Synthesis and Biological Activity Screening of Newly Synthesized Trimethoxyphenyl-Based Analogues as Potential Anticancer Agents

被引：10

作者：

Al-Warhi, Tarfah ^{[1
]}

Abualnaja, Matokah ^{[2
]}

Abu Ali, Ola A. ^{[3
]}

Althobaiti, Fayez ^{[4
]}

Alharthi, Fahad ^{[5
]}

Elsaid, Fahmy G. ^{[6
,7
]}

Shati, Ali A. ^{[6
]}

Fayad, Eman ^{[4
]}

Elghareeb, Doaa ^{[8
,9
]}

Abu Almaaty, Ali H. ^{[10
]}

Zaki, Islam ^{[11
]}

机构：

[1] Princess Nourah Bint Abdulrahman Univ, Dept Chem, Coll Sci, Riyadh 11671, Saudi Arabia

[2] Umm Al Qura Univ, Fac Sci Appl, Dept Chem, Makkah Al Mukarrama 24381, Saudi Arabia

[3] Taif Univ, Dept Chem, Coll Sci, Taif 21944, Saudi Arabia

[4] Taif Univ, Dept Biotechnol, Fac Sci, Taif 21944, Saudi Arabia

[5] Taif Univ, Dept Biol, Coll Sci, Taif 21944, Saudi Arabia

[6] King Khalid Univ, Dept Biol, Coll Sci, Abha 61421, Saudi Arabia

[7] Mansoura Univ, Dept Zool, Fac Sci, Mansoura 35516, Egypt

[8] Umm Al Qura Univ, Dept Biol, Jumum Coll Univ, Mecca 21955, Saudi Arabia

[9] Agr Res Ctr, Agr Genet Engn Res Inst AGERI, Cairo 12619, Egypt

[10] Port Said Univ, Dept Zool, Fac Sci, Port Said 42526, Egypt

[11] Port Said Univ, Dept Organ Pharmaceut Chem, Fac Pharm, Port Said 42526, Egypt

来源：

MOLECULES | 2022年 / 27卷 / 14期

关键词：

diamide; oxazolone; imidazolone; triazinone; cytotoxicity; tubulin; cell cycle analysis; apoptosis;

D O I：

10.3390/molecules27144621

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A group of novel trimethoxyphenyl (TMP)-based analogues were synthesized by varying the azalactone ring of 2-(3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxybenzylidene)oxazolone 1 and characterized using NMR spectral data as well as elemental microanalyses. All synthesized compounds were screened for their cytotoxic activity utilizing the hepatocellular carcinoma (HepG2) cell line. Compounds 9, 10 and 11 exhibited good cytotoxic potency with IC50 values ranging from 1.38 to 3.21 mu M compared to podophyllotoxin (podo) as a reference compound. In addition, compounds 9, 10 and 11 exhibited potent inhibition of beta-tubulin polymerization. DNA flow cytometry analysis of compound 9 shows cell cycle disturbance at the G2/M phase and a significant increase in Annexin-V-positive cells compared with the untreated control. Compound 9 was further studied regarding its apoptotic potential in HepG2 cells; it decreased the level of MMP and Bcl-2 as well as boosted the level of p53 and Bax compared with the control HepG2 cells.

引用

页数：18

共 50 条

[21] Synthesis, Anticancer Screening and Molecular Docking Studies of New Heterocycles with Trimethoxyphenyl Scaffold as Combretastatin Analogues
Ali, Korany A.
Hafez, Naglaa A. Abdel
Elsayed, Mohamed A.
El-Shahawi, Manal M.
El-Hallouty, Salwa M.
Amr, Abd El-Galil E.
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2018, 18 (08) : 717 - 727
[22] Anticancer Studies of Newly Synthesized Thiazole Derivatives: Synthesis, Characterization, Biological Activity, and Molecular Docking
Al-Salmi, Fawziah A.
Alrohaimi, Abdulmohsen H.
El Behery, Mohammed
Megahed, Walaa
Abu Ali, Ola A.
Elsaid, Fahmy G.
Fayad, Eman
Mohammed, Faten Z.
Keshta, Akaber T.
CRYSTALS, 2023, 13 (11)
[23] Synthesis and biological evaluation of quinoline analogues of flavones as potential anticancer agents and tubulin polymerization inhibitors
Shobeiri, Nikta
Rashedi, Maryam
Mosaffa, Fatemeh
Zarghi, Afshin
Ghandadi, Morteza
Ghasemi, Ali
Ghodsi, Razieh
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 114 : 14 - 23
[24] Discovery of Ring-Annulated Analogues of Cannabidiol as Potential Anticancer Agents: Synthesis and Biological Evaluation
Cham, Pankaj Singh
Singh, Ajeet
Jamwal, Ashiya
Singh, Rattandeep
Anand, Radhika
Manhas, Diksha
Sharma, Sucheta
Singh, Varun Pratap
Nandi, Utpal
Singh, Shashank K.
Singh, Parvinder Pal
ACS MEDICINAL CHEMISTRY LETTERS, 2024, 15 (11): : 1832 - 1842
[25] Anticancer activity of newly synthesized azaphenothiazines from NCI’s anticancer screening bank
Krystian Pluta
Małgorzata Jeleń
Beata Morak-Młodawska
Michał Zimecki
Jolanta Artym
Maja Kocięba
Pharmacological Reports, 2010, 62 : 319 - 332
[26] ETPs as anticancer agents: Synthesis and biological activity
Sil, Bruno C.
Hilton, Stephen T.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[27] Anticancer activity of newly synthesized azaphenothiazines from NCI's anticancer screening bank
Pluta, Krystian
Jelen, Malgorzata
Morak-Mlodawska, Beata
Zimecki, Michal
Artym, Jolanta
Kocieba, Maja
PHARMACOLOGICAL REPORTS, 2010, 62 (02) : 319 - 332
[28] Synthesis, biological evaluation and virtual screening of some acridone derivatives as potential anticancer agents
Oyedele, Abiodun S.
Bogan, Deanna N.
Okoro, Cosmas O.
BIOORGANIC & MEDICINAL CHEMISTRY, 2020, 28 (09)
[29] Synthesis of Some Novel Thiophene Analogues as Potential Anticancer Agents
Almatari, Altaf S.
Saeed, Ali
Abdel-Ghani, Ghada E.
Abdullah, Mahmood M. S.
Al-Lohedan, Hamad A.
Abdel-Latif, Ehab
El-Demerdash, Amr
CHEMISTRY & BIODIVERSITY, 2024, 21 (07)
[30] Synthesis of Marine Cyclopeptide Galaxamide Analogues as Potential Anticancer Agents
Li, Daichun
Liao, Xiaojian
Zhong, Shenghui
Zhao, Bingxin
Xu, Shihai
MARINE DRUGS, 2022, 20 (03)

← 1 2 3 4 5 →