Synthese d'un telomere perfluorocarbone derive du tris‐(hydroxymethyl) <sup>14</sup>C et <sup>13</sup>C‐acrylamidomethane (F‐TAC)

Azim, Muhlisun; Madelmont, Jean‐Claude; Rapp, Maryse; Maurizis, Jean‐Claude; Pavia, A. A.; Pucci, Bernard; Veyre, A.

doi:10.1002/jlcr.2580331210

Cited by 3 publications

(2 citation statements)

References 5 publications

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“…It could be prepared via the oxa‐Michael addition of amino‐polyethylene glycol 3 to acrylate [1‐ 14 C]‐ 4 . In turn, [1‐ 14 C]‐acrylate 4 can be prepared via the addition of vinyl magnesium bromide to 14 CO 2 …”

Section: Resultsmentioning

confidence: 99%

Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG)_n) and [1‐¹⁴C]‐CA (PEG)_n via oxa‐Michael addition of amino‐polyethylene glycols to propiolates vs to acrylates

Song

Chen

Lin

et al. 2019

Labelled Comp Radiopharmac

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Synthesis of carboxy-polyethylene glycol-amine (CA (PEG) n ) via oxa-Michael addition of amino-polyethylene glycols to either acrylates or propiolates was investigated. Compared with the oxa-Michael addition to acrylates, the corresponding addition to propiolates was found to proceed under mild reaction conditions and afford the adducts in high yields from a broad scope of substrates. A two-step efficient and convenient synthesis of benzyl [1-14 C]propiolate from 14 CO 2 was therefore developed and utilized as a common synthon to afford practical and high yielding access to [1-14 C]-CA (PEG) n .

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Section: Resultsmentioning

confidence: 99%

Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG)_n) and [1‐¹⁴C]‐CA (PEG)_n via oxa‐Michael addition of amino‐polyethylene glycols to propiolates vs to acrylates

Song

Chen

Lin

et al. 2019

Labelled Comp Radiopharmac

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“…In order to assess the biodisposition of the F8TAC telomer in rat and mouse, we labeled the amide carbonyl group of THAM monomer with 13 C and 14 C [45]. After i.v.…”

Section: Biocompatibility and Bioavailability Of Tham-derived Telomersmentioning

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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Disposition in rat of a new fluorinated, biocompatible, non-ionic telomeric carrier

Maurizis¹,

Azim²,

Rapp³

et al. 1994

Xenobiotica

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1. The disposition of the new fluorinated, biocompatible, non-ionic telomeric carrier trisacryl conjugate (F-TAC) labelled with 13C and 14C on the amide function has been studied in the rat after p.o. and i.v. administration. 2. After i.v. administration, excretion measurements have shown that radioactivity was eliminated mainly in the urine (69% within 24 h), and that faecal excretion was low (8% within 72 h). After p.o. administration, faecal elimination was significantly increased (30% within 72 h). No radioactivity was eliminated as 14CO2, after either route of administration. 3. After i.v. administration, plasma radioactivity exhibited a biphasic decrease, with t1/2 = 20 min for the first phase and 29.5 h for the second phase. The maximal plasma concentration was obtained 40 min after oral dosing, followed by a monoexponential decrease with t1/2 = 38.1 h. The ratio AUC (p.o.)/AUC (i.v.) as an assessment of bioavailability was 0.22. 4. After both i.v. and p.o. administration, a relatively homogeneous concentration of radioactivity was found in most organs, close or below the plasma concentration, indicating that tissues do not exhibit a high affinity for this molecule. In addition, F-TAC did not cross the blood-brain barrier. 5. Analysis of urine and plasma on DOWEX AG1X2 anionic resin showed that < 20% of the radioactivity was bound to this support. 13C- and 19F-nmr analysis of the non-bound radioactivity identified it to unchanged F-TAC, with bound radioactivity being due to polyanionic telomers arising from the hydrolysis of the amide function.(ABSTRACT TRUNCATED AT 250 WORDS)

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Synthese d'un telomere perfluorocarbone derive du tris‐(hydroxymethyl) ¹⁴C et ¹³C‐acrylamidomethane (F‐TAC)

Cited by 3 publications

References 5 publications

Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG)_n) and [1‐¹⁴C]‐CA (PEG)_n via oxa‐Michael addition of amino‐polyethylene glycols to propiolates vs to acrylates

Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG)_n) and [1‐¹⁴C]‐CA (PEG)_n via oxa‐Michael addition of amino‐polyethylene glycols to propiolates vs to acrylates

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

Disposition in rat of a new fluorinated, biocompatible, non-ionic telomeric carrier

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Synthese d'un telomere perfluorocarbone derive du tris‐(hydroxymethyl) 14C et 13C‐acrylamidomethane (F‐TAC)

Cited by 3 publications

References 5 publications

Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG)n) and [1‐14C]‐CA (PEG)n via oxa‐Michael addition of amino‐polyethylene glycols to propiolates vs to acrylates

Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG)n) and [1‐14C]‐CA (PEG)n via oxa‐Michael addition of amino‐polyethylene glycols to propiolates vs to acrylates

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

Disposition in rat of a new fluorinated, biocompatible, non-ionic telomeric carrier

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Synthese d'un telomere perfluorocarbone derive du tris‐(hydroxymethyl) ¹⁴C et ¹³C‐acrylamidomethane (F‐TAC)

Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG)_n) and [1‐¹⁴C]‐CA (PEG)_n via oxa‐Michael addition of amino‐polyethylene glycols to propiolates vs to acrylates

Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG)_n) and [1‐¹⁴C]‐CA (PEG)_n via oxa‐Michael addition of amino‐polyethylene glycols to propiolates vs to acrylates