Abstract
Coumarin and coumarin derivatives have been known for their anti-viral, anti-oxidant, anti-cancer and anti-inflammatory activities. Changes in biological activity when these biologically active compounds are combined with different heterocyclic groups are among the topics of interest to researchers in recent years. Therefore, a series of coumarin–selenophene hybrid compounds have been synthesized. Products are fully characterized by NMR and FT-IR spectroscopic techniques. The prepared compounds are screened for their anti-inflammatory potencies on LPS induced mouse macrophage cell line (RAW 264.7). The results showed that coumarin–selenophene hybrid compounds were not cytotoxic at the tested concentrations on RAW 264.7 macrophages. Also, these compounds decreased TNF- α, IL-6 secretion, and NO, PGE2 production in dose-depended manner. According to our results, coumarin–selenophene hybrid compounds have the capacity to moderate the immune response and a potential anti-inflammatory activity.
Similar content being viewed by others
REFERENCES
Singh, N., Baby, D., Rajguru, J.P., Patil, P.B., Thakkannavar, S.S., and Pujari, V.B., Ann. Afr. Med., 2019, vol. 18, pp. 121–126. https://doi.org/10.4103/aam.aam_56_18
Ma, W.T., Gao, F., Gu, K., and Chen, D.K., Front. Immunol., 2019, vol. 10, p. 1140. https://doi.org/10.3389/fimmu.2019.01140
Johansson, J.U., Woodling, N.S., Shi, J., and Andreasson, K.I., Curr. Immunol Rev., 2015 vol. 11, pp. 125. https://doi.org/10.2174/1573395511666150707181414
Choudhari, S.K., Chaudhary, M., Bagde, S., Gadbail, A.R., and Joshi, V., World J. Surg Oncol., 2013, vol. 11, article no. 118. https://doi.org/10.1186/1477-7819-11-118
Sharma, J.N., Al-Omran, A., and Parvathy, S.S. Inflammopharmacology, 2007, vol. 15., pp. 252–259. https://doi.org/10.1007/s10787-007-0013-x
Simone, M.J. and Tan, Z.S., CNS Neurosci. Ther., 2011, vol. 17, pp. 506–513. https://doi.org/10.1111/j.1755-5949.2010.00173.x
Abdel-Rahman, S., Shaban, N., Haggag, A., Awad, D., Bassiouny, A., and Talaat, I., Asian Pac. J. Cancer Prev., 2016, vol. 16, pp. 8411–8418. https://doi.org/10.7314/apjcp.2015.16.18.8411
Medina, F.G., Marrero, J.G., Macías-Alonso, M., González, M.C., Córdova-Guerrero, I., Teissier García, A.G., and Osegueda-Robles, S., Nat. Prod. Rep., 2015, vol. 32, pp. 1472–1507. https://doi.org/10.1039/C4NP00162A
Tapanyigit, O., Demirkol, O., Güler, E., Ersatır, M., Çam, M.E., and Giray, E.S., Arab J. Chem., 2020, vol. 31, pp. 9105–9117. https://doi.org/10.1016/j.arabjc.2020.10.034
Ersatır, M., Yıldırım, M., and Giray, E.S., Synth. Commun., 2021, vol. 51, pp. 290–301. https://doi.org/10.1080/00397911.2020.1825744
Ersatır, M., Yıldırım, M., Giray, E.S., and Yalın, S., Monatsh. Chemi., 2020, vol. 151, pp. 625–636. https://doi.org/10.1007/s00706-020-02573-x
Borges Bubols, G., Da Rocha Vianna, D., Medina-Remón, A., Von Poser, G., Lamuela-Raventos, R.M., Lucia Eifler-Lima, V., and Garcia, S.C., Rev. Med. Chem., 2013, vol.13, pp. 318–334. https://doi.org/10.2174/138955713804999775
Mandlik, V., Patil, S., Bopanna, R., Basu, S., and Singh, S., PLoS One, 2016 vol. 11, p. 1 https://doi.org/10.1371/journal.pone.0164585
Al-Majedy, Y.K., Kadhum, A.A.H., Al-Amiery, A.A., and Mohamad, A.B., Syst. Rev. Pharm., 2017, vol. 8, pp. 62–70. https://doi.org/10.5530/srp.2017.1.11
Cetin, Y., Microbial Toxins, in Food Safety Engineering. Food Engineering Series, Demirci, A., Feng, H., and Krishnamurthy, K., Eds., Cham: Springer, 2020, pp. 51–83. https://doi.org/10.1007/978-3-030-42660-6_3
Yenjai, C., Sripontan, S., Sriprajun, P., Kittakoop, P., Jintasirikul, A., Tanticharoen, M., and Thebtaranonth, Y., Planta Med., 2000, vol. 66, pp. 277–279. https://doi.org/10.1055/s-2000-8558
Paquin, F., Rivnay, J., Salleo, A., Stingelin, N., and Silva-Acuña, C., J. Mater. Chem. C, 2015, vol. 3, pp. 10715–10722. https://doi.org/10.1039/C5TC02043C
Subudhi, B., Panda, P., Tosh, B., Sahu, S., and Majhi, P., Dhaka Univ. J. Pharm. Sci., 2007, vol. 4, pp. 87–92. https://doi.org/10.3329/dujps.v4i2.207
Chen, L., Deng, H., Cui, H., Fang, J., Zuo, Z., Deng, J., Li, Y., Wang, X., and Zhao, L., Oncotarget, 2018, vol. 9, pp. 7204–7208. https://doi.org/10.18632/oncotarget.23208
Gergely, P., Lang, I., Gonzalez-Cabello, R., and Feher, J., Tokai J. Exp. Clin. Med., 1986, vol. 11, pp. 207–213.
Thomas, V., Giles, D., Basavarajaswamy, P.M.G., Kumar Das, A., and Patel, A., Anticancer Agents Med. Chem., 2017, vol. 17, pp. 415–423. https://doi.org/10.2174/1871520616666160902094739
Zhang, J.M. and An, J., Int. Anesthesiol. Clin., 2007, vol. 45, pp. 27–37. https://doi.org/10.1097/AIA.0b013e318034194e
Chetaille Nézondet, A.L., Poubelle, P.E., and Pelletier, M., J. Leukoc Biol., 2020, vol. 108, pp. 647–657. https://doi.org/10.1002/JLB.5MR0120-218RRR
Alshibl, H.M., Al-Abdullah, E.S., Haiba, M.E., Alkahtani, H.M., Awad, G.E.A., Mahmoud, A.H., Ibrahim, B.M.M., Bari, A., and Villinger, A., Molecules, 2020, vol. 25, p. 3251. https://doi.org/10.3390/molecules25143251
Lin, C.Y., Wang, W.H., Chen, S.H., Chang, Y.W., Hung, L.C., Chen, C.Y., and Chen, Y.H., Int. J. Mol. Sci., 2017, vol. 18, p. 2637. https://doi.org/10.3390/ijms18122637
Sautebin, L., Fitoterapia, 2000, vol. 71, pp. S48–S57. https://doi.org/10.1016/S0367-326X(00)00181-7
Sun, J., Zhang, X., Broderick, M., and Fein, H., Sensors, 2003, vol. 3, pp. 276–284. https://doi.org/10.3390/s30800276
Funding
The research leading to these results received funding from (Scientific Research Committee of Mersin University) under Grant Agreement no. 2021-1-AP4-4227.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
COMPLIANCE WITH ETHICAL STANDARDS
This article does not contain any studies involving animals or human participants performed by any of the authors.
Conflict of Interests
The authors declare that they have no conflicts of interest.
Supplementary Information
Rights and permissions
About this article
Cite this article
Yildirim, M., Unal, Z.N., Ersatir, M. et al. Anti-Inflammatory Effects of Coumarin–Selenophene Derivatives on LPS-Stimulated RAW 264.7 Macrophage Cells. Russ J Bioorg Chem 48, 1209–1214 (2022). https://doi.org/10.1134/S1068162022060279
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1068162022060279