New spectrofluorimetric methods for determination of melatonin in the presence ofN-{2-[1-({3-[2-(acetylamino)ethyl]-5-methoxy-1H-indol-2-yl}methyl)-5-methoxy-1H-indol-3-yl]-ethyl}acetamide: a contaminant in commercial melatonin preparations

Chemistry Central Journal

Mohamed I Attia²  Hany W Darwish¹ 

[1]Department of Analytical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street,ET, 11562, Cairo, Egypt

[2]Department of Pharmaceutical Chemistry, Institute of Pharmacy and Food Chemistry, WürzburgUniversity, Am Hubland, 97074, Würzburg, Germany

关键词: Commercial preparations;    Spectrofluorimetry;    Synthesis;    Contaminants;    Melatonin;   

Others  :  788356
DOI  :  10.1186/1752-153X-6-36

 received in 2012-01-24, accepted in 2012-05-02,  发布年份 2012

【 摘 要 】

Background

Melatonin (MLT) has many health implications, therefore it is of valuable importance to develop specific analytical methods for determination of MLT in the presence of its main contaminant, N-{2-[1-({3-[2-(acetylamino)ethyl]-5-methoxy-1H-indol-2-yl}methyl)-5-methoxy-1H-indol-3-yl]ethyl}acetamide (10). For development of these analytical methods, compound 10 had to be prepared in an adequate amount.

Results

Compound 10 was synthesized in six steps starting from 5-methoxyindole-2-carboxylic acid (1). Analytical performance of the proposed spectrofluorimetric methods was statistically validated with respect to linearity, accuracy, precision and specificity. The proposed methods were successfully applied for the assay of MLT in laboratory prepared mixtures containing up to 60 % of compound 10 and in commercial MLT tablets with recoveries not less than 99.00 %. No interference was observed from common pharmaceutical additives and the results were favorably compared with those obtained by a reference method.

Conclusions

This work describes simple, sensitive, and reliable second derivative spectrofluorimetric method in addition to two multivariate calibration methods, principal component regression (PCR) and partial least square (PLS), for the determination of MLT in the presence of compound 10.

【 授权许可】

   
2012 Darwish and Attia; licensee Chemistry Central Ltd.

【 图 表 】

Figure 1.

Scheme 1

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【 参考文献 】

• [1]Csernus V, Mess B: Biorhythms and pineal gland. Neuroendocrinol Lett 2003, 24:404-411.
• [2]Nosjean O, Ferro M, Coge F, Beauverger P, Henlin J-M, Lefoulon F, Fauchere J-L, Delagrange P, Canet E, Boutin JA: Identification of the Melatonin-binding SiteMT3 as the Quinone Reductase 2. J Biol Chem 2000, 275:31311-31317.
• [3]Genovese T, Mazzon E, Muia C, Bramanti P, De Sarro A, Cuzzocrea S: Attenuation in the evolution of experimental spinal cord trauma by treatment with melatonin. J Pineal Res 2005, 38:198-208.
• [4]Peres MFP: Melatonin, the pineal gland and their implications for headache disorders. Cephalalgia 2005, 25:403-411.
• [5]Witt-Enderby PA, Radio NM, Doctor JS, Davis VL: Therapeutic treatments potentially mediated by melatonin receptors: potential clinical uses in the prevention of osteoporosis, cancer and as an adjuvant therapy. J Pineal Res 2006, 41:297-305.
• [6]Blask DE, Sauer LA, Dauchy RT: Melatonin as a Chronobiotic/Anticancer Agent: Cellular, Biochemical, and Molecular Mechanisms of Action and their Implications for Circadian-Based Cancer Therapy. Curr Top Med Chem 2002, 2:113-132.
• [7]Mills E, Wu P, Seely D, Guyatt G: Melatonin in the treatment of cancer: a systematic review of randomized controlled trials and meta-analysis. J Pineal Res 2005, 39:360-366.
• [8]Sofic E, Rimpapa Z, Kundurovic Z, Sapcanin A, Tahirovic I, Rustembegovic A, Cao G: Antioxidant capacity of the neurohormone melatonin. J Neural Transm 2005, 112:349-358.
• [9]Swygert LA, Back EE, Auerbach SB, Sewell LE, Falk H: Oesinophilia-myalgia syndrome case-associated contaminants in commercially available 5-hydroxytryptophane. J Rheumatol 1993, 20:1711-1717.
• [10]Lissoni P, Ardizzoia A, Tisi E, Rossini F, Barni S, Tancici G, Conti A, Maestroni GJ: Amplification of eosinophilia by melatonin during the immunotherapy of cancer with interleukin-2. J Biol Regul Homeost Agents 1993, 7:34-36.
• [11]Lissoni P, Barni S, Tancini G, Rovelli F, Ardizzoia A, Conti A, Maestroni GJ: A study of the mechanisms involved in the immunostimulatory action of the pineal hormone in cancer patients. Oncology 1993, 50:399-402.
• [12]Williamson BL, Tomlinson AJ, Mishra PK, Gleich GJ, Naylor S: Structural Characterization of Contaminants Found in Commercial Preparations of Melatonin: Similarities to Case-Related Compounds from l-Tryptophan Associated with Eosinophilia-Myalgia Syndrome. Chem Res Toxicol 1998, 11:234-240.
• [13]Murillo JA, García LF: Application of First Derivative Fluorescence Spectrometry to the Simultaneous Determination of Paracetamol and Salicylamide in Pharmaceuticals. Anal Lett 1996, 29:423-438.
• [14]Ni Y, Gong X: Simultaneous spectrophotometric determination of mixtures of food colorants. Anal Chem Acta 1997, 354:163-171.
• [15]Brereton RG: Multilevel multifactor designs for multivariate calibration. Analyst 1997, 122:1521-1529.
• [16]Kramer R: Chemometric techniques for quantitative analysis. Marcel Dekker Inc, New York; 1998.
• [17]Haland DM, Thomas EV: Partial least-squares methods for spectral analyses. 2. Application to simulated and glass spectral data. Anal Chem 1988, 60:1202-1208.
• [18]Gangjee A, Vasudevan A, Queener SF: Synthesis and Biological Evaluation of Nonclassical 2,4-Diamino-5-methylpyrido[2,3-d]pyrimidines with Novel Side Chain Substituents as Potential Inhibitors of Dihydrofolate Reductases. J Med Chem 1997, 40:479-485.
• [19]Lakatosh SA, Luzikov YN, Preobrazhenskaya MN: Synthesis of 6H-pyrrolo[3′,4′:2,3] [1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold. Org Biomol Chem 2003, 1:826-833.
• [20]Attia MI, Witt-Enderby PA, Julius J: Synthesis and pharmacological evaluation of pentacyclic 6a,7-dihydrodiindole and 2,3-dihydrodiindole derivatives as novel melatoninergic ligands. Bioorg Med Chem 2008, 16:7654-7661.
• [21]Bartoli G, Bosco M, Dalpozzo R, Marcantoni E, Massaccesi M, Sambri L: Zn(ClO4)2·6H2O as a Powerful Catalyst for a Practical Acylation of Alcohols with Acid Anhydrides. Eur J Org Chem 2003, 2003:4611-4617.
• [22]Sorouraddin MH, Rashidi MR, Kalhor EG, Zeynali KA: Simultaneous spectrofluorimetric and spectrophotometric determination of melatonin and pyridoxine in pharmaceutical preparations by multivariate calibration methods. Il Farmaco 2005, 60:451-458.
• [23]ICH: Validation of Analytical procedures: Methodology (Q2AR1). International Conference on Harmonization, Food and Drug Administration, USA; . November 1996 and November 2005
• [24]The Merck Index, An Encyclopedia of Chemicals, Drugs and Biologicals 12th edition. ,; 1996:5860.
• [25]Hinchen JD: Practical statistics for chemical Research. 1st edition. , London; 1969.