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Design and Synthesis of Potential New Apoptosis Agents: Hybrid Compounds Containing Perillyl Alcohol and New Constrained Retinoids.

ABSTRACT: Novel retinoids 1-3 containing perillyl alcohol were synthesized through the addition of perillyl alcohol to the activated carboxylic acids (retinoids) promoted by DCC (N, N'-Dicylohexyl cabodiimide). A set of structurally and functionally diverse perillyl alcohol derivatives of retinoids were obtained in good yields (78-82%). Biological evaluation of these novel hybrid compounds (containing retinoids and perillyl alcohol) is currently underway in our laboratory.

SUBMITTER: Das BC

PROVIDER: S-EPMC2849109 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Design and Synthesis of Potential New Apoptosis Agents: Hybrid Compounds Containing Perillyl Alcohol and New Constrained Retinoids.

Das Bhaskar C BC Mahalingam Sakkarapalayam M SM Panda Lipsa L Wang Bo B Campbell Phillp P Evans Todd T

Tetrahedron letters 20100301 11

Novel retinoids 1-3 containing perillyl alcohol were synthesized through the addition of perillyl alcohol to the activated carboxylic acids (retinoids) promoted by DCC (N, N'-Dicylohexyl cabodiimide). A set of structurally and functionally diverse perillyl alcohol derivatives of retinoids were obtained in good yields (78-82%). Biological evaluation of these novel hybrid compounds (containing retinoids and perillyl alcohol) is currently underway in our laboratory. ...[more]

PMID: 20379349

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Antifungal effect of Perillyl alcohol (PA) on C. albicans SC5314

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| S-EPMC2907645 | biostudies-literature

The identification of perillyl alcohol glycosides with improved antiproliferative activity.

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| S-EPMC4161159 | biostudies-literature

Optimal Design of THEDES Based on Perillyl Alcohol and Ibuprofen.

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| S-EPMC3517803 | biostudies-literature

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| S-EPMC2834810 | biostudies-literature

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Anticandidal Effect and Mechanisms of Monoterpenoid, Perillyl Alcohol against Candida albicans.

Project description:This study explored the antifungal potential of perillyl alcohol (PA), a natural monoterpene alcohol, against most prevalent human fungal pathogen C. albicans, its clinical isolates and four non-albicans species of Candida. To resolve the potential mechanisms, we used whole genome transcriptome analyses of PA treated Candida cells to examine the affected cellular circuitry of this pathogen. The transcriptome data revealed a link between calcineurin signaling and PA as among the several categories of PA responsive genes the down regulation of calcineurin signaling gene CNB1 was noteworthy which was also confirmed by both molecular docking and susceptibility assays. We observed that PA treated Candida phenocopied compromised calcineurin pathway stress responses and turned sensitive to alkaline pH, ionic, membrane, salinity, endoplasmic reticulum and serum stresses. Indispensability of functional calcineurin was further confirmed as calcineurin mutant was hypersensitive to PA while constitutively expressed calcineurin strain remained resistant. We explored that PA leads to perturbed membrane integrity as depicted through depleted ergosterol levels and disrupted pH homeostasis. Moreover, PA caused cell wall damage which was evident from hypersensitivity against cell wall perturbing agents (congo red, calcoflour white), SEM and enhanced rate of cell sedimentation. Furthermore, PA inhibited potential virulence traits including morphological transition, biofilm formation and displayed diminished capacity to adhere both to the polystyrene surface and buccal epithelial cells. The study also revealed that PA leads to cell cycle arrest and mitochondrial dysfunction in C. albicans. Together, the present study provides enough evidence for further work on PA so that better strategies could be employed to treat Candida infections.

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Pharmacokinetic properties of the temozolomide perillyl alcohol conjugate (NEO212) in mice.

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| S-EPMC7764505 | biostudies-literature

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