Abstract
In this communication, we feature the synthesis and in-depth characterization of a series of silver(I) complexes obtained from the complexation of quinolin-4-yl Schiff base ligands ((E)-2-((quinolin-4-ylmethylene)amino)phenol La, 2-(quinolin-4-yl)benzo[d]thiazole Lb, (E)-N-(2-fluorophenyl)-1-(quinolin-4-yl)methanimine Lc, (E)-N-(4-chlorophenyl)-1-(quinolin-4-yl)methanimine Ld, (E)-1-(quinolin-4-yl)-N-(p-tolyl)methanimine Le, (E)-1-(quinolin-4-yl)-N-(thiophen-2-ylmethyl)methanimine Lf) and three different silver(I) anions (nitrate, perchlorate and triflate). Structurally, the complexes adopted different coordination geometries, which included distorted linear or distorted tetrahedral geometry. The complexes were evaluated in vitro for their potential antibacterial and antioxidant activities. In addition, their interactions with calf thymus-DNA (CT-DNA) and bovine serum albumin (BSA) were evaluated. All the complexes had a wide spectrum of effective antibacterial activity against gram-positive and gram-negative bacterial and good antioxidant properties. The interactions of the complexes with CT-DNA and BSA were observed to occur either through intercalation or through a minor groove binder, while the interaction of the complexes with BSA reveals that some of the complexes can strongly quench the fluorescence of BSA through the static mechanism. The molecular docking studies of the complexes were also done to further elucidate the modes of interaction with CT-DNA and BSA.
Similar content being viewed by others
Abbreviations
- BSA:
-
Bovine serum albumin
- CLSI:
-
Clinical and Laboratory Standards Institute
- CT-DNA:
-
Calf-thymus deoxyribonucleic acid
- DMSO:
-
Dimethyl sulfoxide
- DNA:
-
Deoxyribonucleic acid
- DPPH:
-
2,2-Diphenyl-1-picrylhydrazyl
- EB:
-
Ethidium bromide
- H342:
-
Hoechst 33342
- FRAP:
-
Ferric reducing antioxidant power
- IC50 :
-
50% Inhibitory concentration
- MHA:
-
Müeller–Hinton agar
- MIC:
-
Minimum inhibitory concentration
- MRSA:
-
Methicillin-resistant staphylococcus aureus
- NB:
-
Nutrient broth
- RNA:
-
Ribonucleic acid
- ROSs:
-
Reactive oxygen species
- TPTZ:
-
Tripyridyltriazine
- Trp:
-
Tryptophan
- Tyr:
-
Tyrosine
References
Abdel-Rahman LH, Abu-Dief AM, El-Khatib RM, Abdel-Fatah SM, Seleem AA (2016) New Cd(II), Mn(II) and Ag(I) Schiff base complexes: synthesis, characterization, DNA binding and antimicrobial activity. IJNC 2(3):83–91. https://doi.org/10.18576/ijnc/020303
Abdel-Rahman LH, Adam MS, Abu-Dief AM, Ahmed HE, Nafady A (2020) Non-linear optical property and biological assays of therapeutic potentials under in vitro conditions of Pd(II), Ag(I) and Cu(II) complexes of 5-diethyl amino-2-({2-[(2-hydroxy-benzylidene)-amino]-phenylimino}-methyl)-phenol. Molecules 25(21):1–24. https://doi.org/10.3390/molecules25215089
Adeleke AA, Islam MS, Olofinsan K, Salau VF, Mocktar C, Omondi B (2021a) Evaluation of substituent bioactivity and anion impact of linear and T-shaped silver(I) pyridinyl complexes as potential antiproliferative, antioxidant, antimicrobial agents and DNA- and BSA-binders. N J Chem 45(35):17827–17846
Adeleke AA, Islam MS, Sanni O, Mocktar C, Zamisa SJ, Omondi B (2021b) Aryl variation and anion effect on CT-DNA binding and in vitro biological studies of pyridinyl Ag(I) complexes. J Inorg Biochem 214:1–17. https://doi.org/10.1016/j.jinorgbio.2020.111266
Adeleke AA, Zamisa SJ, Islam MS, Olofinsan K, Salau VF, Mocktar C, Omondi B (2021c) Quinoline functionalized Schiff base silver(I) complexes: interactions with biomolecules and in vitro cytotoxicity, antioxidant and antimicrobial activities. Molecules 26(5):1205
Adeleke AA, Zamisa SJ, Omondi B (2020) Crystal structure of dichlorido-bis((E)-2-((pyridin-4-ylmethylene)amino)phenol)zinc(II), C24H20Cl2N4O2Zn. Z Kristallogr NCS 235(3):625–628. https://doi.org/10.1515/ncrs-2019-0863
Aguilar CA, Jimenez AB, Silva AR, Kaur N, Thangarasu P, Ramos JM, Singh N (2015) Organic–inorganic hybrid nanoparticles for bacterial inhibition: synthesis and characterization of doped and undoped ONPs with Ag/Au NPs. Molecules 20(4):6002–6021. https://doi.org/10.3390/molecules20046002
Alegaon S, Kashniyal K, Kuncolienkar S, Kavalapure R, Salve P, Palled M et al (2020) Synthesis and biological evaluation of some 4-aminoquinoline derivatives as potential antitubercular agents. Future J Pharm Sci 6(1):1–12. https://doi.org/10.1186/s43094-019-0016-7
Aleksić M, Kapetanović V (2014) An overview of the optical and electrochemical methods for detection of DNA–drug interactions. Acta Chim Slov 61(3):555–573
Ali OAM, El-Medani SM, Ahmed DA, Nassar DA (2014) Metal carbonyl complexes with Schiff bases derived from 2-pyridinecarboxaldehyde: syntheses, spectral, catalytic activity and antimicrobial activity studies. J Mol Struct 1074:713–722. https://doi.org/10.1016/j.molstruc.2014.05.035
Al-Rashida M, Ahsen S (2015) In search of a docking protocol to distinguish between DNA intercalators and groove binders: genetic algorithm vs. shape-complementarity based docking methods. RSC Adv 5(88):72394–72404. https://doi.org/10.1039/c5ra09929c
Alsalme A, Khan RA, Alkathiri AM, Ali MS, Tabassum S, Jaafar M, Al-Lohedan HA (2018) Beta-carboline silver compound binding studies with human serum albumin: a comprehensive multispectroscopic analysis and molecular modeling study. Bioinorg Chem Appl 2018:9782419. https://doi.org/10.1155/2018/9782419
Anjomshoa M, Fatemi SJ, Torkzadeh-Mahani M, Hadadzadeh H (2014) DNA- and BSA-binding studies and anticancer activity against human breast cancer cells (MCF-7) of the zinc(II) complex coordinated by 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine. Spectrochim Acta A 127:511–520. https://doi.org/10.1016/j.saa.2014.02.048
Arjmand F, Sayeed F, Muddassir M (2011) Synthesis of new chiral heterocyclic Schiff base modulated Cu(II)/Zn(II) complexes: their comparative binding studies with CT-DNA, mononucleotides and cleavage activity. J Photochem Photobiol B 103(2):166–179. https://doi.org/10.1016/j.jphotobiol.2011.03.001
Asanin DP, Skaro Bogojevic S, Perdih F, Andrejevic TP, Milivojevic D, Aleksic I et al (2021) Structural characterization, antimicrobial activity and BSA/DNA binding affinity of new silver(I) complexes with thianthrene and 1,8-naphthyridine. Molecules. https://doi.org/10.3390/molecules26071871
Banti CN, Giannoulis AD, Kourkoumelis N, Owczarzak AM, Poyraz M, Kubicki M et al (2012) Mixed ligand–silver(I) complexes with anti-inflammatory agents which can bind to lipoxygenase and calf-thymus DNA, modulating their function and inducing apoptosis. Metallomics 4(6):545–560. https://doi.org/10.1039/c2mt20039b
Barton JK, Olmon ED, Sontz PA (2011) Metal complexes for DNA-mediated charge transport. Coord Chem Rev 255(7–8):619–634. https://doi.org/10.1016/j.ccr.2010.09.002
Bawa S, Kumar S, Drabu S, Kumar R (2010) Structural modifications of quinoline-based antimalarial agents: recent developments. J Pharm Bioallied Sci 2(2):64–71. https://doi.org/10.4103/0975-7406.67002
Bedlovicova Z, Strapac I, Balaz M, Salayova A (2020) A brief overview on antioxidant activity determination of silver nanoparticles. Molecules. https://doi.org/10.3390/molecules25143191
BIOVIA Dassault Systemes (2021). Discovery Studio Visualizer (version 21.1.0.20298). Dassault Systemes, San Diego
Chandra S, Chaurasia M, Tomar D (2018) BSA binding studies of Co(II), Ni(II) and Cu(II) metal complexes of Schiff base derived from 2-hydroxy-4-methoxybenzaldehyde and 2-amino-6-methylbenzothiazole. Egypt J Chem. https://doi.org/10.21608/ejchem.2018.4907.1434
Chanquia SN, Larregui F, Puente V, Labriola C, Lombardo E, Garcia Linares G (2019) Synthesis and biological evaluation of new quinoline derivatives as antileishmanial and antitrypanosomal agents. Bioorg Chem 83:526–534. https://doi.org/10.1016/j.bioorg.2018.10.053
Chen X, Guo C, Kong J (2012) Oxidative stress in neurodegenerative diseases. Neural Regen Res 7(5):376–385. https://doi.org/10.3969/j.issn.1673-5374.2012.05.009
Chen J, Yang J, Ma L, Li J, Shahzad N, Kim CK (2020) Structure–antioxidant activity relationship of methoxy, phenolic hydroxyl, and carboxylic acid groups of phenolic acids. Sci Rep 10(1):2611. https://doi.org/10.1038/s41598-020-59451-z
Cifuentes-Vaca OL, Andrades-Lagos J, Campanini-Salinas J, Laguna A, Vásquez-Velásquez D, Concepción Gimeno M (2019) Silver(I) and copper(I) complexes with a Schiff base derived from 2-aminofluorene with promising antibacterial activity. Inorg Chim Acta 489:275–279. https://doi.org/10.1016/j.ica.2019.02.033
Daravath S, Rambabu A, Shankar DS, Raj S (2019) Structure elucidation of copper(II), cobalt(II) and nickel(II) complexes of benzothiazole derivatives: investigation of DNA binding, nuclease efficacy, free radical scavenging and biocidal properties. Chem Data Collect 24:100293. https://doi.org/10.1016/j.cdc.2019.100293
de la Guardia C, Stephens DE, Dang HT, Quijada M, Larionov OV, Lleonart R (2018) Antiviral activity of novel quinoline derivatives against dengue virus serotype 2. Molecules 23(3):1–11. https://doi.org/10.3390/molecules23030672
Dehghanpour S, Mahmoudi A (2007) Synthesis, structure, and redox properties of copper(I) complexes with phenylpyridin-2-ylmethyleneamine derivatives. Main Group Chem 6(2):121–130. https://doi.org/10.1080/10241220801889025
Duric SZ, Vojnovic S, Andrejevic TP, Stevanovic NL, Savic ND, Nikodinovic-Runic J et al (2020) Antimicrobial activity and DNA/BSA binding affinity of polynuclear silver(I) complexes with 1,2-bis(4-pyridyl)ethane/ethene as bridging ligands. Bioinorg Chem Appl 2020(3812050):1–12. https://doi.org/10.1155/2020/3812050
El Jemli M, Kamal R, Marmouzi I, Zerrouki A, Cherrah Y, Alaoui K (2016) Radical-scavenging activity and ferric reducing ability of Juniperus thurifera (L.), J. oxycedrus (L.), J. phoenicea (L.) and Tetraclinis articulata (L.). Adv Pharmacol Sci 2016:6392656. https://doi.org/10.1155/2016/6392656
Fadda AA, Tawfik EH, Selim YA (2018) Synthesis and biological evaluation of some new thiophene, thiazole, dithiolane derivatives and related compounds. Polycycl Aromat Compd. https://doi.org/10.1080/10406638.2018.1555174
Farrugia L (2012) WinGX and ORTEP for Windows: an update. J Appl Crystallogr 45(4):849–854. https://doi.org/10.1107/S0021889812029111
Gill SC, Von Hippel PH (1989) Calculation of protein extinction coefficients from amino acid sequence data. Anal Biochem 182(2):319–326
Gök Y, Sarı Y, Akkoç S, Özdemir İ, Günal S (2014) Antimicrobial studies of N-heterocyclic carbene silver complexes containing benzimidazol-2-ylidene ligand. Int J Inorg Chem 2014:1–6. https://doi.org/10.1155/2014/191054
Gomathi A, Vijayan P, Viswanathamurthi P, Suresh S, Nandhakumar R, Hashimoto T (2017) Organoruthenium(II) compounds with pyridyl benzoxazole/benzthiazole moiety: studies on DNA/protein binding and enzyme mimetic activities. J Coord Chem 70(10):1645–1666. https://doi.org/10.1080/00958972.2017.1309649
Goswami S, Sen D, Das NK, Fun H-K, Quah CK (2011) A new rhodamine based colorimetric ‘off–on’ fluorescence sensor selective for Pd2+ along with the first bound X-ray crystal structure. Chem Commun 47(32):9101–9103
Gulcin I (2015) Fe(3+)–Fe(2+) transformation method: an important antioxidant assay. Methods Mol Biol 1208:233–246. https://doi.org/10.1007/978-1-4939-1441-8_17
Hajiashrafi T, Salehi S, Kubicki M, Bauzá A, Frontera A, Flanagan KJ, Senge MO (2019) Solid-state supramolecular architectures of a series of Hg(II) halide coordination compounds based on hydroxyl-substituted Schiff base ligands. CrystEngComm 21(41):6301–6312. https://doi.org/10.1039/c9ce01078e
Halder S, Dey A, Ortega-Castro J, Frontera A, Ray PP, Roy P (2016) Irradiation specified conformational change in a small organic compound and its effect on electrical properties. J Phys Chem C 120(44):25557–25563. https://doi.org/10.1021/acs.jpcc.6b10081
Haque RA, Ghdhayeb MZ, Budagumpi S, Salman AW, Ahamed MBK, Majid AMSA (2013) Non-symmetrically substituted N-heterocyclic carbene–Ag(I) complexes of benzimidazol-2-ylidenes: synthesis, crystal structures, anticancer activity and transmetallation studies. Inorg Chim Acta 394:519–525. https://doi.org/10.1016/j.ica.2012.09.013
Hindler JA, Richter SS (2016) Methods for antimicrobial dilution and disk susceptibility testing of infrequently isolated or fastidious bacteria: M45. Clinical and Laboratory Standards Institute
Hong M, Geng H, Niu M, Wang F, Li D, Liu J, Yin H (2014) Organotin(IV) complexes derived from Schiff base N′-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-4-carbohydrazone: synthesis, in vitro cytotoxicities and DNA/BSA interaction. Eur J Med Chem 86:550–561. https://doi.org/10.1016/j.ejmech.2014.08.070
Husain S, Verma SK, Yasin D, Hemlata A, Rizvi MM, Fatma T (2021) Facile green bio-fabricated silver nanoparticles from microchaete infer dose-dependent antioxidant and anti-proliferative activity to mediate cellular apoptosis. Bioorg Chem 107:104535. https://doi.org/10.1016/j.bioorg.2020.104535
İnci D, Aydın R, Vatan Ö, Huriyet H, Zorlu Y, Çoşut B, Çinkılıç N (2019) Cu(II) tyrosinate complexes containing methyl substituted phenanthrolines: synthesis, X-ray crystal structures, biomolecular interactions, antioxidant activity, ROS generation and cytotoxicity. Appl Organomet Chem 33(1):e4652. https://doi.org/10.1002/aoc.4652
Irshad M, Zafaryab M, Singh M, Rizvi MM (2012) Comparative analysis of the antioxidant activity of cassia fistula extracts. Int J Med Chem 2012:157125. https://doi.org/10.1155/2012/157125
İspir E, Toroğlu S, Kayraldız A (2008) Syntheses, characterization, antimicrobial and genotoxic activities of new Schiff bases and their complexes. Transit Met Chem 33(8):953–960. https://doi.org/10.1007/s11243-008-9135-2
Jadhav GR, Deshmukh DG, Medhane VJ, Gaikwad VB, Bholay AD (2016) 2,5-Disubstituted 1,3,4-oxadiazole derivatives of chromeno[4,3-b]pyridine: synthesis and study of antimicrobial potency. Heterocycl Commun 22(3):123–130. https://doi.org/10.1515/hc-2015-0215
Jain S, Chandra V, Jain PK, Pathak K, Pathak D, Vaidya A (2019) Comprehensive review on current developments of quinoline-based anticancer agents. Arab J Chem 12(8):4920–4946. https://doi.org/10.1016/j.arabjc.2016.10.009
Jiménez ABP, Aguilar CAH, Ramos JMV, Thangarasu P (2015) Synergistic antibacterial activity of nanohybrid materials ZnO–Ag and ZnO–Au: synthesis, characterization, and comparative analysis of undoped and doped ZnO nanoparticles. Aust J Chem. https://doi.org/10.1071/ch14123
Jimenez J, Chakraborty I, Rojas-Andrade M, Mascharak PK (2017) Silver complexes of ligands derived from adamantylamines: water-soluble silver-donating compounds with antibacterial properties. J Inorg Biochem 168:13–17. https://doi.org/10.1016/j.jinorgbio.2016.12.009
Jung WK, Koo HC, Kim KW, Shin S, Kim SH, Park YH (2008) Antibacterial activity and mechanism of action of the silver ion in Staphylococcus aureus and Escherichia coli. Appl Environ Microbiol 74(7):2171–2178. https://doi.org/10.1128/AEM.02001-07
Jursic BS, Douelle F, Bowdy K, Stevens ED (2002) A new facile method for preparation of heterocyclic α-iminonitriles and α-oxoacetic acid from heterocyclic aldehydes, p-aminophenol, and sodium cyanide. Tetrahedron Lett 43(30):5361–5365
Kakkar R, Garg R (2002) Theoretical study of tautomeric structures and fluorescence spectra of Hoechst 33258. J Mol Struct THEOCHEM 579(1–3):109–113
Karadag A, Korkmaz N, Aydin A, Akbas H, Tekin S, Yerli Y, Sen F (2020) Metalo components exhibiting significant anticancer and antibacterial properties: a novel sandwich-type like polymeric structure. Sci Rep 10(1):12472. https://doi.org/10.1038/s41598-020-69416-x
Kazemi Z, Rudbari HA, Mirkhani V, Sahihi M, Moghadam M, Tangestaninejad S, Mohammadpoor-Baltork I (2015) Synthesis, characterization, crystal structure, DNA- and HSA-binding studies of a dinuclear Schiff base Zn(II) complex derived from 2-hydroxynaphthaldehyde and 2-picolylamine. J Mol Struct 1096:110–120. https://doi.org/10.1016/j.molstruc.2015.04.033
Kellett A, Molphy Z, Slator C, McKee V, Farrell NP (2019) Molecular methods for assessment of non-covalent metallodrug–DNA interactions. Chem Soc Rev 48(4):971–988. https://doi.org/10.1039/C8CS00157J
Kosiha A, Parthiban C, Elango KP (2018) Metal(II) complexes of bioactive aminonaphthoquinone-based ligand: synthesis, characterization and BSA binding, DNA binding/cleavage, and cytotoxicity studies. J Coord Chem 71(10):1560–1574. https://doi.org/10.1080/00958972.2018.1461846
Kouznetsov VV, Meléndez Gómez CM, Peña JLV, Vargas-Méndez LY (2019) Natural and synthetic quinoline molecules against tropical parasitic pathologies: an analysis of activity and structural evolution for developing new quinoline-based antiprotozoal agents, pp 87–164. https://doi.org/10.1016/b978-0-12-815723-7.00004-3
Kumar RR, Ramesh R (2015) Synthesis, molecular structure and electrochemical properties of nickel(II) benzhydrazone complexes: influence of ligand substitution on DNA/protein interaction, antioxidant activity and cytotoxicity. RSC Adv 5(123):101932–101948. https://doi.org/10.1039/c5ra19530f
Kundu N, Audhya A, Abtab SMT, Ghosh S, Tiekink ERT, Chaudhury M (2010) Anion-controlled assembly of silver(I) complexes of multiring heterocyclic ligands: a structural and photophysical study. Cryst Growth Des 10(3):1269–1282. https://doi.org/10.1021/cg901288h
Li Y, Yang Z-Y, Wang M-F (2010) Synthesis, characterization, DNA binding properties, fluorescence studies and antioxidant activity of transition metal complexes with hesperetin-2-hydroxy benzoyl hydrazone. J Fluoresc 20(4):891–905. https://doi.org/10.1007/s10895-010-0635-z
Li H, Liu C, Dai B, Tang X, Zhang ZJ, Xiong Z, Liu X (2015) Synthesis, conductivity, and electromagnetic wave absorption properties of chiral poly Schiff bases and their silver complexes. J Appl Polym Sci 132(36):1–8. https://doi.org/10.1002/app.42498
Li L-J, Yan QQ, Liu GJ, Yuan Z, Lv ZH, Fu B et al (2017) Synthesis characterization and cytotoxicity studies of platinum(II) complexes with reduced amino pyridine Schiff base and its derivatives as ligands. Biosci Biotechnol Biochem 81(6):1081–1089. https://doi.org/10.1080/09168451.2016.1259550
Mavridis L, Hudson BD, Ritchie DW (2007) Toward high throughput 3D virtual screening using spherical harmonic surface representations. J Chem Inf Model 47(5):1787–1796
Medici S, Peana M, Crisponi G, Nurchi VM, Lachowicz JI, Remelli M, Zoroddu MA (2016) Silver coordination compounds: a new horizon in medicine. Coord Chem Rev 327–328:349–359. https://doi.org/10.1016/j.ccr.2016.05.015
Montalban AG (2011) Quinolines and isoquinolines. Heterocycl Nat Prod Synth 2011:299–339
Mukhopadhyay S, Singh RS, Paitandi RP, Sharma G, Koch B, Pandey DS (2017) Influence of substituents on DNA and protein binding of cyclometalated Ir(III) complexes and anticancer activity. Dalton Trans 46(26):8572–8585. https://doi.org/10.1039/c7dt01015j
Murugavel S, Stephen CJP, Subashini R, AnanthaKrishnan D (2017) Synthesis, structural elucidation, antioxidant, CT-DNA binding and molecular docking studies of novel chloroquinoline derivatives: promising antioxidant and anti-diabetic agents. J Photochem Photobiol B 173:216–230. https://doi.org/10.1016/j.jphotobiol.2017.05.043
Nayak SG, Poojary B (2019) Synthesis of novel Schiff bases containing arylpyrimidines as promising antibacterial agents. Heliyon 5(8):e02318. https://doi.org/10.1016/j.heliyon.2019.e02318
Njogu EM, Omondi B, Nyamori VO (2017a) Coordination polymers and discrete complexes of Ag(I)–N-(pyridylmethylene)anilines: synthesis, crystal structures and photophysical properties. J Coord Chem 70(16):2796–2814. https://doi.org/10.1080/00958972.2017.1370088
Njogu EM, Omondi B, Nyamori VO (2017b) Silver(I)–pyridinyl Schiff base complexes: synthesis, characterisation and antimicrobial studies. J Mol Struct 1135:118–128. https://doi.org/10.1016/j.molstruc.2017.01.061
Njogu EM, Martincigh BS, Omondi B, Nyamori VO (2018) Synthesis, characterization, antimicrobial screening and DNA binding of novel silver(I)–thienylterpyridine and silver(I)–furylterpyridine complexes. Appl Organomet Chem 32(12):e4554. https://doi.org/10.1002/aoc.4554
Oladipo SD, Omondi B, Mocktar C (2019) Synthesis and structural studies of nickel(II)- and copper(II)–N, N′-diarylformamidine dithiocarbamate complexes as antimicrobial and antioxidant agents. Polyhedron 170:712–722. https://doi.org/10.1016/j.poly.2019.06.038
Oladipo SD, Olotu FA, Soliman M, Mocktar C, Omondi B (2020) Formamidine-based thiuram disulfides: synthesis, structural characterization, biological studies, and preliminary cheminformatics evaluation. J Mol Struct. https://doi.org/10.1016/j.molstruc.2020.128553
Öztürk S, Akkurt M, Aydemír E, Fun H-K (2003) N-(4-bromo-2-nitrophenyl)-N-methyl-N′-(quinolin-4-ylmethylene)hydrazine. Acta Crystallogr E 59(4):o488–o489. https://doi.org/10.1107/s1600536803005348
Patel C, Bassin JP, Scott M, Flye J, Hunter AP, Martin L, Goyal M (2016) Synthesis and antimicrobial activity of 1, 2-benzothiazine derivatives. Molecules 21(7):1–16. https://doi.org/10.3390/molecules21070861
Patra GK, Goldberg I (2003a) Supramolecular design of coordination complexes of silver(I) with polyimine ligands: synthesis, materials characterization, and structure of new polymeric and oligomeric materials. Cryst Growth Des 3(3):321–329
Patra GK, Goldberg I (2003b) The synthesis and characterization of a series of bis-bidentate Schiff base ligands and their coordination complexes with silver(I), copper(I) and zinc(II) d 10 metal ions. N J Chem 27(7):1124–1131
Pavithra K, Vadivukkarasi S (2015) Evaluation of free radical scavenging activity of various extracts of leaves from Kedrostis foetidissima (Jacq.) Cogn. Food Sci Hum Wellness 4(1):42–46. https://doi.org/10.1016/j.fshw.2015.02.001
Petzinger E, Geyer J (2006) Drug transporters in pharmacokinetics. Naunyn Schmiedebergs Arch Pharmacol 372(6):465–475. https://doi.org/10.1007/s00210-006-0042-9
Phadte AA, Banerjee S, Mate NA, Banerjee A (2019) Spectroscopic and viscometric determination of DNA-binding modes of some bioactive dibenzodioxins and phenazines. Biochem Biophys Rep 18(100629):1–7. https://doi.org/10.1016/j.bbrep.2019.100629
Phaniendra A, Jestadi DB, Periyasamy L (2015) Free radicals: properties, sources, targets, and their implication in various diseases. Indian J Clin Biochem 30(1):11–26. https://doi.org/10.1007/s12291-014-0446-0
Pricopie AI, Ionut I, Marc G, Arseniu AM, Vlase L, Grozav A et al (2019) Design and synthesis of novel 1,3-thiazole and 2-hydrazinyl-1,3-thiazole derivatives as anti-Candida agents: in vitro antifungal screening, molecular docking study, and spectroscopic investigation of their binding interaction with bovine serum albumin. Molecules. https://doi.org/10.3390/molecules24193435
Pucci D, Barberio G, Bellusci A, Crispini A, La Deda M, Ghedini M, Szerb EI (2005) Induction of columnar mesomorphism in tetracoordinated ionic silver(I) complexes based on chelate 4, 4′-disubstituted 2, 2′-bipyridines. Eur J Inorg Chem 2005(12):2457–2463. https://doi.org/10.1002/ejic.200500002
Puskullu MO, Shirinzadeh H, Nenni M, Gurer-Orhan H, Suzen S (2016) Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues. J Enzyme Inhib Med Chem 31(1):121–125. https://doi.org/10.3109/14756366.2015.1005012
Quin LD, Tyrell JA (2010) Fundamentals of heterocyclic chemistry: importance in nature and in the synthesis of pharmaceuticals. Wiley, New York
Raman N, Sakthivel A, Jeyamurugan R (2009) Synthesis, characterization, DNA binding, photo-induced DNA cleavage, and antimicrobial activity of metal complexes of a Schiff base derived from bis(3-aminophenyl)malonamide. J Coord Chem 62(24):3969–3985. https://doi.org/10.1080/00958970903288294
Rehman SU, Yaseen Z, Husain MA, Sarwar T, Ishqi HM, Tabish M (2014) Interaction of 6 mercaptopurine with calf thymus DNA—deciphering the binding mode and photoinduced DNA damage. PLoS ONE 9(4):e93913. https://doi.org/10.1371/journal.pone.0093913
Ribeiro APC, Anbu S, Alegria E, Fernandes AR, Baptista PV, Mendes R et al (2018) Evaluation of cell toxicity and DNA and protein binding of green synthesized silver nanoparticles. Biomed Pharmacother 101:137–144. https://doi.org/10.1016/j.biopha.2018.02.069
Riechert-Krause F, Weisz K (2013) Indoloquinolines as DNA binding ligands. Heterocycl Commun 19(3):145–166
Senerovic L, Opsenica D, Moric I, Aleksic I, Spasic M, Vasiljevic B (2020) Quinolines and quinolones as antibacterial, antifungal, anti-virulence, antiviral and anti-parasitic agents. Adv Exp Med Biol 1282:37–69. https://doi.org/10.1007/5584_2019_428
Shahabadi N, Hakimi M, Morovati T, Fatahi N (2017) DNA binding affinity of a macrocyclic copper(II) complex: spectroscopic and molecular docking studies. Nucleosides Nucleotides Nucleic Acids 36(8):497–510. https://doi.org/10.1080/15257770.2017.1332370
Shahid-ul-Islam S, Butola BS, Mohammad F (2016) Silver nanomaterials as future colorants and potential antimicrobial agents for natural and synthetic textile materials. RSC Adv 6(50):44232–44247. https://doi.org/10.1039/c6ra05799c
Shanty AA, Mohanan PV (2021) Synthesis, characterization, DNA binding, antibacterial, antidiabetic, molecular docking and DFT studies of Ni(II), Cu(II) and Zn(II) complexes derived from heterocyclic Schiff base. In: Inorganic and nanometal chemistry. Taylor and Francis, pp. 1–16
Sharma D, Revanasiddappa HD, Jayalakshmi B (2019) DNA/BSA interaction and in vitro antimicrobial studies of Mn(III) complexes bearing bidentate N, O donor Schiff bases. J Iran Chem Soc 17(1):43–58. https://doi.org/10.1007/s13738-019-01745-9
Sheldrick G (2008) A short history of SHELX. Acta Crystallogr A 64(1):112–122. https://doi.org/10.1107/S0108767307043930
Suganthi M, Elango KP (2017) Synthesis, characterization and serum albumin binding studies of vitamin K3 derivatives. J Photochem Photobiol B 166:126–135. https://doi.org/10.1016/j.jphotobiol.2016.11.016
Sukri SAM, Heng LY, Karim NHA (2017) Synthesis, characterization and DNA-Binding studies of hydroxyl functionalized platinum(II) salphen complexes. J Fluoresc 27(3):1009–1023. https://doi.org/10.1007/s10895-017-2035-0
Szymańska M, Insińska-Rak M, Dutkiewicz G, Roviello GN, Fik-Jaskółka MA, Patroniak V (2020) Thiophene–benzothiazole dyad ligand and its Ag(I) complex—synthesis, characterization, interactions with DNA and BSA. J Mol Liq. https://doi.org/10.1016/j.molliq.2020.114182
Szymańska M, Pospieszna-Markiewicz I, Mańka M, Insińska-Rak M, Dutkiewicz G, Patroniak V, Fik-Jaskółka MA (2021) Synthesis and spectroscopic investigations of Schiff base ligand and its bimetallic Ag(I) complex as DNA and BSA binders. Biomolecules. https://doi.org/10.3390/biom11101449
Tariq S, Kamboj P, Amir M (2019) Therapeutic advancement of benzothiazole derivatives in the last decennial period. Arch Pharm (Weinh) 352(1):e1800170. https://doi.org/10.1002/ardp.201800170
Tian Z, Song L, Zhao Y, Zang F, Zhao Z, Chen N et al (2015) Spectroscopic study on the interaction between naphthalimide–polyamine conjugates and bovine serum albumin (BSA). Molecules 20(9):16491–16523. https://doi.org/10.3390/molecules200916491
Ulitzur S, Weiser I (1981) Acridine dyes and other DNA-intercalating agents induce the luminescence system of luminous bacteria and their dark variants. Proc Natl Acad Sci USA 78(6):3338–3342
Uremis N, Uremis MM, Tolun FI, Ceylan M, Doganer A, Kurt AH (2017) Synthesis of 2-substituted benzothiazole derivatives and their in vitro anticancer effects and antioxidant activities against pancreatic cancer cells. Anticancer Res 37(11):6381–6389. https://doi.org/10.21873/anticanres.12091
Vallejos J, Brito I, Cardenas A, Bolte M, Conejeros S, Alemany P, Llanos J (2016) Self-assembly of discrete metallocycles versus coordination polymers based on Cu(I) and Ag(I) ions and flexible ligands: structural diversification and luminescent properties. Polymers (Basel) 8(46):1–16. https://doi.org/10.3390/polym8020046
Vamsikrishna N, Kumar MP, Ramesh G, Ganji N, Daravath S, Raj S (2017) DNA interactions and biocidal activity of metal complexes of benzothiazole Schiff bases: synthesis, characterization and validation. J Chem Sci 129(5):609–622. https://doi.org/10.1007/s12039-017-1273-7
Vanekova Z, Hubcik L, Toca-Herrera JL, Furtmuller PG, Mucaji P, Nagy M (2020) Analysis of binding interactions of ramipril and quercetin on human serum albumin: a novel method in affinity evaluation. Molecules 25(3):1–17. https://doi.org/10.3390/molecules25030547
Vijayakumari A, Sinthiya A (2018) Biosynthesis of phytochemicals coated silver nanoparticles using aqueous extract of leaves of cassia alata—characterization, antibacterial and antioxidant activities. Int J Pharm Clin Res 10(5):138–149
Wani TA, Bakheit AH, Abounassif MA, Zargar S (2018) Study of interactions of an anticancer drug neratinib with bovine serum albumin: spectroscopic and molecular docking approach. Front Chem 6:47. https://doi.org/10.3389/fchem.2018.00047
Wolfe A, Shimer GH Jr, Meehan T (1987) Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry 26(20):6392–6396
Wu H-C, Thanasekaran P, Tsai C-H, Wu J-Y, Huang S-M, Wen Y-S, Lu K-L (2006) Self-assembly, reorganization, and photophysical properties of silver(I)–Schiff-base molecular rectangle and polymeric array species. Inorg Chem 45(1):295–303
Wu H, Yuan J, Bai Y, Pan G, Wang H, Kong J et al (2012) Synthesis, structure, DNA-binding properties and antioxidant activity of silver(I) complexes containing V-shaped bis-benzimidazole ligands. Dalton Trans 41(29):8829–8838. https://doi.org/10.1039/c2dt30512g
Xiong Y, Zhang P, Warner RD, Fang Z (2021) In vitro and cellular antioxidant activities of 3-deoxyanthocyanidin colourants. Food Biosci. https://doi.org/10.1016/j.fbio.2021.101171
Yallur BC, Katrahalli U, Krishna PM, Hadagali MD (2019) BSA binding and antibacterial studies of newly synthesized 5,6-dihydroimidazo[2,1-b]thiazole-2-carbaldehyde. Spectrochim Acta A 222:117192. https://doi.org/10.1016/j.saa.2019.117192
Yernale N, Mathada M (2014) Synthesis, characterization, antimicrobial, DNA cleavage, and in vitro cytotoxic studies of some metal complexes of Schiff base ligand derived from thiazole and quinoline moiety. Bioinorg Chem Appl 2014(314963):1–17. https://doi.org/10.1155/2014/314963
Yousuf S, Arjmand F, Tabassum S (2021) Design, synthesis, ligand’s scaffold variation and structure elucidation of Cu(II) complexes; in vitro DNA binding, morphological studies and their anticancer activity. Polyhedron. https://doi.org/10.1016/j.poly.2021.115450
Yu X, Yang Y, Shiyu L, Yao Q, Heting L, Xiaofang L, Pinggui Y (2011) The fluorescence spectroscopic study on the interaction between imidazo[2,1-b]thiazole analogues and bovine serum albumin. Spectrochim Acta A 83(1):322–328. https://doi.org/10.1016/j.saa.2011.08.038
Zhang G, Hu X, Fu P (2012) Spectroscopic studies on the interaction between carbaryl and calf thymus DNA with the use of ethidium bromide as a fluorescence probe. J Photochem Photobiol B 108:53–61. https://doi.org/10.1016/j.jphotobiol.2011.12.011
Acknowledgements
Ms Adesola A. Adeleke acknowledges Olabisi Onabanjo University, Ago-Iwoye, for granting her study leave to pursue the Ph.D. Programme at the University of KwaZulu-Natal. The authors would like to appreciate the University of KwaZulu-Natal and the National Research Foundation of South Africa (Grant Number 119342) for their financial assistance for Ms. Adesola A. Adeleke.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
No potential conflict of interest was reported by the authors.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Adeleke, A.A., Zamisa, S.J., Islam, M.S. et al. A study of structure–activity relationship and anion-controlled quinolinyl Ag(I) complexes as antimicrobial and antioxidant agents as well as their interaction with macromolecules. Biometals 35, 363–394 (2022). https://doi.org/10.1007/s10534-022-00377-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10534-022-00377-6