دورية أكاديمية

A dual-functional sulfone biscompound containing 1,2,3-triazole moiety for decolorization and disinfection of contaminated water.

التفاصيل البيبلوغرافية
العنوان: A dual-functional sulfone biscompound containing 1,2,3-triazole moiety for decolorization and disinfection of contaminated water.
المؤلفون: Radwan EK; Water Pollution Research Department, National Research Centre, 33 El Buhouth St, Dokki, Giza, 12622, Egypt. emadk80@gmail.com., Rashdan HRM; Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Research Institute, National Research Centre, 33 El Buhouth St, Dokki, Giza, 12622, Egypt., Hemdan BA; Water Pollution Research Department, National Research Centre, 33 El Buhouth St, Dokki, Giza, 12622, Egypt., Koryam AA; Water Pollution Research Department, National Research Centre, 33 El Buhouth St, Dokki, Giza, 12622, Egypt., El-Naggar ME; Institute of Textile Research and Technology, National Research Centre, 33 El Bohouth St, Dokki, Giza, 12622, Egypt. mehrez_chem@yahoo.com.
المصدر: Environmental science and pollution research international [Environ Sci Pollut Res Int] 2022 Nov; Vol. 29 (51), pp. 77238-77252. Date of Electronic Publication: 2022 Jun 08.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Springer Country of Publication: Germany NLM ID: 9441769 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1614-7499 (Electronic) Linking ISSN: 09441344 NLM ISO Abbreviation: Environ Sci Pollut Res Int Subsets: MEDLINE
أسماء مطبوعة: Publication: <2013->: Berlin : Springer
Original Publication: Landsberg, Germany : Ecomed
مواضيع طبية MeSH: Disinfection* , Water Pollutants, Chemical*/chemistry, Triazoles/pharmacology ; Coloring Agents/chemistry ; Adsorption ; Kinetics ; Water/chemistry ; Sulfones ; Anti-Bacterial Agents ; Hydrogen-Ion Concentration ; Thermodynamics
مستخلص: Water decontamination from toxic dyes and pathogenic microorganisms is critical for life on Earth. Herein, we report the synthesis of sulfone biscompound containing 1,2,3-triazole moiety and evaluation of its dye decolorization and biocidal and disinfection efficiencies. The decolorization efficiency was tested under different experimental conditions, while the biocidal action was examined against various types of waterborne pathogens, and the disinfection of some pathogenic microbes was executed in artificially contaminated water. The findindgs illustrated that the solution initial pH (pH i ) affected the decolorization efficiency significantly. About complete removal of 10 mg/L malachite green (MG) dye was achieved after 10 min using 3 g/L of the sulfone biscompound at pH i 6. The pseudo-second-order equation suited the adsorption kinetics accurately, while the equilibrium data was suited by Langmuir isotherm model. Electrostatic, n-π, and π-π interactions brought about the adsorption of MG onto the sulfone biscompound. The biocidal results indicated that the sulfone biscompound had a powerful antibacterial potential against the tested bacterial species. Likewise, the distinction trail revealed that after 70-90 min of direct contact with an effective dose, the tested pathogens could be completely eliminated (6-log reduction). Overall, the newly synthesized sulfone biscompound can efficiently remove cationic dyes and disinfect contaminated water.
(© 2022. The Author(s).)
References: Abdel Ghafar HH, Radwan EK, El-Wakeel ST (2020) Removal of hazardous contaminants from water by natural and zwitterionic surfactant-modified clay. ACS Omega 5:6834–6845. (PMID: 10.1021/acsomega.0c00166)
Abdel-Karim A, El-Naggar ME, Radwan EK, Mohamed IM, Azaam M, Kenawy E-R (2021) High-performance mixed-matrix membranes enabled by organically/inorganic modified montmorillonite for the treatment of hazardous textile wastewater. Chem Eng J 405:126964. (PMID: 10.1016/j.cej.2020.126964)
Abou Hammad AB, El Nahwary AM, Hemdan BA, Abia ALK (2020) Nanoceramics and novel functionalized silicate-based magnetic nanocomposites as substitutional disinfectants for water and wastewater purification. Environ Sci Pollut Res 27:26668–26680. (PMID: 10.1007/s11356-020-09073-9)
Abu Elella MH, Goda ES, Gamal H, El-Bahy SM, Nour MA, Yoon KR (2021) Green antimicrobial adsorbent containing grafted xanthan gum/SiO 2 nanocomposites for malachite green dye. Int J Biol Macromol 191:385–395. (PMID: 10.1016/j.ijbiomac.2021.09.040)
Agouram N, El Hadrami EM, Bentama A (2021) 1,2,3-triazoles as biomimetics in peptide science. Molecules 26:2937. (PMID: 10.3390/molecules26102937)
Ahmad J, Naeem S, Ahmad M, Usman AR, Al-Wabel MI (2019) A critical review on organic micropollutants contamination in wastewater and removal through carbon nanotubes. J Environ Manage 246:214–228. (PMID: 10.1016/j.jenvman.2019.05.152)
Alam MA, Shimada K, Jahan A, Khan MW, Bhuiyan MM, Alam M, Matin M (2018) Synthesis, reactions and medicinal importance of cyclic sulfone derivatives: a review. Nat Prod Chem Res 6:2.
Alene AN, Abate GY, Habte AT, Getahun DM (2021) Utilization of a novel low-cost Gibto Lupinus Albus seed peel waste for the removal of malachite green dye: equilibrium, kinetic, and thermodynamic studies. J Chem 2021:6618510. (PMID: 10.1155/2021/6618510)
Aljerf L (2018) High-efficiency extraction of bromocresol purple dye and heavy metals as chromium from industrial effluent by adsorption onto a modified surface of zeolite: kinetics and equilibrium study. J Environ Manage 225:120–132. (PMID: 10.1016/j.jenvman.2018.07.048)
Aljerf L, Williams M, Ajong AB, Onydinma UP, Dehmchi F, Pham VT, Bhatnagar S, Belboukhari N (2021) Comparative study of the biochemical response behavior of some highly toxic minerals on selenosis in rats. Rev Chim 72:9–18. (PMID: 10.37358/RC.21.2.8415)
Appel C, Ma LQ, Rhue RD, Kennelley E (2003) Point of zero charge determination in soils and minerals via traditional methods and detection of electroacoustic mobility. Geoderma 113:77–93. (PMID: 10.1016/S0016-7061(02)00316-6)
Bekçi Z, Özveri C, Seki Y, Yurdakoç K (2008) Sorption of malachite green on chitosan bead. J Hazard Mater 154:254–261. (PMID: 10.1016/j.jhazmat.2007.10.021)
Blanchard G, Maunaye M, Martin G (1984) Removal of heavy metals from waters by means of natural zeolites. Water Res 18:1501–1507. (PMID: 10.1016/0043-1354(84)90124-6)
Cadillo-Benalcazar JJ, Renner A, Giampietro M (2020) A multiscale integrated analysis of the factors characterizing the sustainability of food systems in Europe. J Environ Manage 271:110944. (PMID: 10.1016/j.jenvman.2020.110944)
da SM Forezi L, Lima CG, Amaral AA, Ferreira PG, de Souza MCB, Cunha AC, de C. da Silva F, Ferreira VF (2021) Bioactive 1,2,3‐triazoles: an account on their synthesis, structural diversity and biological applications. Chem Rec 21:2782-2807.
Dubinin MM, Radushkevich LV (1947) The equation of the characteristic curve of the activated charcoal. Proc Acad Sci USSR Phys Chem Sect 55:331–337.
El Bendary MM, Radwan EK, El-Shahat MF (2021) Valorization of secondary resources into silica-based adsorbents: preparation, characterization and application in dye removal from wastewater. Environ Nanotechnol Monit Manag 15:100455.
El Malah T, Nour HF, Radwan EK, Abdel Mageid RE, Khattab TA, Olson MA (2021) A bipyridinium-based polyhydrazone adsorbent that exhibits ultrahigh adsorption capacity for the anionic azo dye, direct blue 71. Chem Eng J 409:128195. (PMID: 10.1016/j.cej.2020.128195)
El Malah T, Farag H, Hemdan BA, Mageid REA, Abdelrahman MT, El-Manawaty MA, Nour HF (2022) Synthesis, in vitro antimicrobial evaluation, and molecular docking studies of new isatin-1,2,3-triazole hybrids. J Mol Struct 1250:131855. (PMID: 10.1016/j.molstruc.2021.131855)
El Nahrawy AM, Abou Hammad AB, Bakr AM, Hemdan BA, Wassel AR (2019) Decontamination of ubiquitous harmful microbial lineages in water using an innovative Zn 2 Ti 0.8 Fe 0.2 O 4 nanostructure: dielectric and terahertz properties. Heliyon 5:e02501.
El Nahrawy AM, Hemdan BA, Mansour A, Elzwawy A, AbouHammad AB (2021) Structural and opto-magnetic properties of nickel magnesium copper zircon silicate nano-composite for suppress the spread of foodborne pathogenic bacteria. Silicon 1–16.
El-Naggar M, El-All A, Amira S, El-Naem SI, Abdalla MM, Rashdan HR (2020) New potent 5α-reductase and aromatase inhibitors derived from 1,2,3-triazole derivative. Molecules 25:672. (PMID: 10.3390/molecules25030672)
Falkinham JO, Pruden A, Edwards M (2015) Opportunistic premise plumbing pathogens: increasingly important pathogens in drinking water. Pathogens 4:373–386. (PMID: 10.3390/pathogens4020373)
Freundlich HMF (1906) Over the adsorption in solution. J Phys Chem 57:385–470.
Gotoh H, Kasaraneni N, Devineni N, Dallo SF, Weitao T (2010) SOS involvement in stress-inducible biofilm formation. Biofouling 26:603–611. (PMID: 10.1080/08927014.2010.501895)
Güler M, Çetintaş S, Bingöl D (2021) Cinnamon bark as low-cost and eco-friendly adsorbent for the removal of indigo carmine and malachite green dyestuffs. Int J Environ Anal Chem 101:735–757. (PMID: 10.1080/03067319.2019.1670171)
Hemdan BA, El Nahrawy AM, Mansour A-FM, Hammad ABA (2019) Green sol–gel synthesis of novel nanoporous copper aluminosilicate for the eradication of pathogenic microbes in drinking water and wastewater treatment. Environ Sci Pollut Res 26:9508–9523. (PMID: 10.1007/s11356-019-04431-8)
Hiba K, Sreekumar K (2021) Multi-arm dendronized polymer as a unimolecular micelle: synthesis, characterization and application as organocatalyst in the synthesis of N-unsubstituted 1, 2, 3-triazoles. React Funct Polym 160:104827. (PMID: 10.1016/j.reactfunctpolym.2021.104827)
Igwegbe CA, Ighalo JO, Onyechi KK, Onukwuli OD (2021) Adsorption of Congo red and malachite green using H 3 PO 4 and NaCl-modified activated carbon from rubber (Hevea brasiliensis) seed shells. Sustain Water Resour Manag 7:63. (PMID: 10.1007/s40899-021-00544-6)
Jiang J-J, Okvitasari AR, Huang F-Y, Tsai C-S (2021) Characteristics, pollution patterns and risks of perfluoroalkyl substances in drinking water sources of Taiwan. Chemosphere 264:128579. (PMID: 10.1016/j.chemosphere.2020.128579)
Kokkinos P, Mantzavinos D, Venieri D (2020) Current trends in the application of nanomaterials for the removal of emerging micropollutants and pathogens from water. Molecules 25:2016. (PMID: 10.3390/molecules25092016)
Kuznetsov A (2021) Azoles: synthesis, properties, applications and perspectives. BoD–Books on Demand.
Langergren S, Svenska BK (1898) Zur theorie der sogenannten adsorption geloester stoffe. Veternskapsakad Handlingar 24:1–39.
Langmuir I (1918) The adsorption of gases on plane surfaces of glass, mica and platinum. J Am Chem Soc 40:1361–1403. (PMID: 10.1021/ja02242a004)
Lin L, Tang S, Wang X, Sun X, Yu A (2021) Hexabromocyclododecane alters malachite green and lead(II) adsorption behaviors onto polystyrene microplastics: Interaction mechanism and competitive effect. Chemosphere 265:129079. (PMID: 10.1016/j.chemosphere.2020.129079)
Luo L-W, Wu Y-H, Yu T, Wang Y-H, Chen G-Q, Tong X, Bai Y, Xu C, Wang H-B, Ikuno N, Hu H-Y (2021) Evaluating method and potential risks of chlorine-resistant bacteria (CRB): a review. Water Res 188:116474. (PMID: 10.1016/j.watres.2020.116474)
Lv J-S, Peng X-M, Kishore B, Zhou C-H (2014) 1,2,3-Triazole-derived naphthalimides as a novel type of potential antimicrobial agents: synthesis, antimicrobial activity, interaction with calf thymus DNA and human serum albumin. Bioorg Med Chem Lett 24:308–313. (PMID: 10.1016/j.bmcl.2013.11.013)
Margha FH, Radwan EK, Badawy MI, Gad-Allah TA (2020) Bi 2 O 3 –BiFeO 3 glass-ceramic: controllable β-/γ-Bi 2 O 3 transformation and application as magnetic solar-driven photocatalyst for water decontamination. ACS Omega 5:14625–14634. (PMID: 10.1021/acsomega.0c01307)
Mo CY, Manning SA, Roggiani M, Culyba MJ, Samuels AN, Sniegowski PD, Goulian M, Kohli RM (2016) Systematically altering bacterial SOS activity under stress reveals therapeutic strategies for potentiating antibiotics. Msphere 1:e00163-e216. (PMID: 10.1128/mSphere.00163-16)
Nour HF, Abdel Mageid RE, Radwan EK, Khattab TA, Olson MA, El Malah T (2021) Adsorption isotherms and kinetic studies for the removal of toxic reactive dyestuffs from contaminated water using a viologen-based covalent polymer. New J Chem 45:18983-18993.
Pedersen DS, Abell A (2011) 1,2,3-Triazoles in peptidomimetic chemistry. Eur J Org Chem 2011:2399–2411. (PMID: 10.1002/ejoc.201100157)
Phukan P, Chetia R, Boruah R, Konwer S, Sarma D (2021) Fabrication of polypyrrole/Cu (II) nanocomposite through liquid/liquid interfacial polymerization: a novel catalyst for synthesis of NH-1,2,3-triazoles in PEG-400. Mater Adv 2:6996–7006. (PMID: 10.1039/D1MA00700A)
Radwan EK, Abdel Ghafar HH, Moursy AS, Langford CH, Bedair AH, Achari G (2017) Adsorptive removal of hazardous organic water pollutants by humic acid–carbon hybrid materials: kinetics and isotherm study. Desalin Water Treat 80:297–305. (PMID: 10.5004/dwt.2017.20930)
Radwan MA, Alshubramy MA, Abdel-Motaal M, Hemdan BA, El-Kady DS (2020) Synthesis, molecular docking and antimicrobial activity of new fused pyrimidine and pyridine derivatives. Bioorg Chem 96:103516. (PMID: 10.1016/j.bioorg.2019.103516)
Radwan EK, El-Naggar ME, Abdel-Karim A, Wassel AR (2021) Multifunctional 3D cationic starch/nanofibrillated cellulose/silver nanoparticles nanocomposite cryogel: synthesis, adsorption, and antibacterial characteristics. Int J Biol Macromol 189:420–431. (PMID: 10.1016/j.ijbiomac.2021.08.108)
Rani UA, Ng LY, Ng CY, Mahmoudi E, Ng Y-S, Mohammad AW (2021) Sustainable production of nitrogen-doped carbon quantum dots for photocatalytic degradation of methylene blue and malachite green. J Water Process Eng 40:101816. (PMID: 10.1016/j.jwpe.2020.101816)
Rashdan HR (2019) Synthesis and biological evaluation of some new pyridines, isoxazoles and isoxazolopyridazines bearing 1,2,3-triazole moiety. Acta Pol Pharm 76:469–482.
Rashdan HR, Abdelmonsef AH, Abou-Krisha MM, Yousef TA (2021a) Synthesis, identification, computer-aided docking studies, and ADMET prediction of novel benzimidazo-1,2,3-triazole based molecules as potential antimicrobial agents. Molecules 26:7119. (PMID: 10.3390/molecules26237119)
Rashdan HR, Abdelmonsef AH, Abou-Krisha MM, Yousef TA (2021b) Synthesis and identification of novel potential thiadiazole based molecules containing 1,2,3-triazole moiety against COVID-19 main protease through structure-guided virtual screening approach.
Reddy ND, Elias AJ (2021) Chlorine and the chemistry of disinfectants. Resonance 26:341–366. (PMID: 10.1007/s12045-021-1135-y)
Redlich O, Peterson DL (1959) A useful adsorption isotherm. J Phys Chem 63:1024–1024. (PMID: 10.1021/j150576a611)
Rubio-Clemente A, Gutiérrez J, Henao H, Melo AM, Pérez JF, Chica E (2021): Adsorption capacity of the biochar obtained from Pinus patula wood micro-gasification for the treatment of polluted water containing malachite green dye. Journal of King Saud University - Engineering Sciences.
Sartape AS, Mandhare AM, Jadhav VV, Raut PD, Anuse MA, Kolekar SS (2017) Removal of malachite green dye from aqueous solution with adsorption technique using Limonia acidissima (wood apple) shell as low cost adsorbent. Arab J Chem 10:S3229–S3238. (PMID: 10.1016/j.arabjc.2013.12.019)
Schulze B, Schubert US (2014) Beyond click chemistry–supramolecular interactions of 1,2,3-triazoles. Chem Soc Rev 43:2522–2571. (PMID: 10.1039/c3cs60386e)
Shojaei S, Shojaei S, Band SS, Farizhandi AAK, Ghoroqi M, Mosavi A (2021) Application of Taguchi method and response surface methodology into the removal of malachite green and auramine-O by NaX nanozeolites. Sci Rep 11:16054. (PMID: 10.1038/s41598-021-95649-5)
Silver LL (2011) Challenges of antibacterial discovery. Clin Microbiol Rev 24:71–109. (PMID: 10.1128/CMR.00030-10)
Sonawane SA, Pore DM (2022) Novel copper tagged supported ionic liquid phase catalyst for the synthesis of 1,4‑disubstituted 1,2,3‑triazoles via Cu-catalyzed azide–alkyne cycloaddition reactions in water. Catalysis Letters, 1–15.
Sun J, Jiang G, Zhu B, Wang X, Liu F, Liu C, Wang Y (2021) Antibacterial properties of recoverable CuZnO@Fe 3 O 4 @GO composites in water treatment. Environ Sci Pollut Res 28:33355–33370. (PMID: 10.1007/s11356-021-12963-1)
Temkin MI, Pyzhev V (1940) Kinetics of ammonia synthesis on promoted iron catalyst. Acta Physiochim URSS 12:327–356.
Thomas J, Jana S, Liekens S, Dehaen W (2016) A single-step acid catalyzed reaction for rapid assembly of NH-1,2,3-triazoles. Chem Commun 52:9236–9239. (PMID: 10.1039/C6CC03744E)
Tohidi A, Chaibakhsh N, Mohammadi A (2021) A novel functionalized chitosan nanoadsorbent for efficient elimination of malachite green from aqueous media. Environ Prog Sustainable Energy 40:e13576. (PMID: 10.1002/ep.13576)
Tran HN, Wang Y-F, You S-J, Chao H-P (2017) Insights into the mechanism of cationic dye adsorption on activated charcoal: the importance of π–π interactions. Process Saf Environ Prot 107:168–180. (PMID: 10.1016/j.psep.2017.02.010)
Wang X, Zhang X, Ding S (2021) 1,2,3-Triazole-based sequence-defined oligomers and polymers. Polym Chem 12:2668–2688. (PMID: 10.1039/D1PY00123J)
Xing X, Zhang X, Zhang K, Le J, Cao Q (2019) Preparation of large-sized graphene from needle coke and the adsorption for malachite green with its graphene oxide. Fullerenes, Nanotubes, Carbon Nanostruct 27:97–105. (PMID: 10.1080/1536383X.2018.1512099)
Zheng Z-J, Wang D, Xu Z, Xu L-W (2015) Synthesis of bi-and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: a family of valuable products by click chemistry. Beilstein J Org Chem 11:2557–2576. (PMID: 10.3762/bjoc.11.276)
فهرسة مساهمة: Keywords: Adsorption; Antimicrobial activity; Cationic dyes; Kinetic and isotherm models; Multi-functional materials
المشرفين على المادة: 0 (Triazoles)
12058M7ORO (malachite green)
0 (Coloring Agents)
0 (Water Pollutants, Chemical)
059QF0KO0R (Water)
0 (Sulfones)
0 (Anti-Bacterial Agents)
تواريخ الأحداث: Date Created: 20220608 Date Completed: 20221021 Latest Revision: 20240316
رمز التحديث: 20240316
مُعرف محوري في PubMed: PMC9581830
DOI: 10.1007/s11356-022-20932-5
PMID: 35676578
قاعدة البيانات: MEDLINE
الوصف
تدمد:1614-7499
DOI:10.1007/s11356-022-20932-5