The synthesis, characterization, and preliminary biological evaluation of 1-β- -arabinofuranosylcytosine-5′-diphosphate- -1,2-dipalmitin

MacCoss, Malcolm; Ryu, Eung K.; Matsushita, Tatsuo

doi:10.1016/0006-291x(78)91220-2

Cited by 39 publications

(24 citation statements)

References 12 publications

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“…Thus, condensation of 17c-g with ara-CMP morpholidate [46] in pyridine gave 18c-g with yields ranging from 15-38% (scheme 4) [43]. Likewise, condensation of 17c and f with cytidine 5 -phosphoromorpholidate [47] gave 19c and f, the C2-epimers of 18c and f, in 29-31% yield [43].…”

Section: Thioether Lipidsmentioning

confidence: 90%

Synthesis of sulfur-containing glycerophospholipids

Davy

Wang

Notter

et al. 2007

Journal of Sulfur Chemistry

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Section: Thioether Lipidsmentioning

confidence: 90%

Synthesis of sulfur-containing glycerophospholipids

Davy

Wang

Notter

et al. 2007

Journal of Sulfur Chemistry

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“…In contrast to a simple suspension of 26 in H 2 O, the sample prepared as described showed good inhibition of cell growth of L1210 cells and of mouse myeloma MPC 11 cells. However, the activity of the ara-C nucleolipid in its micellar form was lower than that of 5'-O-adamantanoyl-ara-C and of 5'-O-palmitoyl-ara-C (29) [36].…”

Section: Fig 2 Liposidomycinsmentioning

confidence: 92%

“…In 1978, MacCoss and co-workers [33] published the synthesis of the single diastereoisomers of 1-b-d-arabinofuranosylcytosine-5'-diphosphate-l-1,2-dipalmitine Fig. 4.…”

Section: Fig 2 Liposidomycinsmentioning

confidence: 99%

Nucleolipids: Natural Occurrence, Synthesis, Molecular Recognition, and Supramolecular Assemblies as Potential Precursors of Life and Bioorganic Materials

Rosemeyer

2005

C&B

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Nucleolipids are hybrid molecules composed of a nucleobase, a nucleoside, a nucleotide or an oligonucleotide (either DNA or RNA), and a lipophilic moiety, which might be either simply a single- or double-chained alkyl (or alkenyl) moiety or a carbocyclic hydrocarbon such as cholesterol, a vitamin, or a bile acid. This review covers all aspects of nucleolipids, namely their natural occurrence, their synthesis, their molecular recognition, as well as aggregation behavior, either in aqueous or non-aqueous solution. Potential future aspects of nucleolipids in material sciences and for the elucidation of biochemical reactions in living cells are discussed.

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“…In the late 1970s and early 1980s, groups began to investigate cytotoxicity after either alkyl chain additions to ara-C or conjugation of ara-C to phospholipids [59,60]. Raetz et al used natural or synthetic phospholipids to chemically modify ara-C.…”

Section: Phospholipid Ara-c Conjugatesmentioning

confidence: 99%

“…Previous investigators have had many successes with phospholipid/nucleoside analog conjugates; however, there are still improvements that can be made to these compounds [59,60,[62][63][64]73]. In our laboratory, we focused on the synthesis of a thioether phospholipid (1-S-dodecyl-2-Odecyl-thioglycero-3-phosphatidic acid) conjugated to either gemcitabine or ara-C [75].…”

Section: Phospholipid Gemcitabine and Ara-c Conjugatesmentioning

confidence: 99%

Lipid Nucleoside Conjugates for the Treatment of Cancer

Richard¹,

Kucera²

2005

CPD

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Phospholipid nucleoside conjugates and nucleosides with chemical additions to the hydroxyl and amino moieties have been used since the 1970s in order to increase the biological activity of the parent compound. Previous investigators have found that adding lipid moieties to ara-C or chemically linking ara-C to a phospholipid creates a prodrug that exhibits superior cytotoxic activity compared to ara-C alone when used in animal tumor models. The novel ara-C molecules reveal different pharmacological profiles from the parent compound such as decreased catabolism by cytidine deaminase, increased plasma half-life, and release of nucleoside monophosphate, a reaction that bypasses the rate limiting initial nucleoside phosphorylation. Additionally, these compounds were able to penetrate the blood-brain barrier and were active against tumor cells implanted i.c. The purpose of this review is to briefly cover the history and successes of previous investigators who have synthesized and tested these phospholipid ara-C conjugates, to discuss recent phospholipid ara-C and fludarabine conjugates, and to discuss the synthetic design and synthesis of a novel phospholipid gemcitabine conjugate. These phospholipid nucleoside conjugates possess the potential to have superior anti-neoplastic cytotoxicity profiles with fewer side effects than the parent nucleoside and merit further investigation.

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The synthesis, characterization, and preliminary biological evaluation of 1-β- -arabinofuranosylcytosine-5′-diphosphate- -1,2-dipalmitin

Cited by 39 publications

References 12 publications

Synthesis of sulfur-containing glycerophospholipids

Synthesis of sulfur-containing glycerophospholipids

Nucleolipids: Natural Occurrence, Synthesis, Molecular Recognition, and Supramolecular Assemblies as Potential Precursors of Life and Bioorganic Materials

Lipid Nucleoside Conjugates for the Treatment of Cancer

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