Efficient and green synthesis of the ninhydrin-pyrogallol adducts in an ionic liquid and investigation of their antibacterial and synergistic effects on Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa

Subject Areas :

shiva khalil moghadam ¹ , Ashraf Sadat shah velayati ² , atousa Aliahmadi ³

1 - Assistant Prof. of Biochemistry ,Young Researchers and Elite Club, Yadegar-e-Imam Khomeini (RAH) shahr-e-Rey Branch, Islamic Azad University, Tehran, Iran
2 - Associate Prof. of Organic Chemistry, Young Researchers and Elite Club, Yadegar-e-Imam Khomeini (RAH) shahr-e-Rey Branch, Islamic Azad University, Tehran, Iran
3 - Assistant Prof. of Microbiology, Medicinal Plants and Drug Research Institute, Shahid Beheshti University, Tehran, Iran

Received: 2019-02-20 Accepted : 2019-10-23 Published : 2020-08-22

Keywords: antibacterial effect, chloramphenicol, Ionic liquid, Synergy, Ninhydrin-pyrrogallol adducts,

Abstract :

Antimicrobial resistance of bacteria is one of the greatest challenges that threatens human health. In order to introduce new compounds with antibacterial effects, two derivatives of ninhydrin-pyroglycol adducts were synthesized by condensation reaction in an ionic liquid as a green solvent and their effects on Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa isolated from hospitalized patients in Taleghani Hospital was investigated. To determine the lowest bacterial growth inhibitory concentration (MIC) broth micro-dilution method was used. Chloramphenicol was used as standard antibiotic. Comparison of the results of two synthetic samples showed that pyrogallol-ninhydrin adduct 1:1 versus the above bacteria was superior to pyrogallol-ninhydrin adduct 1:2. Synergistic antibacterial effects study of 200 µg/ml of pyrogallol-ninhydrin adduct 1:2 or 100 µg/ml of pyrogallol-ninhydrin adduct 1:1 plus chloramphenicol series, showed that the concentration of chloramphenicol growth inhibitors decreased to 50 µg/ml.

References:

[1] Hanlon, G.; “Fundamentals of microbiology” in: Aulton M.E. (Ed.), “Pharmaceutics, The Science of Dosage Form Design”, 2nd Ed., Churchill Livingstone, London, 2002.
[2] Hussain, T.; Pakistan at the verge of potential epidemics by multi-drug resistant pathogenic bacteria, Adv. Life Sci 2, 46-47, 2015.
[3] Hamdan– Partida, A.; Sainz-Espunes, T.; Bustos-Martinez, J.; J. Clinical. Microbiol. 48, 1701-1705, 2010.
[4] Ravat hi, G.; Puri, J.; Jain, B.K.; Bacteriology of burns, Burns 24, 347-349, 1998.
[5] Shittu, A.; Okon, K.; Adesida, S.; Oyedara, O.; Witte, W.; Strommenger, B.; Layer, F.; BMC Microbiology 11, 92-100, 2011.
[6] Borsari, A.; Bucher,B.; Brazzola, P.; Dolina, G.; Clinical Therapeutics 30, 2090-2095, 2008..
[7] Zinsser, H.; Wolfgang, K. Joklik; Amos, D.B.; Willett, H.P.; “Zinsser Microbiology”, 20th Ed., McGraw-Hill Professional Publishing, U.S., 1992.
[8] Vanhems, P.; lepape, A.; Savey, A.; Jambou, A.; Fabry, P.; J. Hosp Infect. 45, 98-106, 2000.
[9] Arvanitidou, M.; Katikaridou, E.; Tsakria, A.; J. Hosp. Infect. 61, 219-240, 2005.
[10] Lee, K.Y.; Seo, J.; Kim, J.N.; Tetrahedron Letters 46, 4505-4508, 2005.
[11] Bengiat, R.; Gil, M.; Klein, A.; Cohen, O.; Cohen, S.; Dubnikova, F.; Tetrahedron 72, 2429-2439, 2016.
[12] Kirilmis, C.; Ahmedzade, M.; Süleyman, S.; Koca, M.; Euro. J. Med Chem.43, 300-308, 2008.
[13] Shazia, N.; Philip, C.; Stevenson, S.; Phythian, J.; Nigel, C.; Veitch David, R.; Tetrahedron 62, 4214-4226, 2006.
[14] Balasaheb, Y.; Agasimundin, Y.S.; Shivkumar, B.; Devanand Shinde, B.; J. Chil. Chem. Soc. 54, 77-79, 2009.
[15] Chetan, B.; Sanganna, B.; Sandip, K.;  Patil, L.; International Journal of Chemical Sciences and Applications 1,  42-49, 2010.
[16] Wasserscheid, P.; Welton, T.; Ionic liquids in Synthesis 21, 223-224, 2003.
[17] Yavari, I.; Kowsari, E.; Tetrahedron Lett. 48, 3753-3756, 2007.
[18] Yavari, I.; Shahvelayati, A.S.; Ghanbari, M.; J. Iran. Chem. Soc. 8, 636-642, 2011.
[19] Shahvelayati, A.S.; Esmaeeli, Z.; J. Sulfur Chem. 33, 319-325, 2012.
[20] Vygodskii, Y.S.; Lozinskaya, E.I.; Shaplov, A.S.; Macromol. Rapid. Commun. 23,676-679, 2002.
[21] Murray, P.; Ellen, B.; Manual of clinical microbiology, 9th Edition, ASM press, USA, 2007.

_||_