In Vivo Anti-Tumor Activity and Toxicological Evaluations of Perillaldehyde 8,9-Epoxide, a Derivative of Perillyl Alcohol

Andrade, Luciana Nalone; Amaral, Ricardo Guimarães; Dória, Grace Anne Azevedo; Fonseca, Cecília Santos; Silva, Tayane Kayane Mariano da; Júnior, Ricardo Luiz Cavalcante Albuquerque; Thomazzi, Sara Maria; Nascimento, Lázaro Gomes do; Carvalho, Adriana Andrade; Sousa, Damião Pergentino de

doi:10.3390/ijms17010032

Cited by 27 publications

(23 citation statements)

References 31 publications

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“…Comparatively, the observed in vivo activity of derivative 5 seems to be better than the perillaldehyde 8,9-epoxide (regarded as the most potent derivative of POH) in terms of the therapeutic dose. 42 As reported by Andrade et al, perillaldehyde 8,9-epoxide exhibited signicant antitumor activity at a higher doses (100/200 mg per kg per day) in comparison with our derivatives. More importantly, histopathological analysis revealed no toxicity to liver, spleen and kidney of mice 19980 | RSC Adv., 2019, 9,[19973][19974][19975][19976][19977][19978][19979][19980][19981][19982] This journal is © The Royal Society of Chemistry 2019 treated with the derivatives 4 and 5.…”

Section: Biological Assayssupporting

confidence: 78%

Novel N-arylamide derivatives of (S)-perillic acid ((S)-PA): in vitro and in vivo cytotoxicity and antitumor evaluation

Mukhtar

Wang

et al. 2019

RSC Adv.

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Section: Biological Assayssupporting

confidence: 78%

Novel N-arylamide derivatives of (S)-perillic acid ((S)-PA): in vitro and in vivo cytotoxicity and antitumor evaluation

Mukhtar

Wang

et al. 2019

RSC Adv.

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“…Perillyl alcohol, a naturally occurring monoterpene found in the essential oils of peppermint and lavender, has been widely studied [18], demonstrating effectiveness against a variety of human tumor cell lines [19][20][21]. The monoterpene, which previously showed cytotoxic and antitumor activities in various experimental models, is already in clinical trials, mainly for cancer treatment [19,22]. The cytotoxicity of perillyl alcohol analog compounds, namely (−)-8,9-perillaldehyde epoxide, (−)-perillaldehyde, (+)-limonene 1,2-epoxide, and (−)-8-hydroxycarvotanacetone, has also been thoroughly characterized [19].…”

Section: Introductionmentioning

confidence: 99%

(+)-Limonene 1,2-Epoxide-Loaded SLNs: Evaluation of Drug Release, Antioxidant Activity, and Cytotoxicity in an HaCaT Cell Line

Souto

Zielińska

Souto

et al. 2020

IJMS

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In this work, we developed a solid lipid nanoparticle (SLN) formulation with (+)-limonene 1,2-epoxide and glycerol monostearate (Lim-SLNs), stabilized with Poloxamer® 188 in aqueous dispersion to modify the release profile of the loaded monoterpene derivative. We also evaluated the role of SLNs in lipid peroxidation and cytotoxicity in a spontaneously transformed aneuploid immortal keratinocyte cell line from adult human skin (the HaCaT cell line). For the cell viability assay, the colorimetric 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay was used. Lim-SLNs with a loading capacity and encapsulation efficiency of 0.39% and 63%, respectively, were produced by high pressure homogenization. A mean particle size of 194 ± 3.4 nm and polydispersity index of 0.244 were recorded for the loaded Lim-SLNs, as compared to 203 ± 1.5 nm (PI 0.213) for the non-loaded (blank) SLNs. The loading of the monoterpene derivative into glycerol monostearate SLNs fitted into the zero-order kinetics, and ameliorated both lipid peroxidation and cytotoxicity in a keratinocyte cell line. A promising formulation for antioxidant and anti-tumoral activities is here proposed.

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“…Perillyl alcohol, a naturally occurring monoterpene found in the essential oils peppermint and lavender, has been widely studied [14], demonstrating effectiveness against a variety of human tumor cell lines [15][16][17]. The monoterpene showed cytotoxicity and antitumor activity in various experimental models, and has already reached clinical trials for cancer treatment [15,18]. The cytotoxicity of perillyl alcohol analogues, such as (-)-8,9-perillaldehyde epoxide, (-)-perillaldehyde, (+)-limonene 1,2-epoxide and (-)-8-hydroxycarvotanacetone, has also been thoroughly characterized [15].…”

Section: Introductionmentioning

confidence: 99%

Perillaldehyde 1,2-epoxide Loaded SLN-Tailored mAb: Production, Physicochemical Characterization and In Vitro Cytotoxicity Profile in MCF-7 Cell Lines

Souto

Zielińska

et al. 2020

Pharmaceutics

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We have developed a new cationic solid lipid nanoparticle (SLN) formulation, composed of Compritol ATO 888, poloxamer 188 and cetyltrimethylammonium bromide (CTAB), to load perillaldehyde 1,2-epoxide, and surface-tailored with a monoclonal antibody for site-specific targeting of human epithelial growth receptor 2 (HER2). Perillaldehyde 1,2-epoxide-loaded cationic SLN (cPa-SLN), with a mean particle size (z-Ave) of 275.31 ± 4.78 nm and polydispersity index (PI) of 0.303 ± 0.081, were produced by high shear homogenization. An encapsulation efficiency of cPa-SLN above 80% was achieved. The release of perillaldehyde 1,2-epoxide from cationic SLN followed the Korsemeyer–Peppas kinetic model, which is typically seen in nanoparticle formulations. The lipid peroxidation of cPa-SLN was assessed by the capacity to produce thiobarbituric acid-reactive substances, while the antioxidant activity was determined by the capacity to scavenge the stable radical DPPH. The surface functionalization of cPa-SLN with the antibody was done via streptavidin-biotin interaction, monitoring z-Ave, PI and ZP of the obtained assembly (cPa-SLN-SAb), as well as its stability in phosphate buffer. The effect of plain cationic SLN (c-SLN, monoterpene free), cPa-SLN and cPa-SLN-SAb onto the MCF-7 cell lines was evaluated in a concentration range from 0.01 to 0.1 mg/mL, confirming that streptavidin adsorption onto cPa-SLN-SAb improved the cell viability in comparison to the cationic cPa-SLN.

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In Vivo Anti-Tumor Activity and Toxicological Evaluations of Perillaldehyde 8,9-Epoxide, a Derivative of Perillyl Alcohol

Cited by 27 publications

References 31 publications

Novel N-arylamide derivatives of (S)-perillic acid ((S)-PA): in vitro and in vivo cytotoxicity and antitumor evaluation

Novel N-arylamide derivatives of (S)-perillic acid ((S)-PA): in vitro and in vivo cytotoxicity and antitumor evaluation

(+)-Limonene 1,2-Epoxide-Loaded SLNs: Evaluation of Drug Release, Antioxidant Activity, and Cytotoxicity in an HaCaT Cell Line

Perillaldehyde 1,2-epoxide Loaded SLN-Tailored mAb: Production, Physicochemical Characterization and In Vitro Cytotoxicity Profile in MCF-7 Cell Lines

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