Journal of Fluorescence

, Volume 21, Issue 3, pp 1061–1067 | Cite as

Solvatochromic and Fluorescence Behavior of Sulfisoxazole

  • Abdulilah Dawoud Bani-Yaseen
Original Paper


The Fluorescence spectroscopic and solvatochromic behavior of Sulfisoxazole, a sulfa drug with antimicrobial activities, in various pure solvents of different polarity and hydrogen bonding capability is reported. The fluorescence emission spectrum of sulfisoxazole was found to be solvent polarity dependent, where a notable red shift in emission maximum was observed with increasing solvent polarity as well as hydrogen bonding capability. The effects of the latter two solvent parameters were quantitatively investigated using the methods of Lippert–Mataga and solvatochromic comparison method (SCM) that is based on the Kamlet-Taft equation. Particularly, the Lippert–Mataga method was applied to estimate the dipole moment of the excited state (μe) upon plotting Stokes shift versus solvent polarizability (Δf), where a value of 11.54 Debye was obtained. On the other hand, applying the multiple regression analysis to the SCM method revealed that solvent polarizability (π*) and hydrogen-bond donor capability (α) approximately equally stabilize sulfisoxazole in the excited state with minor destabilization contribution by the hydrogen-bond acceptor capability (β). These findings revealed that the excited state of sulfisoxazole is stabilized by polar solvents, indicating that this drug molecules exhibit larger dipole moment in the excited state than in the ground state, which in turn implies that a potential intramolecular charge transfer (ICT) occurs after excitation.


Fluorescence spectroscopy Solvatochromism Lippert-Mataga method Solvatochromic comparison method (SCM) Hydrogen bonding Charge transfer Pharmaceutical drug Photophysical properties 


  1. 1.
    Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Kluwer Academic/Plenum Press, New YorkCrossRefGoogle Scholar
  2. 2.
    Garbowski Z, Rorkiewicz K, Rettig W (2003) Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures. Chem Rev 103:3899–4032CrossRefGoogle Scholar
  3. 3.
    Rohatgi-Mukherjee KK (1992) Fundamentals of photochemistry. Wiley Eastern, New DelhiGoogle Scholar
  4. 4.
    Quintero B, Miranda M (2000) Mechanisms of photosensitization induced by drugs: a general survey. Ars Pharmaceutica 41(1):27–46Google Scholar
  5. 5.
    Hans R, Agrawal N, Verma K, Misra R, Ray A, Farooq M (2008) Assessment of the phototoxic potential of cosmetic products. Food Chem Toxicol 46:1653–1658PubMedCrossRefGoogle Scholar
  6. 6.
    Serrano-Perez J, Serrano-Andres L, Merchan M (2008) Photosensitization and phototherapy with furocoumarins: a quantum-chemical study. Chem Phys 347:422–435CrossRefGoogle Scholar
  7. 7.
    Musa K, Eriksson L (2009) Photochemical and photophysical properties, and photodegradation mechanism, of the non-steroid anti-inflammatory drug Flurbiprofen. J Photochem Photobiol A Chem 202(1):48–56CrossRefGoogle Scholar
  8. 8.
    Arantes F, Barbosa L, Alvarenga E, Demuner A, Bezzera D, Ferreira J, Costa-Lotufo L, Pessoa C, Moraes M (2009) Synthesis and cytotoxic activity of α-santonin derivatives. Eur J Med Chem 44(9):3739–3745PubMedCrossRefGoogle Scholar
  9. 9.
    Davids L, Klemann M, Kacerovska D, Pizinger K, Kidson S (2009) New aspects in photodynamic therapy of actinic keratoses. J Photochem Photobiol B Biol 96(3):159–169CrossRefGoogle Scholar
  10. 10.
    Smits T, Moor A (2008) Hypericin phototoxicity induces different modes of cell death in melanoma and human skin cells. J Photochem Photobiol B Biol 91(2–3):67–76Google Scholar
  11. 11.
    Kushibiki T, Sakai M, Awazu K (2009) Differential effects of photodynamic therapy on morphologically distinct tumor cells derived from a single precursor cell. Cancer Lett 268(2):244–251CrossRefGoogle Scholar
  12. 12.
    Jimenez-Banzo A, Sagrista ML, Mora M, Nonell S (2008) Kinetics of singlet oxygen photosensitization in human skin fibroblasts. Free Radic Biol Med 44(11):1926–1934PubMedCrossRefGoogle Scholar
  13. 13.
    Zupan K, Egyki M, Toth K, Fekete A, Herenyi L, Modos K, Csik G (2008) Comparison of the efficiency and the specificity of DNA-bound and free cationic porphyrin in photodynamic virus inactivation. J Photochem Photobiol B Biol 90(2):105–112CrossRefGoogle Scholar
  14. 14.
    Daryany M, Hosseini S, Raie M, Fakharie J, Zarehv A (2008) Study on continuous (254 nm) and pulsed UV (266 and 355 nm) lights on BVD virus inactivation and its effects on biological properties of fetal bovine serum. J Photochem Photobiol B Biol 92(2):120–124Google Scholar
  15. 15.
    Pal SK, Zewail AH (2004) Dynamics of water in biological recognition. Chem Rev 104:2099–2124PubMedCrossRefGoogle Scholar
  16. 16.
    Bilski P, Martinez LJ, Koker EB, Chignell CF (1998) Influence of solvent polarity and proticity on the photochemical properties of norfloxacin. Photochem Photobiol 68(1):20–24PubMedCrossRefGoogle Scholar
  17. 17.
    Plášek J, Hošková B (2010) Solvatochromic effect in the optical spectra of calcofluor and its relation to fluorescent staining of yeast cell walls. J Fluoresc 20(1):343–352PubMedCrossRefGoogle Scholar
  18. 18.
    Garcıa C, Oyola R, Pinero L, Hernandez D, Arce R (2008) Photophysics and photochemistry of imipramine, desimipramine, and clomipramine in several solvents: a fluorescence, 266 nm laser flash, and theoretical study. J Phys Chem B 112:168–178PubMedCrossRefGoogle Scholar
  19. 19.
    Park H-R, Oh C-H, Lee H-C, Lim SR, Yang K, Bark K-M (2004) Spectroscopic properties of various quinolone antibiotics in aqueous—organic solvent mixtures. Photochem Photobiol 80(3):554–564PubMedGoogle Scholar
  20. 20.
    Posokhov Y, Biner H, Içli S (2003) Spectral-luminescent and solvatochromic properties of anticancer drug camptothecin. J Photochem Photobiol A Chem 158(1):13–20CrossRefGoogle Scholar
  21. 21.
    Park KK, Park JW, Hamilton AD (2007) Solvent and pH effects on the fluorescence of 7-(Dimethylamino)-2-Fluorenesulfonate. J Fluoresc 17(4):361–3369PubMedCrossRefGoogle Scholar
  22. 22.
    Umadevi M, Vanelle P, Terme T, Rajkumar BJM, Ramakrishnan V (2008) Spectral investigations of solvatochromism and preferential solvation on 1, 4-dihydroxy-2, 3-dimethyl-9, 10-Anthraquinone. J Fluoresc 18(6):1139–1149PubMedCrossRefGoogle Scholar
  23. 23.
    Liu H-B, Yu D, Shin SC, Park H-R, Park JK, Bark K-M (2009) Spectroscopic properties of quercetin derivatives, quercetin-3-O-rhamnoside and quercetin-3-O-rutinoside, in hydro-organic mixed solvents. Photochem Photobiol 85(4):934–942PubMedCrossRefGoogle Scholar
  24. 24.
    Connor EE (1998) Sulfonamide antibiotics. Prim Care Update Ob Gyns 5:32–35CrossRefGoogle Scholar
  25. 25.
    Brackett CC, Singh H, Block JH (2004) Likelihood and mechanisms of cross-allergenicity between sulfonamide antibiotics and other drugs containing a sulfonamide functional group. Pharmacotherapy 24:856–870PubMedCrossRefGoogle Scholar
  26. 26.
    Supuran CT, Casini A, Scozzafava A (2003) Protease inhibitors of the sulfonamide type: anticancer, antiinflammatory, and antiviral agents. Med Res Rev 23:535–558PubMedCrossRefGoogle Scholar
  27. 27.
    Kim J, Park Y, Choi K (2009) Phototoxicity and oxidative stress responses in Daphnia magna under exposure to sulfathiazole and environmental level ultraviolet B irradiation. Aquat Toxicol 91(1):87–94PubMedCrossRefGoogle Scholar
  28. 28.
    de Liguoro M, Fioretto B, Poltronieri C, Gallina G (2009) The toxicity of sulfamethazine to Daphnia magna and its additivity to other veterinary sulfonamides and trimethoprim. Chemosphere 75:1519–1524PubMedCrossRefGoogle Scholar
  29. 29.
    Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94:2319–2358CrossRefGoogle Scholar
  30. 30.
    Kamlet MJ, Abboud J-LM, Abraham MH, Taft RW (1983) Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, pi.*, alpha., and.beta., and some methods for simplifying the generalized solvatochromic equation. J Org Chem 48:2877–2887CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceTaibah UniversityAl-MAdinah Al-MunawarahKingdom of Saudi Arabia

Personalised recommendations