title: Synthesis of novel fluorescent cyclohexenone derivatives and their partitioning study in ionic micellar media.
abstract: An approach is demonstrated toward the synthesis of four novel cyclohexenone derivatives (CDs) via a convenient route of Michael addition of ethyl acetoacetate. The molecular structures of CDs were confirmed by means of FT-IR, (1)H NMR, EIMS, UV and also by X-ray single crystal structure analysis. CDs are strongly fluorescent compounds and their fluorescent spectra exhibits intense violet fluorescence. To model the binding to biological membranes the behavior of CDs in micellar solutions of a cationic surfactant, cetyltrimethylammonium bromide (CTAB) and an anionic surfactant, sodium dodecylsulfate (SDS) has also been examined. The characteristics of partition and binding interactions of CDs with CTAB and SDS were investigated by UV-Visible and fluorescence spectroscopic techniques. Higher values of all mentioned interactions in case of CTAB, compared to SDS, indicate that there are greater interactions between the CDs and CTAB than with SDS.
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, 45320, Islamabad, Pakistan.
authors.forename: Amir
authors.initials: A
authors.lastname: Badshah
authors.forename: Saleem
authors.initials: S
authors.lastname: Nawaz
authors.forename: Muhammad Faizan
authors.initials: MF
authors.lastname: Nazar
authors.forename: Syed Sakhawat
authors.initials: SS
authors.lastname: Shah
authors.forename: Aurangzeb
authors.initials: A
authors.lastname: Hasan
mesh_terms: D000077286:Cetrimonium; D002593:Cetrimonium Compounds / Q000737:chemistry; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007477:Ions; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008823:Micelles; D012967:Sodium Dodecyl Sulfate / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D013501:Surface-Active Agents / Q000737:chemistry; D014965:X-Rays
chemical_list: D002593:Cetrimonium Compounds; D004396:Coloring Agents; D007477:Ions; D008823:Micelles; D013501:Surface-Active Agents; D012967:Sodium Dodecyl Sulfate; D000077286:Cetrimonium
references.citation: J Med Chem. 1981 Apr;24(4):468-72
references.pmid: 6267282
references.citation: J Med Chem. 1976 Apr;19(4):508-11
references.pmid: 1263202
references.citation: Phytochemistry. 2001 May;57(2):261-5
references.pmid: 11382242
references.citation: Phytochemistry. 2004 Apr;65(8):1123-8
references.pmid: 15110693
references.citation: Luminescence. 2008 Sep-Oct;23(5):350-5
references.pmid: 18500699
references.citation: AAPS PharmSciTech. 2009;10(4):1286-94
references.pmid: 19876741
references.citation: Prog Mol Subcell Biol. 2003;37:231-53
references.pmid: 15825646
references.citation: Biochim Biophys Acta. 2000 Nov 23;1508(1-2):210-34
references.pmid: 11090827
references.citation: Biochim Biophys Acta. 2004 Sep 24;1674(2):205-14
references.pmid: 15374625
references.citation: Biomacromolecules. 2006 Apr;7(4):1350-6
references.pmid: 16602760
references.citation: Chemosphere. 2008 Feb;70(11):1987-94
references.pmid: 17983640
references.citation: Acta Crystallogr Sect E Struct Rep Online. 2008 Dec 10;65(Pt 1):o70
references.pmid: 21581709
references.citation: Curr Med Chem. 2000 Apr;7(4):417-36
references.pmid: 10702617
references.citation: Acta Biochim Pol. 2008;55(2):399-409
references.pmid: 18246206
references.citation: J Phys Chem B. 2007 Nov 15;111(45):12985-92
references.pmid: 17958349