Liquid Crystallinity and Biological Activity of a Novel Amphiphilic Compound

Yoshizawa, Atsushi; Takahashi, Yuuka; Terasawa, Rie; Chiba, Shota; Takahashi, Kenji; Hazawa, Masaharu; Kashiwakura, Ikuo

doi:10.1246/cl.2009.310

Cited by 9 publications

(4 citation statements)

References 13 publications

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“…The mechanisms between the previous and present studies seem to be different because each effective compound and dose was different. Recently, we discovered that a liquid crystal also suppressed the proliferation in human lung cancer cell line A549 [26,27]. Fig.…”

Section: Discussionmentioning

confidence: 97%

Liquid crystal-related compound-induced cell growth suppression and apoptosis in the chronic myelogenous leukemia K562 cell line

et al. 2010

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Liquid crystals are the state of matter existing between the liquid and the crystalline phase, and there is a recent surging interest in its biological effects. Our previous study showed that liquid crystal-related compounds (LCRCs), which are precursors of the liquid crystal, enhanced hematopoietic differentiation at a relatively low concentration (Biol Pharm Bull, 32, 2009). However, biological potentials of LCRCs on tumor cells are unclear. In this study, the biological activity of 16 LCRCs to a chronic myelogenous leukemia cell line, K562, was evaluated. As a result, two compounds, 2-(4-butoxyphenyl)-5-(4-hydroxyphenyl)pyrimidine (compound 7) and 2-{4-(4-hexyloxyphenyl)phenyl}-5-hydroxypyrimidine (compound 9) showed marked growth suppression of K562 cells at μM range. These compounds are similar in structure with a core of three aromatic rings including a pyrimidine ring and residues of one alkyl chain and one hydroxide on either side. In addition, only compound 7 induced the activation of p38 mitogen-activated protein kinase and c-Jun N-terminal kinase, and apoptosis of K562 cells. The contrasting results between compounds 7 and 9 indicate different mechanisms to suppress the cell proliferation between the two compounds. These results suggest the possibility of LCRCs for application as new antitumor drugs.

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Section: Discussionmentioning

confidence: 97%

Liquid crystal-related compound-induced cell growth suppression and apoptosis in the chronic myelogenous leukemia K562 cell line

et al. 2010

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“…[6] Results of earlier studies have demonstrated that some thermotropic liquid-crystalline compounds suppress cell growth in A549 lung cancer cells. [7,8] Furthermore, as described herein, a phenyl benzoate derivative, 4-butylphenyl 4-(6-hydroxyhexyloxy) benzoate, exhibits marked anti-proliferative activity on A549 lung cancer cells. Moreover, it has the ability to form a spherical molecular aggregation in dimethyl sulphoxide (DMSO)-H 2 O mixture solution.…”

Section: Introductionmentioning

confidence: 70%

Effects of liquid crystallinity on anticancer activity of benzoate derivatives possessing a terminal hydroxyl group

et al. 2014

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To elucidate the effects of liquid crystallinity on the anticancer activity of a small mesogenic molecule, we prepared some benzoate derivatives possessing a terminal hydroxyl group and investigated their antiproliferative activity against A549 human lung cancer cells. We also observed their molecular aggregation properties using polarised optical microscopy, differential scanning microscopy and dynamic light scattering. We discuss the structure-property relation of the benzoate derivatives. The results are explained in terms of the octanol-water partition coefficient, topological polar surface area (tPSA) and molecular aggregation ability.

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“…A previous study has shown that amphiphilic LCs have cytostatic effects [11,12]. The present study focuses on the structure-activity relationships (SAR) and functional mechanisms related to various anticancer properties in A549 human lung cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Suppressive effects of liquid crystal compounds on the growth of the A549 human lung cancer cell line

et al. 2010

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The aim of this study was to evaluate the biological activity and pharmacological activity of several amphiphilic liquid-crystalline compounds (LCs), i.e. phenylpyrimidine derivatives possessing D-glucamine and cyanobiphenyl derivatives with a terminal hydroxyl unit, to explore novel anti-cancer functions of the LCs. The anti-cancer properties of the LCs were investigated in A549 human lung cancer cells by assessing cell growth, cell cycle distribution, and cell signaling pathways using a flow cytometer and a Western blot analysis. In addition, the effect of LCs on the growth of WI-38 normal fibroblasts was examined. Consequently, the phenylpyrimidine derivatives and cyanobiphenyl derivatives showed cytostatic effects, causing the suppression of cell growth through G1 phase arrest in A549 cells. Further analyses using phenylpyrimidine derivatives and precursors of a cyanobiphenyl compound demonstrated the structure-activity relationships. One of the phenylpyrimidine derivatives inhibited A549 growth without any toxicity to normal fibroblasts. As a result, a novel pharmacological function was hypothesized to be inherent in the structure of the LCs themselves, and the dependence of the tumor-specific activity on the hydrophobic group of phenylpyrimidine derivatives therefore remains an interesting issue. Our results suggest the possibility that the LCs themselves may act as a novel type of chemotherapeutic agent.

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Liquid Crystallinity and Biological Activity of a Novel Amphiphilic Compound

Cited by 9 publications

References 13 publications

Liquid crystal-related compound-induced cell growth suppression and apoptosis in the chronic myelogenous leukemia K562 cell line

Liquid crystal-related compound-induced cell growth suppression and apoptosis in the chronic myelogenous leukemia K562 cell line

Effects of liquid crystallinity on anticancer activity of benzoate derivatives possessing a terminal hydroxyl group

Suppressive effects of liquid crystal compounds on the growth of the A549 human lung cancer cell line

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