In – Silico Prediction of Biological Activity Spectrum of Some Existing Local Anesthetic Drugs for Their Novel Anti-infective and Anticancer Potential
Keywords:
PASS, Drug Repurposing, Anti-infective, AnticancerAbstract
Cancer and Infectious diseases now a day’s are becoming the major public health issue. The mutations in cancer cell and infectious agents are resulting into new variants which either is resistant or not responding to the current treatment. And discovering novel potential drugs for such new variants is time consuming, complex and laborious process that needs huge money and human efforts. Drug repurposing has attracted attention of world’s scientist as it is one of the promising fields that may give quick and cost effective solution for the treatment of such diseases that are affecting major population of the world by utilizing modern bioinformatics and computational resources. Various computational models utilized as a large source of information such as Pubchem, DrugBank, Chemspider, ChEMBL and PASS contains physicochemical and biological information on drugs.
The PASS estimates the probable biological activity profiles for compounds under study based on their structural formulae presented in MOL file or SD file format. Prediction is based on the analysis of structure activity-relationships for more than 250,000 biologically active substances including drugs, drug-candidates, leads and toxic compounds. So we may use PASS for the prediction of the biological activity spectrum for existing drugs and based on the particular interest to some kind of activity and novelty of pharmacological action, we may choose which activities have to be tested experimentally.
In present work the PASS studies of some already existing Local Anesthetics drugs like Benzocaine, Biphenamine, Butacaine, Cyclomethylcaine and Lidocaine were carried out on the Way2Drug portal on PASS online software version 2.0. The PASS study results obtained had revealed that amongst virtually screened Local Anaesthetic drugs Benzocaine, Biphenamine, Butacaine, Cyclomethylcaine, Lidocaine and Ambucaine have shown good Pa value ranging from 0,880 to 0,573 for Antibacterial Activity targets, 0,861 to 0,551 for Antifungal Activity targets and 0,867 to 0,593 for Anticancer Activity targets which predicts the higher probability for these drugs to be active as Antibacterial agents, Antifungal agents and Anticancer agents respectively. Amongst all virtually screened Local Anesthetic drugs Benzocaine was found to possess potent Antibacterial, Antifungal and Anticancer Activities which may be subjected for further evaluation
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[1] Anand, P., Kunnumakara, A.B., Sundaram, C., Harikumar, K.B., Tharakan, S.T., Lai, O.S., Sung, B. and Aggarwal, B.B. (2008). Cancer is a Preventable Disease that Requires Major Lifestyle Changes. Pharmaceutical Research, 25(9), pp.2097–2116. doi:10.1007/s11095-008-9661-9.
[2] Bhattacharyya, G.S., Doval, D.C., Desai, C.J., Chaturvedi, H., Sharma, S. and Somashekhar, S.P. (2020). Overview of Breast Cancer and Implications of Overtreatment of Early-Stage Breast Cancer: An Indian Perspective. JCO Global Oncology, (6), pp.789–798. doi:10.1200/go.20.00033.
[3] Cancer. (2022). India. [online] 8 Aug. Available at: https://www.india.com/topic/cancer/.
[4] Dhillon, P.K., Mathur, P., Nandakumar, A., Fitzmaurice, C., Kumar, G.A., Mehrotra, R., Shukla, D.K., Rath, G.K., Gupta, P.C., Swaminathan, R., Thakur, J.S., Dey, S., Allen, C., Badwe, R.A., Dikshit, R., Dhaliwal, R.S., Kaur, T., Kataki, A.C., Visweswara, R.N. and Gangadharan, P. (2018). The burden of cancers and their variations across the states of India: the Global Burden of Disease Study 1990–2016. The Lancet Oncology, [online] 19(10), pp.1289–1306. doi:10.1016/s1470-2045(18)30447-9.
[5] Jain, A., Singh, P.K., Chooramani, G., Dixit, P. and Malhotra, H.S. (2016). Drug resistance and associated genetic mutations among patients with suspected MDR-TB in Uttar Pradesh, India. The International Journal of Tuberculosis and Lung Disease, 20(7), pp.870–875. doi:10.5588/ijtld.15.0874.
[6] Kulothungan, V., Sathishkumar, K., Leburu, S., Ramamoorthy, T., Stephen, S., Basavarajappa, D., Tomy, N., Mohan, R., Menon, G.R. and Mathur, P. (2022). Burden of cancers in India - estimates of cancer crude incidence, YLLs, YLDs and DALYs for 2021 and 2025 based on National Cancer Registry Program. BMC Cancer, 22(1). doi:10.1186/s12885-022-09578-1.
[7] Kumar, S., Kushwaha, P.P. and Gupta, S. (2019). Emerging targets in cancer drug resistance. Cancer Drug Resistance. doi:10.20517/cdr.2018.27.
[8] Malik, P.S. and Raina, V. (2015). Lung cancer: prevalent trends & emerging concepts. The Indian journal of medical research, [online] 141(1), pp.5–7. doi:10.4103/0971-5916.154479.
[9] Perillo, B., Di Donato, M., Pezone, A., Di Zazzo, E., Giovannelli, P., Galasso, G., Castoria, G. and Migliaccio, A. (2020). ROS in cancer therapy: the bright side of the moon. Experimental & Molecular Medicine, 52(2), pp.192–203. doi:10.1038/s12276-020-0384-2.
[10] Cha, Y., Erez, T., Reynolds, I.J., Kumar, D., Ross, J., Koytiger, G., Kusko, R., Zeskind, B., Risso, S., Kagan, E., Papapetropoulos, S., Grossman, I. and Laifenfeld, D. (2017a). Drug Repurposing from the Perspective of Pharmaceutical Companies. British Journal of Pharmacology, 175(2), pp.168–180. doi:10.1111/bph.13798.
[11] Cha, Y., Erez, T., Reynolds, I.J., Kumar, D., Ross, J., Koytiger, G., Kusko, R., Zeskind, B., Risso, S., Kagan, E., Papapetropoulos, S., Grossman, I. and Laifenfeld, D. (2017b). Drug Repurposing from the Perspective of Pharmaceutical Companies. British Journal of Pharmacology, 175(2), pp.168–180. doi:10.1111/bph.13798.
[12] Drago, F. and Maldonado, R. eds., (2021). Drug Repurposing for COVID-19 Therapy. Frontiers Research Topics. Frontiers Media SA. doi:10.3389/978-2-88971-485-8.
[13] GNS, H.S., GR, S., Murahari, M. and Krishnamurthy, M. (2019). An Update on Drug Repurposing: Re-written Saga of the Drug’s Fate. Biomedicine & Pharmacotherapy, 110, pp.700–716. doi:10.1016/j.biopha.2018.11.127.
[14] Gysi, D.M., Valle, Í. do, Zitnik, M., Ameli, A., Gan, X., Varol, O., Ghiassian, S.D., Patten, J.J., Davey, R.A., Loscalzo, J. and Barabási, A.-L. (2021). Network Medicine Framework for Identifying drug-repurposing Opportunities for COVID-19. Proceedings of the National Academy of Sciences, [online] 118(19). doi:10.1073/pnas.2025581118.
[15] Law, G.L., Tisoncik-Go, J., Korth, M.J. and Katze, M.G. (2013). Drug repurposing: a Better Approach for Infectious Disease Drug discovery? Current Opinion in Immunology, 25(5), pp.588–592. doi:10.1016/j.coi.2013.08.004.
[16] Low, Z.Y., Farouk, I.A. and Lal, S.K. (2020). Drug Repositioning: New Approaches and Future Prospects for Life-Debilitating Diseases and the COVID-19 Pandemic Outbreak. Viruses, [online] 12(9). doi:10.3390/v12091058.
[17] Oprea, T.I., Bauman, J.E., Bologa, C.G., Buranda, T., Chigaev, A., Edwards, B.S., Jarvik, J.W., Gresham, H.D., Haynes, M.K., Hjelle, B., Hromas, R., Hudson, L., Mackenzie, D.A., Muller, C.Y., Reed, J.C., Simons, P.C., Smagley, Y., Strouse, J., Surviladze, Z. and Thompson, T. (2011). Drug Repurposing from an Academic Perspective. Drug Discovery today. Therapeutic Strategies, [online] 8(3-4), pp.61–69. doi:10.1016/j.ddstr.2011.10.002.
[18] Papapetropoulos, A. and Szabo, C. (2018). Inventing New Therapies without Reinventing the wheel: the Power of Drug Repurposing. British Journal of Pharmacology, 175(2), pp.165–167. doi:10.1111/bph.14081.
[19] Rudrapal, M., Khairnar, S.J. and Jadhav, A.G. (2020). Drug Repurposing (DR): an Emerging Approach in Drug Discovery. Drug Repurposing. [online] doi:10.5772/intechopen.93193.
[20] Sultana, J., Crisafulli, S., Gabbay, F., Lynn, E., Shakir, S. and Trifirò, G. (2020). Challenges for Drug Repurposing in the COVID-19 Pandemic Era. Frontiers in Pharmacology, 11. doi:10.3389/fphar.2020.588654.
[21] Verbaanderd, C., Rooman, I. and Huys, I. (2021). Exploring New Uses for Existing drugs: Innovative Mechanisms to Fund Independent Clinical Research. Trials, 22(1). doi:10.1186/s13063-021-05273-x.
[22] Akram, M., Riaz, M., Wadood, A.W.C., Hazrat, A., Mukhtiar, M., Ahmad Zakki, S., Daniyal, M., Shariati, M.A., Said Khan, F. and Zainab, R. (2020). Medicinal Plants with anti-mutagenic Potential. Biotechnology & Biotechnological Equipment, 34(1), pp.309–318. doi:10.1080/13102818.2020.1749527.
[23] Ammendolia, D.A., Bement, W.M. and Brumell, J.H. (2021). Plasma Membrane integrity: Implications for Health and Disease. BMC Biology, 19(1). doi:10.1186/s12915-021-00972-y.
[24] Aykkal, R. (2016). Phytochemical analysis, antieczematic, anti-inflammatory, and anticancer activities of Iso-caryophyllene 1-16.
[25] Bărbulescu, A., Barbeș, L. and Dumitriu, C.Ș. (2022). Computer-Aided Methods for Molecular Classification. Mathematics, 10(9), p.1543. doi:10.3390/math10091543.
[26] Bulbule, L.D., Godge, R. and Magar, S. (2022). Hydralazine and Isosorbide Dinitrate: an Analytical Review 291-295.
[27] C. A, A. and K., M. (2013). Evaluation of Biological Activity and Qualitative Analysis of 2, 5-dihydroxybenzoic acid from Momordica charantia Fruit.
[28] Costa, R.A., Junior, E.S.A., Bezerra, J. de A., Mar, J.M., Lima, E.S., Pinheiro, M.L.B., Mendonça, D.V.C., Lopes, G.B.P., Branches, A.D.S. and Oliveira, K.M.T. (2019). Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule. Journal of Chemistry, 2019, pp.1–14. doi:10.1155/2019/9627404.
[29] Dirar, A.I., Waddad, A.Y., Mohamed, M.A., Mohamed, M.S., Osman, W.J., Mohammed, M.S., Elbadawi, M.A.A. and Hamdoun, S. (2016). In Silico Pharmacokinetics And Molecular Docking Of Three Leads Isolated From Tarconanthus Camphoratus L. International Journal of Pharmacy and Pharmaceutical Sciences, [online] pp.71–77. Available at: https://innovareacademics.in/journals/index.php/ijpps/article/view/10528/5112 [Accessed 30 Aug. 2022].
[30] Egelkamp, R., Friedrich, I., Hertel, R. and Daniel, R. (2020). From Sequence to function: a New Workflow for Nitrilase Identification. Applied Microbiology and Biotechnology, 104(11), pp.4957–4970. doi:10.1007/s00253-020-10544-9.
[31] Ferrari, I.V. (2021). Open Access in Silico Tools to Predict the ADMET Profiling and PASS (Prediction of Activity Spectra for Substances of Bioactive Compounds of Garlic (Allium Sativum L.). doi:10.1101/2021.07.18.452815.
[32] Kalaimathi, K., Thiyagarajan, G., Vijayakumar, S., Bhavani, K., Karthikeyan, K., Maria Jancy Rani, J., Dass, K., Sureshkumar, J. and Prabhu, S. (2021). Molecular Docking and Network pharmacology-based Approaches to Explore the Potential of Terpenoids for Mycobacterium Tuberculosis. Pharmacological Research - Modern Chinese Medicine, 1, p.100002. doi:10.1016/j.prmcm.2021.100002.
[33] Karthikeyan, K., Doraiswamy, N., Patchaiappan, P. and Kalathil, S.P. (2017). Pharmaco-Toxicological Evaluation of a Novel Anticancer Polyherbal Formulation Using in Silico Method: PASS. Journal of Chemical and Pharmaceutical Sciences, pp.855–863.
[34] Kumaresan, S., Senthilkumar, V., Stephen, A. and Balakumar, B.S. (2014). GC-MS Analysis And Pass-Assisted Prediction Of Biological Activity Spectra Of Extract Of Phomopsis Sp. Isolated From Andrographis Paniculata ,1053-1035.
[35] M. AbdelHakem, A. and M.N. Abdelhafez, E.-S. (2021). Current Trends and Future Perspectives of Antimutagenic Agents. Genotoxicity and Mutagenicity - Mechanisms and Test Methods. doi:10.5772/intechopen.91689.
[36] Mauger, J., Nagasawa, T. and Yamada, H. (1990). Occurrence of a Novel nitrilase, Arylacetonitrilase in Alcaligenes Faecalis JM3. Archives of Microbiology, 155(1), pp.1–6. doi:10.1007/bf00291265.
[37] Montenegro, C., Gonçalves, G., Oliveira Filho, A., Lira, A., Cassiano, T., Lima, N., Barbosa-Filho, J., Diniz, M. and Pessôa, H. (2017a). In Silico Study and Bioprospection of the Antibacterial and Antioxidant Effects of Flavone and Its Hydroxylated Derivatives. Molecules, 22(6), p.869. doi:10.3390/molecules22060869.
[38] Montenegro, C., Gonçalves, G., Oliveira Filho, A., Lira, A., Cassiano, T., Lima, N., Barbosa-Filho, J., Diniz, M. and Pessôa, H. (2017b). In Silico Study and Bioprospection of the Antibacterial and Antioxidant Effects of Flavone and Its Hydroxylated Derivatives. Molecules, 22(6), p.869. doi:10.3390/molecules22060869.
[39] Montenegro, C., Gonçalves, G., Oliveira Filho, A., Lira, A., Cassiano, T., Lima, N., Barbosa-Filho, J., Diniz, M. and Pessôa, H. (2017c). In Silico Study and Bioprospection of the Antibacterial and Antioxidant Effects of Flavone and Its Hydroxylated Derivatives. Molecules, 22(6), p.869. doi:10.3390/molecules22060869.
[40] NAGASAWA, MAUGER, J. and YAMADA, H. (1990). A novel nitrilase, arylacetonitrilase, of Akaligenes faecalis JM3 Purification and characterization. Eur. J. Biochem, pp.765–772.
[41] Oliveira Filho, A.A., Fernandes, H.M.B., Assis, T.J.C.F., Meireles, D.R.P., Edeltrude, s O., Lima, E.O. and Pêssoa, H.L.F. (2015). Pharmacological and Toxicological Analysis of Flavonoid 5,7,4’- Trimethoxyflavone: an in Silico Approach. International Journal of Pharmacognosy and Phytochemical Research, 7(03), pp.431–435.
[42] Penzo, M., Guerrieri, A., Zacchini, F., Treré, D. and Montanaro, L. (2017). RNA Pseudouridylation in Physiology and Medicine: for Better and for Worse. Genes, 8(11), p.301. doi:10.3390/genes8110301.
[43] Shanthi, S. and Sri Nisha Tharani, S. (2016). In Silico Drug Activity Prediction of Chemical Components of Acalypha Indica 443-467.
[44] Spenkuch, F., Motorin, Y. and Helm, M. (2014). Pseudouridine: Still mysterious, but Never a Fake (uridine)! RNA Biology, 11(12), pp.1540–1554. doi:10.4161/15476286.2014.992278.
[45] Tidke*, K.J. and Solanki, P.R. (2020). Microwave Assisted Synthesis Of 2- (Substitutedbenzilidene)-4-Amino Dihydro Thiophen-3(2h)-One (Ia-Ih) And Their Biological Activities On Pass 1185-1194. Jetir, (3).
[46] Tore, S. (1991). Interactions of Transfer RNA Pseudouridine Synthases with RNAs Substituted with Fluorouracil 6139-6144.
[47] Venkatesh, G., Yohannan, Mary, S., Vennila, P., Mary, S. and Govindaraju, M. (2021). Original Article: Quantum Chemical Calculations and Molecular Docking Studies of Some Phenothiazine Derivatives. Organomet. Chem, 1(1), pp.148–158. doi:10.22034/jaoc.2021.303059.1033.
[48] Yuliia, D., Yuri, S., Anastasiia, K. and Khrystyna, B. (2013). Synthesis of New Fused Tricyclic Quinoid Systems and Studying of Their Biological Activity In-Silico 1471-1477.
[49] “Abstracts of QSAR-Related Publications: 3D-QSAR.” QSAR & Combinatorial Science, vol. 27, no. 5, May 2008, pp. 649–662, 10.1002/qsar.200880036.
[50] Avdeef, Alex, et al. “Solubility-Excipient Classification Gradient Maps.” Pharmaceutical Research, vol. 24, no. 3, 24 Jan. 2007, pp. 530–545, 10.1007/s11095-006-9169-0. Accessed 28 Aug. 2022.
[51] Choi, Daeock, et al. “Synthesis and Anticonvulsant Activities of N-Benzyl-2-Acetamidopropionamide Derivatives.” Journal of Medicinal Chemistry, vol. 39, no. 9, 1 Jan. 1996, pp. 1907–1916, 10.1021/jm9508705.
[52] Dawidowski, Maciej, et al. “Synthesis and Anticonvulsant Activity of Novel 2,6-Diketopiperazine Derivatives. Part 2: Perhydropyrido[1,2-a]Pyrazines.” European Journal of Medicinal Chemistry, vol. 48, Feb. 2012, pp. 347–353, 10.1016/j.ejmech.2011.11.032. Accessed 28 Aug. 2022.
[53] Fayle, D R, et al. “The Effect of Butacaine on Adenine Nucleotide Binding and Translocation in Rat Liver Mitochondria.” Biochemical Journal, vol. 148, no. 3, 1 June 1975, pp. 527–531, 10.1042/bj1480527. Accessed 28 Aug. 2022.
[54] Hashemianzadeh, Seyed M., et al. “Quantum Chemical Study of the Host-Guest Inclusion Complexes of the Local Anaesthetic Drugs, Procaine Hydrochloride and Butacaine Hydrochloride, with α- and β-Cyclodextrins.” Monatshefte Für Chemie - Chemical Monthly, vol. 139, no. 7, 9 June 2008, pp. 763–771, 10.1007/s00706-007-0822-z.
[55] Laasch, Henrik. “Relationship between the Octanol-Water Partition Coefficient of Tertiary Amines and Their Effect of ?Selective? Uncoupling of Photophosphorylation.” Planta, vol. 178, no. 4, 1989, pp. 553–560, 10.1007/bf00963826. Accessed 10 Mar. 2022.
[56] Massari, S., and T. Pozzan. “The Interaction of Organic Cations with the Mitochondrial Membrane.” Experientia, vol. 32, no. 7, July 1976, pp. 868–869, 10.1007/bf02003735. Accessed 24 Jan. 2020.
[57] Mishra, Achal, and Radhika Waghela. “A Comparative Study of Approved Drugs for SARS-CoV-2 by Molecular Docking.” Journal of Molecular Docking, vol. 1, no. 1, 30 June 2021, pp. 25–31, 10.33084/jmd.v1i1.2148.
[58] Quintal Bojorquez, Nidia del Carmen, and Maira Rubi Segura Campos. “Traditional and Novel Computer-Aided Drug Design (CADD) Approaches in the Anticancer Drug Discovery Process Computer-Aided Drug Design (CADD) Approaches in the Development of Anticancer Drugs.” Current Cancer Drug Targets, vol. 22, 5 July 2022, 10.2174/1568009622666220705104249.
[59] Ryu, Hokyoung, and Andrew Monk. “Interaction Unit Analysis: A New Interaction Design Framework.” Human-Computer Interaction, vol. 24, no. 4, Oct. 2009, pp. 367–407, 10.1080/07370020903038086. Accessed 7 Mar. 2019.
[60] Selvaraj, Logesh Kumar, et al. “Molecular Docking Studies of Phytoconstituents Identified in Traditional Siddha Polyherbal Formulations against Possible Targets of SARS-CoV-2.” Journal of Molecular Docking, vol. 1, no. 1, 30 June 2021, pp. 15–24, 10.33084/jmd.v1i1.2264.
[61] Shubha, Jayachamarajapura Pranesh, et al. “Kinetics and Mechanistic Chemistry of Oxidation of Butacaine Sulfate by Chloramine-B in Acid Medium.” Bulletin of the Korean Chemical Society, vol. 33, no. 11, 20 Nov. 2012, pp. 3539–3543, 10.5012/bkcs.2012.33.11.3539.
[62] Alves, T.F.R., Morsink, M., Batain, F., Chaud, M.V., Almeida, T., Fernandes, D.A., da Silva, C.F., Souto, E.B. and Severino, P. (2020). Applications of Natural, Semi-Synthetic, and Synthetic Polymers in Cosmetic Formulations. Cosmetics, [online] 7(4), p.75. doi:10.3390/cosmetics7040075.
[63] Curley, R.K. (1986). Contact Sensitivity to the Amide Anesthetics Lidocaine, Prilocaine, and Mepivacaine. Archives of Dermatology, 122(8), p.924. doi:10.1001/archderm.1986.01660200096024.
[64] Dorris, R.L. (1983). A comparison in rat and mouse heart of the ability of several local anesthetics to inhibit monoamine oxidase. Comparative Biochemistry and Physiology Part C: Comparative Pharmacology, 75(2), pp.327–328. doi:10.1016/0742-8413(83)90200-1.
[65] Johnson, R.F., Schenker, S., Roberts, R.K., Desmond, P.V. and Wilkinson, G.R. (1979). Plasma Binding of Benzodiazepines in Humans. Journal of Pharmaceutical Sciences, 68(10), pp.1320–1322. doi:10.1002/jps.2600681034.
[66] Kepes, E.R. (1959). Allergic Reaction To Succinylcholine. Journal of the American Medical Association, 171(5), p.548. doi:10.1001/jama.1959.73010230001011.
[67] Nygard, G., Shelver, W.H. and Wahba Khalil, S.K. (1979). Sensitive High-pressure Liquid Chromatographic Determination of Propranolol in Plasma. Journal of Pharmaceutical Sciences, 68(3), pp.379–381. doi:10.1002/jps.2600680336.
[68] Rabinovitch, M. and Destefano, M. (1975). Cell to substrate adhesion and spreading: Inhibition by cationic anesthetics. Journal of Cellular Physiology, 85(2), pp.189–193. doi:10.1002/jcp.1040850205.
[69] Dong, X., Liu, Y., Yan, J., Jiang, C., Chen, J., Liu, T. and Hu, Y. (2008). Identification of SVM-based classification model, synthesis and evaluation of prenylated flavonoids as vasorelaxant agents. Bioorganic & Medicinal Chemistry, 16(17), pp.8151–8160. doi:10.1016/j.bmc.2008.07.031.
[70] Lehmann, B., Linnér, E. and Wistrand, P.J. (1970). The Pharmacokinetics of Acetazolamide in Relation to Its Use in the Treatment of Glaucoma and to Its Effects as an Inhibitor of Carbonic Anhydrases. Schering Workshop on Pharmacokinetics, Berlin, May 8 and 9, 1969, pp.197–217. doi:10.1016/b978-0-08-017548-5.50019-9.
[71] Linnér, E. and Wistrand, P.J. (1963). Adrenal cortex and aqueous humour dynamics. Experimental Eye Research, 2(2), pp.148–159. doi:10.1016/s0014-4835(63)80007-x.
[72] Tiwari, V. (2022). Pharmacophore screening, denovo designing, retrosynthetic analysis, and combinatorial synthesis of a novel lead VTRA1.1 against RecA protein of Acinetobacter baumannii. Chemical Biology & Drug Design, 99(6), pp.839–856. doi:10.1111/cbdd.14037.
[73] Vilar, S., Quezada, E., Alcaide, C., Orallo, F., Santana, L. and Uriarte, E. (2007). Quantitative Structure Vasodilatory Activity Relationship – Synthesis and ‘In Silico’ and ‘In Vitro’ Evaluation of Resveratrol-Coumarin Hybrids. QSAR & Combinatorial Science, 26(3), pp.317–332. doi:10.1002/qsar.200630006.
[74] de Matos Alves Pinto, L., Kiyoko Yokaichiya, D., Fernandes Fraceto, L. and de Paula, E. (2000). Interaction of Benzocaine with Model Membranes. Biophysical Chemistry, 87(2-3), pp.213–223. doi:10.1016/s0301-4622(00)00196-4.
[75] G, S. (2016). Russian Journal of Physical Chemistry.
[76] HAN, M.İ., GÜROL, G., YILDIRM, T., KALAYCI, S. and ŞAHİN, F. (2017). Synthesis and Antibacterial Activity of Hnew hydrazide-hydrazones Derived from Benzocaine. Marmara Pharmaceutical Journal, 21(4), pp.961–966. doi:10.12991/mpj.2017.34.
[77] Lehr, J., Masters, A. and Pollack, B. (2012). Benzocaine-Induced Methemoglobinemia in the Pediatric Population. Journal of Pediatric Nursing, 27(5), pp.583–588. doi:10.1016/j.pedn.2012.07.003.
[78] Panaitescu, L. and Ottenbrite, R.M. (2002). Biological Effects and Antitumor Activity Induced by Benzocaine Conjugated Anionic Polymers. Journal of Bioactive and Compatible Polymers, 17(5), pp.357–374. doi:10.1177/0883911502017005710.
[79] Park, L., Tom, J., Bui, N., Wilson, M. and Tanbonliong, T. (2020). Comparing the Efficacy of a Compound Topical Anesthetic versus Benzocaine: a Pilot Study. Anesthesia Progress, 67(1), pp.9–15. doi:10.2344/anpr-66-03-05.
[80] Pinto, L.M.A., Melo, P.S., Haun, M. and de Paula, E. (2000). Benzocaine-lipid Membrane Interaction and Its Application in the Development of long-acting, encapsulated, Local Anesthetic Formulations. Biochemical Society Transactions, 28(5), pp.A203–A203. doi:10.1042/bst028a203b.
[81] Plotycya, S., Strontsitska, O., Pysarevska, S., Blazheyevskiy, M. and Dubenska, L. (2018). A New Approach for the Determination of Benzocaine and Procaine in Pharmaceuticals by Single-Sweep Polarography. International Journal of Electrochemistry, [online] 2018, pp.1–10. doi:10.1155/2018/1376231.
[82] Taha, I., Keshk, E.M., Khalil, A.-G.M. and Fekri, A. (2020). Synthesis, characterization, Antibacterial evaluation, 2D-QSAR Modeling and Molecular Docking Studies for Benzocaine Derivatives. Molecular Diversity. doi:10.1007/s11030-020-10138-7.
[83] Taha, I., Keshk, E.M., Khalil, A.-G.M. and Fekri, A. (2021). Benzocaine as a Precursor of Promising derivatives: synthesis, reactions, and Biological Activity. Chemical Papers, 75(12), pp.6181–6215. doi:10.1007/s11696-021-01808-3.
[84] Zhakina, A.Kh., Kurapova, M.Yu., Gazaliev, A.M. and Nurkenov, O.A. (2008). Synthesis and Biological Activity of Certain Derivatives of Anesthesine (Benzocaine). Russian Journal of General Chemistry, 78(6), pp.1253–1254. doi:10.1134/s1070363208060261.
[85] Abyar, F. and Tabrizi, L. (2018). New Multinuclear Scaffold molybdocene-gold Lidocaine complex: DNA/HSA binding, Molecular docking, Cytotoxicity and Mechanistic Insights. Journal of Biomolecular Structure and Dynamics, 37(13), pp.3366–3378. doi:10.1080/07391102.2018.1515114.
[86] Begec, Z., Gulhas, N., Toprak, H.I., Yetkin, G., Kuzucu, C. and Ersoy, M.O. (2007). Comparison of the Antibacterial Activity of Lidocaine 1% versus Alkalinized Lidocaine in Vitro. Current Therapeutic Research, 68(4), pp.242–248. doi:10.1016/j.curtheres.2007.08.007.
[87] Bozdaganyan, M.E. and Orekhov, P.S. (2021). Synergistic Effect of Chemical Penetration Enhancers on Lidocaine Permeability Revealed by Coarse-Grained Molecular Dynamics Simulations. Membranes, 11(6), p.410. doi:10.3390/membranes11060410.
[88] Çelebi, N., Ermiş, S. and Özkan, S. (2014). Development of Topical Hydrogels of Terbinafine Hydrochloride and Evaluation of Their Antifungal Activity. Drug Development and Industrial Pharmacy, 41(4), pp.631–639. doi:10.3109/03639045.2014.891129.
[89] Fels, G. (1996). Tolperisone: Evaluation of the Lidocaine-Like Activity by Molecular Modeling. Archiv Der Pharmazie, 329(4), pp.171–178. doi:10.1002/ardp.19963290402.
[90] Gajraj, R.J., Hodson, M.J., Gillespie, J.A., Kenny, G.N. and Scott, N.B. (1998). Antibacterial Activity of Lidocaine in Mixtures with Diprivan. British Journal of Anaesthesia, 81(3), pp.444–448. doi:10.1093/bja/81.3.444.
[91] Hanck, D.A., Nikitina, E., McNulty, M.M., Fozzard, H.A., Lipkind, G.M. and Sheets, M.F. (2009). Using Lidocaine and Benzocaine to Link Sodium Channel Molecular Conformations to State-Dependent Antiarrhythmic Drug Affinity. Circulation Research, 105(5), pp.492–499. doi:10.1161/circresaha.109.198572.
[92] Jayaram, P., Kennedy, D.J., Yeh, P. and Dragoo, J. (2019). Chondrotoxic Effects of Local Anesthetics on Human Knee Articular Cartilage: a Systematic Review. PM&R, 11(4), pp.379–400. doi:10.1002/pmrj.12007.
[93] Juan, Y. (2016). GW27-e0167 in Silico Studying the Weak Effect of Lidocaine on Acidosis. Journal of the American College of Cardiology, 68(16), pp.C5–C6. doi:10.1016/j.jacc.2016.07.020.
[94] Ley, R.T. and Paluch, A.S. (2016). Understanding the Large Solubility of Lidocaine in 1-n-butyl-3-methylimidazolium Based Ionic Liquids Using Molecular Simulation. The Journal of Chemical Physics, 144(8), p.084501. doi:10.1063/1.4942025.
[95] Li, W., Yan, Y., Chang, Y., Ding, L., Liu, H. and You, Q. (2019). Synthesis, Sciatic Nerve Block Activity Evaluation and Molecular Docking of fluoro-substituted Lidocaine Analogs as Local Anesthetic Agents. Medicinal Chemistry Research, 28(10), pp.1783–1795. doi:10.1007/s00044-019-02415-4.
[96] Li, X., Lv, X., Jiang, Z., Nie, X., Wang, X., Li, T., Zhang, L. and Liu, S. (2020). Application of Intravenous Lidocaine in Obese Patients Undergoing Painless Colonoscopy: a Prospective, Randomized, Double-Blind, Controlled Study. Drug Design, Development and Therapy, Volume 14, pp.3509–3518. doi:10.2147/dddt.s266062.
[97] Liu, H., Dilger, J.P. and Lin, J. (2021). Lidocaine Suppresses Viability and Migration of Human Breast Cancer Cells: TRPM7 as a Target for Some Breast Cancer Cell Lines. Cancers, 13(2), p.234. doi:10.3390/cancers13020234.
[98] McNulty, M.M., Edgerton, G.B., Shah, R.D., Hanck, D.A., Fozzard, H.A. and Lipkind, G.M. (2007). Charge at the Lidocaine Binding Site Residue Phe-1759 Affects Permeation in Human Cardiac voltage-gated Sodium Channels. The Journal of Physiology, 581(2), pp.741–755. doi:10.1113/jphysiol.2007.130161.
[99] Palmeira-de-Oliveira, A., Ramos, A.R., Gaspar, C., Palmeira-de-Oliveira, R., Gouveia, P. and Martinez-de-Oliveira, J. (2012). In VitroAnti-CandidaActivity of Lidocaine and Nitroglycerin: Alone and Combined. Infectious Diseases in Obstetrics and Gynecology, 2012, pp.1–4. doi:10.1155/2012/727248.
[100] Pina-Vaz, C., Rodrigues, A.G., Sansonetty, F., Martinez-De-Oliveira, J., Fonseca, A.F. and Mårdh, P.-A. (2000). Antifungal Activity of Local Anesthetics against Candida Species. Infectious Diseases in Obstetrics and Gynecology, 8(3-4), pp.124–137. doi:10.1155/s1064744900000168.
[101] Rajendiran, N., Mohandoss, T. and Saravanan, J. (2014). Guest:host Interactions of Lidocaine and Prilocaine with Natural cyclodextrins: Spectral and Molecular Modeling Studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 132, pp.387–396. doi:10.1016/j.saa.2014.04.123.
[102] Rodrigues, C., Hernández-González, J., Pedrina, N., Leite, V. and Bruni, A. (2021). In Silico Evaluation of Cucurbit[6]uril as a Potential Detector for Cocaine and Its Adulterants Lidocaine, Caffeine, and Procaine. Journal of the Brazilian Chemical Society. doi:10.21577/0103-5053.20200231.
[103] Small, A., Fetiveau, M., Smith, R. and Colditz, I. (2021). Three Studies Evaluating the Potential for Lidocaine, Bupivacaine or Procaine to Reduce Pain-Related Behaviors following Ring Castration and/or Tail Docking in Lambs. Animals, 11(12), p.3583. doi:10.3390/ani11123583.
[104] Swiety-Pospiech, A., Wojnarowska, Z., Pionteck, J., Pawlus, S., Grzybowski, A., Hensel-Bielowka, S., Grzybowska, K., Szulc, A. and Paluch, M. (2012). High Pressure Study of Molecular Dynamics of Protic Ionic Liquid Lidocaine Hydrochloride. The Journal of Chemical Physics, 136(22), p.224501. doi:10.1063/1.4727885.
[105] Tanguay, J., Callahan, K.M. and D’Avanzo, N. (2019). Characterization of Drug Binding within the HCN1 Channel Pore. Scientific Reports, [online] 9(1). doi:10.1038/s41598-018-37116-2.
[106] Trellakis, S., Lautermann, J. and Lehnerdt, G. (2007). Lidocaine: Neurobiological Targets and Effects on the Auditory System. Tinnitus: Pathophysiology and Treatment, pp.303–322. doi:10.1016/s0079-6123(07)66028-2.
[107] Wang, L., Sun, J., Zhang, X. and Wang, G. (2021). The Effect of Lidocaine on Postoperative Quality of Recovery and Lung Protection of Patients Undergoing Thoracoscopic Radical Resection of Lung Cancer. Drug Design, Development and Therapy, Volume 15, pp.1485–1493. doi:10.2147/dddt.s297642.
[108] Yang, X., Wei, X., Mu, Y., Li, Q. and Liu, J. (2020). A Review of the Mechanism of the Central Analgesic Effect of Lidocaine. Medicine, [online] 99(17), p.e19898. doi:10.1097/MD.0000000000019898.
[109] Yang, X., Zhao, L., Li, M., Yan, L., Zhang, S., Mi, Z., Ren, L. and Xu, J. (2018). Lidocaine Enhances the Effects of Chemotherapeutic Drugs against Bladder Cancer. Scientific Reports, 8(1). doi:10.1038/s41598-017-19026-x.
[110] Zhao, X., Sun, Y. and Li, Z. (2018). Topical Anesthesia Therapy Using lidocaine-loaded Nanostructured Lipid carriers: Tocopheryl Polyethylene Glycol 1000 succinate-modified Transdermal Delivery System. Drug Design, Development and Therapy, Volume 12, pp.4231–4240. doi:10.2147/dddt.s187177.
[111] Zhou, D., Wang, L., Cui, Q., Iftikhar, R., Xia, Y. and Xu, P. (2020). Repositioning Lidocaine as an Anticancer Drug: the Role beyond Anesthesia. Frontiers in Cell and Developmental Biology, 8. doi:10.3389/fcell.2020.00565
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