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Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes

Year 2012, Volume: 40 Issue: 2, 119 - 126, 01.04.2012

Abstract

The UV-VIS behavior of E -1- 2-hydroxy-5-methylphenyl diazenyl naphthalene-2,7-diol and the acrylate derivatives and their chromium complexes were determined in different solvents, pH and temperature. The dyes were found to exist in azo and hydrazone tautomeric equilibrium in solution. And also, the o,o’- dihydroxyazo dyes and chromium complexes were tested for antimicrobial activity against Enterococcus faecalis, Staphylococcus aureus, Pseudomonas aeroginosa, Escherichia coli and Candida albicans. Dye I generally affected all microorganisms, while compounds II, III and IV were more effective against P. aeroginosa and E. coli. Because dye I has an antimicrobial effect on both bacteria and fungus it finds good use in various applications such as textile fiber dyeing, and biomedical studies. Significantly, this dye could also lead to the development of new antifungal drugs.

References

  • 1. A.T. Peters, H.S. Freeman, Colour chemistry, The desing and synthesis of organic dyes and pigments, Barking Essex: Elsevier Applied Science Publisher, (1991) 193.
  • 2. P. Gregory, High-technology applications of organic colorants, New York and London: Plenum Press, (1991) 293.
  • 3. S.C. Catino, R.E. Farris, Azo dyes, In: Grayson M. editor. Concise encyclopedia of chemical technology. New York: John Wiley&Sons, (1985) 142 .
  • 4. H. Kocaokutgen, S. Özkınalı, Characterisation and applications of some o,o’-dihydroxyazo dyes containing a 7-hydroxy group and their chromium complexes on nylon and wool, Dyes and Pigments, 63 (2004) 83.
  • 5. N.M.Rageh, Tautomeric structures, electronic spectra, acid–base properties of some 7-aryl-2,5- diamino-3(4-hydroxyphenyazo)pyrazolo(1,5-a) pyrimidine-6-carbonitriles and effect of their copper(II) complex solutions on some bacteria and fungi, Spectrochimica Acta Part A, 60 (2004) 1917.
  • 6. E. İspir, The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes, Dyes and Pigments, 82 (2009) 13.
  • 7. C. Kirilmis, M. Ahmedzade, S. Sevri, M. Koca, A. Kizirgil, C. Kazaz, Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives, E. J. Med. Chem., 43 (2008) 300.
  • 8. H. Kocaokutgen, S. Özkınalı, Application of some o,o’-dihydroxyazo dyes containing an acryloyloxy group and their chromium complexes on nylon and wool, Textile Research Journal, 74 (2004) 78.
  • 9. M. Dakiky, K. Kanan, M. Khamis, Aggregation of o,o’- Dihydroxyazo Dyes II, Interaction of 2-hydroxy-4- nitrophenylazoresorcinol in DMSO and DMF, Dyes and Pigments, 41 (1999)199.
  • 10. T. Iijima, E. Jojima, L. Antanov, St. Stoyanov, T. Stoyanova, Aggregation and tautomeric properties of CI Acid Red 138, Dyes and Pigments, 37 (1998) 81.
  • 11. M.M.A. Hamed, N.M. Ismail, S.A. Ibrahim, Solvent characteristics in the spectral Behaviour of Eriochrome Black T, Dyes and Pigments, 26 (1994) 297.
  • 12. B.R. Hsieh, Azo-Hydrazone of an o,o’-Dihydroxyazo Dye-A spectroscopic study, Dyes and Pigments, 14 (1990) 165.
  • 13. A.R. Monahan, J.B. Flannery, Hydrogen Bonding in Crystalline Arylazonaphthols, Chemical Physical Letters, 17 (1972) 510.
  • 14. H. Kocaokutgen, M. Gür, M.S. Soylu, P. Lönnecke, Spectroscopic, thermal and crystal structure properties of novel (E)-2,6-dimethyl-4-(4-tertbutylphenyldiazenyl)phenyl acrylate dye, Dyes and Pigments, 67 (2005) 99.
  • 15. H. Kocaokutgen, E. Erdem, I.E. Gümrükçüoğlu, Synthesis of HMFAN and its chromium and cobalt complexes and their application on nylon 6 and wool, J. Soc. Dyers & Colourists, 114 (1998) 93.
  • 16. M. Dakiky, I. Memcova, Aggregaion of o,o’- Dihydroxyazo Dyes I: Concentration, temperature and solvent effect, Dyes and Pigments, 40 (1999)141.
  • 17. H. Khanmohammadi, M. Darvishpour, New azo ligands containing azomethine groups in the pyridazinebased chain: Synthesis and characterization, Dyes and Pigments, 81 (2005) 167.
  • 18. A. El-Shafei, A.A. Fadda, A.M. Khalil, T.A.E. Ameen, F.A. Badria, Synthesis, antitumor evaluation, molecular modeling and quantitative structureactivity relationship (QSAR) of some novel arylazopyrazolodiazine and triazine analogs, Bioorg.&Med. Chem., 17 (2009) 5096.
  • 19. A.E.I. Ahmed, J.N. Hay, M.E. Bushell, J.N. Wardell, G. Cavalli, Biocidal polymers (I): Preparation and biological activity of some novel biocidal polymers based on uramil and its azo-dyes, Reac.& Func.Poly., 68 (2008) 248.

Akriloil Grup İçeren o,o’-Hidroksiazo Boyar Maddelerinin ve Komplekslerinin Tautomerik Yapıları, Absorbsiyon Karakteristikleri ve Antimikrobiyal Aktiviteleri

Year 2012, Volume: 40 Issue: 2, 119 - 126, 01.04.2012

Abstract

E -1- 2-hydroxy-5-methylphenyl diazenyl naphthalene-2,7-diol’ün ve akrilat türevlerinin ve onların krom komplekslerinin farklı çözücüler, pH ve sıcaklıklardaki UV-VIS davranışları tespit edildi. Çözücü içinde boyalar azo ve hidroazo tautomeric dengede bulundu. Aynı zamanda o,o’-dihydroksi azo boyaları ve krom komplekleri Enterococcus faecalis, Staphylococcus aureus, Pseudomonas aeroginosa, Escherichia coli ve Candida albicans antimikrobiyal aktivite açısından test edildi. Boya I genellikle tüm mikroorganizmalar üzerine etkili iken, II, III ve IV’ cü bileşikler P. aeroginosa ve E. coli üzerine daha fazla etkilidir. Boya I hem bakteriler hem de mayalar üzerinde antimikrobiyal etkiye sahip olduğu için, tekstilde lif boyaması ve biyomedikal çalışmalar gibi çeşitli uygulamalarda kullanımı uygun bulunmuştur. Bu boya önemli ölçüde yeni antifungal ilaçların geliştirilmesine yol açabilir

References

  • 1. A.T. Peters, H.S. Freeman, Colour chemistry, The desing and synthesis of organic dyes and pigments, Barking Essex: Elsevier Applied Science Publisher, (1991) 193.
  • 2. P. Gregory, High-technology applications of organic colorants, New York and London: Plenum Press, (1991) 293.
  • 3. S.C. Catino, R.E. Farris, Azo dyes, In: Grayson M. editor. Concise encyclopedia of chemical technology. New York: John Wiley&Sons, (1985) 142 .
  • 4. H. Kocaokutgen, S. Özkınalı, Characterisation and applications of some o,o’-dihydroxyazo dyes containing a 7-hydroxy group and their chromium complexes on nylon and wool, Dyes and Pigments, 63 (2004) 83.
  • 5. N.M.Rageh, Tautomeric structures, electronic spectra, acid–base properties of some 7-aryl-2,5- diamino-3(4-hydroxyphenyazo)pyrazolo(1,5-a) pyrimidine-6-carbonitriles and effect of their copper(II) complex solutions on some bacteria and fungi, Spectrochimica Acta Part A, 60 (2004) 1917.
  • 6. E. İspir, The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes, Dyes and Pigments, 82 (2009) 13.
  • 7. C. Kirilmis, M. Ahmedzade, S. Sevri, M. Koca, A. Kizirgil, C. Kazaz, Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives, E. J. Med. Chem., 43 (2008) 300.
  • 8. H. Kocaokutgen, S. Özkınalı, Application of some o,o’-dihydroxyazo dyes containing an acryloyloxy group and their chromium complexes on nylon and wool, Textile Research Journal, 74 (2004) 78.
  • 9. M. Dakiky, K. Kanan, M. Khamis, Aggregation of o,o’- Dihydroxyazo Dyes II, Interaction of 2-hydroxy-4- nitrophenylazoresorcinol in DMSO and DMF, Dyes and Pigments, 41 (1999)199.
  • 10. T. Iijima, E. Jojima, L. Antanov, St. Stoyanov, T. Stoyanova, Aggregation and tautomeric properties of CI Acid Red 138, Dyes and Pigments, 37 (1998) 81.
  • 11. M.M.A. Hamed, N.M. Ismail, S.A. Ibrahim, Solvent characteristics in the spectral Behaviour of Eriochrome Black T, Dyes and Pigments, 26 (1994) 297.
  • 12. B.R. Hsieh, Azo-Hydrazone of an o,o’-Dihydroxyazo Dye-A spectroscopic study, Dyes and Pigments, 14 (1990) 165.
  • 13. A.R. Monahan, J.B. Flannery, Hydrogen Bonding in Crystalline Arylazonaphthols, Chemical Physical Letters, 17 (1972) 510.
  • 14. H. Kocaokutgen, M. Gür, M.S. Soylu, P. Lönnecke, Spectroscopic, thermal and crystal structure properties of novel (E)-2,6-dimethyl-4-(4-tertbutylphenyldiazenyl)phenyl acrylate dye, Dyes and Pigments, 67 (2005) 99.
  • 15. H. Kocaokutgen, E. Erdem, I.E. Gümrükçüoğlu, Synthesis of HMFAN and its chromium and cobalt complexes and their application on nylon 6 and wool, J. Soc. Dyers & Colourists, 114 (1998) 93.
  • 16. M. Dakiky, I. Memcova, Aggregaion of o,o’- Dihydroxyazo Dyes I: Concentration, temperature and solvent effect, Dyes and Pigments, 40 (1999)141.
  • 17. H. Khanmohammadi, M. Darvishpour, New azo ligands containing azomethine groups in the pyridazinebased chain: Synthesis and characterization, Dyes and Pigments, 81 (2005) 167.
  • 18. A. El-Shafei, A.A. Fadda, A.M. Khalil, T.A.E. Ameen, F.A. Badria, Synthesis, antitumor evaluation, molecular modeling and quantitative structureactivity relationship (QSAR) of some novel arylazopyrazolodiazine and triazine analogs, Bioorg.&Med. Chem., 17 (2009) 5096.
  • 19. A.E.I. Ahmed, J.N. Hay, M.E. Bushell, J.N. Wardell, G. Cavalli, Biocidal polymers (I): Preparation and biological activity of some novel biocidal polymers based on uramil and its azo-dyes, Reac.& Func.Poly., 68 (2008) 248.
There are 19 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Gülçin Alp Avcı This is me

Sevil Ozkınalı This is me

Aydın Özlük This is me

Emre Avci This is me

Hasan Kocaokutgen This is me

Publication Date April 1, 2012
Published in Issue Year 2012 Volume: 40 Issue: 2

Cite

APA Avcı, G. A., Ozkınalı, S., Özlük, A., Avci, E., et al. (2012). Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes. Hacettepe Journal of Biology and Chemistry, 40(2), 119-126.
AMA Avcı GA, Ozkınalı S, Özlük A, Avci E, Kocaokutgen H. Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes. HJBC. April 2012;40(2):119-126.
Chicago Avcı, Gülçin Alp, Sevil Ozkınalı, Aydın Özlük, Emre Avci, and Hasan Kocaokutgen. “Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes”. Hacettepe Journal of Biology and Chemistry 40, no. 2 (April 2012): 119-26.
EndNote Avcı GA, Ozkınalı S, Özlük A, Avci E, Kocaokutgen H (April 1, 2012) Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes. Hacettepe Journal of Biology and Chemistry 40 2 119–126.
IEEE G. A. Avcı, S. Ozkınalı, A. Özlük, E. Avci, and H. Kocaokutgen, “Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes”, HJBC, vol. 40, no. 2, pp. 119–126, 2012.
ISNAD Avcı, Gülçin Alp et al. “Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes”. Hacettepe Journal of Biology and Chemistry 40/2 (April 2012), 119-126.
JAMA Avcı GA, Ozkınalı S, Özlük A, Avci E, Kocaokutgen H. Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes. HJBC. 2012;40:119–126.
MLA Avcı, Gülçin Alp et al. “Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes”. Hacettepe Journal of Biology and Chemistry, vol. 40, no. 2, 2012, pp. 119-26.
Vancouver Avcı GA, Ozkınalı S, Özlük A, Avci E, Kocaokutgen H. Antimicrobial Activities, Absorption Characteristics and Tautomeric Structures of o,o’-Hydroxyazo Dyes Containing an Acryloyloxy Group and Their Chromium Complexes. HJBC. 2012;40(2):119-26.

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