Synthesis,Characterization and Chemiluminescence of 10-Methylacridinium Esters

doi:10.7517/j.issn.1674-0475.2008.04.257

Abstract

Abstract: The acridine esters are known chemiluminescent molecules with good quantum yield.As a chemiluminescnet regent,they are essentially composed of two parts:acridine ring and leaving group.Modifications on the leaving group have been made to yield four new derivatives with different substituents.And their molecular structures were characterized with ¹HNMR,¹³CNMR,IR and MS.All of them showed reasonable chemiluminescent kinetics and good quantum yields.The hydrolytic stability of the target compounds were tested by chemiluminescent method.

Key words: acridinium ester, leaving group, chemiluminescent kinetics, chemiluminescent quantum yield, hydrolytic stability

CLC Number:

MU Xiao-jing, LIU Min, YAN Shu-shan. Synthesis,Characterization and Chemiluminescence of 10-Methylacridinium Esters[J]. Imaging Science and Photochemistry, 2008, 26(4): 257-264.

References

[1] Dodeigne C,Thunus L,Lejeune R.Chemiluminescence as a diagnostic tool[J].Talanta,2000,51(3):415-439.
[2] Kricka LJ.Clinical applications of chemiluminescence[J].Anal.Chi m.Acta,2003,500:279-286.
[3] King D W,Cooper WJ,Rusak S A,et al.Flowinjection analysis of H₂O₂ in natural waters using acridiniumester chemiluminescence:method development and opti mization using a kinetic model[J].Anal.Chem.,2007,79(11):4169-4176.
[4] Kuruvilla E,Ramaiah D.Selectiveinteractions of a fewacridiniumderivatives withsingle strand DNA:study of pho-tophysical and DNAbindinginteractions[J].J.Phys.Chem.,2007,111B:6549-6556.
[5] Natrajan A,Jiang Q,Sharpe D,et al.High quantumyield acridiniumcompounds and their use in i mproving assay sensitivity[P].WO Patent,2006130736,2006-12-07.
[6] Brown R C,Weeks I,Fisher M,et al.Employment of a phenoxy-substituted acridiniumester as along-lived chemi-luminescent indicator of glucose oxidase activity andits applicationin an alkaline phosphatase amplification cascadei m-munoassay[J].Anal.Biochem.,1998,259:142-151.
[7] McCapra F.Chemical mechanisms in bioluminescence[J].Acc.Chem.Res.,1976,9(6):201-208.
[8] Sato N.Synthesis and properties of newluminescent10-carboxymethylacridiniumderivatives[J].Tetrahedron Lett.,1996,37(47):8519-8522.
[9] Sato N,Mochizuki H,Kanamori T,et al.Acridiniumcompounds andconjugatesthereof[P].US Patent,5594112,1997-01-14.
[10] Smith K,Li Z,Yang J,et al.Synthesis and properties of novel chemiluminescent biological probes:substituted4-(2-succini midyloxycarbonylethyl)phenyl10-methylacridinium-9-carboxylate trifluoromethanesulphonate[J].J.Pho-tochem.Photobiol.,2000,132A(3):181-191.
[11] Denise M W,Burton DJ.Pregeneration,spectroscopic detection andchemical reactivity of(trifluoromethyl)copper,an elusive and complex species[J].J.Am.Chem.Soc.,1986,108(4):832-834.
[12] Burton DJ,Denise M W.Aremarkably si mple preparation of(trifluoromethyl)cadmiumand-zinc reagents directly fromdifluorodihalomethanes[J].J.Am.Chem.Soc.,1985,107(17):5014-5015.
[13] Weeks I,Rutter A,Li Z,et al.Chemiluminescent compounds[P].US Patent,2007166759,2007-07-19.
[14] Weeks I,Rutter A,Li Z,et al.Chemiluminescent acridiniumcompoundsthat emit chemiluminescence belowpH12and materials labelled therewith for use in assays[P].GB Patent,2405407,2005-03-02.

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