<i>In Vitro</i>Evaluation and Characterization of Newly Designed Alkylamidophospholipid Analogues as Anti-Human Immunodeficiency Virus Type 1 Agents

Kucera, Louis S.; Iyer, Nathan; Morris‐Natschke, Susan L.; Chen, S. Y.; Gümüş, Fatma; Ishaq, Khalid S.; Herrmann, Dieter B.

doi:10.1177/095632029800900207

Cited by 8 publications

(4 citation statements)

References 17 publications

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“…All chemicals and solvents were purchased from Sigma-Aldrich and Fisher Scientific except dFdC, which was purchased from the Wake Forest University Baptist Medical Center Pharmacy. NMR data of the lipid intermediates were consistent with those previously reported. , All reactions were carried out under N 2 and extremely dry conditions. Aqueous solubility and partition coefficient measurements were tested as previously described …”

Section: Methodssupporting

confidence: 85%

“…NMR data of the lipid intermediates were consistent with those previously reported. 14,15 All reactions were carried out under N2 and extremely dry conditions. Aqueous solubility and partition coefficient measurements were tested as previously described.…”

Section: Methodsmentioning

confidence: 99%

“…The phospholipid was synthesized as previously published (see Supporting Information for Scheme 1). , Briefly, 3-mercapto-1,2-propanediol ( 1 ) was reacted with bromododecane in ethanol/KOH to yield 1- S -dodecyl-2,3-glycerol ( 2 ). The primary OH was protected by reacting 2 with triphenylmethyl chloride in pyridine.…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and Cytotoxic Activity of Two Novel 1-Dodecylthio-2-decyloxypropyl-3-phosphatidic Acid Conjugates with Gemcitabine and Cytosine Arabinoside

et al. 2003

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Cytosine arabinoside (ara-C) and gemcitabine (dFdC) are two standard chemotherapy drugs used in the treatment of patients with various cancers. To alter the pharmacokinetic and pharmacodynamic properties of these molecules, we conjugated a synthetic phospholipid to both ara-C and dFdC and investigated their chemotherapeutic potential. The dFdC conjugate had greater cytotoxic activity compared with the ara-C conjugate and demonstrated notable cytotoxicity against all human cell lines tested.

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Section: Methodssupporting

confidence: 85%

Section: Methodsmentioning

confidence: 99%

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Synthesis and Cytotoxic Activity of Two Novel 1-Dodecylthio-2-decyloxypropyl-3-phosphatidic Acid Conjugates with Gemcitabine and Cytosine Arabinoside

et al. 2003

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“…These drawbacks of nucleoside therapeutics provoke a profound interest in the search of prodrugs exhibiting an effectiveness superior to that of the parent drug. Among such derivatives, conjugates of nucleosides and phospholipids attracted attention and it was demonstrated that these derivatives display advantageous biological properties over free nucleosides (Ryu et al 1982;Shuto et al 1995;Vodovozova et al 1996;Herrmann et al 1997;Brachwitz et al 1998Brachwitz et al , 1999Kucera et al 1998;Mavromoustakos et al 2001;Alexander et al 2003; for a review, see Morris-Natschke et al 2003).…”

Section: Introductionmentioning

confidence: 98%

A comparison of enzymatic phosphorylation and phosphatidylation of β-l- and β-d-nucleosides

et al. 2007

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Enzymatic 5'-monophosphorylation and 5'-phosphatidylation of a number of beta-L- and beta-D-nucleosides was investigated. The first reaction, catalyzed by nucleoside phosphotransferase (NPT) from Erwinia herbicola, consisted of the transfer of the phosphate residue from p-nitrophenylphosphate (p-NPP) to the 5'-hydroxyl group of nucleoside; the second was the phospholipase D (PLD)-catalyzed transphosphatidylation of L-alpha-lecithin with a series of beta-L- and beta-D-nucleosides as the phosphatidyl acceptor resulted in the formation of the respective phospholipid-nucleoside conjugates. Some beta-L-nucleosides displayed similar or even higher substrate activity compared to the beta-D-enantiomers.

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Lipids and retroviruses

Raulin

2000

Lipids

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The role that lipids may play in enveloped viruses is reviewed. Small lipid molecules can influence retrovirus binding to cell receptors, plasma membrane fusion, and transcription. Palmitoylation following myristoylation of viral glycoproteins is required at the transmembrane level for signal transduction as well as for virion budding and maturation. Cholesterol, ether lipids, phospholipids, platelet-activating factor, phosphatidic acids, diacylglycerols, and several analogs and derivatives influence human immunodeficiency virus (HIV) activity; when conjugated with inhibitors of the viral reverse transcriptase (RT) or aspartyl protease these compounds increase drug effectiveness. On the other hand, L-carnitine, in association with the mitochondrial cardiolipins, inhibits myopathy due to continued prescription of drugs [AZT (zidovudine), ddl (didanoside), or ddC (zalcitabine)], and the redox couple of alpha-lipoic-dihydrolipoic acid prevents production of the reactive oxygen species that trigger apoptosis of infected cells, with sphingomyelin breakdown to ceramides. Retroviral infection induces a shift from phospholipid to neutral fat synthesis in host cells, and a long antiviral, i.e., antiprotease, treatment may lead to lipodystrophy. Multitherapy involving lipids and their analogs in association with anti-RT and antiproteases might enhance the inhibition of growth and proliferation of retroviruses.

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In VitroEvaluation and Characterization of Newly Designed Alkylamidophospholipid Analogues as Anti-Human Immunodeficiency Virus Type 1 Agents

Cited by 8 publications

References 17 publications

Synthesis and Cytotoxic Activity of Two Novel 1-Dodecylthio-2-decyloxypropyl-3-phosphatidic Acid Conjugates with Gemcitabine and Cytosine Arabinoside

Synthesis and Cytotoxic Activity of Two Novel 1-Dodecylthio-2-decyloxypropyl-3-phosphatidic Acid Conjugates with Gemcitabine and Cytosine Arabinoside

A comparison of enzymatic phosphorylation and phosphatidylation of β-l- and β-d-nucleosides

Lipids and retroviruses

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