Home Indole based prostate cancer agents
Article
Licensed
Unlicensed Requires Authentication

Indole based prostate cancer agents

  • Sunil Kumar , Madhuri T. Patil and Deepak B. Salunke EMAIL logo
Published/Copyright: January 13, 2022
Become an author with De Gruyter Brill

Abstract

Cancer weakens the immune system which fails to fight against the rapidly growing cells. Among the various types of cancers, prostate cancer (PCa) is causing greater number of deaths in men after lung cancer, demanding advancement to prevent, detect and treat PCa. Several small molecule heterocycles and few peptides are being used as oncological drugs targeting PCa. Heterocycles are playing crucial role in the development of novel cancer chemotherapeutics as well as immunotherapeutics. Indole skeleton, being a privileged structure has been extensively used for the discovery of novel anticancer agents and the application of indole derivatives against breast cancer is well documented. The present article highlights the usefulness of indole linked heterocyclic compounds as well as the fused indole derivatives against prostate cancer.


Corresponding author: Deepak B. Salunke, Department of Chemistry and Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India; and National Interdisciplinary Centre of Vaccine, Immunotherapeutics and Antimicrobials, Panjab University, Chandigarh 160014, India, E-mail:

Acknowledgments

SK thank SERB, New Delhi for the research fellowship in the form of National Post-Doctoral Fellowship Scheme (No. PDF/2017/03021). MTP is thankful to DST for the award of project under Women Scientist Scheme A (SR/WOS-A/CS-132/2016). DBS is thankful to DBT New Delhi for the award of Ramalingaswami Fellowship (BT/RLF/Re-entry/16/2013).

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. U.S. Cancer Statistics Working Group. U.S. Cancer statistics data visualizations tool, based on November 2017 submission data (1999–2015). U.S. Department of Health and Human Services, Centers for Disease Control and Prevention and National Cancer Institute; 2018. Available from: www.cdc.gov/cancer/dataviz.Search in Google Scholar

2. Pietro, GD, Chornokur, G, Kumar, NB, Davis, C, Park, JY. Racial differences in the diagnosis and treatment of prostate cancer. Int Neurourol J 2016;20:S112–9. https://doi.org/10.5213/inj.1632722.361.Search in Google Scholar PubMed PubMed Central

3. Li, J, Mercer, E, Gou, X, Lu, Y-J. Ethnical disparities of prostate cancer predisposition: genetic polymorphisms in androgen-related genes. Am J Cancer Res 2013;3:127–51.Search in Google Scholar

4. Howlader, N, Noone, AM, Krapcho, M, Miller, D, Brest, A, Yu, M, et al., editors. SEER cancer statistics review, 1975–2016. Bethesda, MD: National Cancer Institute; 2019. Available from: https://seer.cancer.gov/csr/1975_2016/, based on November 2018 SEER data submission, posted to the SEER web site.Search in Google Scholar

5. (i)Sobel, RE, Sadar, MD. Cell lines used in prostate cancer research: a compendium of old and new lines--part 2. J Urol 2005;173:360–72. https://doi.org/10.1097/01.ju.0000149989.01263.dc.(ii)Sobel, RE, Sadar, MD. Cell lines used in prostate cancer research: a compendium of old and new lines--part 1. J Urol 2005;173:342–59. https://doi.org/10.1097/01.ju.0000141580.30910.57.Search in Google Scholar PubMed

6. Cunningham, D, You, Z. In vitro and in vivo model systems used in prostate cancer research. J Biol Methods 2015;2:e17. https://doi.org/10.14440/jbm.2015.63.Search in Google Scholar PubMed PubMed Central

7. Lin, D, Xue, H, Wang, Y, Wu, R, Watahiki, A, Dong, X, et al.. Next generation patient-derived prostate cancer xenograft models. Asian J Androl 2014;16:407–12. https://doi.org/10.4103/1008-682X.125394.Search in Google Scholar PubMed PubMed Central

8. Wang, Y, Revelo, MP, Sudilovsky, D, Cao, M, Chen, WG, Goetz, L, et al.. Development and characterization of efficient xenograft models for benign and malignant human prostate tissue. Prostate 2005;64:149–59. https://doi.org/10.1002/pros.20225.Search in Google Scholar PubMed

9. Ilardi, EA, Vitaku, E, Njardarson, JT. An in-pharm-ative educational poster anthology highlighting the therapeutic agents that chronicle our medicinal history. J Chem Educ 2013;90:1403–5. https://doi.org/10.1021/ed4002317.Search in Google Scholar

10. Dadashpour, S, Emami, S. Indole in the target-based design of anticancer agents: a versatile scaffold with diverse mechanisms. Eur J Med Chem 2018;150:9–29. https://doi.org/10.1016/j.ejmech.2018.02.065.Search in Google Scholar PubMed

11. Corsello, MA, Kima, J, Garg, NK. Indole diterpenoid natural products as the inspiration for new synthetic methods and strategies. Chem Sci 2017;8:5836–44. https://doi.org/10.1039/c7sc01248a.Search in Google Scholar PubMed PubMed Central

12. Alves, FRD, Barreiro, EJ, Fraga, CA. From nature to drug discovery: the indole scaffold as a ‘privileged structure’. Mini Rev Med Chem 2009;9:782–93. https://doi.org/10.2174/138955709788452649.Search in Google Scholar PubMed

13. Welsch, ME, Snyder, SA, Stockwell, BR. Privileged scaffolds for library design and drug discovery. Curr Opin Chem Biol 2010;14:347–61. https://doi.org/10.1016/j.cbpa.2010.02.018.Search in Google Scholar PubMed PubMed Central

14. Weng, T, Qiu, X, Wang, J, Li, Z, Bian, J. Recent discovery of indoleamine-2,3-dioxygenase 1 inhibitors targeting cancer immunotherapy. Eur J Med Chem 2018;143:656–69. https://doi.org/10.1016/j.ejmech.2017.11.088.Search in Google Scholar PubMed

15. Selvan, SR, Dowling, JP, Kelly, WK, Lin, J. Indoleamine 2,3-dioxygenase (IDO): Biology and target in cancer immunotherapies. Curr Cancer Drug Targets 2016;16:755–64. https://doi.org/10.2174/1568009615666151030102250.Search in Google Scholar PubMed

16. Sidhu, JS, Singla, R, Mayank, Jaitak, V. Indole derivatives as anticancer agents for breast cancer therapy: a review. Anti Cancer Agents Med Chem 2015;16:160–73. https://doi.org/10.2174/1871520615666150520144217.Search in Google Scholar PubMed

17. Aggarwal, BB, Ichikawa, H. Molecular targets and anticancer potential of indole-3-carbinol and its derivatives. Cell Cycle 2005;4:1201–15. https://doi.org/10.4161/cc.4.9.1993.Search in Google Scholar PubMed

18. Neave, AS, Sarup, SM, Seidelin, M, Duus, F, Vang, O. Characterization of the N-methoxyindole-3-carbinol (NI3C)-induced cell cycle arrest in human colon cancer cell lines. Toxicol Sci 2005;83:126–35. https://doi.org/10.1093/toxsci/kfi008.Search in Google Scholar PubMed

19. Nachshon-Kedmi, M, Yannai, S, Haj, A, Fares, FA. Indole-3-carbinol and 3,3′-diindolylmethane induce apoptosis in human prostate cancer cells. Food Chem Toxicol 2003;41:745–52. https://doi.org/10.1016/s0278-6915(03)00004-8.Search in Google Scholar PubMed

20. Quash, G, Fournet, G, Courvoisier, C, Martinez, RM, Chantepie, J, Paret, MJ, et al.. Aldehyde dehydrogenase inhibitors: α,β-acetylenic N-substituted aminothiolesters are reversible growth inhibitors of normal epithelial but irreversible apoptogens for cancer epithelial cells from human prostate in culture. Eur J Med Chem 2008;43:906–16. https://doi.org/10.1016/j.ejmech.2007.06.004.Search in Google Scholar PubMed

21. Zhou, Q, Zhu, J, Chen, J, Ji, P, Qiao, C. N-Arylsulfonylsubstituted-1H indole derivatives as small molecule dual inhibitors of signal transducer and activator of transcription 3 (STAT3) and tubulin. Bioorg Med Chem 2018;26:96–106. https://doi.org/10.1016/j.bmc.2017.11.023.Search in Google Scholar PubMed

22. Hwang, DJ, He, Y, Ponnusamy, S, Mohler, ML, Thiyagarajan, T, McEwan, IJ, et al.. New generation of selective androgen receptor degraders: our initial design, synthesis, and biological evaluation of new compounds with enzalutamide-resistant prostate cancer activity. J Med Chem 2019;62:491–511. https://doi.org/10.1021/acs.jmedchem.8b00973.Search in Google Scholar PubMed

23. Goswami, R, Wohlfahrt, G, Törmäkangas, O, Moilanen, A, Lakshminarasimhan, A, Nagaraj, J, et al.. Structure-guided discovery of 2-aryl/pyridin-2-yl-1H-indole derivatives as potent and selective hepsin inhibitors. Bioorg Med Chem Lett 2015;25:5619–314. https://doi.org/10.1016/j.bmcl.2015.09.042.Search in Google Scholar PubMed

24. Ban, F, Leblanc, E, Li, H, Munuganti, RSN, Frewin, K, Rennie, PS, et al.. Discovery of 1H-indole-2-carboxamides as novel inhibitors of the androgen receptor binding function 3 (BF3). J Med Chem 2014;57:6867–77. https://doi.org/10.1021/jm500684r.Search in Google Scholar PubMed

25. Munuganti, RSN, Hassona, MDH, Leblanc, E, Frewin, K, Singh, K, Ma, D, et al.. Identification of a potent antiandrogen that targets the BF3 site of the androgen receptor and inhibits enzalutamide-resistant prostate cancer. Chem Biol 2014;21:1476–85. https://doi.org/10.1016/j.chembiol.2014.09.012.Search in Google Scholar PubMed

26. Chen, J, Ahn, S, Wang, J, Lu, Y, Dalton, JT, Miller, DD, et al.. Discovery of novel 2-aryl-4-benzoyl-imidazole (ABI-III) analogues targeting tubulin polymerization as antiproliferative agents. J Med Chem 2012;55:7285–9. https://doi.org/10.1021/jm300564b.Search in Google Scholar PubMed PubMed Central

27. Liss, MA, Thompson, IM. Prostate cancer prevention with 5-alpha reductase inhibitors: concepts and controversies. Curr Opin Urol 2018;28:42–5. https://doi.org/10.1097/mou.0000000000000464.Search in Google Scholar PubMed

28. Nakai, H, Terashima, H, Arai, Y. Benzoylaminophenoxybutanoic acid derivatives. Ono pharmaceutical Co., Ltd. EP 0 291 245, 1988. Chem Abstr 1989;110:212384t, 708.Search in Google Scholar

29. Takami, H, Koshimura, H, Kishibayashi, N, Ishii, A, Nonaka, H, Aoyama, S, et al.. Indole derivatives as a new class of steroid 5α-reductase inhibitors. J Med Chem 1996;39:5047–52. https://doi.org/10.1021/jm9601819.Search in Google Scholar PubMed

30. (a)Wang, L, Sloper, DT, Addo, SN, Tian, D, Slaton, JW, Xing, C. WL-276, an antagonist against Bcl-2 proteins, overcomes drug resistance and suppresses prostate tumor growth. Cancer Res 2008;68:4377–83. https://doi.org/10.1158/0008-5472.can-07-6590.(b)Liu, T, Wan, Y, Liu, R, Ma, L, Li, M, Fang, H. Design, synthesis and preliminary biological evaluation of indole-3-carboxylic acid-based skeleton of Bcl-2/Mcl-1 dual inhibitors. Bioorg Med Chem 2017;25:1939–48. https://doi.org/10.1016/j.bmc.2017.02.014.Search in Google Scholar

31. Xu, G, Liu, T, Zhou, Y, Yang, X, Fang, H. 1-phenyl-1H-indole derivatives as a new class of Bcl-2/Mcl-1 dual inhibitors: design, synthesis, and preliminary biological evaluation. Bioorg Med Chem 2017;25:5548–56. https://doi.org/10.1016/j.bmc.2017.08.024.Search in Google Scholar PubMed

32. Yang, D, Wang, P, Liu, J, Xing, H, Liu, Y, Xie, W, et al.. Design, synthesis and evaluation of novel indole derivatives as Akt inhibitors. Bioorg Med Chem 2014;22:366–73. https://doi.org/10.1016/j.bmc.2013.11.022.Search in Google Scholar PubMed

33. Kamal, A, Srikanth, YV, Khan, MN, Shaik, TB, Ashraf, M. Synthesis of 3,3′-diindolyloxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity. Bioorg Med Chem Lett 2010;20:5229–31. https://doi.org/10.1016/j.bmcl.2010.06.152.Search in Google Scholar PubMed

34. Xiang, Q, Wang, C, Zhang, Y, Xue, X, Song, M, Zhang, C, et al.. Discovery and optimization of 1-(1H-indol-1-yl)ethanone derivatives as CBP/EP610 bromodomain inhibitors for the treatment of castration-resistant prostate cancer. Eur J Med Chem 2018;147:238–52. https://doi.org/10.1016/j.ejmech.2018.01.087.Search in Google Scholar PubMed

35. Shaveta, Singh, P. Structural optimization of indole-based compounds for highly promising anti-cancer activities: structure activity relationship studies and identification of lead molecules. Eur J Med Chem 2014;74:440–50. https://doi.org/10.1016/j.ejmech.2013.12.047.Search in Google Scholar PubMed

36. Purushottamachar, P, Godbole, AM, Gediya, LK, Martin, MS, Vasaitis, TS, Kwegyir-Afful, AK, et al.. Systematic structure modifications of multitarget prostate cancer drug candidate galeterone to produce novel androgen receptor down-regulating agents as an approach to treatment of advanced prostate cancer. J Med Chem 2013;56:4880–98. https://doi.org/10.1021/jm400048v.Search in Google Scholar PubMed PubMed Central

37. Jain, HKD, Zhang, C, Zhou, S, Zhou, H, Ma, J, Liu, X, et al.. Synthesis and structure–activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein. Bioorg Med Chem Lett 2008;16:4626–51. https://doi.org/10.1016/j.bmc.2008.02.050.Search in Google Scholar PubMed PubMed Central

38. Singh, P, Kaur, P, Luxami, V, Kaur, S, Kumar, S. Syntheses and anti-cancer activities of 2-[1-(indol-3-yl-/pyrimidin-5-yl-/pyridine-2-yl-/quinolin-2-yl)-but-3-enylamino]-2-phenyl-ethanols. Bioorg Med Chem 2007;15:2386–95. https://doi.org/10.1016/j.bmc.2007.01.018.Search in Google Scholar PubMed

39. Panathur, N, Dalimba, UK, Koushik, PV, Alvala, M, Yogeeswari, P, Sriram, D, et al.. Identification and characterization of novel indole based small molecules as anticancer agents through SIRT1 inhibition. Eur J Med Chem 2013;69:125–38. https://doi.org/10.1016/j.ejmech.2013.08.018.Search in Google Scholar PubMed

40. Kong, S, McBurney, MW, Fang, D. Sirtuin 1 in immune regulation and autoimmunity. Immunol Cell Biol 2012;90:6–13. https://doi.org/10.1038/icb.2011.102.Search in Google Scholar PubMed

41. Blum, CA, Ellis, JL, Loh, C, Ng, PY, Perni, RB, Stein, RL. SIRT1 modulation as a novel approach to the treatment of diseases of aging. J Med Chem 2011;54:417–32. https://doi.org/10.1021/jm100861p.Search in Google Scholar PubMed

42. Kojima, K, Fujita, Y, Nozawa, Y, Deguchi, T, Ito, M. MiR‐34a attenuates paclitaxel‐resistance of hormone‐refractory prostate cancer PC3 cells through direct and indirect mechanisms. Prostate 2010;70:1501–12. https://doi.org/10.1002/pros.21185.Search in Google Scholar PubMed

43. Nakane, K, Fujita, Y, Terazawa, R, Atsumi, Y, Kato, T, Nozawa, Y, et al.. Inhibition of cortactin and SIRT1 expression attenuates migration and invasion of prostate cancer DU145 cells. Int J Urol 2012;19:71–9. https://doi.org/10.1111/j.1442-2042.2011.02888.x.Search in Google Scholar PubMed

44. Ramya, PVS, Angapelly, S, Guntuku, L, Digwal, CS, Babu, BN, Naidu, VGM, et al.. Synthesis and biological evaluation of curcumin inspired indole analogues as tubulin polymerization inhibitors. Eur J Med Chem 2017;127:100–14. https://doi.org/10.1016/j.ejmech.2016.12.043.Search in Google Scholar PubMed

45. Wang, Q, Arnst, KE, Wang, Y, Kumar, G, Ma, D, White, SW, et al.. Structure-guided design, synthesis, and biological evaluation of (2-(1H-Indol-3-yl)-1H-(imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone (ABI-231) analogues targeting the colchicine binding site in tubulin. J Med Chem 2019;62:6734–50. https://doi.org/10.1021/acs.jmedchem.9b00706.Search in Google Scholar PubMed

46. Saravanan, K, Elancheran, R, Divakar, S, Anand, SA, Ramanathan, M, Kotoky, J. Design, synthesis and biological evaluation of 2-(4-phenylthiazol-2-yl) isoindoline-1,3-dione derivatives as anti-prostate cancer agents. Bioorg Med Chem Lett 2017;27:1199–204. https://doi.org/10.1016/j.bmcl.2017.01.065.Search in Google Scholar PubMed

47. Kovvuri, J, Nagaraju, B, Nayak, VL, Akunuri, RK, Rao, MPN, Ajitha, A, et al.. Design, synthesis and biological evaluation of new b-carboline bisindole compounds as DNA binding, photocleavage agents and topoisomerase I inhibitors. Eur J Med Chem 2018;143:1563–77. https://doi.org/10.1016/j.ejmech.2017.10.054.Search in Google Scholar PubMed

48. Balasubramanian, BN, Laurent, DR, Saulnier, MG, Long, BH, Bachand, C, Beaulieu, F, et al.. Design and synthesis of a fluoroindolocarbazole series as selective topoisomerase I active agents. Discovery of water-soluble 3,9-difluoro-12,13-dihydro-13-[6-amino-β-d-glucopyranosyl]-5H,13H-benzo[b]-thienyl[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (BMS-251873) with curative antitumor activity against prostate carcinoma xenograft tumor model. J Med Chem 2004;47:1609–12. https://doi.org/10.1021/jm034197s.Search in Google Scholar PubMed

49. Barraja, P, Diana, P, Lauria, A, Montalbano, A, Almerico, M, Dattolo, G, et al.. Synthesis and antiproliferative activity of [1,2,3,5]tetrazino[5,4-a]indoles, a new class of azolo-tetrazinones. Bioorg Med Chem 2005;13:295–610. https://doi.org/10.1016/j.bmc.2004.10.028.Search in Google Scholar PubMed

50. Zhao, N, Li, Z-L, Li, D-H, Sun, Y-T, Shan, D-T, Bai, J, et al.. Quinolone and indole alkaloids from the fruits of Euodia rutaecarpa and their cytotoxicity against two human cancer cell lines. Phytochemistry 2015;109:133–9. https://doi.org/10.1016/j.phytochem.2014.10.020.Search in Google Scholar PubMed

51. Liew, SY, Looi, CY, Paydar, MJ, Cheah, FK, Leong, KH, Wong, WF, et al.. Subditine, a new monoterpenoid indole alkaloid from bark of Nauclea subdita (Korth.) steud. Induces apoptosis in human prostate cancer cells. PLoS One 2014;9:1–13:e87286. https://doi.org/10.1371/journal.pone.0087286.Search in Google Scholar PubMed PubMed Central

52. Lobo, G, Monasterios, M, Rodrigues, J, Gamboa, N, Capparelli, MV, Martínez-Cuevas, J, et al.. Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9. Eur J Med Chem 2015;96:281–95. https://doi.org/10.1016/j.ejmech.2015.04.023.Search in Google Scholar PubMed

53. Liu, J, Zhao, M, Qian, K, Zhang, X, Lee, K-H, Wu, J, et al.. Benzyl 1,2,3,5,11,11a-hexahydro-3,3-dimethyl-1-oxo-6H-imidazo[3′,4′:1,2]pyridin[3,4-b]indole-2-substituted acetates: one-pot-preparation, anti-tumor activity, docking toward DNA and 3D QSAR analysis. Bioorg Med Chem 2010;18:1910–7. https://doi.org/10.1016/j.bmc.2010.01.038.Search in Google Scholar PubMed

54. Chaniyara, R, Tala, SK, Chen, C-W, Zang, X, Kakadiya, R, Lin, LF, et al.. Novel antitumor indolizino[6,7-b]indoles with multiple modes of action: DNA cross-linking and topoisomerase I and II inhibition. J Med Chem 2013;56:1544–63. https://doi.org/10.1021/jm301788a.Search in Google Scholar PubMed

55. Hundsdörfer, C, Hemmerling, HJ, Götz, C, Totzke, F, Bednarski, P, Borgne, ML, et al.. Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors. Bioorg Med Chem 2012;20:2282–9.10.1016/j.bmc.2012.02.017Search in Google Scholar PubMed

56. Yan, J, Hu, J, An, B, Huang, L, Li, X. Design, synthesis and biological evaluation of cyclic-ndole derivatives as anti-tumor agents via the inhibition of tubulin polymerization. Eur J Med Chem 2017;125:663–75. https://doi.org/10.1016/j.ejmech.2016.09.056.Search in Google Scholar PubMed

Published Online: 2022-01-13

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Reviews
  3. Recent endeavors in microbial remediation of micro- and nanoplastics
  4. Metal nanoparticles and its application on phenolic and heavy metal pollutants
  5. The story of nitrogen
  6. Recent development of imidazole derivatives as potential anticancer agents
  7. Indole based prostate cancer agents
  8. Lawsone (2-hydroxy-1,4-naphthaquinone) derived anticancer agents
  9. Small modular nuclear reactors are mostly bad policy
  10. A holistic environmental investigation of complementary energy in Alberta
  11. Green synthesis of various saturated S-heterocyclic scaffolds: an update
  12. Recent advances of heterocycle based anticancer hybrids
  13. Molecular docking and MD: mimicking the real biological process
  14. Synthesis of quinazolinone and quinazoline derivatives using green chemistry approach
  15. Nuclear fusion: the promise of endless energy
  16. Finance for Green Chemistry through Currency Mix
  17. Synthesis of bioactive scaffolds catalyzed by agro-waste-based solvent medium
  18. Recent developments in the green synthesis of biologically relevant cinnolines and phthalazines
  19. Detection of Rapid Eye Movement Behaviour Sleep Disorder using Time and Frequency Analysis of EEG Signal Applied on C4-A1 Channels
  20. Recent developments in C–C bond formation catalyzed by solid supported palladium: a greener perspective
  21. Visible-light-mediated metal-free C–Si bond formation reactions
  22. An overview of quinoxaline synthesis by green methods: recent reports
  23. Naturally occurring, natural product inspired and synthetic heterocyclic anti-cancer drugs
  24. Synthesis of bioactive natural products and their analogs at room temperature – an update
  25. One-pot multi-component synthesis of diverse bioactive heterocyclic scaffolds involving 6-aminouracil or its N-methyl derivatives as a versatile reagent
  26. Synthesis of new horizons in benzothiazole scaffold and used in anticancer drug development
  27. Triazine based chemical entities for anticancer activity
  28. Modification of kaolinite/muscovite clay for the removal of Pb(II) ions from aqueous media
  29. In silico design of ACE2 mutants for competitive binding of SARS-CoV-2 receptor binding domain with hACE2
  30. Computational study of Cu n AgAu (n = 1–4) clusters invoking DFT based descriptors
  31. Development of an online assessment system to evaluate knowledge on chemical safety and security
  32. Developing a questionnaire for diabetes mellitus type 2 risk effects and precondition factors – multivariate statistical paths
  33. Antioxidant and antibacterial activities of two xanthones derivatives isolated from the leaves extract of Anthocleista schweinfurthii Gilg (Loganiaceae)
  34. The stability increase of α-amylase enzyme from Aspergillus fumigatus using dimethyladipimidate
  35. Sustainability of ameliorative potentials of urea spiked poultry manure biochar types in simulated sodic soils
  36. Cytotoxicity test and antibacterial assay on the compound produced by the isolation and modification of artonin E from Artocarpus kemando Miq.
  37. Effects of alum, soda ash, and carbon dioxide on 40–50 year old concrete wastewater tanks
Downloaded on 8.11.2025 from https://www.degruyterbrill.com/document/doi/10.1515/psr-2021-0131/pdf
Scroll to top button