PMID- 37546528
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20230808
IS  - 1319-0164 (Print)
IS  - 2213-7475 (Electronic)
IS  - 1319-0164 (Linking)
VI  - 31
IP  - 9
DP  - 2023 Sep
TI  - Synthesis, anti-amoebic activity and molecular docking simulation of eugenol 
      derivatives against Acanthamoeba sp.
PG  - 101703
LID - 10.1016/j.jsps.2023.101703 [doi]
LID - 101703
AB  - Amoebae of the genus Acanthamoeba can cause diseases such as amoebic keratitis 
      and granulomatous amoebic encephalitis. Until now, treatment options for these 
      diseases have not been fully effective and have several drawbacks. Therefore, 
      research into new drugs is needed for more effective treatment of Acanthamoeba 
      infections. Eugenol, a phenolic aromatic compound mainly derived from cloves, has 
      a variety of pharmaceutical properties. In this study, nine eugenol derivatives 
      (K1-K9), consisting of five new and four known compounds, were synthesized and 
      screened for their antiamoebic properties against Acanthamoeba sp. The structure 
      of these compounds was characterized spectroscopically by Fourier transform 
      infrared (FTIR), Ultraviolet-Visible (UV-Vis), (1)H and (13)C Nuclear Magnetic 
      Resonance (NMR) and mass spectrometer (MS). The derived molecules were screened 
      for antiamoebic activity by determining IC(50) values based on 
      3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and 
      observation of amoeba morphological changes by light and fluorescence microscopy. 
      Most of the tested compounds possessed strong to moderate cytotoxic effects 
      against trophozoite cells with IC(50) values ranging from 0.61 to 24.83 mug/mL. 
      Observation of amoebae morphology by light microscopy showed that the compounds 
      caused the transformed cells to be roundish and reduced in size. Furthermore, 
      fluorescence microscopy observation using acridine orange (AO) and propidium 
      iodide (PI) (AO/PI) staining showed that the cells have damaged membranes by 
      displaying a green cytoplasm with orange-stained lysosomes. Acidification of the 
      lysosomal structure indicated disruption of the internal structure of 
      Acanthamoeba cells when treated with eugenol derivatives. The observed biological 
      results were also confirmed by interaction simulations based on molecular docking 
      between eugenol derivatives and Acanthamoeba profilin. These interactions could 
      affect the actin-binding ability of the protein, disrupting the shape and 
      mobility of Acanthamoeba. The overall results of this study demonstrate that 
      eugenol derivatives can be considered as potential drugs against infections 
      caused by Acanthamoeba.
CI  - (c) 2023 The Authors.
FAU - Zamli, Khairunisa Mohd
AU  - Zamli KM
AD  - Faculty of Science and Marine Environment, Universiti Malaysia Terengganu, 21030 
      Kuala Nerus, Terengganu, Malaysia.
FAU - Hashim, Fatimah
AU  - Hashim F
AD  - Biological Security and Sustainability Research Group, Faculty of Science and 
      Marine Environment, Universiti Malaysia Terengganu, 21030 Kuala Nerus, 
      Terengganu, Malaysia.
FAU - Razali, Siti Aisyah
AU  - Razali SA
AD  - Biological Security and Sustainability Research Group, Faculty of Science and 
      Marine Environment, Universiti Malaysia Terengganu, 21030 Kuala Nerus, 
      Terengganu, Malaysia.
FAU - Yusoff, Hanis Mohd
AU  - Yusoff HM
AD  - Faculty of Science and Marine Environment, Universiti Malaysia Terengganu, 21030 
      Kuala Nerus, Terengganu, Malaysia.
AD  - Advanced Nano Materials (ANoMa) Research Group, Faculty of Science and Marine 
      Environment, Universiti Malaysia Terengganu, 21030 Kuala Nerus, Terengganu, 
      Malaysia.
FAU - Mohamad, Habsah
AU  - Mohamad H
AD  - Institute of Biotechnology Marine, Universiti Malaysia Terengganu, 21030 Kuala 
      Nerus, Terengganu, Malaysia.
FAU - Abdullah, Fauziah
AU  - Abdullah F
AD  - Phytochemistry Programme, Natural Products Division, Forest Research Institute of 
      Malaysia, 52109 Kepong, Selangor, Malaysia.
FAU - Asari, Asnuzilawati
AU  - Asari A
AD  - Faculty of Science and Marine Environment, Universiti Malaysia Terengganu, 21030 
      Kuala Nerus, Terengganu, Malaysia.
AD  - Advanced Nano Materials (ANoMa) Research Group, Faculty of Science and Marine 
      Environment, Universiti Malaysia Terengganu, 21030 Kuala Nerus, Terengganu, 
      Malaysia.
LA  - eng
PT  - Journal Article
DEP - 20230718
PL  - Saudi Arabia
TA  - Saudi Pharm J
JT  - Saudi pharmaceutical journal : SPJ : the official publication of the Saudi 
      Pharmaceutical Society
JID - 9705695
PMC - PMC10400915
OTO - NOTNLM
OT  - Anti-amoebic
OT  - Cytotoxicity
OT  - Eugenol derivatives
OT  - MTT assay
OT  - Synthesis
COIS- The authors declare that they have no known competing financial interests or 
      personal relationships that could have appeared to influence the work reported in 
      this paper.
EDAT- 2023/08/07 06:42
MHDA- 2023/08/07 06:43
PMCR- 2023/07/18
CRDT- 2023/08/07 04:38
PHST- 2022/12/27 00:00 [received]
PHST- 2023/07/10 00:00 [accepted]
PHST- 2023/08/07 06:43 [medline]
PHST- 2023/08/07 06:42 [pubmed]
PHST- 2023/08/07 04:38 [entrez]
PHST- 2023/07/18 00:00 [pmc-release]
AID - S1319-0164(23)00198-6 [pii]
AID - 101703 [pii]
AID - 10.1016/j.jsps.2023.101703 [doi]
PST - ppublish
SO  - Saudi Pharm J. 2023 Sep;31(9):101703. doi: 10.1016/j.jsps.2023.101703. Epub 2023 
      Jul 18.