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Antimicrobial azo molecules: a review

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Abstract

Among the photochromes superfamily, azobenzene subgroup is the most extensively produced and used scaffold for many applications. However, the emergence of MDR (multi-drug resistant) bacterial strains brought to light the urgent need of efficient antimicrobial molecules. In that context, this review aims to compile the different approaches coupling azobenzene and antimicrobial activity. Thus, this paper will focus on mono-azo, bis-azo and tetra-azo dyes, surfactant-azo molecules, organometallic azo dyes and photochromic azo materials with antimicrobial activities.

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References

  1. K.G. Yager, C.J. Barrett, J. Photochem. Photobiol., A 182, 250–261 (2006)

    Article  CAS  Google Scholar 

  2. M.G. Pamar, P. Govender, K. Muthusamy, R.W.M. Krause, H.M. Nanjundaswamy, Orient. J. Chem. 29, 969–974 (2013)

    Article  CAS  Google Scholar 

  3. L. Hu, X. Cao, L. Chen, J. Zheng, J. Lu, X. Sun, H. Gu, Chem. Commun. 48, 3445–3447 (2012)

    Article  CAS  Google Scholar 

  4. D. Combita, P. Concepción, A. Corma, J. Catal. 311, 339–349 (2014)

    Article  CAS  Google Scholar 

  5. S.K. Surampudi, H.R. Patel, G. Nagarjuna, D. Venkataraman, Chem. Commun. (2013). https://doi.org/10.1039/c3cc43797c

    Article  Google Scholar 

  6. N.A. Noureldin, J.W. Bellegarde, Synthesis 6, 939–942 (1999)

    Article  Google Scholar 

  7. A.K. Flatt, S.M. Dirk, J.C. Henderson, D.E. Shen, J. Su, M.A. Reed, J.M. Tour, Tetrahedron 59, 8555–8570 (2003)

    Article  CAS  Google Scholar 

  8. G. Haberhauer, C. Kallweit, C. Wölper, D. Bläser, Angew. Chem., Int. Ed. 52, 7879–7882 (2013)

    Article  CAS  Google Scholar 

  9. C. Zhang, N. Jiao, Angew. Chem., Int. Ed. 49, 6174–6177 (2010)

    Article  CAS  Google Scholar 

  10. S. Bellotto, R. Reuter, C. Heinis, H.A. Wegner, J. Org. Chem. 76, 9826–9834 (2011)

    Article  CAS  PubMed  Google Scholar 

  11. P. Viehmann, S. Hecht, Beilstein J. Org. Chem. 8, 1825–1830 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. M. Schönberger, D. Trauner, Angew. Chem., Int. Ed. 53, 3264–3267 (2014)

    Article  CAS  Google Scholar 

  13. T. Takeuchi, T. Mori, A. Kuwahara, T. Ohta, A. Oshita, H. Sunayama, Y. Kitayama, T. Ooya, Angew. Chem., Int. Ed. 53, 12765–12770 (2014)

    Article  CAS  Google Scholar 

  14. A.M. Rosales, K.M. Mabry, E.M. Nehls, K.S. Anseth, Biomacromol 16, 798–806 (2015)

    Article  CAS  Google Scholar 

  15. G. Granucci, M. Persico, Theor. Chem. Acc. 117, 1131–1143 (2007)

    Article  CAS  Google Scholar 

  16. I. Conti, M. Garavelli, G. Orlandi, J. Am. Chem. Soc. 130, 5216–5230 (2008)

    Article  CAS  PubMed  Google Scholar 

  17. R.L. Klug, R. Burcl, J. Phys. Chem. A 114, 6401–6407 (2010)

    Article  CAS  PubMed  Google Scholar 

  18. H.M.D. Bandara, P.N. Basa, J. Yan, C.E. Camire, J.C. MacDonald, R.K. Jackson, S.C. Burdette, Eur. J. Org. Chem. 2013, 4794–4803 (2013)

    Article  CAS  Google Scholar 

  19. P.-F. Loos, J. Preat, A.D. Laurent, C. Michaux, D. Jacquemin, E.A. Perpète, X. Assfeld, J. Chem. Theory Comput. 4, 637–645 (2008)

    Article  CAS  PubMed  Google Scholar 

  20. M. Pederzoli, J. Pittner, M. Barbatti, H. Lischka, J. Phys. Chem. A 115, 11136–11143 (2011)

    Article  CAS  PubMed  Google Scholar 

  21. O. Weingart, Z. Lan, A. Koslowski, W. Thiel, J. Phys. Chem. Lett. 2, 1506–1509 (2011)

    Article  CAS  Google Scholar 

  22. H. Leube, in K. ed. by I. Dyes (Wiley-VCH Verlag GmbH & Co. KGaA, Hunger, 2002), pp. 339–425

    Google Scholar 

  23. J. Chr, Larsen. Trends Food Sci. Technol. 19, S64–S69 (2008)

    Article  CAS  Google Scholar 

  24. G. Vives, J. Kang, K.F. Kelly, J.M. Tour, Org. Lett. 11, 5602–5605 (2009)

    Article  CAS  PubMed  Google Scholar 

  25. T. Sasaki, J.M. Tour, Org. Lett. 10, 897–900 (2008)

    Article  CAS  PubMed  Google Scholar 

  26. Y. Shirai, T. Sasaki, J.M. Guerrero, B.-C. Yu, P. Hodge, J.M. Tour, ACS Nano 2, 97–106 (2008)

    Article  CAS  PubMed  Google Scholar 

  27. N. Drillaud, E. Banaszak-Léonard, I. Pezron, C. Len, J. Org. Chem. 77, 9553–9561 (2012)

    Article  CAS  PubMed  Google Scholar 

  28. M. Billamboz, F. Mangin, N. Drillaud, C. Chevrin-Villette, E. Banaszak-Léonard, C. Len, J. Org. Chem. 79, 493–500 (2014)

    Article  CAS  PubMed  Google Scholar 

  29. T.J. Sorensen, K. Kjaer, D.W. Breiby, B.W. Laursen, Langmuir 24, 3223–3227 (2008)

    Article  CAS  PubMed  Google Scholar 

  30. E. Léonard, F. Mangin, C. Villette, M. Billamboz, C. Len, Catal. Sci. Technol. 6, 379–398 (2016)

    Google Scholar 

  31. R. Rajaganesh, A. Gopal, T. Mohan Das, A. Ajayaghosh, Org. Lett. 14, 748–751 (2012)

    Article  CAS  PubMed  Google Scholar 

  32. G. Galli, E. Chiellini, Liq. Cryst. 33, 1297–1301 (2006)

    Article  CAS  Google Scholar 

  33. S.S. Subala, B.S. Sundar, S.S. Sastry, J. Chem. 2013, e939406 (2013)

    Article  CAS  Google Scholar 

  34. “WHO publishes list of bacteria for which new antibiotics are urgently needed,” can be found under http://www.who.int/news-room/detail/27-02-2017-who-publishes-list-of-bacteria-for-which-new-antibiotics-are-urgently-needed (2017)

  35. G. Oros, T. Cserhati, E. Forgacs, Chemosphere 52, 185–193 (2003)

    Article  CAS  PubMed  Google Scholar 

  36. M.R. Yazdanbakhsh, H. Yousefi, M. Mamaghani, E.O. Moradi, M. Rassa, H. Pouramir, M. Bagheri, J. Mol. Liq. 169, 21–26 (2012)

    Article  CAS  Google Scholar 

  37. Z. Seferoğlu, E. Yalçın, B. Babür, N. Seferoğlu, T. Hökelek, E. Yılmaz, E. Şahin, Spectrochim. Acta, Part A 113, 314–324 (2013)

    Article  CAS  Google Scholar 

  38. S.M. Al-Mousawi, M.A. El-Apasery, H.M. Mahmoud, Molecules 17, 11495–11506 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. Z.H. Aiube, A.H. Samir, I.S.H.A.-R. Al-Kadi, Int. J. Eng. Sci. Res. Technol. 5, 750–760 (2016)

    CAS  Google Scholar 

  40. A.M. Al-Etaibi, M.A. El-Apasery, H.M. Mahmoud, N.A. Al-Awadi, Molecules 17, 4266–4280 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. C.T.K. Kumar, J. Keshavayya, T. Rajesh, S.K. Peethambar, R.A.S. Ali, Chem. Sci. Trans. 2, 1346–1351 (2013)

    Google Scholar 

  42. H.M. Ali, S.Q. Badr, M.F. Hassan Al-Kinani, IOP Conf. Ser.: Mater. Sci. Eng. 571, 012102 (2019)

    Article  CAS  Google Scholar 

  43. S. Piotto, S. Concilio, L. Sessa, R. Diana, G. Torrens, C. Juan, U. Caruso, P. Iannelli, Molecules 22, 1372/1 (2017)

    Article  CAS  Google Scholar 

  44. S. Erişkin, N. Şener, S. Yavuz, İ Şener, Med. Chem. Res. 23, 3733–3743 (2014)

    Article  CAS  Google Scholar 

  45. H.F. Rizk, S.A. Ibrahim, M.A. El-Borai, Dyes Pigm. 112, 86–92 (2015)

    Article  CAS  Google Scholar 

  46. H. Singh, J. Sindhu, J.M. Khurana, C. Sharma, K.R. Aneja, RSC Adv. 4, 5915–5926 (2014)

    Article  CAS  Google Scholar 

  47. A.H. Shridhar, J. Keshavayya, H.J. Hoskeri, R.A.S. Ali, Int. Res. J. Pure Appl. Chem. 1, 119–129 (2011)

    Article  CAS  Google Scholar 

  48. M. Ghasemian, A. Kakanejadifard, T. Karami, Spectrochim. Acta, Part A 168, 190–198 (2016)

    Article  CAS  Google Scholar 

  49. H. Kaur, S.M. Lim, K. Ramasamy, M. Vasudevan, S.A.A. Shah, B. Narasimhan, Arab. J. Chem. 13, 377–392 (2020)

    Article  CAS  Google Scholar 

  50. M. Köse, N. Kurtoglu, Ö. Gümüşsu, M. Tutak, V. McKee, D. Karakaş, M. Kurtoglu, J. Mol. Struct. 1053, 89–99 (2013)

    Article  CAS  Google Scholar 

  51. H. Shaki, K. Gharanjig, A. Khosravi, Biotechnol. Prog. 31, 1086–1095 (2015)

    Article  CAS  PubMed  Google Scholar 

  52. H.E. Gaffer, Color. Technol. 135, 484–500 (2019)

    Article  CAS  Google Scholar 

  53. J.K. Vinodkumar, J. Mol. Struct. 1186, 404–412 (2019)

    Article  CAS  Google Scholar 

  54. H.Z. Shams, R.M. Mohareb, M.H. Helal, A.E.-S. Mahmoud, Molecules 16, 6271–6305 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. A.A. Ghoneim, N.M. Morsy, J. Iran. Chem. Soc 15, 2567–2572 (2018)

    Article  CAS  Google Scholar 

  56. E.O. Moradi Rufchahi, H. Pouramir, M.R. Yazdanbakhsh, H. Yousefi, M. Bagheri, M. Rassa, Chin. Chem. Lett. 24, 425–428 (2013)

    Article  CAS  Google Scholar 

  57. M. Gür, J. Heterocycl. Chem. 56, 980–987 (2019)

    Article  CAS  Google Scholar 

  58. S. Kinali-Demirci, S. Demirci, M. Kurt, Spectroc. Acta A 106, 12–18 (2013)

    Article  CAS  Google Scholar 

  59. N.N. Pesyan, D. Soleimani, N.H. Jazani, Turk. J. Chem. 39, 998–1011 (2015)

    Article  CAS  Google Scholar 

  60. H.N. Chopde, R. Pagadala, J.S. Meshram, V. Jetti, J. Heterocycl. Chem. 47, 1361–1366 (2010)

    Article  CAS  Google Scholar 

  61. W. Li, Y. Li, X. Yin, Y. Liang, J. Li, C. Wang, Y. Lan, H. Wang, Y. Ju, G. Li, Tetrahedron Lett. 57, 2539–2543 (2016)

    Article  CAS  Google Scholar 

  62. G. Singh, A. Saroa, S. Girdhar, S. Rani, D. Choquesillo-Lazarte, S.C. Sahoo, Appl. Organomet. Chem. 29, 549–555 (2015)

    Article  CAS  Google Scholar 

  63. Y.Q. Yeoh, J. Yu, S.W. Polyak, J.R. Horsley, A.D. Abell, Chem. Bio. Chem. 19, 2591–2597 (2018)

    Article  CAS  PubMed  Google Scholar 

  64. Y.Q. Yeoh, J.R. Horsley, J. Yu, S.W. Polyak, B. Jovcevski, A.D. Abell, Chem. Med. Chem. 15, 1505–1508 (2020)

    Article  CAS  PubMed  Google Scholar 

  65. W.A. Velema, J.P. van der Berg, M.J. Hansen, W. Szymanski, A.J.M. Driessen, B.L. Feringa, Nat. Chem. 5, 924–928 (2013)

    Article  CAS  PubMed  Google Scholar 

  66. P.S. Jogi, J. Meshram, J. Sheikh, T. Ben Hadda, Med. Chem. Res. 22, 4202–4210 (2013)

    Article  CAS  Google Scholar 

  67. H. Khanmohammadi, M. Pass, K. Rezaeian, G. Talei, J. Mol. Struct. 1072, 232–237 (2014)

    Article  CAS  Google Scholar 

  68. Ç. Karabacak, T. Tilki, B.Ö. Tuncer, M. Cengiz, Res. Chem. Intermed. 41, 1985–1999 (2015)

    Article  CAS  Google Scholar 

  69. F. Karcı, F. Karcı, A. Demirçalı, M. Yamaç, J. Mol. Liq. 187, 302–308 (2013)

    Article  CAS  Google Scholar 

  70. N. Şener, H.J.A. Mohammed, S. Yerlikaya, Y. Celik Altunoglu, M. Gür, M.C. Baloglu, İ Şener, Dyes Pigm. 157, 11–19 (2018)

    Article  CAS  Google Scholar 

  71. J.R. Ames, M.D. Ryan, P. Kovacic, J. Free Radic. Biol. Med. 2, 377–391 (1986)

    Article  CAS  PubMed  Google Scholar 

  72. H.M. Patel, Eur. J. Chem. 3, 44–50 (2012)

    Article  CAS  Google Scholar 

  73. S.P. Denyer, J.-Y. Maillard, J. Appl. Microbiol. 92, 35S-45S (2002)

    Article  PubMed  Google Scholar 

  74. T.K. Mazu, B.A. Bricker, H. Flores-Rozas, S.Y. Ablordeppey, Mini Rev. Med. Chem. 16, 555–578 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  75. S. Buffet-Bataillon, P. Tattevin, M. Bonnaure-Mallet, A. Jolivet-Gougeon, Int. J. Antimicrob. Agents 39, 381–389 (2012)

    Article  CAS  PubMed  Google Scholar 

  76. A. Franche, A. Fayeulle, L. Lins, M. Billamboz, I. Pezron, M. Deleu, E. Léonard, Bioorg. Chem. 94, 103399 (2020)

    Article  CAS  PubMed  Google Scholar 

  77. S. Liu, J. Ma, D. Zhao, Dyes Pigm. 75, 255–262 (2007)

    Article  CAS  Google Scholar 

  78. Y. Hu, W. Zou, V. Julita, R. Ramanathan, R.F. Tabor, R. Nixon-Luke, G. Bryant, V. Bansal, B.L. Wilkinson, Chem. Sci. 7, 6628–6634 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  79. J. Salta, R.I. Benhamou, I.M. Herzog, M. Fridman, Chem. Eur. J. 23, 12724–12728 (2017)

    Article  CAS  PubMed  Google Scholar 

  80. M.G. Roberson, J.M. Duncan, K.J. Flieth, L.M. Geary, M.J. Tucker, RSC Adv. 10, 21464–21472 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  81. X. Wang, Y. Liu, Y. Lin, Y. Han, J. Huang, J. Zhou, Y. Yan, A.C.S. Appl, Bio Mater. 2, 447–453 (2019)

    CAS  Google Scholar 

  82. I.M.A. Awad, A.H. Osman, A.A.M. Aly, Phosphorus Sulfur Silicon Relat. Elem. 178, 1339–1352 (2003)

    Article  CAS  Google Scholar 

  83. I.M.A. Awad, A.A.M. Aly, Synth. React. Inorg. Met.-Org. Chem. 21, 375 (1991)

    Article  CAS  Google Scholar 

  84. A.M. Badawi, E.M.S. Azzam, S.M.I. Morsy, Bioorg. Med. Chem. 14, 8661–8665 (2006)

    Article  CAS  PubMed  Google Scholar 

  85. S. Bal, S. Bal, A. Erener, H. Halipci, S. Akar, Chem. Pap. 68, 352–361 (2014)

    Article  CAS  Google Scholar 

  86. A.Z. El-Sonbati, A.A. El-Bindary, G.G. Mohamed, Sh.M. Morgan, W.M.I. Hassan, A.K. Elkholy, J. Mol. Liq. 218, 16–34 (2016)

    Article  CAS  Google Scholar 

  87. V.A. Modhavadiya, Asian J. Biochem. Pharm. Res. 2, 114–120 (2012)

    CAS  Google Scholar 

  88. W.H. Mahmoud, M.M. Omar, F.N. Sayed, J. Therm. Anal. Calorim. 124, 1071–1089 (2016)

    Article  CAS  Google Scholar 

  89. A.E.I. Ahmed, J.N. Hay, M.E. Bushell, J.N. Wardell, G. Cavalli, React. Funct. Polym. 68, 248–260 (2008)

    Article  CAS  Google Scholar 

  90. Q. Bian, S. Chen, Y. Xing, D. Yuan, L. Lv, G. Wang, Acta Biomater. 76, 39–45 (2018)

    Article  CAS  PubMed  Google Scholar 

  91. S. Concilio, S. Piotto, L. Sessa, P. Iannelli, A. Porta, E.C. Calabrese, M.R. Galdi, L. Incarnato, A.I.P. Conf, Proc. 1459, 256–258 (2012)

    CAS  Google Scholar 

  92. S. Piotto, S. Concilio, L. Sessa, P. Iannelli, A. Porta, E.C. Calabrese, M.R. Galdi, L. Incarnato, Polym. Compos. 34, 1489–1492 (2013)

    Article  CAS  Google Scholar 

  93. S. Concilio, P. Iannelli, L. Sessa, R. Olivieri, A. Porta, F.D. Santis, R. Pantani, S. Piotto, J. Appl. Polym. Sci. 132, 42357–42365 (2015)

    Article  CAS  Google Scholar 

  94. S. Concilio, L. Sessa, A.M. Petrone, A. Porta, R. Diana, P. Iannelli, S. Piotto, Molecules 22, 875/1 (2017)

    Article  CAS  Google Scholar 

  95. B.C. Dixit, H.M. Patel, R.B. Dixit, D.J. Desai, J. Serb. Chem. Soc. 75, 605–614 (2010)

    Article  CAS  Google Scholar 

  96. M.A. El-Borai, H.F. Rizk, G.B. El-Hefnawy, H.F. El-Sayed, S.A. Ibrahim, Fibers Polym. 14, 2061–2068 (2013)

    Article  CAS  Google Scholar 

  97. S.K. Zadafiya, G.M. Malik, Fibers Polym. 14, 904–908 (2013)

    Article  CAS  Google Scholar 

  98. H.E. Gaffer, I.I. Althagafi, Pigm. Resin Technol. 49, 207–214 (2020)

    Article  CAS  Google Scholar 

  99. H.A. Mohamed, B.F. Abdel-Wahab, H.M. Fahmy, Polycycl. Aromat. Compd. (2020). https://doi.org/10.1080/10406638.2020.1723655

    Article  Google Scholar 

  100. N. Parekh, K. Maheria, Fibers Polym. 13, 162–168 (2012)

    Article  CAS  Google Scholar 

  101. V.K. Jain, H.C. Mandalia, N. Bhojak, Fibers Polym. 11, 363–371 (2010)

    Article  CAS  Google Scholar 

  102. A.G. Püntener, R. Pedrazzi, T. Clausen, K. Hunger, W. Bauer, M. Filosa, E. Ross, in K. ed. by I. Dyes (Wiley-VCH Verlag GmbH & Co. KGaA, Hunger, 2002), pp. 427–541

    Google Scholar 

  103. S. Samanta, A.A. Beharry, O. Sadovski, T.M. McCormick, A. Babalhavaeji, V. Tropepe, G.A. Woolley, J. Am. Chem. Soc. 135, 9777–9784 (2013)

    Article  CAS  PubMed  Google Scholar 

  104. M.C. Basheer, Y. Oka, M. Mathews, N. Tamaoki, Chem.—Eur. J. 16, 3489–3496 (2010)

    Article  CAS  PubMed  Google Scholar 

  105. B.-C. Yu, Y. Shirai, J.M. Tour, Tetrahedron 62, 10303–10310 (2006)

    Article  CAS  Google Scholar 

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The authors would like to thank TIMR (UTC, ESCOM) and Yncrea Hauts-de-France for their support.

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Banaszak-Leonard, E., Fayeulle, A., Franche, A. et al. Antimicrobial azo molecules: a review. J IRAN CHEM SOC 18, 2829–2851 (2021). https://doi.org/10.1007/s13738-021-02238-4

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