Synthesis and anti-tumor activity of vinyl polymers containing 5-fluorouracils attached via carbamoyl bonds to organosilicon groups

Ouchi, Tatsuro; Hagita, Kazuo; Kwashima, M.; Inoi, Takeshi; Tashiro, Tazuko

doi:10.1016/0168-3659(88)90040-5

Cited by 17 publications

(8 citation statements)

References 8 publications

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“…On increasing the generation of dendritic compound, the in vitro antitumor activities of the dendrimer(G‐2)/5‐FU conjugate were higher due to increasing 5‐FU content and increased spacer length with ester linkages with keeping the cytotoxicities against normal cells low. This is good agreement with the published results 21, 22…”

Section: Resultssupporting

confidence: 94%

“…This is good agreement with the published results. 21,22 In vivo antitumor activity against mice bearing sarcoma 180 The in vivo antitumor activities of the conjugates against mice bearing sarcoma 180 tumor cell line were summarized in Table II. The ratio, T/C was used as the index of the antitumor activity: As shown in Table II, G-1/5-FU, and G-2/5-FU conjugates were showed higher antitumor activities at all dosages due to slower hydrolysis and the introduction of ascorbic acid as a pseudotarget moiety.…”

Section: In Vitro Cytotoxicity Of the Conjugatesmentioning

confidence: 99%

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Antitumor and antiangiogenic active dendrimer/5‐fluorouracil conjugates

Lee

Bala

Lee

et al. 2013

J Biomedical Materials Res

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Antitumor and antiangiogenic active dendritic compounds conjugated with 5-fluorouracil (5-FU) were synthesized and characterized. First, the core structure based on ascorbic acid and dicarboxylic acid was synthesized, amidated with ethylenediamine. For the synthesis of higher generated dendrimer, it was reacted further with methyl acrylate to increase molecular weight through Michael addition reaction, followed by the continuous repeating amidation reaction, finally, used to synthesize covalently bound dendrimer/5-FU conjugates. The in vitro cytotoxicities of the conjugates was evaluated with mouse mammary carcinoma, mouse leukemia, and human histiocytic lymphoma as cancer cell lines and mouse liver cells as a normal cell line, and showed lower values than 5-FU. The in vivo antitumor activities of the conjugates against mice bearing sarcoma 180 tumor cell line were better than 5-FU. Especially, Second generated dendrimer (G-2)/5-FU conjugates showed excellent in vivo antitumor as well as antiangiogenic activities evaluated by the embryo chorioallantoic membrane assay due to slow hydrolysis rate and the amount of 5-FU released.

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Section: Resultssupporting

confidence: 94%

Section: In Vitro Cytotoxicity Of the Conjugatesmentioning

confidence: 99%

Antitumor and antiangiogenic active dendrimer/5‐fluorouracil conjugates

Lee

Bala

Lee

et al. 2013

J Biomedical Materials Res

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“…In addition, the compounds 7 and 9 with ester linkage showed different antitumor activity and cytotoxicities, which may be associated with the different spacer lengths. Basically, the antitumor activity of the conjugates with ester linkages increased with increasing the average molecular weight [24,25].…”

Section: Syntheses Of Antitumor and Antiangiogenic Compoundsmentioning

confidence: 97%

Syntheses and Evaluations of Antitumor and Antiangiogenic Compounds Conjugated with 5-Fluorouracil and Ascorbic Acid

Lee

Kim

et al. 2008

Journal of Bioactive and Compatible Polymers

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The new multifunctional antitumor conjugates containing ascorbic acid and 5-fluorouracil (5-FU) were synthesized from bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, ascorbic acid and/or a chain spacer, followed by condensation with 5-FU. The synthesized conjugates were identified by 1 H and 13 C NMR spectroscopies and elemental analysis. The in vitro cytotoxicities of these conjugates were determined and their antitumor activity was evaluated. The IC 50 values (drug concentration for 50% inhibition of tumor growth) indicated that the synthesized conjugates were better inhibitors against cancer cells and were lower in cytotoxicity than the free 5-FU. The in vivo antitumor activity of the conjugates was examined against mice bearing the sarcoma 180 tumor cells. The life spans (T/C) of mice treated with the conjugates were higher than for the free 5-FU. In addition, the synthesized conjugates showed excellent antiangiogenic activity, based on the embryo chorioallantoic membrane assay.

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“…For example, 5fluorouracil can be applied locally or orally in the therapy of the alimentary tract, urinary bladder and prostate gland cancers. The conjugations of this therapeutic agent as a pendant group to polyethylene glycol (Ouchi et al, 1986(Ouchi et al, , 1992 or to vinyl polymer chain as substituent form examples of its macromolecular prodrugs (Ouchi et al, 1988).…”

Section: Fig 1 Structure Of the Macromolecular Prodrugsmentioning

confidence: 99%