Towards efficient ciprofloxacin adsorption using magnetic hybrid nanoparticles prepared with κ-, ι-, and λ-carrageenan
Abstract
Abstract
The efficient removal of the antibiotic ciprofloxacin (CIP) from aqueous samples using magnetic nanosorbents prepared using three sulfated polysaccharides, κ-, ι- and λ-carrageenan and an alkoxysilane agent containing a reactive epoxide ring is described. The prepared nanosorbents were characterized in detail using FTIR spectroscopy, solid-state
29
Si and
13
C NMR spectroscopy and elemental microanalysis. The synthesis method was more effective for incorporating higher amounts of κ-carrageenan in the siliceous shells. Although being less sulfated, κ-carrageenan is cheaper than the other carrageenan tested. The CIP adsorption was a cooperative process, well described by the Dubinin–Radushkevich isotherm, with maximum adsorption capacities of 878, 969 and 865 mg/g for κ-, ι- and λ-carrageenan sorbents, respectively. Overall, the produced magnetic nanosorbents are among the best magnetic systems with high adsorptive efficiency for CIP. It is suggested that protonated CIP molecules are exchanged with ester sulfate counterions of carrageenan at the particles’ surface as the main pathway for CIP adsorption. The adsorption process was exothermic and entropically favorable for the three sorbents. However, at 298 K, the adsorption was spontaneous for κ-carrageenan-based sorbents and non-spontaneous for ι- and λ-carrageenan particles. The magnetic sorbents could be reused and maintained their ability towards CIP removal up to four cycles. The removal efficiency in wastewater was enhanced with the sorbent dose.
Graphical abstract
Magnetic carrageenan nanosorbents were prepared using three carrageenan polysaccharides (κ-, ι-, and λ-carrageenan). The resulting magnetic particles removed the antibiotic ciprofloxacin efficiently from ultra-pure water and wastewater samples. Magnetic features enabled the fast magnetic separation of the nanosorbents from water.
Keywords
- Carrageenan,
- Hybrids,
- Ciprofloxacin,
- Magnetite nanoparticles,
- Water treatment,
- Adsorption
References
- Sabri et al. (2020) Fate of antibiotics and antibiotic resistance genes during conventional and additional treatment technologies in wastewater treatment plants https://doi.org/10.1016/j.scitotenv.2020.140199
- Tavengwa et al. (2022) Challenges and future directions in the analysis of emerging pollutants in aqueous environments (pp. 373-379) Elsevier https://doi.org/10.1016/B978-0-12-822850-0.00016-8
- Sanganyado et al. (2022) The fate of emerging pollutants in aquatic systems: an overview (pp. 119-135) Elsevier https://doi.org/10.1016/B978-0-12-822850-0.00002-8
- Burke et al. (2016) Occurrence of antibiotics in surface and groundwater of a drinking water catchment area in germany (pp. 652-659) https://doi.org/10.2175/106143016X14609975746604
- Boy-Roura et al. (2018) Towards the understanding of antibiotic occurrence and transport in groundwater: findings from the Baix Fluvià alluvial aquifer (NE Catalonia, Spain) (pp. 1387-1406) https://doi.org/10.1016/j.scitotenv.2017.09.012
- Gu et al. (2019) Occurrence and risk assessment of antibiotics in manure, soil, wastewater, groundwater from livestock and poultry farms in Xuzhou, China (pp. 590-596) https://doi.org/10.1007/s00128-019-02692-0
- Van Doorslaer et al. (2014) Fluoroquinolone antibiotics: an emerging class of environmental micropollutants (pp. 250-269) https://doi.org/10.1016/j.scitotenv.2014.08.075
- Rasheed et al. (2019) Environmentally-related contaminants of high concern: potential sources and analytical modalities for detection, quantification, and treatment (pp. 52-66) https://doi.org/10.1016/j.envint.2018.11.038
- Sivagami et al. (2020) Antibiotic usage, residues and resistance genes from food animals to human and environment: an Indian scenario https://doi.org/10.1016/j.jece.2018.02.029
- Ahmadzadeh et al. (2017) Removal of ciprofloxacin from hospital wastewater using electrocoagulation technique by aluminum electrode: optimization and modelling through response surface methodology (pp. 538-547) https://doi.org/10.1016/j.psep.2017.04.026
- El-Shafey et al. (2012) Ciprofloxacin adsorption from aqueous solution onto chemically prepared carbon from date palm leaflets (pp. 1579-1586) https://doi.org/10.1016/S1001-0742(11)60949-2
- Igwegbe et al. (2021) Adsorption of ciprofloxacin from water: a comprehensive review (pp. 57-77) https://doi.org/10.1016/j.jiec.2020.09.023
- Zhang et al. (2016) A novel aluminum-graphite dual-ion battery https://doi.org/10.1002/aenm.201502588
- Wang et al. (2018) Reversible calcium alloying enables a practical room-temperature rechargeable calcium-ion battery with a high discharge voltage (pp. 667-672) https://doi.org/10.1038/s41557-018-0045-4
- Mu et al. (2020) Molecular grafting towards high-fraction active nanodots implanted in N-doped carbon for sodium dual-ion batteries (pp. 1-12)
- Chen et al. (2019) Enhanced photoresponsivity of a GaAs nanowire metal-semiconductor-metal photodetector by adjusting the fermi level (pp. 33188-33193) https://doi.org/10.1021/acsami.9b07891
- Li et al. (2018) Optical properties of quasi-type-II structure in GaAs/GaAsSb/GaAs coaxial single quantum-well nanowires https://doi.org/10.1063/1.5053844
- Tang et al. (2020) Competitive-type pressure-dependent immunosensor for highly sensitive detection of diacetoxyscirpenol in wheat via monoclonal antibody (pp. 3563-3571) https://doi.org/10.1021/acs.analchem.9b03933
- Zhu et al. (2020) Dual-phase CsPbCl3–Cs4PbCl6 perovskite films for self-powered, visible-blind UV photodetectors with fast response (pp. 32961-32969) https://doi.org/10.1021/acsami.0c09910
- Xu et al. (2021) Quantum chemical study on the adsorption of megazol drug on the pristine BC3 nanosheet (pp. 63-69) https://doi.org/10.1080/10610278.2021.1938049
- Zhao et al. (2022) Electro-reduction of N2 on nanostructured materials and the design strategies of advanced catalysts based on descriptors https://doi.org/10.1016/j.mtphys.2022.100609
- Girardi et al. (2011) Biodegradation of ciprofloxacin in water and soil and its effects on the microbial communities (pp. 22-30) https://doi.org/10.1016/j.jhazmat.2011.10.004
- Wei et al. (2013) Distinct photolytic mechanisms and products for different dissociation species of ciprofloxacin (pp. 4284-4290) https://doi.org/10.1021/es400425b
- Couto et al. (2020) Assessing potential of nanofiltration, reverse osmosis and membrane distillation drinking water treatment for pharmaceutically active compounds (PhACs) removal https://doi.org/10.1016/j.jwpe.2019.101029
- Mu et al. (2019) Electrochemical degradation of ciprofloxacin with a Sb-doped SnO2 electrode: performance, influencing factors and degradation pathways (pp. 29796-29804) https://doi.org/10.1039/C9RA04860J
- Fallah et al. (2021) Toxicity and remediation of pharmaceuticals and pesticides using metal oxides and carbon nanomaterials https://doi.org/10.1016/j.chemosphere.2021.130055
- Biswal and Balasubramanian (2022) Adsorptive removal of sulfonamides, tetracyclines and quinolones from wastewater and water using carbon-based materials: Recent developments and future directions https://doi.org/10.1016/j.jclepro.2022.131421
- Ahmad et al. (2019) Synthesis and characterization of molecularly imprinted magnetite nanomaterials as a novel adsorbent for the removal of heavy metals from aqueous solution (pp. 4239-4252) https://doi.org/10.1016/j.jmrt.2019.07.034
- Soares et al. (2020) Recent advances on magnetic biosorbents and their applications for water treatment (pp. 151-164) https://doi.org/10.1007/s10311-019-00931-8
- Zare et al. (2021) Water decontamination using bio-based, chemically functionalized, doped, and ionic liquid-enhanced adsorbents: review (pp. 3075-3114) https://doi.org/10.1007/s10311-021-01207-w
- Theamwong et al. (2021) Activated carbons from waste Cassia bakeriana seed pods as high-performance adsorbents for toxic anionic dye and ciprofloxacin antibiotic remediation https://doi.org/10.1016/j.biortech.2021.125832
- Wang et al. (2021) Ciprofloxacin removal by ultrasound-enhanced carbon nanotubes/permanganate process: in situ generation of free reactive manganese species via electron transfer https://doi.org/10.1016/j.watres.2021.117393
- Huang et al. (2020) Preparation of a three-dimensional porous graphene oxide–kaolinite–poly(vinyl alcohol) composite for efficient adsorption and removal of ciprofloxacin (pp. 10895-10904) https://doi.org/10.1021/acs.langmuir.0c00654
- Hu et al. (2020) Removal of ciprofloxacin with aluminum-pillared kaolin sodium alginate beads (CA-Al-KABs): kinetics, isotherms, and BBD model
- Falyouna et al. (2022) Encapsulation of iron nanoparticles with magnesium hydroxide shell for remarkable removal of ciprofloxacin from contaminated water (pp. 813-827) https://doi.org/10.1016/j.jcis.2021.07.154
- Laabd et al. (2021) A novel mesoporous Hydroxyapatite@Montmorillonite hybrid composite for high-performance removal of emerging Ciprofloxacin antibiotic from water: Integrated experimental and Monte Carlo computational assessment https://doi.org/10.1016/j.molliq.2021.116705
- Yang et al. (2022) Efficient with low-cost removal and adsorption mechanisms of norfloxacin, ciprofloxacin and ofloxacin on modified thermal kaolin: experimental and theoretical studies https://doi.org/10.1016/j.jhazmat.2022.128500
- Jiang et al. (2013) Removal of ciprofloxacin from water by birnessite (pp. 362-369) https://doi.org/10.1016/j.jhazmat.2013.02.015
- Soares et al. (2019) Magnetic nanosorbents with siliceous hybrid shells of alginic acid and carrageenan for removal of ciprofloxacin (pp. 827-841) https://doi.org/10.1016/j.ijbiomac.2019.08.030
- Yaashikaa et al. (2022) Review on biopolymers and composites—evolving material as adsorbents in removal of environmental pollutants https://doi.org/10.1016/j.envres.2022.113114
- Dang et al. (2022) Current application of algae derivatives for bioplastic production: a review https://doi.org/10.1016/j.biortech.2022.126698
- Guo et al. (2022) Carrageenan oligosaccharides: a comprehensive review of preparation, isolation, purification, structure, biological activities and applications https://doi.org/10.1016/j.algal.2021.102593
- Zia et al. (2017) A review on synthesis, properties and applications of natural polymer based carrageenan blends and composites (pp. 282-301) https://doi.org/10.1016/j.ijbiomac.2016.11.095
- Papageorgiou et al. (2017) Novel isocyanate-modified carrageenan polymer materials: preparation, characterization and application adsorbent materials of pharmaceuticals https://doi.org/10.3390/polym9110595
- Soares et al. (2016) Hybrid nanoadsorbents for the magnetically assisted removal of metoprolol from water (pp. 560-569) https://doi.org/10.1016/j.cej.2016.05.079
- Sharma et al. (2022) A comprehensive review on the removal of noxious pollutants using carrageenan based advanced adsorbents https://doi.org/10.1016/j.chemosphere.2021.133100
- Mohd Yusop et al. (2021) Preparation and characterization of new sol–gel hybrid inulin–TEOS adsorbent https://doi.org/10.3390/polym13081295
- Benvenuti et al. (2020) Hybrid sol–gel silica adsorbent material based on grape stalk applied to cationic dye removal (pp. 1-10) https://doi.org/10.1002/ep.13398
- Samiey et al. (2014) Organic-inorganic hybrid polymers as adsorbents for removal of heavy metal ions from solutions: a review (pp. 673-726) https://doi.org/10.3390/ma7020673
- Soares et al. (2021) A versatile synthetic route towards gelatin-silica hybrids and magnetic composite colloidal nanoparticles https://doi.org/10.1007/s42114-021-00386-y
- Huang and Keller (2013) Magnetic nanoparticle adsorbents for emerging organic contaminants (pp. 731-736) https://doi.org/10.1021/sc400047q
- Kharissova et al. (2015) Magnetic adsorbents based on micro- and nano-structured materials (pp. 6695-6719) https://doi.org/10.1039/C4RA11423J
- Malek et al. (2021) Fly ash modified magnetic chitosan-polyvinyl alcohol blend for reactive orange 16 dye removal: adsorption parametric optimization (pp. 464-476) https://doi.org/10.1016/j.ijbiomac.2021.08.160
- Reghioua et al. (2021) Parametric optimization by Box-Behnken design for synthesis of magnetic chitosan-benzil/ZnO/Fe3O4 nanocomposite and textile dye removal https://doi.org/10.1016/j.jece.2021.105166
- Soares et al. (2019) Magnetic quaternary chitosan hybrid nanoparticles for the efficient uptake of diclofenac from water (pp. 35-44) https://doi.org/10.1016/j.carbpol.2018.09.030
- Oliveira-Silva et al. (2015) Magnetic chelating nanoprobes for enrichment and selective recovery of metalloproteases from human saliva (pp. 238-249) https://doi.org/10.1039/C4TB01189A
- Stöber et al. (1968) Controlled growth of monodisperse silica spheres in the micron size range (pp. 62-69) https://doi.org/10.1016/0021-9797(68)90272-5
- Soares et al. (2021) On the efficient removal, regeneration and reuse of quaternary chitosan magnetite nanosorbents for glyphosate herbicide in water https://doi.org/10.1016/j.jece.2021.105189
- Gómez-Ordóñez and Rupérez (2011) FTIR-ATR spectroscopy as a tool for polysaccharide identification in edible brown and red seaweeds (pp. 1514-1520) https://doi.org/10.1016/j.foodhyd.2011.02.009
- Prado-Fernández et al. (2003) Quantitation of κ-, ι- and λ-carrageenans by mid-infrared spectroscopy and PLS regression (pp. 23-37) https://doi.org/10.1016/S0003-2670(02)01592-1
- Pereira et al. (2009) Identification of selected seaweed polysaccharides (phycocolloids) by vibrational spectroscopy (FTIR-ATR and FT-Raman) (pp. 1903-1909) https://doi.org/10.1016/j.foodhyd.2008.11.014
- Pereira et al. (2013) Analysis by vibrational spectroscopy of seaweed polysaccharides with potential use in food, pharmaceutical, and cosmetic industries (pp. 1-7) https://doi.org/10.1155/2013/537202
- Soares et al. (2019) Trimethyl chitosan/siloxane-hybrid coated Fe3O4 nanoparticles for the uptake of sulfamethoxazole from water https://doi.org/10.3390/molecules24101958
- Wang et al. (2018) Synthesis of phosphated k-carrageenan and its application for flame-retardant waterborne epoxy https://doi.org/10.3390/polym10111268
- Soares et al. (2015) Carrageenan-silica hybrid nanoparticles prepared by a non-emulsion method (pp. 4588-4594) https://doi.org/10.1002/ejic.201500450
- Ouyang et al. (2015) Thermal stability and magnetic properties of polyvinylidene fluoride/magnetite nanocomposites (pp. 4553-4564) https://doi.org/10.3390/ma8074553
- Mahdavinia et al. (2014) Study of adsorption of cationic dye on magnetic kappa-carrageenan/PVA nanocomposite hydrogels (pp. 1578-1587) https://doi.org/10.1016/j.jece.2014.05.020
- Long et al. (2015) New method for the immobilization of pullulanase onto hybrid magnetic (Fe3O4–κ-carrageenan) nanoparticles by electrostatic coupling with pullulanase/chitosan complex (pp. 3534-3542) https://doi.org/10.1021/jf505981t
- Kulal and Badalamoole (2020) Hybrid nanocomposite of kappa-carrageenan and magnetite as adsorbent material for water purification (pp. 542-553) https://doi.org/10.1016/j.ijbiomac.2020.09.202
- Silva et al. (2017) Multifunctional organic–inorganic hybrids based on cellulose acetate and 3-glycidoxypropyltrimethoxysilane (pp. 114-126) https://doi.org/10.1007/s10971-016-4089-x
- Vueva et al. (2018) Silica/alginate hybrid biomaterials and assessment of their covalent coupling (pp. 1-12) https://doi.org/10.1016/j.apmt.2017.12.011
- van de Velde et al. (2004) The revised NMR chemical shift data of carrageenans (pp. 2309-2313) https://doi.org/10.1016/j.carres.2004.07.015
- Turquois et al. (1996) Composition of carrageenan blends inferred from 13C-NMR and infrared spectroscopic analysis (pp. 269-278) https://doi.org/10.1016/S0144-8617(96)00031-8
- Silva et al. (2010) Anticoagulant activity, paw edema and pleurisy induced carrageenan: action of major types of commercial carrageenans (pp. 26-33) https://doi.org/10.1016/j.carbpol.2009.07.010
- Babonneau et al. (2010) Solid-state nuclear magnetic resonance: A valuable tool to explore organic-inorganic interfaces in silica-based hybrid materials (pp. 58-68) https://doi.org/10.1016/j.crci.2009.08.001
- Barberena-Fernández et al. (2015) Interaction of TEOS with cementitious materials: Chemical and physical effects (pp. 145-152) https://doi.org/10.1016/j.cemconcomp.2014.09.010
- Chen et al. (2019) Multivariate optimization of ciprofloxacin removal by polyvinylpyrrolidone stabilized NZVI/Cu bimetallic particles (pp. 183-192) https://doi.org/10.1016/j.cej.2019.02.051
- Schefer et al. (2014) Unravelling secondary structure changes on individual anionic polysaccharide chains by atomic force microscopy (pp. 5376-5379) https://doi.org/10.1002/anie.201402855
- Khan et al. (2020) Development of Mn-PBA on GO sheets for adsorptive removal of ciprofloxacin from water: kinetics, isothermal, thermodynamic and mechanistic studies https://doi.org/10.1016/j.matchemphys.2020.122737
- Lagergren (1907) Springer-Verlag
- Ho and McKay (1999) Pseudo-second order model for sorption processes (pp. 451-465) https://doi.org/10.1016/S0032-9592(98)00112-5
- Chien and Clayton (1980) Application of Elovich equation to the kinetics of phosphate release and sorption in soils https://doi.org/10.2136/sssaj1980.03615995004400020013x
- Bui and Choi (2009) Adsorptive removal of selected pharmaceuticals by mesoporous silica SBA-15 (pp. 602-608) https://doi.org/10.1016/j.jhazmat.2009.02.072
- Sotelo et al. (2012) Adsorption of pharmaceutical compounds and an endocrine disruptor from aqueous solutions by carbon materials (pp. 640-652) https://doi.org/10.1080/03601234.2012.668462
- Wu et al. (2009) Characteristics of Elovich equation used for the analysis of adsorption kinetics in dye-chitosan systems (pp. 366-373) https://doi.org/10.1016/j.cej.2009.01.014
- Langmuir (1918) The adsorption of gases on plane surfaces of glass, mica and platinum (pp. 1361-1403) https://doi.org/10.1021/ja02242a004
- Freundlich (1906) Concerning adsorption in solutions (pp. 444-448)
- Dubinin and Radushkevich (1947) Equation of the characteristic curve of activated charcoal (pp. 331-333)
- Togue Kamga (2019) Modeling adsorption mechanism of paraquat onto Ayous (Triplochiton scleroxylon) wood sawdust https://doi.org/10.1007/s13201-018-0879-3
- Ayawei et al. (2017) Modelling and interpretation of adsorption isotherms https://doi.org/10.1155/2017/3039817
- Çelebi et al. (2007) A radiotracer study of the adsorption behavior of aqueous Ba2+ ions on nanoparticles of zero-valent iron (pp. 761-767) https://doi.org/10.1016/j.jhazmat.2007.06.122
- Mutavdžić Pavlović et al. (2017) Isotherm, kinetic, and thermodynamic study of ciprofloxacin sorption on sediments (pp. 10091-10106) https://doi.org/10.1007/s11356-017-8461-3
- Awe et al. (2020) Preparation and characterisation of activated carbon from Vitisvinifera leaf litter and its adsorption performance for aqueous phenanthrene https://doi.org/10.1186/s13765-020-00494-1
- Nazraz et al. (2019) Chitosan-based sorbent for efficient removal and extraction of ciprofloxacin and norfloxacin from aqueous solutions https://doi.org/10.1007/s00604-019-3563-x
- Wang et al. (2015) Preparation of a specific bamboo based activated carbon and its application for ciprofloxacin removal (pp. 32-39) https://doi.org/10.1016/j.scitotenv.2015.06.087
- Zhang et al. (2017) Response surface methodology approach for optimization of ciprofloxacin adsorption using activated carbon derived from the residue of desilicated rice husk (pp. 316-325) https://doi.org/10.1016/j.molliq.2017.04.022
- Huang et al. (2014) Adsorption of tetracycline and ciprofloxacin on activated carbon prepared from lignin with H3PO4 activation (pp. 2678-2687) https://doi.org/10.1080/19443994.2013.833873
- Privar et al. (2019) Metal-chelate sorbents based on carboxyalkylchitosans: Ciprofloxacin uptake by Cu(II) and Al(III)-chelated cryogels of N-(2-carboxyethyl)chitosan (pp. 806-811) https://doi.org/10.1016/j.ijbiomac.2019.03.122
- Zhuang et al. (2017) Enhanced adsorption removal of antibiotics from aqueous solutions by modified alginate/graphene double network porous hydrogel (pp. 250-259) https://doi.org/10.1016/j.jcis.2017.07.033
- Li et al. (2019) Ionically cross-linked sodium alginate/ĸ-carrageenan double-network gel beads with low-swelling, enhanced mechanical properties, and excellent adsorption performance (pp. 1091-1103) https://doi.org/10.1016/j.cej.2019.05.007
- Wang et al. (2016) Removal of ciprofloxacin from aqueous solution by a magnetic chitosan grafted graphene oxide composite (pp. 188-194) https://doi.org/10.1016/j.molliq.2016.07.037
- Zhou et al. (2019) A novel Fe3O4/graphene oxide/citrus peel-derived bio-char based nanocomposite with enhanced adsorption affinity and sensitivity of ciprofloxacin and sparfloxacin https://doi.org/10.1016/j.biortech.2019.121951
- Álvarez-Torrellas et al. (2017) Effective adsorption of non-biodegradable pharmaceuticals from hospital wastewater with different carbon materials (pp. 319-329) https://doi.org/10.1016/j.cej.2017.03.077
- Yu et al. (2019) κ-Carrageenan/Sodium alginate double-network hydrogel with enhanced mechanical properties, anti-swelling, and adsorption capacity https://doi.org/10.1016/j.chemosphere.2019.124417
- Rasoulzadeh et al. (2019) Mechanistic investigation of ciprofloxacin recovery by magnetite–imprinted chitosan nanocomposite: Isotherm, kinetic, thermodynamic and reusability studies (pp. 712-721) https://doi.org/10.1016/j.ijbiomac.2019.04.139
- Zhao et al. (2018) Sodium alginate/graphene oxide hydrogel beads as permeable reactive barrier material for the remediation of ciprofloxacin-contaminated groundwater (pp. 612-620) https://doi.org/10.1016/j.chemosphere.2018.02.157
- Saha et al. (2011) Insight into adsorption thermodynamics (pp. 349-364) InTech
- Husein (2013) Adsorption and removal of mercury ions from aqueous solution using raw and chemically modified Egyptian mandarin peel (pp. 6761-6769) https://doi.org/10.1080/19443994.2013.801793
- Liu (2015) Cooperative adsorption on solid surfaces (pp. 224-238) https://doi.org/10.1016/j.jcis.2015.03.013
- Maheshwari et al. (2013) Kinetics, equilibrium and thermodynamics of ciprofloxacin hydrochloride removal by adsorption on coal fly ash and activated alumina (pp. 7241-7254) https://doi.org/10.1080/19443994.2013.775076
- Soares et al. (2017) Highly efficient removal of dye from water using magnetic carrageenan/silica hybrid nano-adsorbents https://doi.org/10.1007/s11270-017-3281-0
- Nemati Sani et al. (2019) Catalytic ozonation of ciprofloxacin using γ-Al2O3 nanoparticles in synthetic and real wastewaters https://doi.org/10.1016/j.jwpe.2019.100894
- Das et al. (2020) Montmorillonite impregnated electrospun cellulose acetate nanofiber sorptive membrane for ciprofloxacin removal from wastewater https://doi.org/10.1016/j.jwpe.2020.101497
- Wang et al. (2010) Cation exchange interaction between antibiotic ciprofloxacin and montmorillonite (pp. 309-314) https://doi.org/10.1016/j.jhazmat.2010.07.025
- Wang et al. (2020) Removal of ciprofloxacin as an emerging pollutant: a novel application for bauxite residue reuse https://doi.org/10.1016/j.jclepro.2020.120049
- Wang et al. (2016) Effect of humic acid on ciprofloxacin removal by magnetic multifunctional resins https://doi.org/10.1038/srep30331
- Ma et al. (2017) Interaction processes of ciprofloxacin with graphene oxide and reduced graphene oxide in the presence of montmorillonite in simulated gastrointestinal fluids https://doi.org/10.1038/s41598-017-02620-4
- Inglezakis et al. (2018) Insights into the S-shaped sorption isotherms and their dimensionless forms (pp. 166-176) https://doi.org/10.1016/j.micromeso.2018.06.026
- Li et al. (2018) The effect of molecular shape on oligomerization of hydrophobic drugs: molecular simulations of ciprofloxacin and nutlin https://doi.org/10.1063/1.5013056
- Pavli et al. (2011) Doxazosin–carrageenan interactions: a novel approach for studying drug–polymer interactions and relation to controlled drug release (pp. 110-119) https://doi.org/10.1016/j.ijpharm.2011.09.019
- Liu et al. (2017) Adsorption of sulfamethoxazole (SMZ) and ciprofloxacin (CIP) by humic acid (HA): characteristics and mechanism (pp. 50449-50458) https://doi.org/10.1039/C7RA06231A
- Zhang et al. (2019) Fundamental insights into ciprofloxacin adsorption by sulfate-reducing bacteria sludge: Mechanisms and thermodynamics https://doi.org/10.1016/j.cej.2019.122103
10.1007/s40097-022-00498-x