Research Article
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Year 2024, , 889 - 898, 15.05.2024
https://doi.org/10.18596/jotcsa.1369980

Abstract

References

  • 1. McGinity JW. Drug Stability: Principles and Practices. Journal of Pharmaceutical Sciences. 1991;80(1):98.
  • 2. Ohannesian L, Streeter A. Handbook of pharmaceutical analysis: CRC Press; 2001.
  • 3. Fiese E, Hagen T. Preformulation In: The Theory and Practice of Industrial Pharmacy. Lachman L, Lieberman HA, Kanig JL. Varghese Publishing House; 1990.
  • 4. Wadke DA, Serajuddin AT, Jacobson H. Preformulation testing. Pharmaceutical dosage forms: Tablets. 1989; 1:1-73.
  • 5. Carstensen JT. Pharmaceutical preformulation: crc Press; 1998.
  • 6. Gibson M. Pharmaceutical preformulation and formulation. Drugs the pharmaceutical sciences. 2001; 199:199.
  • 7. Adeyeye MC, Brittain H. Drug-excipient interaction occurrences during solid dosage form development. THE PHARMACEUTICAL SCIENCES. 2008; 178:357.
  • 8. Leite RS, Macedo RO, Torres SM, Batista CCN, Baltazar LO, Neto SL, et al. Evaluation of thermal stability and parameters of dissolution of nifedipine crystals. Journal of thermal analysis calorimetry. 2013;111(3):2117-23.
  • 9. Kocevska S, Maggioni GM, Crouse SH, Prasad R, Rousseau RW, Grover MA. Effect of ion interactions on the Raman spectrum of NO3−: Toward monitoring of low-activity nuclear waste at Hanford. Chemical Engineering Research Design. 2022; 181:173-94.
  • 10. Lagerman CE, Grover MA, Rousseau RW, Bommarius AS. Reactor Design and Optimization of α-Amino Ester Hydrolase-Catalyzed Synthesis of Cephalexin. Frontiers in Bioengineering Biotechnology. 2022;10.
  • 11. Wiesław W, Krystyna S, Cezary C, Leszek Ł, Alicja M. Photophysical properties of (p-hydroxy) phenylglycine. Journal of Photochemistry Photobiology A: Chemistry. 1997;102(2-3):189-95.
  • 12. Kaneko I, Fearon DT, Austen K. Inhibition of the alternative pathway of human complement in vitro by a natural microbial product, complestatin. Journal of immunology. 1980;124(3):1194-8.
  • 13. Báthori NB, Bourne SA. Crystal Structure of D (−)-amino-(4-hydroxyphenyl) acetate, the Zwitter Ionic Form of Biologically Active D (−)-4-hydroxyphenylglycine. Journal of Chemical Crystallography. 2009; 39:539-43.
  • 14. Li S, Cao M, Li Y, Yang J, Zhao M, Song H. Three pairs of Pb (II), Cd (II) and Cu (II) enantiomeric coordination compounds based on D-(−)-and L-(+)-4-Hydroxyphenylglycine: Synthesis, structures and properties. Journal of Molecular Structure. 2022; 1255:132451.
  • 15. Zhong Q-S, Xia W-Y, Liu B-C, Xu C-W, Li N. Co0. 85Se on three-dimensional hierarchical porous graphene-like carbon for highly effective oxygen evolution reaction. International Journal of Hydrogen Energy. 2019;44(21):10182-9.
  • 16. Mostaghasi E, Zarepour A, Zarrabi A. Folic acid armed Fe3O4-HPG nanoparticles as a safe nano vehicle for biomedical theranostics. Journal of the Taiwan Institute of Chemical Engineers. 2018; 82:33-41.
  • 17. Liu B-C, Chen S-L, Ling X-Y, Li Q-X, Xu C-W, Liu Z-L. High activity of NiCo 2 O 4 promoted Pt on three-dimensional graphene-like carbon for glycerol electrooxidation in an alkaline medium. RSC advances. 2020;10(41):24705-11.
  • 18. He Y, Cheng Z, Qin Y, Xu B, Ning L, Zhou L. Facile synthesis and functionalization of hyperbranched polyglycerol capped magnetic Fe3O4 nanoparticles for efficient dye removal. Materials Letters. 2015; 151:100-3.
  • 19. Kosmidis J, Williams J, Andrews J, Goodall J, Geddes A. Amoxycillin-pharmacology, bacteriology and clinical studies. Brit J Clin Practice. 1972;26(7):341-6.
  • 20. Chen C-X, Wu Q, Liu B-K, Lv D-S, Lin X-F. Anhydrous tert-pentanol as a novel media for the efficient enzymatic synthesis of amoxicillin. Enzyme microbial technology. 2008;42(7):601-7.
  • 21. Youshko MI, Moody HM, Bukhanov AL, Boosten WH, Švedas VK. Penicillin acylase‐catalyzed synthesis of β‐lactam antibiotics in highly condensed aqueous systems: Beneficial impact of kinetic substrate supersaturation: Biotechnology bioengineering. 2004;85(3):323-9.
  • 22. Giron D, Goldbronn C, Mutz M, Pfeffer S, Piechon P, Schwab P. Solid state characterizations of pharmaceutical hydrates. Journal of thermal analysis calorimetry. 2002; 68:453-65.
  • 23. Ergin M. Purification of amoxicillin trihydrate in the presence of degradation products by different washing methods. CrystEngComm. 2021;23(46):8121-30.
  • 24. ERGİN M. Yıkama Metodu Kullanılarak Saflaştırılan Amoksisilin Trihidratın Taguchi Yöntemi ile Optimizasyonu. Journal of the Institute of Science Technology. 2022;12(2):933-45.
  • 25. Hsi KH, Kenny M, Simi A, Myerson AS. Purification of structurally similar compounds by the formation of impurity co-former complexes in solution. Crystal growth design. 2013;13(4):1577-82.
  • 26. Hsi KHY, Concepcion AJ, Kenny M, Magzoub AA, Myerson AS. Purification of amoxicillin trihydrate by impurity-coformer complexation in solution. CrystEngComm. 2013;15(34):6776-81.
  • 27. YAŞA H. Synthesis, characterization, and evaluation of antioxidant activity of new $\gamma $-and $\delta $-imino esters. Turkish Journal of Chemistry. 2018;42(4):1105-12.
  • 28. Onar HÇ, Vardar BA. Synthesis and antioxidant activity of novel 8-formyl-4-substitued coumarins. Bulletin of the Chemical Society of Ethiopia. 2018;32(1):175-8.
  • 29. YAŞA H, Ergin MF, ERGİN A, ALKAN G. Importance of inert gases for chemical transportation. Proceedings Book. 2016:825.
  • 30. Ergin M, Yasa H. Determination of amoxicillin trihydrate impurities 4-HPG and 6-APA by means of ultraviolet spectroscopy. Methods Applications in Fluorescence. 2022.
  • 31. Celik Onar H, Ergin MF, Yasa H. Investigating the Role of Citric Acid as a Natural Acid on the Crystallization of Amoxicillin Trihydrate. ACS Omega. 2023;8(39):36344-54.
  • 32. Nugrahani I, Asyarie S, Soewandhi SN, Ibrahim S. Solid state interaction between amoxicillin trihydrate and potassium Clavulanate. Malays J Pharm Sci. 2007;5(1):45-57.
  • 33. Bisson-Boutelliez C, Fontanay S, Finance C, Kedzierewicz F. Preparation and physicochemical characterization of amoxicillin β-cyclodextrin complexes. Aaps Pharmscitech. 2010; 11:574-81.
  • 34. Bhattacharya A, Araullo-Mcadams C, Meier MB. Crystallization induced asymmetric transformation: synthesis of Dp-hydroxyphenylglycine. Synthetic communications. 1994;24(17):2449-59.
  • 35. Fogazzi GB, Cantu M, Saglimbeni L, Daudon M. Amoxycillin, a rare but possible cause of crystalluria. Nephrology Dialysis Transplantation. 2003;18(1):212-4.
  • 36. Yokozeki K, Nakamori S, Eguchi C, Yamada K, Mitsugi K. Screening of Microorganisms Producing d-p-Hydroxyphenyl-glycine from Dl-5-(-Hydroxyphenyty) hydantoin. Agricultural biological chemistry. 1987;51(2):355-62.
  • 37. Bhat SA, Ahmad SJJoMS. FTIR, FT-Raman and UV–Vis spectral studies of d-tyrosine molecule. 2016; 1105:169-77.
  • 38. Feng S, Shan N, Carpenter KJ. Crystallization of amoxicillin trihydrate in the presence of degradation products. Organic process research development. 2006;10(6):1212-8.
  • 39. Pharmacopeia U. USP 39-NF34. The United States Pharmacopeial. 2016.

Investigation of Thermodynamic and Morphological Properties of Crystalline 4-HPG (4-hydroxyphenylglycine) Using Raman, PXRD and DTA/TGA

Year 2024, , 889 - 898, 15.05.2024
https://doi.org/10.18596/jotcsa.1369980

Abstract

This study focuses on the detailed physical characterization of 4-HPG, a significant impurity found in some of the most commonly prescribed β-lactam antibiotics worldwide. Various analytical techniques, including X-ray powder diffractometry, dynamic light scattering, scanning electron microscopy, Fourier-transform infrared, and Raman spectroscopy, were employed to characterize the properties of 4-HPG crystals. XRD analysis revealed the crystallinity and small crystallite sizes of 4-HPG particles, supported by DLS and SEM analyses. FT-IR and Raman spectroscopy results exhibited excellent agreement, providing insight into the structural characterization of 4-HPG. Thermal analysis revealed a two-stage degradation feature of 4-HPG. Overall, this study contributes to a better understanding of 4-HPG's structure and its impact on antibiotic stability.

References

  • 1. McGinity JW. Drug Stability: Principles and Practices. Journal of Pharmaceutical Sciences. 1991;80(1):98.
  • 2. Ohannesian L, Streeter A. Handbook of pharmaceutical analysis: CRC Press; 2001.
  • 3. Fiese E, Hagen T. Preformulation In: The Theory and Practice of Industrial Pharmacy. Lachman L, Lieberman HA, Kanig JL. Varghese Publishing House; 1990.
  • 4. Wadke DA, Serajuddin AT, Jacobson H. Preformulation testing. Pharmaceutical dosage forms: Tablets. 1989; 1:1-73.
  • 5. Carstensen JT. Pharmaceutical preformulation: crc Press; 1998.
  • 6. Gibson M. Pharmaceutical preformulation and formulation. Drugs the pharmaceutical sciences. 2001; 199:199.
  • 7. Adeyeye MC, Brittain H. Drug-excipient interaction occurrences during solid dosage form development. THE PHARMACEUTICAL SCIENCES. 2008; 178:357.
  • 8. Leite RS, Macedo RO, Torres SM, Batista CCN, Baltazar LO, Neto SL, et al. Evaluation of thermal stability and parameters of dissolution of nifedipine crystals. Journal of thermal analysis calorimetry. 2013;111(3):2117-23.
  • 9. Kocevska S, Maggioni GM, Crouse SH, Prasad R, Rousseau RW, Grover MA. Effect of ion interactions on the Raman spectrum of NO3−: Toward monitoring of low-activity nuclear waste at Hanford. Chemical Engineering Research Design. 2022; 181:173-94.
  • 10. Lagerman CE, Grover MA, Rousseau RW, Bommarius AS. Reactor Design and Optimization of α-Amino Ester Hydrolase-Catalyzed Synthesis of Cephalexin. Frontiers in Bioengineering Biotechnology. 2022;10.
  • 11. Wiesław W, Krystyna S, Cezary C, Leszek Ł, Alicja M. Photophysical properties of (p-hydroxy) phenylglycine. Journal of Photochemistry Photobiology A: Chemistry. 1997;102(2-3):189-95.
  • 12. Kaneko I, Fearon DT, Austen K. Inhibition of the alternative pathway of human complement in vitro by a natural microbial product, complestatin. Journal of immunology. 1980;124(3):1194-8.
  • 13. Báthori NB, Bourne SA. Crystal Structure of D (−)-amino-(4-hydroxyphenyl) acetate, the Zwitter Ionic Form of Biologically Active D (−)-4-hydroxyphenylglycine. Journal of Chemical Crystallography. 2009; 39:539-43.
  • 14. Li S, Cao M, Li Y, Yang J, Zhao M, Song H. Three pairs of Pb (II), Cd (II) and Cu (II) enantiomeric coordination compounds based on D-(−)-and L-(+)-4-Hydroxyphenylglycine: Synthesis, structures and properties. Journal of Molecular Structure. 2022; 1255:132451.
  • 15. Zhong Q-S, Xia W-Y, Liu B-C, Xu C-W, Li N. Co0. 85Se on three-dimensional hierarchical porous graphene-like carbon for highly effective oxygen evolution reaction. International Journal of Hydrogen Energy. 2019;44(21):10182-9.
  • 16. Mostaghasi E, Zarepour A, Zarrabi A. Folic acid armed Fe3O4-HPG nanoparticles as a safe nano vehicle for biomedical theranostics. Journal of the Taiwan Institute of Chemical Engineers. 2018; 82:33-41.
  • 17. Liu B-C, Chen S-L, Ling X-Y, Li Q-X, Xu C-W, Liu Z-L. High activity of NiCo 2 O 4 promoted Pt on three-dimensional graphene-like carbon for glycerol electrooxidation in an alkaline medium. RSC advances. 2020;10(41):24705-11.
  • 18. He Y, Cheng Z, Qin Y, Xu B, Ning L, Zhou L. Facile synthesis and functionalization of hyperbranched polyglycerol capped magnetic Fe3O4 nanoparticles for efficient dye removal. Materials Letters. 2015; 151:100-3.
  • 19. Kosmidis J, Williams J, Andrews J, Goodall J, Geddes A. Amoxycillin-pharmacology, bacteriology and clinical studies. Brit J Clin Practice. 1972;26(7):341-6.
  • 20. Chen C-X, Wu Q, Liu B-K, Lv D-S, Lin X-F. Anhydrous tert-pentanol as a novel media for the efficient enzymatic synthesis of amoxicillin. Enzyme microbial technology. 2008;42(7):601-7.
  • 21. Youshko MI, Moody HM, Bukhanov AL, Boosten WH, Švedas VK. Penicillin acylase‐catalyzed synthesis of β‐lactam antibiotics in highly condensed aqueous systems: Beneficial impact of kinetic substrate supersaturation: Biotechnology bioengineering. 2004;85(3):323-9.
  • 22. Giron D, Goldbronn C, Mutz M, Pfeffer S, Piechon P, Schwab P. Solid state characterizations of pharmaceutical hydrates. Journal of thermal analysis calorimetry. 2002; 68:453-65.
  • 23. Ergin M. Purification of amoxicillin trihydrate in the presence of degradation products by different washing methods. CrystEngComm. 2021;23(46):8121-30.
  • 24. ERGİN M. Yıkama Metodu Kullanılarak Saflaştırılan Amoksisilin Trihidratın Taguchi Yöntemi ile Optimizasyonu. Journal of the Institute of Science Technology. 2022;12(2):933-45.
  • 25. Hsi KH, Kenny M, Simi A, Myerson AS. Purification of structurally similar compounds by the formation of impurity co-former complexes in solution. Crystal growth design. 2013;13(4):1577-82.
  • 26. Hsi KHY, Concepcion AJ, Kenny M, Magzoub AA, Myerson AS. Purification of amoxicillin trihydrate by impurity-coformer complexation in solution. CrystEngComm. 2013;15(34):6776-81.
  • 27. YAŞA H. Synthesis, characterization, and evaluation of antioxidant activity of new $\gamma $-and $\delta $-imino esters. Turkish Journal of Chemistry. 2018;42(4):1105-12.
  • 28. Onar HÇ, Vardar BA. Synthesis and antioxidant activity of novel 8-formyl-4-substitued coumarins. Bulletin of the Chemical Society of Ethiopia. 2018;32(1):175-8.
  • 29. YAŞA H, Ergin MF, ERGİN A, ALKAN G. Importance of inert gases for chemical transportation. Proceedings Book. 2016:825.
  • 30. Ergin M, Yasa H. Determination of amoxicillin trihydrate impurities 4-HPG and 6-APA by means of ultraviolet spectroscopy. Methods Applications in Fluorescence. 2022.
  • 31. Celik Onar H, Ergin MF, Yasa H. Investigating the Role of Citric Acid as a Natural Acid on the Crystallization of Amoxicillin Trihydrate. ACS Omega. 2023;8(39):36344-54.
  • 32. Nugrahani I, Asyarie S, Soewandhi SN, Ibrahim S. Solid state interaction between amoxicillin trihydrate and potassium Clavulanate. Malays J Pharm Sci. 2007;5(1):45-57.
  • 33. Bisson-Boutelliez C, Fontanay S, Finance C, Kedzierewicz F. Preparation and physicochemical characterization of amoxicillin β-cyclodextrin complexes. Aaps Pharmscitech. 2010; 11:574-81.
  • 34. Bhattacharya A, Araullo-Mcadams C, Meier MB. Crystallization induced asymmetric transformation: synthesis of Dp-hydroxyphenylglycine. Synthetic communications. 1994;24(17):2449-59.
  • 35. Fogazzi GB, Cantu M, Saglimbeni L, Daudon M. Amoxycillin, a rare but possible cause of crystalluria. Nephrology Dialysis Transplantation. 2003;18(1):212-4.
  • 36. Yokozeki K, Nakamori S, Eguchi C, Yamada K, Mitsugi K. Screening of Microorganisms Producing d-p-Hydroxyphenyl-glycine from Dl-5-(-Hydroxyphenyty) hydantoin. Agricultural biological chemistry. 1987;51(2):355-62.
  • 37. Bhat SA, Ahmad SJJoMS. FTIR, FT-Raman and UV–Vis spectral studies of d-tyrosine molecule. 2016; 1105:169-77.
  • 38. Feng S, Shan N, Carpenter KJ. Crystallization of amoxicillin trihydrate in the presence of degradation products. Organic process research development. 2006;10(6):1212-8.
  • 39. Pharmacopeia U. USP 39-NF34. The United States Pharmacopeial. 2016.
There are 39 citations in total.

Details

Primary Language English
Subjects Instrumental Methods
Journal Section RESEARCH ARTICLES
Authors

Mustafa Ergin 0000-0003-4158-368X

Publication Date May 15, 2024
Submission Date October 2, 2023
Acceptance Date March 25, 2024
Published in Issue Year 2024

Cite

Vancouver Ergin M. Investigation of Thermodynamic and Morphological Properties of Crystalline 4-HPG (4-hydroxyphenylglycine) Using Raman, PXRD and DTA/TGA. JOTCSA. 2024;11(2):889-98.