Synthesis and preliminary biological assessments of a new class of amphiphilic telomers bearing 5-fluorouracil moieties

The present contribution reports on an original new class of acid-labile thermosensitive polyacrylamides, namely poly(tris(hydroxymethyl)acrylamidomethane-co-(5-acrylamido-5-hydroxymethyl-2,2-dimethyl-1,3-dioxane)) (P(THAM-co-pTHAM)), in which pTHAM only differed from THAM by an acetal group. The lower critical solution temperature (LCST) was controlled by varying the comonomer composition. Additionally, the properties of these new statistical copolymers were investigated and proved that such chemical structures were interesting for smart applications, notably for drug delivery due to the biocompatibility of low molecular weight PTHAM already demonstrated.

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“…1 H NMR (DMSO-d 6 ) d (ppm): 1-2 (Ha, Hb); 3.5-4 (Hd); 4.5-5.4 (Hg); 7.1-7.5 (Hc). 13 C NMR (DMSO-d 6 …”

Section: Methodsmentioning

confidence: 99%

Poly(tris(hydroxymethyl)acrylamidomethane)-based copolymers: a new class of acid-labile thermosensitive polymers

et al. 2012

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“…In order to verify the hypothesis that THAM-derived telomers could be used as a drug delivery system, various biological assays were performed using antimitotic agents such as Arabinofuranosylcytosine (Ara-C) [49] or 5-Fluorouracil [50]. Scheme 5.…”

Section: Drug Transport and Releasementioning

confidence: 99%

Amphiphilic Oligomers: A New Kind of Macromolecular Carrier of Antimitotic Drugs

Contino‐Pépin¹,

Maurizis²,

Pucci

2002

CMCACA

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The last three decades have seen the development of new concepts in the biomedical and medical field based on the principle of drug carrying and in vivo pharmaco-targeting using synthetic carriers such as nanoparticles, liposomes or polymers. This review deals with the synthesis and biomedical applications of a new kind of macromolecular compounds: end-capped oligomers called telomers. The telomers, derived from Tris(hydroxymethyl)aminomethane bearing either a hydro- or a fluorocarbon tail, are described. Their functionality and biocompatibility enhance their potential in the biomedical and medical fields. Such compounds exhibit no cytotoxicity and are able to cross cell membranes by endocytosis. After i.v or per os administration in the animal, they exhibit a very good bio-availability and a homogeneous distribution in all tissues without any accumulation. Their ability to carry in vivo antimitotic drugs has been shown. Moreover, the grafting of different glycoside moieties onto the hydroxyl groups of telomers allows the selective targeting of specific receptors called integrins. Finally, we have shown the potential use of telomers bearing specific peptide ligands, such as RGD sequences, in the selective carrying of antimitotic drugs to the angiogenic zone surrounding tumors.

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“…They can be divided into two kinds of methods. One kind is chemical modification, such as synthesis of low molecular weight 5-FU derivatives, 24 conjugation with polymeric materials, 25 conjugation with peptide, 26 or modification with palmitic acid. 22 The other kind is based on nanocarriers, such as liposomes, 27 nanoparticles, 28 micelles, 29,30 and SLN.…”

Section: Introductionmentioning

confidence: 99%

Engineering of lipid prodrug-based, hyaluronic acid-decorated nanostructured lipid carriers platform for 5-fluorouracil and cisplatin combination gastric cancer therapy

Qu¹,

Zhou²,

Chen³

et al. 2015

IJN

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Purpose The first-line chemotherapy treatment protocol for gastric cancer is combination chemotherapy of 5-fluorouracil (5-FU) and cisplatin (CDDP). The aim of this study was to engineer prodrug-based nanostructured lipid carriers (NLC) platform for codelivery of 5-FU and CDDP to enhance therapy and decrease toxicity. Methods First, 5-FU-stearic acid lipid conjugate was synthesized by two steps. Second, 5-FU-stearic acid prodrug and CDDP were loaded in NLC. Finally, hyaluronic acid (HA) was coated onto NLC surface. Average size, zeta potential, and drug loading capacity of NLC were evaluated. Human gastric cancer cell line BGC823 (BGC823 cells) was used for the testing of in vitro cytotoxicity assays. In vivo antitumor activity of NLC was evaluated in mice bearing BGC823 cells model. Results HA-coated 5-FU-stearic acid prodrug and CDDP-loaded NLC (HA-FU/C-NLC) showed a synergistic effect in combination therapy and displayed the greatest antitumor activity than all of the free drugs or uncoated NLC in vitro and in vivo. Conclusion This work reveals that HA-coated NLC could be used as a novel carrier to code-liver 5-FU and CDDP for gastric cancer therapy. HA-FU/C-NLC could be a promising targeted and combinational therapy in nanomedicine.

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Synthesis and preliminary biological assessments of a new class of amphiphilic telomers bearing 5-fluorouracil moieties

Cited by 14 publications

References 7 publications

Poly(tris(hydroxymethyl)acrylamidomethane)-based copolymers: a new class of acid-labile thermosensitive polymers

Poly(tris(hydroxymethyl)acrylamidomethane)-based copolymers: a new class of acid-labile thermosensitive polymers

Amphiphilic Oligomers: A New Kind of Macromolecular Carrier of Antimitotic Drugs

Engineering of lipid prodrug-based, hyaluronic acid-decorated nanostructured lipid carriers platform for 5-fluorouracil and cisplatin combination gastric cancer therapy

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