Literature DB >> 29695549

In Vitro Anti-tumor Activity of Azulene Amide Derivatives.

Toshiki Wada1, Ryota Maruyama1, Yuta Irie1, Masashi Hashimoto1, Hidetsugu Wakabayashi2, Noriyuki Okudaira3, Yoshihiro Uesawa4, Hajime Kagaya4, Hiroshi Sakagami5.   

Abstract

BACKGROUND/AIM: There exist few research articles regarding the anticancer activity of azulene-related compounds. We investigated here the relative cytotoxicity of 10 azulene amide derivatives against cancer and normal cells.
MATERIALS AND METHODS: Cytotoxicity against four human oral squamous cell carcinoma (OSCC) cell lines and three human oral normal cells (gingival fibroblasts, periodontal ligament fibroblasts and pulp cells) was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetra-zolium bromide method. Antitumor activity was evaluated by tumor-specificity (TS) (ratio of mean 50% cytotoxic concentration (CC50) against normal cells to that against OSCC cell lines) and potency-selectivity expression (PSE) (ratio of TS to CC50 against tumor cells). Apoptosis-inducing activity was evaluated by cleavage of poly ADP-ribose polymerase and caspase-3 with western blot analysis.
RESULTS: N-Propylguaiazulenecarboxamide [1] showed the highest TS and PSE values, compared to that of doxorubicin, and induced apoptosis in two OSCC cell lines. QSAR analysis demonstrated that their tumor-specificity of azulene amide derivatives was correlated with hydrophobicity and molecular shape.
CONCLUSION: Compound [1] can be considered as a lead compound for manufacturing new anticancer drug candidates. Copyright
© 2018, International Institute of Anticancer Research (Dr. George J. Delinasios), All rights reserved.

Entities:  

Keywords:  Azulene amides; apoptosis; cytotoxicity; hydrophobicity; molecular shape; tumor specificity

Mesh:

Substances:

Year:  2018        PMID: 29695549      PMCID: PMC6000805          DOI: 10.21873/invivo.11264

Source DB:  PubMed          Journal:  In Vivo        ISSN: 0258-851X            Impact factor:   2.155


  17 in total

1.  Quantitative Structure-Cytotoxicity Relationship of 3-Styryl-2H-chromenes.

Authors:  Yoshihiro Uesawa; Hiroshi Sakagami; Mariko Ishihara; Hajime Kagaya; Taisei Kanamoto; Shigemi Terakubo; Hideki Nakashima; Hideaki Yahagi; Koichi Takao; Yoshiaki Sugita
Journal:  Anticancer Res       Date:  2015-10       Impact factor: 2.480

2.  Antioxidant activity of guaiazulene and protection against paracetamol hepatotoxicity in rats.

Authors:  A P Kourounakis; E A Rekka; P N Kourounakis
Journal:  J Pharm Pharmacol       Date:  1997-09       Impact factor: 3.765

3.  [A new human cell line derived from human carcinoma of the gingiva. I. Its establishment and morphological studies].

Authors:  M Horikoshi; Y Kimura; H Nagura; T Ono; H Ito
Journal:  Nihon Koku Geka Gakkai Zasshi       Date:  1974

4.  Azulene analogs of pharmacologic agents. I. Amides.

Authors:  P H Doukas; T J Speaker
Journal:  J Pharm Sci       Date:  1971-02       Impact factor: 3.534

5.  Hormetic and anti-radiation effects of tropolone-related compounds.

Authors:  Kaori Kantoh; Manami Ono; Yuko Nakamura; Yukio Nakamura; Ken Hashimoto; Hiroshi Sakagami; Hidetsugu Wakabayashi
Journal:  In Vivo       Date:  2010 Nov-Dec       Impact factor: 2.155

6.  Cytotoxic activity of guaiazulene on gingival fibroblasts and the influence of light exposure on guaiazulene-induced cell death.

Authors:  Jessica Fiori; Gabriella Teti; Roberto Gotti; Giovanni Mazzotti; Mirella Falconi
Journal:  Toxicol In Vitro       Date:  2010-09-18       Impact factor: 3.500

7.  Effect of guaiazulene on some cytochrome P450 activities. Implication in the metabolic activation and hepatotoxicity of paracetamol.

Authors:  A P Kourounakis; E A Rekka; P N Kourounakis
Journal:  Arch Pharm (Weinheim)       Date:  1997 Jan-Feb       Impact factor: 3.751

8.  Comparison of cardioprotective efficacy of two thromboxane A2 receptor antagonists.

Authors:  Zhi-Dong Ge; John A Auchampach; Galen M Piper; Garrett J Gross
Journal:  J Cardiovasc Pharmacol       Date:  2003-03       Impact factor: 3.105

9.  Enhancement of Cytotoxicity of Three Apoptosis-inducing Agents Against Human Oral Squamous Cell Carcinoma Cell Line by Benzoxazinotropone.

Authors:  Yukiko Tomikoshi; Maki Nomura; Noriyuki Okudaira; Hiroshi Sakagami; Hidetsugu Wakabayashi
Journal:  In Vivo       Date:  2016 09-10       Impact factor: 2.155

10.  Guaiazulene biochemical activity and cytotoxic and genotoxic effects on rat neuron and N2a neuroblastom cells.

Authors:  Basak Togar; Hasan Turkez; Ahmet Hacimuftuoglu; Abdulgani Tatar; Fatime Geyikoglu
Journal:  J Intercult Ethnopharmacol       Date:  2015-01-03
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  3 in total

Review 1.  Development of Heterocycle-Substituted and Fused Azulenes in the Last Decade (2010-2020).

Authors:  Taku Shoji; Tetsuo Okujima; Shunji Ito
Journal:  Int J Mol Sci       Date:  2020-09-25       Impact factor: 5.923

2.  Tumor-Specificity, Neurotoxicity, and Possible Involvement of the Nuclear Receptor Response Pathway of 4,6,8-Trimethyl Azulene Amide Derivatives.

Authors:  Kotone Naitoh; Yuta Orihara; Hiroshi Sakagami; Takumi Miura; Keitaro Satoh; Shigeru Amano; Kenjiro Bandow; Yosuke Iijima; Kota Kurosaki; Yoshihiro Uesawa; Masashi Hashimoto; Hidetsugu Wakabayashi
Journal:  Int J Mol Sci       Date:  2022-02-26       Impact factor: 5.923

3.  Guaiazulene derivative 1,2,3,4-tetrahydroazuleno[1,2-b] tropone reduces the production of ATP by inhibiting electron transfer complex II.

Authors:  Chieko Kasami; Jun-Ichi Yamaguchi; Hideki Inoue
Journal:  FEBS Open Bio       Date:  2021-09-21       Impact factor: 2.693

  3 in total

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