A review on Schiff base as a bioactive ligand

Purakala ISSN: 0971-2143 (UGC Care Journal) Vol-31-Issue-39-May-2020 A review on Schiff base as a bioactive ligand Swati Kolhe Department of Chemistry, Baburaoji Gholap College Sangvi, Pune, Maharashtra. 411027 Dipak Patil Department of Chemistry, Sardar Vallabhabhai Patel Arts and Science College, Ainpur, Dist. Jalgaon, Maharashtra. 425507 Email: dbpatil37@gmail.com Abstract Schiff bases are obtained from condensation of primary amines with carbonyl compounds. Schiff bases play an important role in inorganic chemistry due to formation of very stable complexes with various transition and inner-transition metals. There are several applications of Schiff bases in the field of biological activities which include antifungal, antimicrobial, antibacterial, anticancer, antioxidant, DNA cleavage, anti-inflammatory etc. Design of a new chemotherapeutic Schiff bases and their metal complexes is now attracting the attention of medicinal chemists. In this review article the biological applications of Schiff bases are summarized. Keywords: Schiff base, antifungal, antimicrobial, antioxidant. Introduction Schiff bases have been known since 1864 when Hugo Schiff reported the condensation of primary amines with carbonyls compounds (Tobriya, 2014). A Schiff base which is also known as imine or azomethine is a nitrogen analogue of an aldehyde or ketone in which the carbonyl group has been replaced by an imine or azomethine group. Schiff bases with aromatic aldehyde are more stable due to conjugated system whereas Schiff bases of aliphatic aldehyde are unstable and they readily get polymerized. Ligands with heterocyclic molecules containing heteroatoms like N, O, S and in azomethine derivatives, C=N linkage is important for biological activities. The presence of lone pair of electrons in sp2 hybridized orbital of nitrogen atom of the azomethine is of considerable chemical and biological importance. Schiff Bases are good chelating agents; generally bi- or tri- dentate ligands are more capable of forming very stable complexes with transition metals. Therefore, Schiff bases metal complexes were widely investigated for their antifungal, antimicrobial, antibacterial, anticancer, antioxidant, DNA cleavage, anti-inflammatory activities (Tobriya, 2014). Schiff bases played an important role as ligands even a century after their discovery in coordination chemistry. Schiff bases are an important class of ligands in co-ordination chemistry. Schiff bases and their metal complexes have been shown to be promising leads not only for synthetic but also for structural research due to their relatively simple synthesis and structural diversity and have been widely investigated, due to their marvellous chemical properties and applications in various fields (Abu-Dief and Mohamed, 2015; Kolhe and Patil, 2019). The chelating capability and biological applications of metal complexes have attracted remarkable attention and they can work as models for biologically significant P a g e | 284 Copyright ⓒ 2020Authors Purakala (UGC Care Journal) ISSN: 0971-2143 Vol-31-Issue-39-May-2020 species. It is believed that the biological activity is related to the hydrogen bonding through the imino group of Schiff bases with the active centers of the cell constituents. Schiff base as a bioactive ligand Antimicrobial The main classes of antimicrobial agents are disinfectants which kill a wide range of microorganisms on non-living surfaces to prevent the spread of illness. Some Schiff bases are known to be promising antifungal agents. (El-Sherif et al., 2012) have prepared Schiff base namely 2aminomethylthiophenyl-4-bromosalicylaldehyde (ATS) (4-bromo-2-(thiophen-2- yl-imino) methylphenol) and its metal complexes. The ligand and their complexes have been screened for their antimicrobial activities against the gram-positive & gram-negative bacteria. Metal complexes possess better antitumor activity than the free ligand thiophene derivatives have intensively antibacterial and antitumor activities. (Amer et al., 2013) have synthesized copper (II) complexes of Schiff bases derived from 7H-2,6-diaminopurine and 4H-3,5diamino1,2,4-triazole with 2-pyridinecarbaldehyde, salicylaldehyde, 2,4dihydroxybenzaldehyde and 2-hydroxy1-naphthaldehyde. These complexes were tested for their in vitro antimicrobial activities against some bacterial and fungal strains. Similarly, anti-tumor activities for some complexes have been evaluated. The results of the antibacterial activity of the tested ligands and their complexes showed moderate activity against E. coli and S. aureus when compared with the standard drug, tetracycline. (Reiss et al., 2018) have synthesized complexes of Co (II), Ni (II) and Cu (II) with the Schiff base derived from ceftazidime and salicylaldehyde. These complexes were tested for in vitro antibacterial activity against selected Gram-negative and Gram-positive bacterial strains, and they exhibited an antibacterial activity superior to that of the Schiff base ligand. Similarly, (Al-Shaalan, 2011) have prepared Schiff base hydrazone ligand and its complexes with Cu (II), Ni (II), Co (II), Mn (II), UO2 (VI) and Fe (II). The ligand and its complexes were tested against a strain of Gram-positive bacteria (Staphylococcus aureus), Gram negative bacteria (Escherichia coli), and fungi (Candida albicans). The tested compounds exhibited high antibacterial activities. In another study, (El-Sherif et al., 2012) have synthesized Schiff base ligand, 1,4-bis[(2-hydroxybenzaldehyde) propyl] piperazine, and its Cu (II), Ni (II) and Co (II) metal complexes. The ligand and its complexes have been screened for their antimicrobial activity against Gram-positive & Gram-negative bacteria. The results indicate that, the three complexes exhibited moderate activity against the fungal strains when compared with standard Amphotericin. Whereas, (Shaabani et al., 2013) have synthesized the Schiff base methyl 2-pyridyl ketone semicarbazone from the condensation of methyl 2-pyridyl ketone and semicarbazide & its complexes. The antimicrobial activity of Schiff base and the complexes was investigated against some bacteria and fungi. The complexes revealed enhanced antibacterial activity than ligand, and this increase in the activity of the metal complexes can be explained on the basis of the chelation theory. Moreover, (Kathiravan et al., 2014) have prepared Pyrene containing Schiff base molecule, namely 4-[(pyren-1ylmethylene) amino] phenol. The antimicrobial studies were carried out against both Gram-positive and Gram-negative bacterial species and also fungal species. The result shows ligand can act as an excellent antimicrobial agent and as a photolabeling agent. In addition, (Rahman et al., 2015) have synthesized azomethine amino ligands derived from the condensation of 3-methoxysalicylaldehyde or 4diethylaminosalicylaldehyde with α-amino acids (L-phenylalanine (P) and DL-tryptophan P a g e | 285 Copyright ⓒ 2020Authors Purakala (UGC Care Journal) ISSN: 0971-2143 Vol-31-Issue-39-May-2020 (T)). The antimicrobial effects of the ligands and their complexes were screened against some Gram- positive & Gram-negative bacteria. The results of these studies indicate that the metal complexes exhibit a stronger antibacterial and antifungal efficiency compared to their corresponding ligands. (Tohidian et al., 2016) have synthesized two Nano- sized Schiff base complexes [M(L)], where L= 2, 2'-((1E, 1E’) -(1, 2 phenylene bis (azanylylidene)) bis (methanylylidene)) bis (4-bromo phenolato) and M=Cu or Zn. In vitro antimicrobial activities of the compounds against some Gram-positive and Gram-negative bacteria and fungus strain were investigated. It was found that Cu (II) complex showed higher antibacterial activity than the Zn (II) complex. In another study, (Abdel‐Rahman et al., 2017) have synthesized a novel Schiff base, namely Z-3-((2-((E)-(2-hydroxynaphthyl) methylene) amino)-5-nitrophenylimino)-1,3dihydroindin-2-one, by the condensation of 2-hydroxy-1-naphthaldehyde and isatin with 4-nitro-o-phenylenediamine. In addition, Ni (II)and Cu (II)complexes of the Schiff base ligand were prepared. The prepared Schiff base ligand and its complexes were screened for their bactericidal and fungicidal activities. The results show that the Cu (II) complex has higher antibacterial activity than the Ni (II) complex. Recently, (Fekri et al., 2017) have synthesized Schiff base and its complexes by condensation of benzohydrazide and salicylaldehyde. Their antibacterial activities were examined against Gram-positive and Gram-negative bacteria. The results of these studies indicated that all compounds had antibacterial activity against Gram-positive bacteria. Similarly, (Khajoee Nejad et al., 2018) have synthesized a tridentate Schiff base ligand, (E)‐ 3‐ ((2‐ hydroxy‐ 3‐ methoxybenzylidene) amino) ‐ 2‐ methylquinazolin‐ 4(3H) ‐ one, and its mixed‐ ligand Ni (II) complex. Furthermore, in‐ vitro antimicrobial studies were performed that indicated the great antibacterial activities of the Ni (II) complex against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Bacillus cereus bacteria. Effect Of substituent Substituents have remarkable impact on biological activities of Schiff bases and its metal complexes. The high-negative potential shows that the metal ion is highly stabilized by the strong donor properties of the substituents which overcome the acceptor property. Generally, the electron withdrawing and electron releasing nature and the position of substituents present in the phenyl ring (figure-1) affect the antimicrobial activities; the presence of substituents at the o-position lowers the antimicrobial activity whereas the substituents at the m- and p-positions give higher antimicrobial activity. Inhibition is improved with the introduction of an electron withdrawing nitro group in the phenyl ring (Justin Dhanaraj and Sivasankaran Nair, 2009). The order of the antimicrobial activity of the synthesized compounds (based on the substituent present in the phenyl ring) is as follows: NO2 > H >OCH3 P a g e | 286 Copyright ⓒ 2020Authors Purakala ISSN: 0971-2143 (UGC Care Journal) Vol-31-Issue-39-May-2020 NO2 N N N N X Where X= H, p-NO2, p-OCH3 Figure-1. Synthesized Schiff base ligand. Antibacterial The increase in the mortality rate associated with infectious diseases is directly related to bacteria that exhibit multiple resistances to antibiotics. The lack of effective treatments is the main cause of this problem. (Parsaee and Mohammadi, 2017) have synthesized some macrocyclic bridged dianilines tetradentate with N-4 coordination sphere Schiff base ligands and their nickel (II) complexes with general formula [(Ni2 LCl4), where L = (C20H14 N2X)2, X=SO2, O, CH2]. All the Schiff bases and their complexes have been detected in vitro both for antibacterial activity against gram-negative and gram-positive bacteria. The nickel (II) complexes were found to be more active than the free macrocycle Schiff bases. Whereas, (Chaudhary and Mishra, 2017) have synthesized Schiff base ligand by the condensation of amoxicillin trihydrate and nicotinaldehyde. Similarly, its metal complexes of Co (II), Ni (II), Cu (II), and Zn (II) were also synthesized. The in vitro antibacterial activity of all the compounds, at their two different concentrations, was screened against some bacterial pathogens and showed better activity compared to parent drug and control drug. Recently, (Al Zoubi et al., 2018) have synthesized an Azo‐ Schiff base ligand by reaction of m‐ hydroxy benzoic acid with (Schiff base B) of 3‐ [2‐ (1H–indol‐ 3‐ yl) ‐ ethylamine] ‐ 1.5‐ dimethyl‐ 2‐ phenyl‐ 2,3‐ dihydro‐ 1H‐ pyrazol‐ 4‐ ylamine. This synthesized ligand was used for complexation with different metal ions like Ni (II), Co (II), Pd (II) and Pt (IV). The biological activities of Schiff base and its complexes had been tested in vitro against, some Gram-positive and Gram-negative bacteria. A comparative study of the values of ligand and the complexes indicate that the metal complexes exhibit higher antimicrobial activity than the free ligand. Antioxidant Antioxidant compounds may function as free radical scavengers, which play important role in food and chemical material degradation, and significantly delay or prevent the oxidation of easily oxidable substrates (Patil, 2013). Therefore, the importance of searching for antioxidants has greatly increased in the recent years. P a g e | 287 Copyright ⓒ 2020Authors Purakala (UGC Care Journal) ISSN: 0971-2143 Vol-31-Issue-39-May-2020 (Kostova and Saso, 2013) have prepared Schiff base 1-(4-Aminoantipyrine)-3tosylurea and its three lanthanide (III) complexes, M(H2 L)3.3NO3 [where M= Nd (III), Sm (III) and Eu (III)]. Antioxidant activity of the ligand and its complexes was determined by superoxide and hydroxyl radical scavenging methods. Ln (III) complexes inhibit stronger antioxidant activity than the ligand alone. Whereas, (Gomes et al., 2014) have synthesized 8-Hydroxyquinoline Schiff-base & its Cu (II) complex. Then Antioxidant activity of the ligand and its complex was determined. Recently, (Demetgül and Beyazit, 2018) have synthesized a chromonefunctionalized chitosan Schiff base and its cross-linked derivative. The in vitro antioxidant activity of high molecular chitosan and its chromone derivatives was evaluated. The results showed that both of the chitosan-chromone derivatives have good antioxidant potential which might be due to the phenolic group introduced after chemical modification of chitosan with a chromone derivative. Similarly, (Singh et al., 2014) have prepared acylated chitosan Schiff base utilizing 3,5-di-tert-butyl-4-hydroxybenzaldehyde. Schiff base were evaluated against antioxidant, anticorrosion, antifriction, and antiwear properties. Antibacterial and antifungal Fungal infections are not usually limited to the superficial tissues; indeed, a significant increase in life threatening systemic fungal infections has been reported. The fundamental reason for this is the increasing number of patients at risk, including those with advanced age, major surgery, immunosuppressive therapy, acquired immunodeficiency syndrome (AIDS), cancer treatment, and solid-organ and hematopoietic stem cell transplantation. The search and development of more effective antifungal agents are mandatory and some Schiff bases are known to be promising antifungal agents. (Malik et al., 2011) have prepared a Schiff’s base of 5-acetamido-1,3,4-thiadiazole2-sulphonamide with Mn (II), Fe (II), Ni (II), Cu (II) metal ions. The ligand and its complexes were screened for antifungal activity against the tested pathogenic fungal species by the well agar method. (Ashraf et al., 2011) have synthesized three biologically active amino substituted Schiff bases with general formula, R1 N=CHR2. Where R1 = 2-amino-benzthiazole, 4amino-salicylic acid and 4-aminophenol. R2 =4-chlorobenzaldehyde, 2-chlorobenzaldehyde, salicylaldehyde, vanillin and benzaldehyde. The free ligands and their metal complexes have been screened for their in vitro biological activities against bacteria, fungi and yeast. The metal complexes show more potent activities compared with Schiff base ligands. The synthesized Schiff bases from 2-amino-Benzthiazole, 4amino-Salicylic acid and 4-aminophenol are shown in figure 2. P a g e | 288 Copyright ⓒ 2020Authors Purakala ISSN: 0971-2143 (UGC Care Journal) Vol-31-Issue-39-May-2020 OH HO COOH N S N N N CH CH CH R1 R1 R2 R2 R3 R1 R2 R3 R3 R1= H,OH,Cl R2= H,OCH3 R3= H,OH,Cl Figure-2. Structures of the Schiff bases synthesized from 2-amino-Benzthiazole, 4-amino-Salicylic acid and 4-aminophenol In addition, (Rizwana and Lakshmi, 2012) have synthesized Schiff base derived from o- vanillin with allylthiourea and its metal complexes of Zn (II), Ni (II) and Cu (II). The ligand and its metal complexes were screened for antibacterial activity against Klebsiella pneumonia, Bacillus cereus and Pseudomonas aeruginosa and fungicidal activity against Aspergillus Niger, Candida albicans and Candida kefyr. The results revealed that the synthesized compounds were more potent against all the microbes under investigation. Moreover, (Abu-Khadra et al., 2016) have synthesized a series of Ag, Cd (II), Ce (III), Co (II), Cr (III), Fe (III), Ni (II) and Pb (II) complexes with (E)-N-(4-(2hydroxybenzylideneamino) phenylsulfonyl. Complexes have been screened for their antibacterial activity against some Gram-negative & Gram-positive bacteria. Similarly, antifungal was also done. Cd (II), Ce (III), Co (II), Cr (III), Fe (III), Ni (II) and Pb (II) complexes with (E)-N-(4-(2-hydroxybenzylideneamino) phenylsulfonyl) showing promising antimicrobial activity. R1 R2 O R3 H R5 R4 Benzaldehyde moiety Table-1. Different biological activities shown by benzaldehyde moiety. Metal (II) R2 R3 R4 R5 Activity R1 complexes Antimicrobial P a g e | 289 OH H H Br H OH OCH3 H H H Cu and Zn Ni Copyright ⓒ 2020Authors Reference (Tohidian et al., 2016) (Khajoee Purakala ISSN: 0971-2143 (UGC Care Journal) Vol-31-Issue-39-May-2020 Nejad et al., 2018) Antimicrobial and antioxidant Co, Ni and Mn OH CH3 CH(CH3)2 -H H H H N(CH3)2 H H Antifungal, Antibacterial, Antimicrobial Mn, Fe, Co, Ni, Cu and Zn (Tadavi et al., 2018) (Khan et al., 2013) Recently, (Goyat et al., 2018) have synthesized a series of tellurium (IV) complexes from Schiff base i.e. 5-chlorosalicylaldehyde-3aminopyridine Schiff base. The Schiff base and some of their tellurium (IV) complexes were tested for antifungal and antibacterial activities. Moreover, several biological activities shown by Schiff bases derived from benzaldehyde and salicylaldehyde have shown in table 1 and 2. HO R1 H R2 O R4 R3 Salicylaldehyde moiety Table-2. Different biological activities shown by Salicylaldehyde moiety. Activity R1 R2 R3 R4 Metal complexes H H H H Co (II), Ni (II) and Cu (II) OCH3 H H H H N(Et)2 H H Fe (II) and Cu (II) H H H H Mn (II), Fe (II), Ni (II) and Cu (II) H H Br H Cu (II), Ni (II), Co (II), Pd (II) and Pt (II) H H H H Cu (II) and Co (II) H H H H Cd (II), Ce (III), Co (II), Cr (III), Fe (III), Ni (II) and Pb (II) H H Cl H Tellurium (IV) H H H H Cu (II) H H Br H Cu (II), Ni (II), Mn (II), Co (II) Antimicrobial Antifungal Antibacterial and antifungal Antibacterial and antitumor Antimicrobial and P a g e | 290 Reference (El-Sherif et al., 2012; Reiss et al., 2018) Fe (II) and Cu (II) Copyright ⓒ 2020Authors (Rahman et al., 2015) (Malik et al., 2011) (Sönmez et al., 2003) (Ahmadi and Amani, 2012) (AbuKhadra et al., 2016) (Goyat et al., 2018) (Amer et al., 2013) (El-Sherif Purakala ISSN: 0971-2143 (UGC Care Journal) Vol-31-Issue-39-May-2020 antitumor Antimicrobial and antioxidant and Zn (II) H H SO3Na H Cu (II), Ni (II) and Zn (II) and Eldebss, 2011) (HosseiniYazdi et al., 2017) Schiff bases showing multiple bio-activities (Al-Amiery et al., 2012) have prepared 2-(2-imino-1-methylimidazolidin-4-ylidene) hydrazine carbothioamide (IMHC) by the reaction of creatinine with thiosemicarbazide. The complex was screened for antifungal, antibacterial & antioxidant activities against selected bacteria. Similarly, they also did the density functional theory (DFT) study of complex. Similarly, (Sirajuddin et al., 2013) have synthesized three Schiff base compounds of N’substituted benzohydrazide and sulfonohydrazide derivatives: N’-(2-hydroxy-3methoxybenzylidene)-4-tert-butylbenzohydrazide (1), N-(5-bromo-2hydroxybenzylidene)-4-tert-butylbenzohydrazide (2) and N’-(2-hydroxy-3methoxybenzylidene)-4-methylbenzenesulfonohydrazide (3). The DNA binding of the compounds1–3with Sodium salt of Salmon fish sperm DNA (SS-DNA) has been carried out with absorption spectroscopy. The synthesized compounds were tested against Grampositive and Gram-negative bacteria & antifungal activity against fungal strains. The synthesized compounds were found an effective scavenging of the stable DPPH radical, DPPH as potent as standard antioxidant agent, ascorbic acid. In another study, (Khan et al., 2013) have synthesized transition metal complexes derived from the reaction of 4(4(dimethylamino) benzylideneamino) benzoic acid and Mn (II), Fe (II), Co (II), Ni (II), Cu (II) and Zn (II). In addition, the biological activity was evaluated by conducting in vitro antibacterial, anti-fungal and anti-leishmanial screenings. All the complexes were found more active than the ligand. (Rezki et al., 2015) have synthesized a new series of 2,5disubstituted-1,3,4-thiadiazole tethered 1,2,4-triazole, 1,3,4-thiadiazole, 1,3,4-oxadiazole and Schiff base derivatives. All compounds were screened for their antibacterial, antifungal and antiproliferative activity. Moreover, (Rauf et al., 2017) have synthesized a Schiff base, 1-((2, 4-dimethylphenylimino) methyl) naphthalen-2-ol abbreviated as (HL) and its four metallic complexes [(L2 VO), (L2Sn), (L2 Zn) and (L2Co)]. The compounds were tested for anti-dietic, triglyceride, cholesterol, anti-microbial, anti-fungal and enzyme inhibition activities. The results revealed that ligand and its complexes are promising new therapeutic options as these compounds exhibit strong activity against cancer cells, diabetics, fungal and microbial inhibition. Recently, (Jawoor et al., 2018) have synthesized the Co (II), Ni (II), and Cu (II) complexes of the Schiff base derived from 8-formyl-7hydroxy-4-methylcoumarin and 2-hydrazino benzothiazole. All the synthesized compounds were tested against anticancer, antimicrobial, DNA cleavage and anti-TB activity. The synthesized metal complexes exhibited enhanced activity against the tested bacterial and fungal strains as compared to free ligand. The results of the DNA-cleavage activity suggest that the ligand and its metal complexes can cleave CT-DNA at different degrees. Among all these synthesized compounds, the Cu (II) complex exhibits good cleaving ability compared to other newly synthesized metal complexes. Antibacterial & Anticancer Cancer is a class of diseases in which a group of cells display uncontrolled growth and even sometimes metastasis. It continues as a serious public unhealthiness throughout the P a g e | 291 Copyright ⓒ 2020Authors Purakala (UGC Care Journal) ISSN: 0971-2143 Vol-31-Issue-39-May-2020 world as the most feared diagnosis. It is the second leading reason of human death after cardiovascular diseases in developing as well as in developed countries (Gharamaleki et al., 2016). Currently, the treatment for cancer primarily includes surgery and chemotherapy, but the curative effects of the existing chemotherapeutic drugs are not good enough and they have plentiful side effects. The development of more effective drugs for treating cancer patients has been a main attempt over the past 50 years. In recent years, various Schiff bases derivatives have been found to be associated with anticancer properties. (Ebrahimipour et al., 2015) have synthesized three Oxido-vanadium(V) complexes, [VO2(L)] [NH(Et)3] (1), [VO(L)(PrO)] (2) and [VO(L)(BuO)] (3), containing deprotonated form of the tridentate Schiff base ligand 1-(((5-chloro-2-oxidophenyl) imino) methyl) naphthalen-2-olate [L2]. The anticancer activities of the complexes have been also investigated against Michigan Cancer Foundation (MCF-7) (breast cancer) cells. According to the obtained results, all the complexes possess higher anticancer activity than VO (acac)2. (Mahmoud et al., 2016) have synthesized Schiff base ligand (H2L) was prepared through condensation of 2,6-diaminopyridine and o-benzoyl benzoic acid. Also, its Cr (III), Mn (II), Fe (III), Co (II), Ni (II), Cu (II), Zn (II) and Cd (II) metal complexes were prepared. The synthesized ligand and its complexes were screened for antimicrobial activities against Gram-positive & Gram-negative bacteria and fungal strain. Anticancer activities of the ligand and its metal complexes against human breast cancer cell line Michigan Cancer Foundation (MCF7) were investigated. The ligand and metal complexes are found to possess appreciable antibacterial activity, except the Fe (III) complex which has no activity against B. subtilis and E. coli and the Cd (II) complex which also has no activity against S. aureus. The Co (II), Ni (II) and Cd (II) complexes have high antifungal activity. In addition, the cytotoxicity of the Cu (II) complex indicates a higher anticancer activity than the others. Conclusion Schiff bases and their metal complexes are one of the most important chemical classes of compounds having a common integral feature of a variety of structural diversity and of active medicinal agents. 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