Abstract
The fragmentation behavior of two antineoplastic curcumin analogues with a structural backbone of 1,5-diaryl-3-oxo-1,4-pentadiene was studied using ESI-MS/MS. Tandem mass spectrometric analysis confirmed their molecular structure and identified their diagnostic product ions that will be used for qualitative and quantitative applications. Two curcumin analogues (designated as NC2067 and NC2081) have been studied using a triple quadrupole linear ion trap hybrid mass spectrometer (Qq-LIT-MS). It was observed that the two compounds behave in the same manner during MS/MS analysis. The fragmentation of the 3,5-bis(benzylidene)-4-piperidone was mainly based on cleavage within the 4-piperidone ring. However, the side chain fragmentation was mainly observed on the carbon-nitrogen and carbon-oxygen bonds. Based on this behavior, a general fragmentation pattern has been established.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Aggarwal BB, Kumar A, Bharti AC (2003) Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res 23(1A):363–398
Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB (2007) Bioavailability of curcumin: problems and promises. Mol Pharm 4(6):807–818
Shaikh J, Ankola DD, Beniwal V, Singh D, Kumar MNV (2009) Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Eur J Pharm Sci 37(3):223–230
Anand P, Thomas SG, Kunnumakkara AB, Sundaram C, Harikumar KB, Sung B, Tharakan ST, Misra K, Priyadarsini IK, Rajasekharan KN (2008) Biological activities of curcumin and its analogues (congeners) made by man and mother nature. Biochem Pharmacol 76(11):1590–1611
Das U, Sharma RK, Dimmock JR (2009) 1, 5-diaryl-3-oxo-1,4-pentadienes: a case for antineoplastics with multiple targets. Curr Med Chem 16(16):2001
Das S, Das U, Selvakumar P, Sharma RK, Balzarini J, De Clercq E, Molnár J, Serly J, Baráth Z, Schatte G (2009) 3, 5‐Bis (benzylidene)‐4‐oxo‐1‐phosphonopiperidines and related diethyl esters: potent cytotoxins with multi‐drug‐resistance reverting properties. ChemMedChem 4(11):1831–1840
Das U, Alcorn J, Shrivastav A, Sharma RK, De Clercq E, Balzarini J, Dimmock JR (2007) Design, synthesis and cytotoxic properties of novel 1-[4-(2-alkylaminoethoxy) phenylcarbonyl]-3, 5-bis (arylidene)-4-piperidones and related compounds. Eur J Med Chem 42(1):71–80
Das U, Sakagami H, Chu Q, Wang Q, Kawase M, Selvakumar P, Sharma RK, Dimmock JR (2010) 3, 5-Bis (benzylidene)-1-[4-2-(morpholin-4-yl) ethoxyphenylcarbonyl]-4-piperidone hydrochloride: a lead tumor-specific cytotoxin which induces apoptosis and autophagy. Bioorg Med Chem Lett 20(3):912–917
Gillespie TA, Winger BE (2011) Mass spectrometry for small molecule pharmaceutical product development: a review. Mass Spectrom Rev 30(3):479–490
Korfmacher WA (ed) (2011) Mass spectrometry for drug discovery and drug development. Wiley, Hoboken
Gross JH (2011) Tandem mass spectrometry. Mass spectrometry. Springer, Berlin/Heidelberg, 415–478
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer Science+Business Media Dordrecht
About this paper
Cite this paper
Awad, H., Das, U., Dimmock, J., El-Aneed, A. (2014). Tandem Mass Spectrometric Analysis of Novel Antineoplastic Curcumin Analogues. In: Banoub, J. (eds) Detection of Chemical, Biological, Radiological and Nuclear Agents for the Prevention of Terrorism. NATO Science for Peace and Security Series A: Chemistry and Biology. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-9238-7_15
Download citation
DOI: https://doi.org/10.1007/978-94-017-9238-7_15
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-017-9237-0
Online ISBN: 978-94-017-9238-7
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)