Synthesis and anticancer activities of fatty acid analogs of podophyllotoxin

Mustafa, Jamal; Khan, Shabana I.; Ma, Guoyi; Walker, Larry; Khan, Ikhlas A.

doi:10.1007/s11745-004-1215-5

Cited by 75 publications

(101 citation statements)

References 12 publications

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“…The in vivo application of this polyphenol has resulted in tumor regression in murine models, although tumor regrowth would take place after treatment. Other limitations such as poor solubility in water and tumor resistance have inspired clinicians and scientists to develop water soluble compounds to overcome its solubility [143], and to join podophyllotoxin with other molecules like fatty acids to overcome tumor resistance and improve pharmacological efficacy [144]. In terms of epidemiological studies, podophyllotoxin is used in anticancer preparations along with other chemicals [145][146][147][148].…”

Section: Lignansmentioning

confidence: 99%

The Role of Phenolic Compounds in the Fight against Cancer – A Review

Carocho¹,

Ferreira

2013

ACAMC

233

144

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Abstract:Cancer is a worldwide scourge; it's the leading cause of death in developed countries and is increasing in developing countries. Mankind has been trying with effort to find better and cheaper treatments with fewer side effects, to reduce the incidence of the disease and its consequent mortality. For many years, phenolic compounds have been intensely studied for their antitumor, proapoptotic and antiangiogenic effects. In recent years, the usage of these compounds has increased considerably.This manuscript intends to structurally characterize the different phenolic compounds (flavonoids, hydroxycinnamates, hydroxybenzoates, coumarins, xanthones, chalcones, stilbenes, lignins and lignans) and their metabolic pathways as well as review the most important results regarding these compounds and their derivatives in cancer treatment and prevention both in tumor cell lines in vitro, in murine models in vivo and finally some results regarding human trials.

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Section: Lignansmentioning

confidence: 99%

The Role of Phenolic Compounds in the Fight against Cancer – A Review

Carocho¹,

Ferreira

2013

ACAMC

233

144

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“…The in vitro cytotoxicities of peptides 3-6 were tested against four human cancer cell lines and two noncancerous mammalian kidney cell lines up to a concentration of 23.8 mg mL À1 using a neutral red assay procedure, as described earlier. [24,25] None of the peptides showed any cytotoxic effects up to the highest test concentration. The antimicrobial activities discussed above led to the identification of the hexapeptide Orn-d-Trp-d-Phe-Ile-d-Phe-His(1-Bzl)-NH 2 (3) as a lead compound, which provides an interesting pharmacophore for the design of more potent AMPs.…”

Section: Resultsmentioning

confidence: 94%

New Antimicrobial Hexapeptides: Synthesis, Antimicrobial Activities, Cytotoxicity, and Mechanistic Studies

et al. 2009

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Synthetic antimicrobial peptides have recently emerged as promising candidates against drug‐resistant pathogens. We identified a novel hexapeptide, Orn‐D‐Trp‐D‐Phe‐Ile‐D‐Phe‐His(1‐Bzl)‐NH2, which exhibits broad‐spectrum antifungal and antibacterial activity. A lead optimization was undertaken by conducting a full amino acid scan with various proteinogenic and non‐proteinogenic amino acids depending on the hydrophobic or positive‐charge character of residues at various positions along the sequence. The hexapeptide was also cyclized to study the correlation between the linear and cyclic structures and their respective antimicrobial activities. The synthesized peptides were found to be active against the fungus Candida albicans and Gram‐positive bacteria such as methicillin‐resistant Staphylococcus aureus and methicillin‐resistant Staphylococcus epidermidis, as well as the Gram‐negative bacterium Escherichia coli; MIC values for the most potent structures were in the range of 1–5 μg mL−1 (IC50 values in the range of 0.02–2 μg mL−1). Most of the synthesized peptides showed no cytotoxic effects in an MTT assay up to the highest test concentration of 200 μg mL−1. A tryptophan fluorescence quenching study was performed in the presence of negatively charged and zwitterionic model membranes, mimicking bacterial and mammalian membranes, respectively. The results of the fluorescence study demonstrate that the tested peptides are selective toward bacterial over mammalian cells; this is associated with a preferential interaction between the peptides and the negatively charged phospholipids of bacterial cells.

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“…The experimental procedures are similar to those detailed in our earlier publication [15]. Octadec-Z-9,12-dienoic acid, 4-dimethylaminopyridine (DMAP), 1,3-dibromopropane, butyl lithium (BuLi; 6 M solution in THF), triphenylphosphine, 4-hydroxybenzaldehyde, p-anisaldehyde, hexamethylphosphoramide (HMPA), and acetone (99.51) were procured from Aldrich Chemicals (Milwaukee, WI, USA), and dicyclohexyl carbodiimide (DCC) was purchased from Fluka Chemical Corporation (Hauppauge, NY, USA).…”

Section: Methodsmentioning

confidence: 99%

Synthesis, spectroscopic and anti‐tumor studies of polyphenol‐linoleates derived from natural polyphenols

Mustafa

Khan

Ferreira

et al. 2007

Euro J Lipid Sci & Tech

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An efficient first synthesis of di-, hexa-and octa-esters (octadeca-Z-9,12-dienoates, linoleates) from natural 1,5-bis-(4'-hydroxyphenyl)penta-Z-1,4-diene (Ginkgo biloba L.), (-)-epigallocatechin and (-)-epigallocatechin-3-O-gallate (jasmine tea/green tea), respectively, was developed. Using dicyclohexyl carbodiimide as an activating reagent in the presence of a catalytic amount of 4-dimethylaminopyridine in the polyesterification reactions gave di-, hexa-and octa-products (4), (7), and (8), respectively, in quantitative yields. A three-step efficient procedure for the synthesis of 1,5-bis-[4'-O-(octadec-Z-9",12"-dienoate)phenyl]penta-Z-1,4-diene (4) was also developed. The key step in the synthesis involved a stereoselective Wittig diolefination reaction that produced the penta-Z-1,4-diene system of (4). 1 H and 13 C NMR and MS techniques confirmed the structures of the esters. The esterified compounds were tested for in vitro anti-tumor activities against four and three human cancer cell lines at NCNPR and at NCI, respectively. They were found inactive as they failed to inhibit 50% growth of these cancer cells.

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Synthesis and anticancer activities of fatty acid analogs of podophyllotoxin

Cited by 75 publications

References 12 publications

The Role of Phenolic Compounds in the Fight against Cancer – A Review

The Role of Phenolic Compounds in the Fight against Cancer – A Review

New Antimicrobial Hexapeptides: Synthesis, Antimicrobial Activities, Cytotoxicity, and Mechanistic Studies

Synthesis, spectroscopic and anti‐tumor studies of polyphenol‐linoleates derived from natural polyphenols

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