. ter Horst, Isonicotinamide selfassociation:The link between solvent and polymorph nucleation, Chem. Commun. 48(2012) 4983-4985.

[13] H. Kitano, T. Tanaka, I. Hirasawa, Study of polymorphic control in an ethanol-water binary solvent, J. Cryst. Growth 469(2017) 54-58.

[14] R. Paus, Y. Ji, Modeling and predicting the influence of variable factors on dissolution of crystalline pharmaceuticals, Chem. Eng. Sci. 145(2016) 10-20.

[15] M. Jim, K.-J. Kim, Solubility of forms I and Ⅱ of clopidogrel hydrogen sulfate in formic acid, N-Methylpyrrolidone, and N,N-dimethylformamide, J. Chem. Eng. Data 57(2012) 598-602.

[16] R. Bonfilio, J.S. Leal, O.M. Santos, G.R. Pereira, A.C. Doriguetto, M.B. de Araújo, Analysis of chlorthalidone polymorphs in raw materials and tablets and the effect of forms I and Ⅱ on the dissolution properties of drug products, J. Pharm. Biomed. Anal. 88(2014) 562-570.

[17] D. Hirai, Y. Iwao, S.-I. Kimura, S. Noguchi, S. Itai, Mathematical model to analyze the dissolution behavior of metastable crystals or amorphous drug accompanied with a solid-liquid interface reaction, Int. J. Pharm. 522(2017) 58-65.

[18] S. Katti, T. Seshadri, M. Viswamitra, Structure and conformation of didodium guanosine-5'-phosphate heptahydrate C10H13N5O8PNa2.7H₂O, Curr. Sci. 49(1980) 533-535.

[19] S. Katti, T. Seshadri, M. Viswamitra, Structure of disodium guanosine 5'-phosphate heptahydrate, Acta Crystallogr. B Struct. Crystallogr. Cryst. Chem. 37(1981) 1825-1832.

[20] B.S. Liu, H. Sun, J.K. Wang, Q.X. Yin, Solubility of disodium 5'-guanylate heptahydrate in aqueous methanol mixtures, Food Chem. 128(2011) 218-221.

[21] R. Zhang, J. Ma, J. Li, Y. Jiang, M. Zheng, Effect of pH, temperature and solvent mole ratio on solubility of disodium 5'-guanylate in water + ethanol system, Fluid Phase Equilib. 303(2011) 35-39.

[22] F. Zou, W. Zhuang, J. Wu, J. Zhou, P. Yang, Q. Liu, Y. Chen, H. Ying, Determination of metastable zone widths and the primary nucleation and growth mechanisms for the crystallization of disodium guanosine 5'-monophosphate from a water-ethanol system, Ind. Eng. Chem. Res. 54(2015) 137-145.

[23] F. Zou, Q. Chen, P. Yang, J. Zhou, J. Wu, W. Zhuang, H. Ying, Solution-mediated polymorphic transformation:From amorphous to crystals of disodium guanosine 5'-monophosphate in ethanol, Ind. Eng. Chem. Res. 56(2017) 8274-8282.

[24] Y. Mo, L. Dang, H. Wei, Solubility of α-form and β-form of L-glutamic acid in different aqueous solvent mixtures, Fluid Phase Equilib. 300(2011) 105-109.

[25] F. Zou, W. Zhuang, J. Wu, J. Zhou, Q. Liu, Y. Chen, J. Xie, C. Zhu, T. Guo, H. Ying, Experimental measurement and modelling of solubility of inosine-5'-monophosphate disodium in pure and mixed solvents, J. Chem. Thermodyn. 77(2014) 14-22.

[26] F. Zou, W. Zhuang, Q. Chen, P. Yang, C. Lin, P. Jiao, J. Zhou, J. Wu, H. Ying, Solvent effects on nucleation of disodium guanosine 5'-monophosphate in anti-solvent/water mixtures, CrystEngComm 18(2016) 6653-6663.

[27] A.-T. Nguyen, J. Kang, W.-S. Kim, Noncommon ion effect on phase transformation of guanosine 5-monophosphate disodium in antisolvent crystallization, Ind. Eng. Chem. Res. 54(2015) 5784-5792.

[28] H. Kamio, H. Nakamachi, Water of crystallization in disodium 5'-inosinate and disodium 5'-guanylate and their mixed crystal formation, Yakugaku zasshi, J. Pharm. Soc. Jpn. 87(1967) 1436-1441.

[29] B. Li, Y. Wu, J. Zhu, K. Chen, B. Wu, L. Ji, Determination and correlation of solubility and mixing properties of isonicotinamide (form Ⅱ) in some pure solvents, Thermochim. Acta 627(2016) 55-60.

[30] Y. Liu, Z.-P. Zhao, J. Cui, G. Ren, Solubility of amorphous clopidogrel hydrogen sulfate in different pure solvents, J. Chem. Eng. Data 60(2015) 2442-2446.

[31] I. Montes, C.Q. Lai, D. Sanabria, Like dissolves like:A classroom demonstration and a guided-inquiry experiment for organic chemistry, J. Chem. Educ. 80(2003) 447-449.

[32] H. Tajmir Riahi, T. Theophanides, A Fourier transform infrared study of the electrophilic attack at the N7-site of guanosine-5'-monophosphate, Can. J. Chem. 62(1984) 266-272.

[33] J. Kang, N.A. Tuan, J.-M. Kim, S.-M. Chang, W.-S. Kim, Study of phase transformation of guanosine 5'-monophosphate in drowning-out crystallization, Appl. Biochem. Biotechnol. 160(2010) 561-573.

[34] A.-T. Nguyen, J. Kang, W.-S. Kim, Influence of salt additives on phase transformation of guanosine 5-monophosphate disodium in anti-solvent crystallization, J. Cryst. Growth 373(2013) 82-87.

[35] G. Kaptay, The Gibbs equation versus the kelvin and the Gibbs-Thomson equations to describe nucleation and equilibrium of nano-materials, J. Nanosci. Nanotechnol. 12(2012) 2625-2633.

[36] C.A. Hunter, J.F. McCabe, A. Spitaleri, Solvent effects of the structures of prenucleation aggregates of carbamazepine, Cryst. Eng. Comm. 14(2012) 7115-7117.

[37] K. Fucke, G.J. McIntyre, M.H. Lemée-Cailleau, C. Wilkinson, A.J. Edwards, J.A. Howard, J.W. Steed, Insights into the crystallisation process from anhydrous, hydrated and solvated crystal forms of diatrizoic acid, Chem. Eur. J. 21(2015) 1036-1047.

[38] L. Yang, Q. Yin, B. Hou, Y. Wang, Y. Bao, J. Wang, H. Hao, Solubility and thermodynamic stability of the enantiotropic polymorphs of 2, 3, 5-trimethyl-1, 4-diacetoxybenzene, Ind. Eng. Chem. Res. 52(2013) 2477-2485.

Transformation of microstructure and phase of disodium guanosine 5'-monophosphate: Thermodynamic perspectives

Transformation of microstructure and phase of disodium guanosine 5'-monophosphate: Thermodynamic perspectives

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