Abstract
The absorption and fluorescence spectra of sulfamethoxazole (SMO), sulfisoxazole (SFO), sulfathiazole (STO) and sulfanilamide (SAM) in different solvents, pH and β-cyclodextrin (β-CD) have been analyzed. The inclusion complexes of the above sulfa drugs with β-CD were investigated by UV-visible spectroscopy, fluorometry, DFT, SEM, FT-IR and 1H NMR. The solvent study indicates that the position of the substituent (oxazole or thiazole group) in the SAM molecule (R–SO2–NH-group) is not the key factor to change the absorption and emission behavior of these sulpha drug molecules. In aqueous solution, a single fluorescence band (340 nm) was observed whereas in solutions of β-CD dual emission (430 nm) was noticed in sulpha drug compounds. Formation of the inclusion complex in SMO, SFO and STO should result dual emission which is due to a Twisted Intramolecular Charge Transfer band (TICT). The β-CD study indicates that (i) sulpha drugs form 1:1 inclusion complexes with β-CD and (ii) the red shift and the presence of TICT in the β-CD medium confirms heterocyclic ring encapsulated in the β-CD cavity with the aniline ring present on the out side of the β-CD cavity.
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Scypinski, S., Love, J.L.C.: Cyclodextrin-induced room-temperature phosphorescence of nitrogen heterocycles and bridged biphenyls. Anal. Chem. 56, 331–336 (1984)
Muñoz de la Peña, A., Durán Merás, I., Salinas, F., Warner, I.M., Ndou, T.T.: Cyclodextrin-induced fluid solution room temperature phosphorescence from acenaphthene in the presence of 2-bromoethanol. Anal. Chim. Acta 255, 351–336 (1991)
Szente, L., Szejtli, J.: Non-chromatographic analytical uses of cyclodextrins. Analyst 123, 735–741 (1998)
Okamoto, H., Uetake, A., Tamaya, R., Nakajima, T., Sagara, K., Ito, Y.: Simultaneous determination of eleven ingredients in ophthalmic solutions by cyclodextrin-modified micellar electrokinetic chromatography with tetrabutylammonium salt. J. Chromatogr. A 888, 299–308 (2000)
Mora Diez, N., Muñoz de la Peña, A., Mahedero Garcia, M.C., Bohoyo Gil, D., Canada-Canada, F.: Fluorimetric determination of sulphaguanidine and sulphamethoxazole by host-guest complexation in β-cyclodextrin and partial least squares calibration. J. Fluoresc. 17, 309–318 (2007)
Marek, J., Marek, J.: Farmakoterapie vnitrnich nemoci (Pharmacotherapy of Internal Diseases). Grada Publishing, Prague (1998), pp. 159
Msagati, T.A.M., Nindi, M.M.: Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection. Talanta 64, 87–100 (2004)
Bridges, J.W., Gifford, L.A., Hayes, W.P., Miller, J.N., Thorburn Burns, D.: Luminescence properties of sulfonamide drugs. Anal. Chem. 46, 1010–1017 (1974)
Sterling, J.M., Haney, W.G.: Spectrophotofluorometric analysis of procainamide and sulfadiazine in presence of primary aliphatic amines based on reaction with fluorescamine. J. Pharm. Sci. 63, 1448–1450 (1974)
Arthur, J., de Silva, F., Strojny, N.: Spectrofluorometric determination of pharmaceuticals containing aromatic or aliphatic primary amino groups as their fluorescamine (Fluram) derivatives. Anal. Chem. 47, 714–718 (1975)
Stewart, J.T., RE, Wilkin: Determination of sulfonamides and local anesthetics with 9-chloroacridine by quenching fluorometry. J. Pharm. Sci. 61, 432–433 (1972)
Pang, G.F., Cao, Y.Z., Fan, C.L., Zhang, J.J., Li, X.M., Li, Z.Y., Jia, G.Q.: Liquid chromatography fluorescence detection for simultaneous analysis of sulfonamide residues in honey. Anal. Bioanal. Chem. 376, 534–541 (2003)
Maudens, E., Zhang, G.-F., Lambert, W.E.: Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection. J. Chromatogr. 1047, 85–92 (2004)
Jorgenson, M.J., Hartter, D.R.: A critical re-evaluation of the Hammett acidity function at moderate and high acid concentrations of sulfuric acid. New H 0 values based solely on a set of primary aniline indicators. J. Am. Chem. Soc. 85, 878–883 (1963)
Yagil, G.: The effect of ionic hydration on equilibria and rates in concentrated electrolyte solutions. IV. The H− scale in concentrated hydroxide solutions. J. Phys. Chem. 71, 1045–1052 (1967)
Rajendiran, N., Swaminathan, M.: Luminescence characteristics of 4,4′-diaminodiphenyl methane in different solvents and at various pH. Spectrochim. Acta A 52, 1785–1792 (1996)
Rajendran, N., Swaminathan, M.: Photoluminescence of 4,4′-diaminodiphenyl. Bull. Chem. Soc. Jpn. 68, 2797–2802 (1995)
Rajendiran, N., Swaminathan, M.: Unusual spectral shifts of bis(4-amino phenyl) ether. Bull. Chem. Soc. Jpn. 69, 2447–2452 (1996)
Dey, J.K., Dogra, S.K.: Solvatochromism and prototropism in 2-(aminophenyl) benzothiazoles. Bull. Chem. Soc. Jpn. 64, 3142–3152 (1991)
Mishra, A.K., Dogra, S.K.: Effect of solvents and pH on the spectral behavior of 2-(p-aminophenyl)benzimidazole. Bull. Chem. Soc. Jpn. 58, 3587–3592 (1985)
Dey, J.K., Dogra, S.K.: Spectral characteristics of three different isomeric 2-(amino phenyl) benzoxazoles: effect of solvents and acid concentrations. Chem. Phys. 143, 97–107 (1990)
Bilot, L., Kawasaki, A.: Zur theory des einflusses von loesungsmitteln auf die elektronenspektren der molekuele. Z. Naturforsch. A 17, 621–630 (1962)
Reichardt, C.: Empirical parameters of solvent polarity as linear free-energy relationships. Angew. Chem. Int. Ed. English 18, 98–110 (1979)
Mishra, A.K., Dogra, S.K.: Absorption and fluorescence spectra of 2-amino benzimidazole: effect of different solvents and pH on spectral behavior. Indian J. Chem. A 24, 815–819 (1985)
Swaminathan, M., Dogra, S.K.: Solvent and Ph dependence of absorption and fluorescence spectra of 5-aminoindazole: biprotonic phototautomerism of singly protonated species. J. Am. Chem. Soc. 105, 6223–6228 (1983)
Stalin, T., Rajendiran, N.: Intra molecular charge transfer effects on 3-aminobenzoic acid. Chem. Phys. 322, 311–322 (2006)
Stalin, T., Rajendiran, N.: Intramolecular charge transfer effect associated with hydrogen bonding on 2-aminobenzoic acid. J. Photochem. Photobiol. A, Chem. 182, 137–150 (2006)
Stalin, T., Rajendiran, N.: Solvatochromism, prototropism and complexation of para-aminobenzoic acid. J. Incl. Phenom. Macrocycl. Chem. 55, 21–29 (2006)
Muthu Prabhu, A., Rajendiran, N.: Unusual spectral shifts on fast violet-B and benzanilide: effect of solvents, pH and β-cyclodextrin. Spectrochim. Acta A 74, 484–497 (2009)
Muthu Prabhu, A., Rajendiran, N.: Azo-ammonium tautomerism and assembly behavior of inclusion complexes of β-cyclodextrin with 4-amino, 2′,3-dimethyl azobenzene and 4-amino azobenzene. Ind. J. Chem. 49A, 407–417 (2010)
Kim, Y., Yoon, M., Kim, D.: Excited-state intramolecular proton transfer coupled-charge transfer of p-N,N-dimethylaminosalicylic acid in aqueous β-cyclodextrin solutions. J. Photochem. Photobiol. A 138, 167–175 (2001)
Kim, T.H., Cho, D.W., Yoon, M., Kim, D.: Observation of hydrogen-bonding effects on twisted intramolecular charge transfer of p-(N,N-diethylamino)benzoic acid in aqueous cyclodextrin solutions. J. Phys. Chem. 100, 15670–15676 (1996)
Jiang, Y.B.: Effect of cyclodextrin inclusion complex formation on the twisted intramolecular charge transfer (TICT) of the included compound: the p-dimethyl aminobenzoic acid-β-cyclodextrin system. J. Photochem. Photobiol. A, Chem. 88, 109–116 (1995)
Jiang, Y.B.: Fluorescence spectroscopic investigation of the effect of α-cyclodextrin on the twisted intramolecular charge transfer of p-dimethylaminobenzoic acid in aqueous media. Appl. Spectrosc. 48, 1169–1173 (1994)
Stalin, T., Rajendiran, N.: Photophysical behavior of 4-hydroxy-3,5-dimethoxy benzoic acid in different solvents, pH and β-cyclodextrin. J. Photochem. Photobiol. A, Chem. 177, 144–155 (2006)
Stalin, T., Rajendiran, N.: Photophysical properties of 4-hydroxy-3-methoxy benzoic acid. J. Mol. Struct. 794, 35–45 (2006)
Rajendiran, N., Balasubramanian, T.: Intramolecular charge transfer effects on 4-hydroxy-3-methoxy benzaldehyde. Spectrochim. Acta A 69, 822–829 (2008)
Rajendiran, N., Balasubramanian, T.: Dual luminescence of syringaldazine. Spectrochim. Acta A 68, 894–904 (2007)
Agbaria, RA, Uzar, B., Gill, D.: Fluorescence of 1,6-naphthalenediol with cyclodextrins. J. Phys. Chem. 93, 3855–3859 (1989)
Sandra, S., Dogra, S.K.: Spectral characteristics of 2-(2′-aminophenyl)benzimidazole in β-cyclodextrin. J. Photochem. Photobiol. A, Chem. 101, 221–227 (1996)
Krishnamoorthy, G., Dogra, S.K.: Dual fluorescence of 2-(4′-N,N-dimethyl amino phenyl)benzimidazole: effect of β-cyclodextrin and pH. J. Photochem. Photobiol. A, Chem. 123, 109–119 (1999)
Das, S.: Inclusion complexation of 2-(4′N,N-dimethyl aminophenyl)-1H-naphth[2,3-d]imidazole by β-cyclodextrin: effect on the twisted intramolecular charge transfer emission. Chem. Phys. Lett. 361, 21–28 (2002)
Benesi, A., Hildebrand, J.H.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2703–2707 (1949)
Bhattacharya, K., Chowdhury, M.: Environmental and magnetic field effects on exciplex and twisted charge transfer emission. Chem. Rev. 93, 507–535 (1993)
Panja, S., Bangal, P.R., Chakravorty, S.: Modulation of photophysics due to orientational selectivity of 4-N,N-dimethylaminocinnamladehyde β-cyclodextrin inclusion complex in different solvents. Chem. Phys. Lett. 329, 377–385 (2000)
Testa, A.C.: Evidence for a hydrogen bonded dimer as a fluorescence quenching channel in 4,5-diphenylimidazole. J. Luminesci. 50, 243–248 (1991)
Modiano, S.H., Dresner, J., Lim, B.C.: Intramolecular photoassociation and photoinduced charge transfer in bridged diaryl compounds. 1. Photoassociation in the lowest triplet state of 2,2′-dinaphthylmethane and 2,2′-dinaphthyl ether. J. Phys. Chem. 95, 9144–9151 (1991)
Muthu Prabhu, A.A., Siva, S., Sankaranarayanan, R.K., Rajendiran, N.: Intra molecular proton transfer effects on 2,6-diaminopyridine. J. Fluoresc. 20, 43–54 (2010)
Lehman, J., Klienpeter, E.: 1H NMR spectroscopy as a probe of intermolecular interactions in β-cyclodextrin inclusion compounds. J. Incl. Phenom. 10, 233–239 (1991)
Rath, M.C., Palit, D.K., Mukherjee, T.: Effects of organised media on the excited-state proton transfer in 2-(2′-pyridyl)benzimidazole. J. Chem. Soc. Faraday Trans. 94, 1189–1196 (1998)
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Muthu Prabhu, A.A., Venkatesh, G. & Rajendiran, N. Spectral Characteristics of Sulfa Drugs: Effect of Solvents, pH and β-Cyclodextrin. J Solution Chem 39, 1061–1086 (2010). https://doi.org/10.1007/s10953-010-9559-0
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DOI: https://doi.org/10.1007/s10953-010-9559-0