The Journal of the Convergence on Culture Technology (문화기술의 융합)

The International Promotion Agency of Culture Technology (국제문화기술진흥원)
권호 표지
DOI QR코드

DOI QR Code

Theoretical Study on Structural Properties of Triptan Derivatives

트립탄 유도체의 구조적 특성에 관한 이론적 연구

  • Chul Jae Lee (Division of Cosmetics Chemistry, Yeungnam College of Science & Technology) ;
  • Ki Young Nam (Department of Dentistry, College of Medicine, Keimyung University)
  • 이철재 (영남이공대학교 화장품화공계열) ;
  • 남기영 (계명대학교 의과대학 치과학교실)
  • Received : 2023.05.25
  • Accepted : 2023.07.02
  • Published : 2023.07.31
Download PDF
⟨ Previous Next ⟩

Abstract

Tryptane derivatives are substances that treat acute migraines, and many studies have been conducted on analysis methods such as chromatography, electrochemistry, spectroscopy, and capillary electrophysiology. Recently, analytical chemists have become more interested in drug analysis and solving fundamental problems of biological importance. Therefore, in this study, the chemical properties of each derivative were investigated by calculating the total energy, band gap, electrostatic potential, and charge of Sumatriptan, Lizatriptan, Naratriptan, and Eletriptan using HyperChem8.0's semi-empirical PM3 method. As a result of this study, in the case of Sumatriptan, Naratriptan, and Eletriptan, chemical reactions are expected to proceed centering on oxygen and nitrogen atoms bonded to sulfur atoms. In addition, in the case of Rizatriptan without a sulfur atom, it was shown that the chemical reaction proceeds at the 17th and 19th nitrogens of the 5-membered heterocyclic compound.

트립탄 유도체는 급성 편두통을 치료하는 물질로 크로마토그래피, 전기화학, 분광학 및 모세관 전기영동학 등의 분석법과 관련된 연구가 많이 진행되었다. 최근 분석화학자들의 약물 분석과 생물학적 중요성에 대한 근본적인 문제 해결에 더욱 관심이 깊어지고 있다. 따라서 본 연구에서는 트립탄 유도체의 분자단위 수준의 구조적 특성을 알아보기 위하여 HyperChem8.0의 반경험적 PM3 방법을 이용하여 수마트립탄, 리자트립탄, 나라트립탄 그리고 엘레트립탄의 전체에너지, 밴드갭, 정전포텐셜, 전하량을 계산하여 각 유도체의 분자 구조적 변화에 따른 화학적 특성을 조사하였다. 본 연구의 결과 수마트립탄, 나라트립탄 그리고 엘레트립탄의 경우 황 원자에 결합된 산소와 질소 원자를 중심으로 화학작용이 진행될 것으로 예상된다. 또한, 황원자가 없는 리자트립탄의 경우는 5원헤테로 고리화합물의 17, 19번 질소에서 화학작용이 진행될 것으로 나타났다.

Keywords

References

  1. Stewart, W. F., Lipton, R. B., Chee, E., Sawyer, J. and Silberstein, S. D., Menstrual cycle and headache in a population sample of migraineurs. Neurology 55, 1517-1523, (2000). https://doi.org/10.1212/WNL.55.10.1517
  2. Hargraves, R. J. and Shepherd, S. L., Pathophy siology of migraine new insights. Canadian Journal of Neurological Sciences 26, 12-19, (1999). https://doi.org/10.1017/S0317167100000147
  3. Bowers, G. D., Clegg, C. P., Hughes, S. C., Harker, A. J. and Lambert, S., Automated SPE and tandem MS without HPLC columns for quantifying drugs at the picogram level. LC GC 15, 48-53, (1997).
  4. Kerns, E. H., Rourick, R. A., Volk, K. J. and Lee, M. S., Buspirone metabolite structure profile using a standard liquid chromatographicmass spectrometric protocol. Journal of Chro matography B, Biomedical Sciences and Applications, 698, 133-145, (1997). https://doi.org/10.1016/S0378-4347(97)00254-5
  5. Dear, G. J., Harrelson, J.C., Jones, A. E., Johnson, T. E. and S. Pleasance, Identification of the urinary and biliary conjugated metabolites of the neuromuscular blocker 51W89 by liquid chromatography/ mass spectrometry. Rapid Communications in Mass Spectrometry, 9, 1457-1464, (1995). https://doi.org/10.1002/rcm.1290091425
  6. Mogili, R., Kanala, K., Challa, B. R., Chandu, B. R. and Bannoth,C. K., Chromatographia, 74, 585, (2011).
  7. Stanislav, R., Ondrej, K., Robert, K and Jaroslav, H. New Synthesis of Rizatriptan Based on Radical Cyclization, Collect. Czech. Chem. Commun,.73, 1, 116-126, (2008). https://doi.org/10.1135/cccc20080116
  8. Muthumariappan, A. Sakthivel, K. Chen, S. M. Chen, T. W. Elgorban, A. M. Elshikhc, M. S. and Marraiki, N., Evaluating an effective electrocatalyst for the rapid determination of triptan drug (Maxaltt) from (mono and binary) transition metal (Co, Mn, CoMn, MnCo) oxides via electrochemical approaches, New J. Chem., 44, 605~613, (2020). DOI: 10.1039/c9nj04462k
  9. Dunne, M. and Andrew, P., Fully automated assay for the determination of sumatriptan in human serum using solid-phase extraction and high-performance liquid chromatography with electrochemical detection. Journal of Pharma ceutical and Biomedical Analysis 14, 721-726, (1996). https://doi.org/10.1016/0731-7085(95)01688-0
  10. Shields, K.G., Goadsby, P.J., Serotonin receptors modulate trigeminovascular responses in ventro posteromedial nucleus of thalamus: a migraine target? Neurobiol Dis, 23, 491-501, (2006). https://doi.org/10.1016/j.nbd.2006.04.003
  11. Bartsch, T., Knight, Y.E., Goadsby, P.J., Activation of 5-HT(1B/1D) receptor in the periaqueductal gray inhibits nociception. Ann Neurol, 56, 371-81. (2004) https://doi.org/10.1002/ana.20193
  12. Silberstein, S.D., Elkind, A.H., Schreiber, C., Keywood, C., A randomized trial of frovatriptan for the intermittent prevention of menstrual migraine. Neurology, 63, 261-9, (2004). https://doi.org/10.1212/01.WNL.0000134620.30129.D6
  13. Adelman, J.U., Calhoun. A., A randomized trial of frovatriptan for the intermittent prevention of menstrual migraine. Neurology, 64, 931, (2005).
  14. Stewart, J.P., J. Comput. Chem. 10, (2), 209 (1989).
  15. HyperChem, Molecular visualization and imulation program package, Hypercube, Gainsville, Fl. (1995~2011).
  16. Lee, C.J., Choi, J.W., Jang, W.G., Theoretical Studies on the Electrical Characteristics of the Anthocyanin Derivatives, JCCT, 4, (4), (343~348).
  17. Lee, C.J., Kim, J.M.Theoretical Study on the Selective Reduction of Chiral [2-(diphenyl hydroxy-methyl)pyrrolidine]-AlH Derivatives and Aromatic Ketone, JCCT, 7, (2), (389~394)
  18. Laliwala1, S. K., Mehta1, V. N., Rohit1, J. V. Kailasa, S. K., Citrate-modified silver nanoparticles as a colorimetric probe forsimultaneous detection of four triptan-family drugs, Sensors and Actuators B 197, 254~263, (2014). http://dx.doi.org/10.1016/j.snb.2014.02.087