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Simultaneous Determination of Cysteamine and Cystamine in Cosmetics by Ion-Pairing Reversed-Phase High-Performance Liquid Chromatography

  • Kim, Yejin (College of Pharmacy, Chung-Ang University) ;
  • Na, Dong Hee (College of Pharmacy, Chung-Ang University)
  • Received : 2019.02.21
  • Accepted : 2019.03.10
  • Published : 2019.04.15

Abstract

Cysteamine has been used in cosmetics as an antioxidant, a hair straightening agent, and a hair waving agent. However, recent studies indicate that cysteamine can act as an allergen to hairdressers. The objective of this study was to develop and validate a simple and effective reversed-phase high-performance liquid chromatography (RP-HPLC) method for the measurement of cysteamine and its dimer, cystamine. Sodium 1-heptanesulfonate (NaHpSO) was used as an ion-pairing agent to improve chromatographic performance. Separation was performed on a Gemini C18 column ($250mm{\times}4.6mm$, $5{\mu}m$ particle size) using a mobile phase composed of 85:15 (v/v) 4 mM NaHpSO in 0.1% phosphoric acid:acetonitrile. UV absorbance was monitored at 215 nm. The RP-HPLC method developed in this study was validated for specificity, linearity, limit of detection, limit of quantitation, precision, accuracy, and recovery. Cysteamine and cystamine were chromatographically resolved from other reducing agents such as thioglycolic acid and cysteine. Extraction using water and chloroform resulted in the recovery for cysteamine and cystamine ranging from 100.2-102.7% and 90.6-98.7%, respectively. This validated RP-HPLC method would be useful for quality control and monitoring of cysteamine and cystamine in cosmetics.

Keywords

References

  1. Coloso, R.M., Hirschberger, L.L., Dominy, J.E., Lee, J.I. and Stipanuk, M.H. (2006) Cysteamine dioxygenase: evidence for the physiological conversion of cysteamine to hypotaurine in rat and mouse tissues. Adv. Exp. Med. Biol., 583, 25-36. https://doi.org/10.1007/978-0-387-33504-9_3
  2. Besouw, M., Masereeuw, R., van den Heuvel, L. and Levtchenko, E. (2013) Cysteamine: an old drug with new potential. Drug Discov. Today, 18, 785-792. https://doi.org/10.1016/j.drudis.2013.02.003
  3. Charrier, C., Rodger, C., Robertson, J., Kowalczuk, A., Shand, N., Fraser-Pitt, D., Mercer, D. and O'Neil, D. (2014) Cysteamine (Lynovex(R)), a novel mucoactive antimicrobial & antibiofilm agent for the treatment of cystic fibrosis. Orphanet J. Rare Dis., 9, 189. https://doi.org/10.1186/s13023-014-0189-2
  4. Medic, G., van der Weijden, M., Karabis, A. and Hemels, M. (2017) A systematic literature review of cysteamine bitartrate in the treatment of nephropathic cystinosis. Curr. Med. Res. Opin., 33, 2065-2076. https://doi.org/10.1080/03007995.2017.1354288
  5. Marks, J.G., Jr., Belsito, D.V., DeLeo, V.A., Fowler, J.F., Jr., Fransway, A.F., Maibach, H.I., Mathias, C.G., Pratt, M.D., Rietschel, R.L., Sherertz, E.F., Storrs, F.J. and Taylor, J.S. (2000) North American Contact Dermatitis Group patch-test results, 1996-1998. Arch. Dermatol., 136, 272-273. https://doi.org/10.1001/archderm.136.2.272
  6. Landers, M.C., Law, S. and Storrs, F.J. (2003) Permanentwave dermatitis: contact allergy to cysteamine hydrochloride. Am. J. Contact Dermat., 14, 157-160.
  7. Uter, W., Bensefa-Colas, L., Frosch, P., Gimenez-Arnau, A., John, S.M., Lepoittevin, J.P., Liden, C., White, I.R. and Duus Johansen, J. (2015) Patch testing with hair cosmetic series in Europe: a critical review and recommendation. Contact Derm., 73, 69-81. https://doi.org/10.1111/cod.12424
  8. Nishioka, K., Koizumi, A. and Takita, Y. (2019) Allergic contact dermatitis caused by cysteamine hydrochloride in permanent wave agent-A new allergen for hairdressers in Japan. Contact Derm., 80, 174-175. https://doi.org/10.1111/cod.13150
  9. Kusmierek, K., Chwatko, G., Glowacki, R. and Bald, E. (2009) Determination of endogenous thiols and thiol drugs in urine by HPLC with ultraviolet detection. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 877, 3300-3308. https://doi.org/10.1016/j.jchromb.2009.03.038
  10. Garcia, A.J. and Apitz-Castro, R. (2002) Plasma total homocysteine quantification: an improvement of the classical high-performance liquid chromatographic method with fluorescence detection of the thiol-SBD derivatives. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 779, 359-363. https://doi.org/10.1016/S1570-0232(02)00401-4
  11. Ichinose, S., Nakamura, M., Maeda, M., Ikeda, R., Wada, M., Nakazato, M., Ohba, Y., Takamura, N., Maeda, T., Aoyagi, K. and Nakashima, K. (2009) A validated HPLC-fluorescence method with a semi-micro column for routine determination of homocysteine, cysteine and cysteamine, and the relation between the thiol derivatives in normal human plasma. Biomed. Chromatogr., 23, 935-939. https://doi.org/10.1002/bmc.1205
  12. Kusmierek, K. and Bald, E. (2008) Measurement of reduced and total mercaptamine in urine using liquid chromatography with ultraviolet detection. Biomed. Chromatogr., 22, 441-445. https://doi.org/10.1002/bmc.959
  13. Kusmierek, K., Chwatko, G., Glowacki, R., Kubalczyk, P. and Bald, E. (2011) Ultraviolet derivatization of low-molecular-mass thiols for high performance liquid chromatography and capillary electrophoresis analysis. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 879, 1290-1307. https://doi.org/10.1016/j.jchromb.2010.10.035
  14. Kataoka, H., Imamura, Y., Tanaka, H. and Makita, M. (1993) Determination of cysteamine and cystamine by gas chromatography with flame photometric detection. J. Pharm. Biomed. Anal., 11, 963-969. https://doi.org/10.1016/0731-7085(93)80056-7
  15. Kataoka, H., Tanaka, H. and Makita, M. (1994) Determination of total cysteamine in urine and plasma samples by gas chromatography with flame photometric detection. J. Chromatogr. B, Biomed. Appl., 657, 9-13. https://doi.org/10.1016/0378-4347(94)80063-4
  16. ICH (2005) ICH Harmonised Tripartite Guideline Q2(R1):Validationof Analytical Procedures, ICH, Geneva.
  17. Park, E.J., Na, D.H., Shin, Y.H. and Lee, K.C. (2008) Liquid chromatography-mass spectrometric method for the sensitive determination of niflumic acid in human plasma and its application to pharmacokinetic study of talniflumate tablet. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 876, 159-162. https://doi.org/10.1016/j.jchromb.2008.10.010
  18. Yoon, J., Kim, Y., Kim, K.B., Park, E.J. and Na, D.H. (2018) Reversed-phase high-performance liquid chromatographic method for the determination of Permaton Red (D&C Red No. 36) in cosmetics. Bull. Korean Chem. Soc., 39, 1219-1222. https://doi.org/10.1002/bkcs.11567
  19. Park, E.J., Kim, M.S., Choi, Y.L., Shin, Y.H., Lee, H.S. and Na, D.H. (2012) Liquid chromatography-tandem mass spectrometry to determine the stability of collagen pentapeptide (KTTKS) in rat skin. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 905, 113-117. https://doi.org/10.1016/j.jchromb.2012.08.010
  20. Isaksson, M. and van der Walle, H. (2007) Occupational contact allergy to cysteamine hydrochloride in permanentwave solutions. Contact Derm., 56, 295-296. https://doi.org/10.1111/j.1600-0536.2006.01019.x