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Synthesis 2011(9): 1494-1500  
DOI: 10.1055/s-0030-1259991
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Coumarin Conjugates of Biological Thiols for Fluorescent Detection and Estimation

Alan R. Katritzky*a, Tarek S. Ibrahima,b, Srinivasa R. Talaa, Nader E. Abo-Dyaa,b, Zakaria K. Abdel-Samiib, Said A. El-Fekyb
a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
Fax: +1(352)3920554; e-Mail: katritzky@chem.ufl.edu;
b Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig 44519, Egypt
Further Information

Publication History

Received 2 February 2011
Publication Date:
05 April 2011 (online)

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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

    References

  • 1a Oae S. Doi JT. Organic Sulfur Chemistry: Structure and Mechanisms   CRC Press; Boca Raton: 1992. 
    Google Scholar
  • 1b Movassagh B. Balalaie S. Shaygan P. ARKIVOC  2007,  (xiii):  47 
    Google Scholar
  • 2 Halliwell B. Nutr. Rev.  1994,  52:  253 
    Google Scholar
  • 3 Ivanov AR. Nazimov IV. Baratova L. J. Chromatogr., A  2000,  895:  157 
    CrossrefGoogle Scholar
  • 4 Kumar V. Fausto N. Abbas A. Aster J. Robbins & Cotran Pathologic Basis of Disease   8th ed.:  W. H. Saunders; Philadelphia: 2009. 
    Google Scholar
  • 5 Giles NM. Giles IG. Jacob C. Biochem. Biophys. Res. Commun.  2003,  300:  1 
    CrossrefGoogle Scholar
  • 6a Sass JO. Endres W. J. Chromatogr., A  1997,  776:  342 
    Google Scholar
  • 6b Huang YF. Chang HT. Anal. Chem.  2006,  78:  1485 
    Google Scholar
  • 7 Cao XN. Li JH. Xu HH. Lin L. Xian YZ. Yamamoto K. Jin LT. Biomed. Chromatogr.  2004,  18:  564 
    CrossrefGoogle Scholar
  • 8a Chen SJ. Chang HT. Anal. Chem.  2004,  76:  3727 
    Google Scholar
  • 8b Shen CC. Tseng WL. Hsieh MM. J. Chromatogr., A  2009,  1216:  288 
    Google Scholar
  • 9 Wen M. Liu H. Zhang F. Zhu Y. Liu D. Tian Y. Wu Q. Chem. Commun.  2009,  4530 
    Google Scholar
  • 10 Burford N. Eelman MD. Mahony DE. Morash M. Chem. Commun.  2003,  146 
    Google Scholar
  • 11a Zeng Y. Zhang G. Zhang D. Anal. Chim. Acta  2008,  627:  254 
    Google Scholar
  • 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 
    Google Scholar
  • 11c Yang SJ. Tian XZ. Shin I. Org. Lett.  2009,  11:  3438 
    Google Scholar
  • 11d Zhang D. Zhang M. Liu Z. Yu M. Li FY. Yi T. Huang C. Tetrahedron Lett.  2006,  47:  7093 
    Google Scholar
  • 12a Duan L. Xu Y. Qian X. Wang F. Liu J. Cheng T. Tetrahedron Lett.  2008,  49:  6624 
    Google Scholar
  • 12b Shibata A. Furukawa K. Abe H. Tsuneda S. Ito Y. Bioorg. Med. Chem. Lett.  2008,  18:  2246 
    Google Scholar
  • 12c Matsumoto T. Urano Y. Shoda T. Kojima H. Nagano T. Org. Lett.  2007,  9:  3375 
    Google Scholar
  • 12d Bouffard J. Kim Y. Swager TM. Weissleder R. Hilderbrand SA. Org. Lett.  2008,  10:  37 
    Google Scholar
  • 12e Zhang M. Li M. Zhao Q. Li F. Zhang D. Zhang J. Yi T. Huang C. Tetrahedron Lett.  2007,  48:  2329 
    Google Scholar
  • 12f Tanaka FJ. Mase N. Barbas CF. Chem. Commun.  2004,  1762 
    Google Scholar
  • 12g Song HY. Nagi MH. Song ZY. MacAry PA. Hobley J. Lear MJ. Org. Biomol. Chem.  2009,  7:  3400 
    Google Scholar
  • 12h Wang S.-P. Deng W.-J. Sun D. Yan M. Zheng H. Xu J.-G. Org. Biomol. Chem.  2009,  7:  4017 
    Google Scholar
  • 12i Hong V. Kislukhin AA. Finn MG. J. Am. Chem. Soc.  2009,  131:  9986 
    Google Scholar
  • 12j Lee KS. Kim TK. Lee JH. Kim HJ. Hong JI. Chem. Commun.  2008,  6173 
    Google Scholar
  • 12k Lee JH. Lim CS. Tian YS. Han JH. Cho BR. J. Am. Chem. Soc.  2010,  132:  1216 
    Google Scholar
  • 12l Liu J. Bao C. Zhong X. Zhao C. Zhu L. Chem. Commun.  2010,  46:  2971 
    Google Scholar
  • 12m Yi L. Li H. Sun L. Liu L. Zhang C. Xi Z. Angew. Chem. Int. Ed.  2009,  48:  4034 
    Google Scholar
  • 13a Signore G. Nifosi R. Albertazzi L. Storti B. Bizzarri R. J. Am. Chem. Soc.  2010,  132:  1276 
    Google Scholar
  • 13b Kim TK. Lee DN. Kim HJ. Tetrahedron Lett.  2008,  49:  4879 
    Google Scholar
  • 13c Lin W. Long L. Tan W. Chem. Commun.  2010,  46:  1503 
    Google Scholar
  • 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 
    Google Scholar
  • 14 Katritzky AR. Angrish P. Todadze E. Synlett  2009,  2392 
    Article in Thieme ConnectGoogle Scholar
  • 15a Katritzky AR. Narindoshvili T. Angrish P. Synthesis  2008,  2013 
    Google Scholar
  • 15b Katritzky AR. Yoshioka M. Narindoshvili T. Chung A. Johnson JV. Org. Biomol. Chem.  2008,  6:  4582 
    Google Scholar
  • 15c Katritzky AR. Abdelmajeid A. Tala SR. Amine MS. Steel PJ. Synthesis  2011,  83 
    Google Scholar
  • 16 Katritzky AR. Tala SR. Abo-Dya NE. Gyanda K. El-Gendy BM. Abdel-Samii ZK. Steel PJ. J. Org. Chem.  2009,  74:  7165 
    CrossrefGoogle Scholar
  • 17 Katritzky AR. Abo-Dya NE. Tala SR. Ghazvini-Zadeh EH. Bajaj K. El-Feky SA. Synlett  2010,  1337 
    Article in Thieme ConnectGoogle Scholar
  • 18 Katritzky AR. Shestopalov AA. Suzuki K. Synthesis  2004,  1806 
    Article in Thieme ConnectGoogle Scholar