Chiral differentiation of the noscapine and hydrastine stereoisomers by electrospray ionization tandem mass spectrometry

Journal of Mass Spectrometry

Volumn 50, Issue 1, 2015, Pages 240-246

  Nagy, Tibor ^a   Kuki, Ákos ^a   Antal, Borbála ^a   Nagy, Lajos ^a   Purgel, Mihály ^b   Sipos, Attila ^c   Nagy, Miklós ^a   Zsuga, Miklós ^a   Kéki, Sándor ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b MTA DE Homogeneous Catalysis and Reaction Mechanisms Research Group   (Hungary)

^c UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Chiral differentiation; Chiral mass spectrometry; Hydrastine; Noscapine; Stereoisomers; Survival yield

Indexed keywords

AMINO ACIDS; DIMERS; ELECTROSPRAY IONIZATION; ISOMERS; MASS SPECTROMETRY; QUANTUM CHEMISTRY;

CHIRAL DIFFERENTIATIONS; HYDRASTINE; NOSCAPINE; STEREOISOMERS; SURVIVAL YIELD;

STEREOCHEMISTRY;

DEXTRO LYSINE; HETERODIMER; HYDRASTINE; NOSCAPINE; TYROSINE; BENZYLISOQUINOLINE DERIVATIVE; CATION; LITHIUM; LYSINE; SODIUM;

ARTICLE; CHIRALITY; COLLISIONALLY ACTIVATED DISSOCIATION; DRUG DETERMINATION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; ELECTROSPRAY QUADRUPOLE TIME OF FLIGHT TANDEM MASS SPECTROMETRY; ENANTIOMER; PRIORITY JOURNAL; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY; CHEMICAL MODEL; CHEMISTRY; DIMERIZATION; PROCEDURES; QUANTUM THEORY;

BENZYLISOQUINOLINES; CATIONS; DIMERIZATION; LITHIUM; LYSINE; MODELS, CHEMICAL; NOSCAPINE; QUANTUM THEORY; SODIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; TYROSINE;

EID: 84921520207     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.3527     Document Type: Article

References (34)

1. S. Zughaier, P. Karna, D. Stephens, R. Aneja. Potent anti-inflammatory activity of novel microtubule-modulating brominated noscapine analogs. PLoS One 2010, 5(2), e9165.
2. M. Mahmoudian, N. Mojaverian. Effect of noscapine, the antitussive opioid alkaloid, on bradykinin-induced smooth muscle contraction in the isolated ileum of the guinea-pig. Acta Physiol. Hung. 2001, 88, 231.
3. M. Mahmoudian, P. Rahimi-Moghaddam. The Anti-Cancer Activity of Noscapine: A Review. Recent Patents Anti-Cancer 2009, 4, 92.
4. N. Jhaveri, H. Cho, S. Torres, W. Wang, A. H. Schönthal, N. A. Petasis, S. G. Louie, F. M. Hofman, T. C. Chen. Noscapine inhibits tumor growth in TMZ-resistant gliomas. Cancer Lett. 2011, 312, 245.
5. W. Su, L. Huang, Q. Ao, Q. Zhang, X. Tian, Y. Fang, Y. Lu. Noscapine sensitizes chemoresistant ovarian cancer cells to cisplatin through inhibition of HIF-1a. Cancer Lett. 2011, 305, 94.
6. Z. Yang, M. Liu, X. Peng, X. Lei, L. Zhang, W. Dong. Noscapine induces mitochondria-mediated apoptosis in human colon cancer cells in vivo and in vitro. Biochem. Biophys. Res. Commun. 2012, 421, 627.
7. M. Chougule, M. R. Patel, R. Sachdeva, T. Jackson, M. Singh. Anticancer activity of Noscapine, an opioid alkaloid in combination with Cisplatin in human non-small cell lung cancer. Lung Cancer 2011, 71, 271.
8. J. R. Holtman, Jr., P. A. Crooks, J. K. Johnson-Hardy, M. Hojomat, M. Kleven, E. P. Wala. Effects of norketamine enantiomers in rodent models of persistent pain. Pharmacol. Biochem. Behav. 2008, 90, 676.
9. W. R. Henderson, Jr., E. R. Banerjee, E. Y. Chi. Differential effects of (S)- and (R)-enantiomers of albuterol in a mouse asthma model. J. Allergy Clin. Immunol. 2005, 116, 332.
10. L. Wu, F. G. Vogt. A review of recent advances in mass spectrometric methods for gas-phase chiral analysis of pharmaceutical and biological compounds. J. Pharm. Biomed. Anal. 2012, 69, 133.
11. L. Wu, W. Andy Tao, R. G. Cooks. Kinetic method for the simultaneous chiral analysisof different amino acids in mixtures. J. Mass Spectrom. 2003, 38, 386.
12. A. R. M. Hyyryläinen, J. M. H. Pakarinen, P. Vainiotalo, G. Stαjer, F. Fülöp. Diastereochemical Differentiation of β-Amino Acids Using Host-Guest Complexes Studied by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. J. Am. Soc. Mass Spectrom. 2007, 18, 1038.
13. M. Vincenti, A. Irico. Gas-phase interactions of calixarene- and resorcinarene-cavitands with molecular guests studied by mass spectrometry. Int. J. Mass Spectrom. 2002, 214, 23.
14. M. Shizuma, M. Ohta, H. Yamada, Y. Takai, T. Nakaoki, T. Takeda, M. Sawada. Enantioselective complexation of chiral linear hosts containing monosaccharide moieties with chiral organic amines. Tetrahedron 2002, 58, 4319.
15. A. R. M. Hyyryläinen, J. M. H. Pakarinen, E. Forró, F. Fülöp, P. Vainiotalo. Chiral Differentiation of Some Cyclopentane and Cyclohexane β-Amino Acid Enantiomers Through Ion/Molecule Reactions. J. Am. Soc. Mass Spectrom. 2009, 20, 1235.
16. S. P. Gaucher, J. A. Leary. Influence of metal ion and coordination geometry on gas phase dissociation and stereochemical differentiation of N glycosides. Int. J. Mass Spectrom. 2000, 197, 139.
17. C.-T. Yu, Y.-L. Guo, G.-Q. Chen, Y.-W. Zhong. Recognition of Zinc(II) Ion Complexes Composed of Bicyclo[3.3.0] Octane-2, 6-Diol and s-Naproxen Probed by Collisional-Induced Dissociation. J. Am. Soc. Mass Spectrom. 2004, 15, 795.
18. K. Giles, J. L. Wildgoose, D. J. Langridge, I. Campuzano. A method for direct measurement of ion mobilities using a travelling wave ion guide. Int. J. Mass Spectrom. 2010, 298, 10.
19. V. Domalain, V. Tognetti, M. Hubert-Roux, C. M. Lange, L. Joubert, J. Baudoux, J. Rouden, C. Afonso. Role of Cationized and Multimers Formation for Diastereomers Differentation by Ion Mobility-Mass Spectrometry. J. Am. Soc. Mass Spectrom. 2013, 24, 1437.
20. A. Memboeuf, L. Jullien, R. Lartia, B. Brasme, Y. Gimbert. Tandem Mass Spectrometric Analysis of a Mixture of Isobars Using the Survival Yield Technique. J. Am. Soc. Mass Spectrom. 2011, 22, 1744.
21. S. Daikoku, T. Ako, R. Kato, I. Ohtsuka, O. Kanie. Discrimination of 16 Structural Isomers of Fucosyl Galactoside Based on Energy-Resolved Mass Spectrometry. J. Am. Soc. Mass Spectrom. 2007, 18, 1873
22. Z.-P. Yao, T. S. M. Wan, K.-P. Kwong, C.-T. Che. Chiral analysis by electrospray ionization mass spectrometry/mass spectrometry. 1. Chiral recognition of 19 common amino acids. Anal. Chem. 2000, 72, 5383.
23. Gy. Gaál, P. Kerekes, R. Bognár. About the accompanying alkaloids of morphine VI. Preparation of the narcotine isomers. J. Prakt. Chem. 1971, 313, 935.
24. P. Kerekes, Gy. Gaal, R. Bognar. Elimination of phenolic hydroxyl group: Conversion of (-)-α-narcotine into (-)-β-hydrastine. Acta Chim. Hung. 1980, 103, 339.
25. T.M. Kertesz, L. H. Hall, D.W. Hill, D. F. Grant. CE50: Quantifying Collision Induced Dissociation Energy for Small Molecule Characterization and Identification. J. Am. Soc. Mass Spectrom. 2009, 20, 1759.
26. Y. Zhao, D. G. Truhlar. The M60 suite of density functional for main group thermochemistry, thermichemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M60-class functional and12 other functional. Theor. Chem. Acc. 2008, 120, 215.
27. W. J. Hehre, R. Ditchfield, J. A. Pople. Self-ConsistentMolecular Orbital Methods. XII. Further Extensions of Gaussian-Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules. J. Chem. Phys. 1972, 56, 2257.
28. L. F. Pacios, P. A. Christiansen. Ab initio relativistic effective potentials with spin-orbit operators. I. Li through Ar. J. Chem. Phys. 1985, 82, 2664.
29. M.M. Hurley, L. F. Pacios, P. A. Christiansen. Ab initio relativistic effective potentials with spin-orbit operators. II. K through Kr. J. Chem. Phys. 1986, 84, 6840.
30. R. B. Ross, J. M. Powers, T. Atashroo, W. C. Ermler, L. A. LaJohn, P. A. Christiansen. Ab initio relativistic effective potentials with spin- orbit operators. IV. Cs through Rn, R. B. Ross. J. Chem. Phys. 1990, 93, 6654.
31. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox. Gaussian 09. Gaussian, Inc.: Wallingford CT, 2009.
32. P. Henfeng. A non-covalent dimer formed in electrospray ionisation mass spectrometry behaving as a precursor for fragmentations. Rapid Commun. Mass Spectrom. 2008, 22, 3555.
33. C.Müller, B. Kanawati, T.M. Rock, S. Forcisi, F.Moritz, P. Schmitt-Kopplin. Dimer ion formation and intermolecular fragmentation of 1, 2- diacylglycerols revealed by electrospray ionization Fourier transformion cyclotron resonance mass spectrometry for more comprehensive lipid analysis. Rapid Commun. Mass Spectrom. 2014, 28, 1735.
34. M. Sawada, Y. Okumura, H. Yamada, Y. Takai, S. Takahashi, T. Kaneda, K. Hirose, S. Misumi. Cross-chiral Examinations of Molecular Enantioselective Recognition by Fast Atom Bombardment Mass Spectrometry: Host-Guest Complexations Between Chiral Crown Ethers and Chiral Organic Ammonium Ions. Org. Mass. Spectrom. 1993, 28, 1525.