Abstract
Using nanosized metal substrates, surface-enhanced Raman scattering (SERS) is a tool for improving the Raman signal of biomolecules. For detection, SERS has gained much popularity and an important role in determining chemical composition. In the present study, SERS spectra of 2-methyl-4-(4-methylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine (olanzapine) (MPTB) were investigated on silver and silver-gold metal substrates (SERSitive, Warsaw, Poland) at different concentrations. Also, different chemical and electronic properties are investigated using DFT calculations. The ring and other functional modes in SERS change in frequency values with variations in intensity for all concentrations. The molecule is oriented in a tilted manner with respect to Ag and Ag-Au.
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Al-Otaibi JS, Almuqrin AH, Mary YS, Mary YS, Thomas R (2020) Cocrystals of hydrochlorothiazide with picolinamide, tetramethylpyrazine and piperazine: quantum mechanical studies, docking and modelling of the photovoltaic efficiency for DSSC. J Mol Model 26:256. https://doi.org/10.1007/s00894-020-04528-9
Alzoman NZ, Mary YS, Panicker CY, Al-Swaidan IA, El-Emam AA, Al-Deeb OA, Al-Saadi AA, Van Alsenoy C, War JA (2015) Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO-LUMO, NBO, MEP analysis and molecular docking study of 2-[(4-chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-(phenylsulfanyl)-pyrimidine—5-carbonitrile, a potential chemotherapeutic agent. Spectrochim Acta 139:413–424. https://doi.org/10.1016/j.saa.2014,12.043
Beegum S, Mary YS, Mary YS, Thomas R, Armakovic S, Armakovic SJ, Zitko J, Dolezal M, Van Alsenoy C (2020) Exploring the detailed spectroscopic characteristics, chemical and biological activity of two cyanopyrazine-2-carboxamide derivatives using experimental and theoretical tools. Spectrochim Acta. https://doi.org/10.1016/j.saa.2019.117414
Bymaster FP, Falcone JF, Bauzon D, Kennedy JS, Schenck K, DeLapp NW, Cohen ML (2001) Potent antagonism of5-HT(3) and 5-HT(6) receptors by olanzapine. Eur J Pharmacol 430:341–349. https://doi.org/10.1016/s0014-2999(01)01399-1
Chandu B, Bharati MSS, Albrycht P, Rao SV (2020) Fabrication of nanocages on nickel using femtosecond laser ablation and trace level detection of malachite green and Nile blue dyes using surface enhanced Raman spectroscopic technique. Opt Laser Technol 131:106454. https://doi.org/10.1016/j.optlastec.2020.106454
Chowdhury J, Ghosh M, Misra TN (2000) Surface enhanced Raman scattering of 2,2’- biquinoline adsorbed on colloidal silver particles. Spectrochim Acta. https://doi.org/10.1016/S1386-1425(00)00263-8
Chowdhury J, Ghosh M, Misra TN (2000a) pH-dependent surface enhanced Raman scattering of 8-hydroxy quinoline adsorbed on silver hydrosol. J Colloid Interface Sci 228:372–378. https://doi.org/10.1006/jcis.2000.6977
Chowdhury J, Ghosh M, Pal P, Misra TN (2003) Concentration dependent surface enhanced resonance Raman scattering of a porphyrin derivative adsorbed on colloidal silver particles. J Colloid Interface Sci 263:318–326
Cinta S, Iliescu T, Astilean S, David L, Cozar O, Kiefer W (1999) 1,4-Benzodiazepine drugs adsorption on the Ag colloidal surface. J Mol Struct 482–483:685–688. https://doi.org/10.1016/j.molstruc
Coccurello R, D’Amato FR, Moles A (2008) Chronic administration of olanzapine affects behavior satiey sequence and feeding behavior in female mice. Eat Weight Disord 13:e55-60
R. Dennington, T. Keith, J. Millam (2009) Semichem Inc., Shawnee Mission KS, GaussView, Version 5
El-Azab AS, Mary YS, Panicker CY, Abdel-Aziz AAM, El-Sherbeny MA, Van Alsenoy C (2016) DFT and experimental (FT-IR and FT-Raman) investigation of vibrational spectroscopy and molecular docking studies of 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)acetamide. J Mol Struct 1113:133–145
Fogarasi G, Zhou X, Taylor PW, Pulay P (1992) The calculation of ab initio molecular geometries: efficient optimization by natural internal coordinates and empirical correction by offset forces. J Am Chem Soc 114:8191–8201. https://doi.org/10.1021/ja00047a032
Foresman JB (1996) In: Frisch E (ed) Exploring chemistry with electronic structure methods: a guide to using Gaussian, Pittsburg, USA
Forisz E, David L, Cozar O, Craciun C, Venter M, Kilyen M (1997) IR and ESR study of Cu(II)-nitrazepam complexes. J Mol Struct 408–409:195–199. https://doi.org/10.1016/S0022-2860(96)09633-0
Fornasaro S, Gurian E, Pagarin S, Genova E, Stocco G, Decorti G, Sergo V, Bonifacio A (2021) Ergothioneine, a dietary amino acid with a high relevance for the interpretation of label-free surface enhanced Raman scattering (SERS) spectra of many biological samples. Spectrochim Acta 246:119024. https://doi.org/10.1016/j.saa.2020.119024
Gan L-L, Lu Y-H, Zhou C-H (2009) Advances in the research of piperazine compounds as enzyme inhibitors. Chin J Biochem Pharm 30:127–131
Gaussian 09, Revision B.01, M.J. Frisch, G.W. Trucks et al. (2010) Gaussian, Inc., Wallingford CT
Gebavi H, Gasparic V, Risovic D, Baran N, Albrycht PH, Ivanda M (2019) Features and advantages of flexible silicon nanowires for SERS applications. Beilstein J Nanotechnol 10:725–734
Kim SK, Joo TH, Suh SW, Kim MS (1986) Surface enhanced Raman scattering (SERS) of nucleic acid components in silver sols: adenine series. J Raman Spectrosc 17:381–386. https://doi.org/10.1002/jrs.1250170503
Laabaissi T, Bouassiria M, Oudda H, Zarrok H, Zarrouk A, Elmidaouti A, Lakhrissi L, Lakhrissi B, Essassi E, Touir R (2016) Adsorption and corrosion inhibition efficiency effect of benzodiazepine derivative on carbon steel in 2.0 MH3po4 medium. J Mater Enviorn Sci 7:1538–1548
Lai HS, Li GK, Xu FG, Zhang ZM (2020) Metal-organic frameworks: opportunities and challenges for surface enhanced Raman scattering- a review. J Mater Chem C 8:2952–2963. https://doi.org/10.1039/D0TC00040J
Lee HK, Lee YH, Koh CSL, Phan-Quang GC, Han X, Lay CL, Sim HYF, Kao YC, An Q, Ling XY (2019) Designing surface enhanced Raman scattering (SERS) platforms beyond hotspot engineering: emerging opportunities in analyte manipulations and hybrid materials. Chem Soc Rev 48:731–756. https://doi.org/10.1039/C7CS00786H
Liang S, Jamieson LE, Faulds K, Graham D (2017) Surface enhanced Raman spectroscopy for in vivo biosensing. Nat Rev Chem 1:0060. https://doi.org/10.1038/s41570-017-0060
Liu H, Li C, Song R, Xu S (2020) A 3D multilayer curved plasmonic coupling array with abundant and uniform hot spots for surface enhanced Raman scattering. J Phys d: Appl Phys 53:055101. https://doi.org/10.1088/1361-6463/ab550b
Li Y, Jiang L, Zou Y, Song Z, Jin S (2021) Highly reproducible SERS sensor based on self assembled Au nanocubic monolayer film for sensitive and quantitative detection of glutathione. Appl Surf Sci 540:148381. https://doi.org/10.1016/j.apsusc.2020.148381
Martin JML, Van Alsenoy C (2007) GAR2PED, a program to obtain a potential energy distribution from a Gaussian archive record. University of Antwerp, Belgium
Mary YS, Raju K, Yildiz I, Temiz-Arpaci O, Nogueira HIS, Grandeiro CM, Van Alsenoy C (2012) FT-IR, FT-Raman, SERS and computational study of 5-ethylsulphonyl-2-(o-chlorobenzyl)benzoxazole. Spectrochim Acta 96:617–625. https://doi.org/10.1016/j.saa.2012.07.006
Mary YS, Jojo PJ, Van Alsenoy C, Kaur M, Siddegowda MS, Yathirajan HS, Nogueira HIS, Cruz SMA (2014a) Vibrational spectroscopic studies (FT-IR, FT-Raman, SERS) and quantum chemical calculations on cyclobenzaprinium. Spectrochim Acta 120:340–350. https://doi.org/10.1016/j.saa.2013.10.020
Mary YS, Panicker CY, Varghese HT, Van Alsenoy C, Prochazkov M, Sevcik R, Pazdera P (2014b) Acid-base properties, FT-IR, FT-Raman spectroscopy and computational study of 1-(pyrid-4-yl)piperazine. Spectrochim Acta 121:436–444. https://doi.org/10.1016/j.saa.2013.10.119
Mary YS, Jojo PJ, Van Alsenoy C, Kaur M, Siddegowda MS, Yathirajan HS, Nogueira HIS, Cruz SMA (2014c) Vibrational spectroscopic (FT-IR, FT-Raman, SERS) and quantum chemical calculations of 3-(10,10-dimethyl-anthracen-9-ylidene)-N, N, N-trimethyl propanaminiium chloride (Melitracenium chloride). Spectrochim Acta Part A Mol Biomol Spectrosc 120:370–380. https://doi.org/10.1016/j.saa.2013.10.021
Mary YS, Panicker CY, Kavitha CN, Yathirajan HS, Siddegowda MS, Cruz SMA, Nogueira HIS, Al-Saadi AA, Van Alsenoy C, War JA (2015) Spectroscopic investigation (FT-IR, FT-Raman and SERS), vibrational assignments, HOMO-LUMO analysis and molecular docking study of Opipramol. Spectrochim Acta 137:547–559. https://doi.org/10.1016/j.saa.2014.08.106
Meltzer HY (2004) What’s a typical about atypical antipsychotic drugs? Curr Opin Pharmacol 4:53–57. https://doi.org/10.1016/j.coph.2003.09.010
Moore TJ, Mattison DR (2017) Adult utilization of psychiatric drugs and differences by sex and race. JAMA Intern Med 177:274–275. https://doi.org/10.1001/jamainternmed.2016.7507
Murugan E, Santhoshkumar S, Govindaraju S, Palanichamy M (2021) Silver nanoparticles decorated g-C3N4: an efficient SERS substrate for monitoring catalytic reduction and selective Hg2+ ions detection. Spectrochim Acta 246:119036. https://doi.org/10.1016/j.saa.2020.119036
Nemeckova D, Mary YS, Panicker CY, Varghese HT, Van Alsenoy C, Prochazkova M, Pazdera P, Al-Saadi AA (2015) 1-Alkyl-1-methylpiperazine-1,4-diium salts: Synthetic, acid-base, XRD-analytical, FT-IR, FT-Raman spectral and quantum chemical study. J Mol Struct 1094:210–236. https://doi.org/10.1016/j.molstruc.2015.03.051
Osterrieth JWM, Wright D, Noh H, Kung CW, Vulpe D, Li A, Park JE, Van Duyne RP, Moghadam PZ, Baumberg JJ, Farha OK, Airen-Jimenez DF (2019) Core-shell gold nanorod@zirconium-based metal-organic framework composites as in situ size-selective Raman probes. J Am Chem Soc 141:3893–3900
Palasti DJ, Albryct P, Janovszky P, Paszkowska K, Geretovszky Z, Galbacs G (2020) Nanoparticle enhanced laser induced breakdown spectroscopy of liquid samples by using modified surface-enhanced Raman scattering substrates. Spectrochim Acta B 166:105793
Panicker CY, Varghese HT, John A, Philip D, Istvan K, Keresztury G (2002) FT-IR, FT-Raman and FT-SERS spectra of 4-aminosalicylic acid sodium salt dihydrate. Spectrochim Acta 58:281–287. https://doi.org/10.1016/S1386-1425(01)00541-8
Peng Y, Lin C, Long L, Masaki T, Tang M, Yang L, Liu J, Huang Z, Li Z, Luo X, Lombardi JR, Yang Y (2021) Charge-transfer resonance and electromagnetic enhancement synergistically enabling MXenes with excellent SERS sensitivity for SARS-Cov-2S protein detection. Nano-Micro Lett 13:52. https://doi.org/10.1007/s40820-020-00565-4
Pergolese B, Bigotto A (2001) Surface enhanced Raman spectroscopic studies of 1H-indazole on silver sols. Spectrochim Acta 57:1191–1197. https://doi.org/10.1016/S1386-1425(00)00459-5
Rabahi A, Hamdi SM, Rachedi Y, Hamdi M, Talhi O, Paz FAA, Silva ASM, Fadila B, Malika H, Kamel T (2014) 2D-NMR, X-ray crystallography and theoretical studies of the reaction mechanism for the synthesis of 1,5-benzodiazepines from dehydroacetic acid derivatives and o-phenylenediamines. J Mol Struct 1061:97–103. https://doi.org/10.1016/j.molstruc.2013.12.082
Raj A, Mary YS, Panicker CY, Varghese HT, Raju K (2013) IR, Raman, SERS and computational study of 2-(benzylsulfanyl)-3,5-dintrobenzoic acid. Spectrochim Acta 113:28–36. https://doi.org/10.1016/j.saa.2013.04.096
Renjith R, Mary YS, Panicker CY, Varghese HT, Pakosinska-Parys M, Van Alsenoy C, Manojkumar TK (2014) Spectroscopic(FT-IR, FT-Raman), first order hyperpolarizability, NBO analysis, HOMO and LUMO analysis of 1,7,8,9-tetrachloro-10,10-dimethoxy-4-[3-(4-phenylpiperazin-1-yl)propyl]-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione by density functional methods. Spectrochim Acta. https://doi.org/10.1016/j.saa.2014.01.045
Renjith R, Mary YS, Panicker CY, Varghese HT, Pakosinska-Parys M, Van Alsenoy C, Al-Saadi AA (2014) Spectroscopic (FT-IR, FT-Raman) investigations and quantum chemical calculations of 1,7,8,9-tetrachloro-10.10-dimethoxy-4-(3–4-(3-methoxyphenyl)piperazin-1ylpropy-1}-4-azatricyclo-5.2.1.0(2,6)dec-8-ene-3,5-dione. Spectrochim Acta 129:438–450
Richter L, Albrycht P, Ksiezopolska-Gocalska M, Pobozy E, Bachlinski R, Sashuk V, Paczesny J, Holyst R (2020) Fast and efficient deposition of broad range of analytes on substrates for surface enhanced Raman spectroscopy. Biosen Bioelectron. https://doi.org/10.1016/j.bios.2020.112124
Roeges NPG (1994) A guide to the complete interpretation of infrared spectra of organic structures. Wiley, New York
Sebhaoui J, El Bakri Y, El Aoufir Y, Anouar EH, Guenbour A, Nasser AA, Essassi EM (2019) Synthesis, NMR characterization, DFT and anti-corrosion on carbon steel in 1M HCl of two novel, 1,5-benzodiazepines. J Mol Struct 1182:123–130. https://doi.org/10.1016/j.molstruc.2019.01.037
Shahabadi N, Bagheri S (2015) Spectroscopic and molecular docking studies on the interaction of the drug olanzapine with calf thymus DNA. Spectrochim Acta 136:1454–1459. https://doi.org/10.1016/j.saa.2014.10.036
Thomas R, Mary YS, Resmi KS, Narayana B, Sarojini BK, Vijayakumar G, Van Alsenoy C (2019) Two neoteric pyrazole compounds as potential anti-cancer agents: synthesis, electronic structure, physic-chemical properties and docking analysis. J Mol Struct 1181:455–466. https://doi.org/10.1016/j.molstruc.2019.01.003
Turker-Kaya S, Mutlu O, Celikyurt IK, Akar F, Ulak G (2016) Tianeptine, olanzapine and fluxetine show similar restoring effects on stress induced molecular changes in mice brain: an FT-IR study. Spectrochim Acta. https://doi.org/10.1016/j.saa.2016.02.038
Vikesland PJ (2018) Nanosensors for water quality monitoring. Nat Nanotechnol 12:651–660. https://doi.org/10.1038/s41565-018-0209-9
Votaw VR, Geyer R, Rieselbach MM, McHugh RK (2019) The epidemiology of benzodiazepine misuse: a systematic review. Drug Alcohol Depend 200:95–114. https://doi.org/10.1016/j.drugalcdep.2019.02.033
Wang J, Hu Y, Yu X, Zhuang X, Wang Q, Jiang N, Hu J (2021) Recyclable and ultrasensitive SERS sensing platform: deposition of atomically precise Ag152 nanoclusters on surface of plasmonic 3D ZnO-NC/AuNP arrays. Appl Surf Sci 540:148324. https://doi.org/10.1016/j.apsusc.2020.148324
Wawrzycka-Gorczyca I, Borowski P, Osypiuk-Tomasik J, Azur LM, Koziol AE (2007) Crystal structure of olanzapine and its solvates Part 3. Two and three-component solvates with water, ethanol, butan-2ol and dichloromethane. J Mol Struct. https://doi.org/10.1016/j.molstruc.2006.07.017
Xu H, Zhuang X (2019) Atypical antipsychotics-induced metabolic syndrome and non-alcoholic fatty liver disease: a critical review. Neuropsychiatr Dis Treat 15:2087–2099. https://doi.org/10.2147/NDT.S208061
Xu M, Tu GP, Ji MW, Wan XD, Liu JJ, Liu J, Rong HP, Yang YL, Wang C, Zhang JT (2019) Vacuum-tuned-atmosphere induced assembly of Au@Ag core/shell nanocubes into multi-dimensional superstructures and the ultrasensitive IAPP proteins SERS detection. Nano Res. https://doi.org/10.1007/s12274-019-2325-8
Xu F, Shang W, Ma G, Zhu Y, Wu M (2021) Metal organic framework wrapped gold nanourchin assembled on filter membrane for fast and sensitive SERS analysis. Sens Actuators, B Chem 326:128968. https://doi.org/10.1016/j.snb.2020.128968
Yu HK, Peng YS, Yang Y, Li ZY (2019) Plasmon enhanced light-matter interactions and applications. NPJ Comput Mater 5:45. https://doi.org/10.1038/s41524-019-0184-1
Zhang R, Jiang W, Liang Z, Luo X, Yang Q (2018) Study of equilibrium solubility, heat of absorption and speciation of CO2 absorption into aqueous 2-methylpiperazine (2MPZ) solution. Ind Eng Chem Res 57:17496–17503. https://doi.org/10.1021/acs.iecr.8b03104
Zhu X, Liu P, Xue T, Ge Y, Ai S, Sheng Y, Wu R, Xu L, Tang K, Wen Y (2021) A novel graphene-like titanium carbide MXene/Au-Ag nanoshuttles bifunctional nanosensor for electrochemical and SERS intelligent analysis of ultra-trace carbendazim coupled with machine learning. Ceram Int 47:173–184. https://doi.org/10.1016/j.ceramint.2020.08.121
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This research was funded by the Deanship of Scientific Research at Princess Nourah bint Abdulrahman University through the Fast-track Research Funding Program.
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JSA, MKG, and PA helped in experimental setup, conceptualization, methodology, data curation, writing, validation. YSM and YSM contributed to conceptualization, methodology, data curation, writing, software, validation.
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Al-Otaibi, J.S., Albrycht, P., Mary, Y.S. et al. Concentration-dependent SERS profile of olanzapine on silver and silver-gold metallic substrates. Chem. Pap. 75, 6059–6072 (2021). https://doi.org/10.1007/s11696-021-01783-9
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DOI: https://doi.org/10.1007/s11696-021-01783-9