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Synthesis 2011(9): 1494-1500
DOI: 10.1055/s-0030-1259991
DOI: 10.1055/s-0030-1259991
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of Coumarin Conjugates of Biological Thiols for Fluorescent Detection and Estimation
Further Information
Received
2 February 2011
Publication Date:
05 April 2011 (online)
Publication History
Publication Date:
05 April 2011 (online)

Abstract
Coumarin-labeled thioesters are efficiently prepared from biological thiols using N-coumarin-3-carbonyl benzotriazoles. Absorption (λabs), fluorescence (λem) wavelength maxima and quantum yields (φ) for the thioesters are measured in buffer solution at physiological pH 7.4. Quantum yields (φ = 0.0318-0.1068) of four of the products are higher than their precursor 7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-one (φ = 0.0195), suggesting that derivatives of this type could be suitable for quantitative thiol assays.
Key words
fluorescence - acylation - coumarin - thiols - benzotriazoles - peptides - amino acids - heterocycles
- Supporting Information for this article is available online:
- Supporting Information
- 1a
Oae S.Doi JT. Organic Sulfur Chemistry: Structure and Mechanisms CRC Press; Boca Raton: 1992. - 1b
Movassagh B.Balalaie S.Shaygan P. ARKIVOC 2007, (xiii): 47 - 2
Halliwell B. Nutr. Rev. 1994, 52: 253 - 3
Ivanov AR.Nazimov IV.Baratova L. J. Chromatogr., A 2000, 895: 157 - 4
Kumar V.Fausto N.Abbas A.Aster J. Robbins & Cotran Pathologic Basis of Disease 8th ed.: W. H. Saunders; Philadelphia: 2009. - 5
Giles NM.Giles IG.Jacob C. Biochem. Biophys. Res. Commun. 2003, 300: 1 - 6a
Sass JO.Endres W. J. Chromatogr., A 1997, 776: 342 - 6b
Huang YF.Chang HT. Anal. Chem. 2006, 78: 1485 - 7
Cao XN.Li JH.Xu HH.Lin L.Xian YZ.Yamamoto K.Jin LT. Biomed. Chromatogr. 2004, 18: 564 - 8a
Chen SJ.Chang HT. Anal. Chem. 2004, 76: 3727 - 8b
Shen CC.Tseng WL.Hsieh MM. J. Chromatogr., A 2009, 1216: 288 - 9
Wen M.Liu H.Zhang F.Zhu Y.Liu D.Tian Y.Wu Q. Chem. Commun. 2009, 4530 - 10
Burford N.Eelman MD.Mahony DE.Morash M. Chem. Commun. 2003, 146 - 11a
Zeng Y.Zhang G.Zhang D. Anal. Chim. Acta 2008, 627: 254 - 11b
Ros-Lis JV.Garcia B.Jiménez D.Martínez-Máňez R.Sancenón F.Soto J.Gonzalvo F.Valldecabres MC. J. Am. Chem. Soc. 2004, 126: 4064 - 11c
Yang SJ.Tian XZ.Shin I. Org. Lett. 2009, 11: 3438 - 11d
Zhang D.Zhang M.Liu Z.Yu M.Li FY.Yi T.Huang C. Tetrahedron Lett. 2006, 47: 7093 - 12a
Duan L.Xu Y.Qian X.Wang F.Liu J.Cheng T. Tetrahedron Lett. 2008, 49: 6624 - 12b
Shibata A.Furukawa K.Abe H.Tsuneda S.Ito Y. Bioorg. Med. Chem. Lett. 2008, 18: 2246 - 12c
Matsumoto T.Urano Y.Shoda T.Kojima H.Nagano T. Org. Lett. 2007, 9: 3375 - 12d
Bouffard J.Kim Y.Swager TM.Weissleder R.Hilderbrand SA. Org. Lett. 2008, 10: 37 - 12e
Zhang M.Li M.Zhao Q.Li F.Zhang D.Zhang J.Yi T.Huang C. Tetrahedron Lett. 2007, 48: 2329 - 12f
Tanaka FJ.Mase N.Barbas CF. Chem. Commun. 2004, 1762 - 12g
Song HY.Nagi MH.Song ZY.MacAry PA.Hobley J.Lear MJ. Org. Biomol. Chem. 2009, 7: 3400 - 12h
Wang S.-P.Deng W.-J.Sun D.Yan M.Zheng H.Xu J.-G. Org. Biomol. Chem. 2009, 7: 4017 - 12i
Hong V.Kislukhin AA.Finn MG. J. Am. Chem. Soc. 2009, 131: 9986 - 12j
Lee KS.Kim TK.Lee JH.Kim HJ.Hong JI. Chem. Commun. 2008, 6173 - 12k
Lee JH.Lim CS.Tian YS.Han JH.Cho BR. J. Am. Chem. Soc. 2010, 132: 1216 - 12l
Liu J.Bao C.Zhong X.Zhao C.Zhu L. Chem. Commun. 2010, 46: 2971 - 12m
Yi L.Li H.Sun L.Liu L.Zhang C.Xi Z. Angew. Chem. Int. Ed. 2009, 48: 4034 - 13a
Signore G.Nifosi R.Albertazzi L.Storti B.Bizzarri R. J. Am. Chem. Soc. 2010, 132: 1276 - 13b
Kim TK.Lee DN.Kim HJ. Tetrahedron Lett. 2008, 49: 4879 - 13c
Lin W.Long L.Tan W. Chem. Commun. 2010, 46: 1503 - 13d
Jung HS.Ko KC.Kim G.-H.Lee A.-R.Na Y.-C.Kang C.Lee JY.Kim JS. Org. Lett. 2011, 13: 1498 - 14
Katritzky AR.Angrish P.Todadze E. Synlett 2009, 2392 - 15a
Katritzky AR.Narindoshvili T.Angrish P. Synthesis 2008, 2013 - 15b
Katritzky AR.Yoshioka M.Narindoshvili T.Chung A.Johnson JV. Org. Biomol. Chem. 2008, 6: 4582 - 15c
Katritzky AR.Abdelmajeid A.Tala SR.Amine MS.Steel PJ. Synthesis 2011, 83 - 16
Katritzky AR.Tala SR.Abo-Dya NE.Gyanda K.El-Gendy BM.Abdel-Samii ZK.Steel PJ. J. Org. Chem. 2009, 74: 7165 - 17
Katritzky AR.Abo-Dya NE.Tala SR.Ghazvini-Zadeh EH.Bajaj K.El-Feky SA. Synlett 2010, 1337 - 18
Katritzky AR.Shestopalov AA.Suzuki K. Synthesis 2004, 1806