Structural Significance of the Benzoyl Group at the C-3′-N Position of Paclitaxel for Nitric Oxide and Tumor Necrosis Factor Production by Murine Macrophages

Kirikae, Teruo; Ojima, Iwao; Ma, Zhuping; Kirikae, Fumiko; Hirai, Yoshikazu; Nakano, Masayasu

doi:10.1006/bbrc.1998.8409

Cited by 21 publications

(17 citation statements)

References 36 publications

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“…Occupancy of the high-affinity binding sites on microtubules with a taxane analog that binds selectively to these sites shifts the equilibrium binding of paclitaxel toward the site responsible for gene induction. Results by Kirakae et al [20] also fit a model analogous to that depicted in Fig. 8 However, their data suggest that taxanes can be agonists, antagonists, or partial agonists at the low-affinity site responsible for gene induction.…”

Section: Additional Components Of the Lps Receptor Signaling Complex:mentioning

confidence: 92%

“…Of 11 compounds examined, including docetaxel, only paclitaxel and its 7-acetyl analog induced TNFa expression. Likewise, Kirikae observed that taxane-induced TNFa and NO production in murine peritoneal macrophages was very sensitive to changes at the C-3V-N position [19,20]. Among a group of 12 paclitaxel analogs consisting of 11 aryl-substituted benzamides and the C-3V-( p-phenyl) phenylacetamide, only six compounds retained the ability to stimulate production of TNFa and NO in murine macrophages.…”

Section: Additional Components Of the Lps Receptor Signaling Complex:mentioning

confidence: 97%

“…Overall, the structures associated with induction of COX-2, TNFa [18,20,21,29], or NO synthase [20,21] in murine macrophages are greatly restricted compared to the structures associated with gene induction in human monocytes (vide infra) or OVCA 420 cells Fig. 7.…”

Section: Additional Components Of the Lps Receptor Signaling Complex:mentioning

confidence: 99%

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The immunopharmacology of paclitaxel (Taxol®), docetaxel (Taxotere®), and related agents

Fitzpatrick

Wheeler

2003

International Immunopharmacology

103

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Section: Additional Components Of the Lps Receptor Signaling Complex:mentioning

confidence: 92%

Section: Additional Components Of the Lps Receptor Signaling Complex:mentioning

confidence: 97%

See 1 more Smart Citation

The immunopharmacology of paclitaxel (Taxol®), docetaxel (Taxotere®), and related agents

Fitzpatrick

Wheeler

2003

International Immunopharmacology

103

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“…A multiplicity of pathways appears to play a role in cytotoxicity with the relative importance of each not completely elucidated. The activities include apoptosis, microtubule arrest, cell cycle disruption, DNA fragmentation [161], inhibition of DNA synthesis [162], interference with membrane function [163], topoisomerase inhibition, and induction of NO production [164].…”

Section: Paclitaxel (Taxol)mentioning

confidence: 99%

Mechanisms of Anti-Cancer Agents Emphasis on Oxidative Stress and Electron Transfer

Kovacic

Osuna²

2000

CPD

150

105

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A large body of evidence has accumulated indicating involvement of oxidative stress (OS) in the mode of action of various bioactive substances, including those of the immune system. The data for anticancer drugs (main and miscellaneous) are summarized herein. Although diverse origins pertain, reactive oxygen species (ROS) are frequently generated by redox cycling via electron transfer (ET) groups, such as quinones (or phenolic precursors), metal complexes (or complexors), aromatic nitro compounds (or reduced products) and conjugated imines (or iminium species). We believe it is not coincidental that these functionalities are frequently found in anticancer agents or their metabolites. Generally, the ET moieties display reduction potentials in the physiologically active range. Often ROS are also implicated in more traditional rationales, namely, enzyme inhibition, membrane or DNA insult, and interference with DNA or protein synthesis. A multi-faceted approach to mechanism appears to be the most logical. Significantly, the unifying theme of ET-OS also applies to other drug categories, as well as to toxins, carcinogens, hormones, and enzymes. Since this theoretical framework aids in our understanding of drug action, it can serve as a useful tool in the design of more active and safer pharmaceuticals.

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“…Peritoneal Mö were prepared from C3H/HeN mice according to the procedures described previously [31]. Brie¯y, murine peritoneal exudate cells (PEC) were isolated by peritoneal lavage 4 days after intraperitoneal injection of 1.5 ml of thioglycolate broth 3%.…”

Section: Cell Preparationsmentioning

confidence: 99%

Non-standard biological activities of lipopolysaccharide from Helicobacter pylori

Matsuyama¹,

Kirikae

et al. 2001

Journal of Medical Microbiology

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As assessed by the lipopolysaccharide (LPS)-speci®c chromogenic Limulus amoebocyte lysate (LAL) assay, Helicobacter pylori LPS extracted by the phenol-water procedure showed full potency to coagulate LAL, as did LPS from Salmonella minnesota and Escherichia coli. However, pretreatment of H. pylori LPS with polymyxin B, which easily destroys the endotoxic activity of enterobacterial LPS/lipid A, had little effect on the LAL coagulation activity, although the same treatment of E. coli LPS markedly diminished its activity. The H. pylori LPS induced very weak production of nitric oxide (NO) or tumour necrosis factor (TNF) by murine macrophages and TNF by human peripheral whole blood in vitro in comparison with S. minnesota LPS. These ®ndings indicate that H. pylori LPS has the unique endotoxic characteristic of retaining full LAL coagulation activity with polymyxin B resistance, despite losing its endotoxic potencies such as the ability to induce NO and TNF production.

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Structural Significance of the Benzoyl Group at the C-3′-N Position of Paclitaxel for Nitric Oxide and Tumor Necrosis Factor Production by Murine Macrophages

Cited by 21 publications

References 36 publications

The immunopharmacology of paclitaxel (Taxol®), docetaxel (Taxotere®), and related agents

The immunopharmacology of paclitaxel (Taxol®), docetaxel (Taxotere®), and related agents

Mechanisms of Anti-Cancer Agents Emphasis on Oxidative Stress and Electron Transfer

Non-standard biological activities of lipopolysaccharide from Helicobacter pylori

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