Abstract
Sulfamethoxazolyl-azo-phenols [SMX–N=N–C6H2(R)(R/)–OH] (1a, 2a) and their Cu(II) complexes, [Cu(SMX–N=N–C6H2(R)(R/)–O)2] (1b, 2b) (R = p-OMe, R/ = H, 1a/1b; R = p-Cl, R/ = m-CH3, 2a/2b) show antibacterial sensitivity against Gram-positive bacteria, B. subtillis; IC50: 281.47 ± 1.84 μM (1a), 126.39 ± 1.66 μM (1b), and 279.94 ± 3.15 μM (2a), 123.62 ± 1.27 μM(2b), and Gram-negative bacteria, E. coli; IC50: 204.66 ± 3.31 μM (1a) and 89.05 ± 1.48 μM (1b), 223.13 ± 2.71 μM (2a), and 98.26 ± 1.59 μM (2b). Interaction of DNA with free ligand (1a and 2a) is insignificant, while the complexes (1b and 2b) interact strongly and the binding constants are K b, 8.413 × 104 M−1 (1b) and 6.56 × 105 M−1 (2b). Optimized structures of the compounds are docked with protein structure of DHPS (E. coli) to propose the most favoured binding mode of the drugs in the active site. The in silico test of the compound helps to understand drug metabolism, drug–protein interactions, and toxicity (ADMET).
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Abbreviations
- ADMET:
-
Absorption, distribution, metabolism, and excretion-toxicity in pharmacokinetics
- ATCC:
-
American-type culture collection
- B3LYP:
-
Becke, three-parameter, Lee–Yang–Parr
- CAMD:
-
Computer-aided molecular design
- DFT:
-
Density functional theory
- DHPS:
-
Dihydropteroate synthase
- PDB:
-
Protein data bank
- SMX:
-
Sulfamethoxazole
- TD DFT:
-
Time-dependent density functional theory
References
Walsh C, Wencewicz T (2016) Antibiotics: challenges, mechanisms, opportunities. ASM Press
Madigan M, Martinko J, Stahl D, Clark D (2012) Brock biology of microorganisms (13th ed.). Pearson Education, p 797
Anderson RJ, Groundwater PW, Todd A, Worsley AJ (2012) Sulfonamide antibacterial agents. In: Antibacterial agents: chemistry, mode of action, mechanisms of resistance and clinical applications. Wiley
Slatore GC, Tilles AS (2004) Immunol Allergy Clin N Am 24:477–490
Choquet-Kastylevsky G, Vial T, Descotes J (2002) Curr Allergy Asthma Rep 2:16–25
Lavergne SN, Wang H, Callan HE, Park BK, Naisbitt DJ (2009) J Pharmacol Exp Ther 331:372–381
Naisbitt DJ, Farrell J, Gordon FS, Maggs LJ, Burkhart C, Pichler JW, Pirmohamed M, Park KB (2002) Mol Pharmacol 62:628–637
Sánchez S, Demain AL (eds) (2015) Antibiotics: current innovations and future trends. Caister Academic Press
Clopton RE, Smith A (2002) J Parasitol 88:786–789
Mondal S, Mandal SM, Mondal TK, Sinha C (2015) Spectrochim Acta Part A 150:268–279
Mondal S, Bhanja AK, Ojha D, Mondal TK, Chattopadhyay D, Sinha C (2015) RSC Adv 5:73626–73638
Das D, Sahu N, Mondal S, Roy S, Dutta P, Gupta S, Mondal TK, Sinha C (2015) Polyhedron 99:77–86
Sahu N, Das D, Mondal S, Roy S, Dutta P, Sepay N, Gupta S, Lopez-Torres E, Sinha C (2016) New J Chem 40:5019–5031
Wu CY, Chen LH, Hwang WS, Chen HS (2004) J Organomet Chem 689:2192–2200
Luckey TD, Venugopal B (1977) Metal Toxicity in mammals, vol 1. Plenum Press, New York
Bult A (1983) In: Sigel H (ed) Metal ions in biological systems. Marcel Dekker, New York
Nogrady Th (1988) Medicinal chemistry, 2nd edn. Oxford University Press, New York
Chen F, Askari MS, Ottenwaelder X (2013) Inorg Chim Acta 407:25–30
Chohan ZH, Shad HA, Youssoufi MH, Hadda TB (2010) Eur J Med Chem 45:2893–2901
Ozturk F, Bulut I, Bulut A (2015) Spectrochim Acta A 138:891–899
Weder JE, Dillon CT, Hambley TW, Kennedy BJ, Lay PA, Ray Biffin J, Regtop HL, Davies NM (2002) Coord Chem Rev 232:95–126
Macıas B, Garcıa I, Villa MV, Borras J, Gonzalez-Alvarez M, Castineiras A (2003) J Inorg Biochem 96:367–374
Bertini I, Gray HB, Lippard SJ, Valentine JS (eds) (1994) Bioinorganic chemistry. University Science Books, Mill Valley
Yousuf I, Arjmand F, Tabassum S, Toupet L, Khan RA, Siddiqui MA (2015) Dalton Trans 44:10330–10342
Kremer E, Facchin G, Estévez E, Alborés P, Baran EJ, Ellena J, Torre MH (2006) J Inorg Biochem 100:1167–1175
Torre MH, Facchin G, Kremer E, Castellano EE, Piro Oscar E, Baran Enrique J (2003) J Inorg Biochem 94:200–204
Dimiza F, Perdih F, Tangoulis V, Turel I, Kessissoglou DP, Psomas G (2011) J Inorg Biochem 105:476–489
Macı́as B, Garcı́a I, Villa MV, Borrás J, González-Álvarez M, Castiñeiras A (2003) J Inorg Biochem 96:367–374
García-Giménez JL, Hernández-Gil J, Martínez-Ruíz A, Castiñeiras A, González ML, Pallardó FV, Borrás J, Piña GA (2013) J Inorg Biochem 121:167–178
Vogel AI, Tatchell AR, Furnis BS, Hannaford AJ (1996) Vogel’s textbook of practical organic chemistry (5th Edition). Longman
Bain GA, Berry JF (2008) J Chem Ed 85:532–536
Bruker, Program name (2001) Bruker AXS Inc., Madison
Blessing RH (1995) Acta Crystallogr A 51:33–38
Sheldrick GM (2008) Acta Crystallogr A 64:112–122
Farrugia LJ (1997) J Appl Crystallogr 30:565
Farrugia LJ (1999) J Appl Crystallogr 32:837–838
Bergeron RJ, Roberts WP (1978) Anal Biochem 90:844–848
Hay PJ, Wadt WRJ (1985) J Chem Phys 82:299–310
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) GAUSSIAN 09, Revision D.01. Gaussian Inc., Wallingford
Frisch A, Nielson AB, Holder AJ (2000) GAUSSVIEW user manual. Gaussian Inc, Pittsburgh
Hay PJ, Wadt WR (1985) J Chem Phys 82:270–273
Wadt WR, Hay PJ (1985) J Chem Phys 284:284–298
Casida ME, Jamorski C, Casida KC, Salahub DR (1998) J Chem Phys 108:4439–4449
Barone V, Cossi M (1998) J Phys Chem A 102:1995–2001
Cossi M, Barone V (2001) J Chem Phys 115:4708–4717
Cossi M, Rega N, Scalmani G, Barone V (2003) J Comput Chem 24:669–681
Discovery Studio 3.5 is a product of Accelrys Inc, San Diego
Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (2001) Adv Drug Deliv Rev 46:3–26
Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD (2002) J Med Chem 45:2615–2623
Ojha PK, Roy K (2010) Eur J Med Chem 45:4645–4656
Tabassum S, Afzal M, Arjmand F (2014) Eur J Med Chem 74:694–702
Bhunia P, Bannerjee D, Datta P, Raghavaiah P, Slawin AMZ, Woollins JD, Ribas J, Sinha C (2010) Eur J Inorg Chem 311:311–321
Das D, Sahu N, Roy S, Dutta P, Mondal S, Torres EL, Sinha C (2015) Spectrochim Acta Part A 137:560–568
Frezza M, Hindo S, Chen D, Davenport A, Schmitt S, Tomco D, Dou QP (2010) Curr Pharm Des 16:1813–1825
Acknowledgements
Financial support from West Bengal Department of Science and Technology (228/1(10)/(Sanc.)/ST/P/S&T/9G-16/2012), Kolkata and University Grants Commission (F.42-333/2013(SR)), New Delhi is gratefully acknowledged. Miss. Ananya Das Mahapatra, NICED, Kolkata, is thankfully acknowledged for help.
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Sahu, N., Mondal, S., Sepay, N. et al. Antibacterial activities of sulfamethoxazolyl-azo-phenols and their Cu(II) complexes along with molecular docking properties. J Biol Inorg Chem 22, 833–850 (2017). https://doi.org/10.1007/s00775-017-1461-4
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DOI: https://doi.org/10.1007/s00775-017-1461-4