Regioselective synthesis and biological profiling of butyric and phenylalkylcarboxylic esters derivated from D-mannose and xylitol: influence of alkyl chain length on acute toxicity

Pouillart, P.; Douillet, Olivier; Scappini, Barbara; Gozzini, Antonella; Santini, Valeria; Grossi, Alberto; Pagliai, Gabriella; Strippoli, Pierluigi; Rigacci, Luigi; Ronco, G.; Villa, Pierre

doi:10.1016/s0928-0987(98)00011-6

Cited by 23 publications

(16 citation statements)

References 25 publications

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“…However, 13 C NMR data of simple esters of xylitol have been reported. 34 -41 Thus, 1-acylxylitol esters have been analysed using CDCl 3 as solvent 34 and deuterated pyridine, 35,36 and these data reveal that 13 C NMR signals for wileyonlinelibrary.com/journal/pi 37 and also that of the pentaacetate of xylitol in CDCl 3 , 38 and a mixed acid pentaacylxylitol, and includes 1,5-dibenzoyltriacetate in CDCl 3 . 39 However, for us the work of Cramer et al 40 is very informative; thus, along with presenting 1 H NMR data, the 13 C NMR analyses of various acylated species obtained from the enzyme-catalysed reaction of xylitol with saturated fatty acids in DMSO-d 6 showed that mainly the 1-acylxylitol, 2-acylxylitol and 1,5-diacylxylitol esters were obtained.…”

Section: Nmr Analyses Of Pxs Prepolymer and Pxs Gelmentioning

confidence: 99%

Characterization of the prepolymer and gel of biocompatible poly(xylitol sebacate) in comparison with poly(glycerol sebacate) using a combination of mass spectrometry and nuclear magnetic resonance

Moorhoff

Cook

et al. 2014

Polymer International

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Atmospheric pressure chemical ionization (negative ion) and electrospray ionization (positive and negative ion) mass spectrometry and nuclear magnetic resonance ( 1 H NMR and 13 C NMR) were used to characterize the prepolymer (i.e. uncrosslinked) poly(xylitol sebacate) (PXS), prepared by condensation of xylitol [X] and sebacic acid [S], and this was compared with poly(glycerol sebacate) (PGS), prepared by condensation of glycerol [G] and [S]. The PXS prepolymer, prepared at 118 ∘ C/24 h, gave predominantly 1-acyl-[XS] and 1,5-diacyl-[SXS] species and smaller amounts of 2-acyl substitutions. At 130 ∘ C/24 h an increase of the amount of the 1-acyl and 1,5-diacyl substitutions in the [(SX) n ], [S(XS) n ] and [(XS) n X] series was identified, as was found for the analogous PGS prepolymer ([(SG) n ], [S(GS) n ] and [(GS) n G] series). Novel tetrahydrofuranyl species were found in the PXS prepolymer. Further polymerization of the PXS prepolymer gave a gel which when analysed using 13 C NMR was shown to mainly contain 1-acyl and 1,5-diacyl substitutions.

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Section: Nmr Analyses Of Pxs Prepolymer and Pxs Gelmentioning

confidence: 99%

Characterization of the prepolymer and gel of biocompatible poly(xylitol sebacate) in comparison with poly(glycerol sebacate) using a combination of mass spectrometry and nuclear magnetic resonance

Moorhoff

Cook

et al. 2014

Polymer International

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“…These newly synthesized molecules are formed by a mannose or a xylitol bound as ester to one to five butyrate moieties. Details of chemistry, synthesis and structure of these molecules are reported elsewhere ( Pouillart, 1998). Butyrate derivatives were freshly prepared immediately before experiments and used in cell cultures at the final concentrations of 0.1, 0.5 and 1 m M .…”

Section: Methodsmentioning

confidence: 99%

“…Most recently, preliminary results of a trial have been reported in which sodium phenylbutyrate was given to patients affected by myelodysplastic syndromes ( Gore et al , 1996 ). Considering these experiences, we have analysed the in vitro anti‐leukaemic effects of three newly synthesized stable monosaccharide butyrate derivatives ( Pouillart et al , 1998 ). In these compounds a mannose molecule is bound as ester to one to five butyrate moieties, conferring pharmacological stability.…”

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confidence: 99%

Butyrate‐stable monosaccharide derivatives induce maturation and apoptosis in human acute myeloid leukaemia cells

et al. 1998

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The rapid degradation and subsequent lack of efficacy of n-butyric acid in vivo has been improved by the synthesis of monosaccharide stable pro-drugs of butyric acid. We studied the effects of D1 (O-n-butanoyl-2,3-O-isopropylidene-alpha-D-mannofuranoside), G1 (1-O-n-butanoyl-D,L-xylitol), and F1 (1-O-n-butanoyl 2,3-O-isopropylidene-D,L-xylitol) on the maturation and proliferation of AML cell lines HL 60 and FLG 29.1 and of purified blast cells from 10 cases of de novo acute myeloid leukaemia (AML). AML cell maturation was measured by surface antigen expression, morphology and cytochemistry. Toxicology in mice was also evaluated (DL50 1000 mg/kg). In HL 60 cells G1 and D1 increased the expression of CD15 and CD11a (presenting 62% of promyelo-metamyelocytes), and in 7/10 cases of primary AMLs that of CD11a, CD11b, CD15, and myeloperoxidase. D1, G1 and F1 induced a dose-dependent inhibition of tritiated thymidine uptake. Apoptosis (evaluated by flow cytometry and agarose gel electrophoresis) was induced in AML blasts by D1 and F1 (79% and 94% respectively for HL 60 cells) and, with less effect, by G1 (27%). The persistence of maturative and apoptotic activity in these new pro-drugs of butyric acid, hydrolysed only inside the tumour cell, suggests a possible use in differentiation therapy of myelodysplastic syndromes and AMLs.

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“…[19][20] The sugar moieties present in these esters can increase drug water solubility, decrease toxicity, and contribute to the bioactivity of the natural products. Hence, sugar esters are used as anticancer agents, 21 insecticides, 22 antibacterial, and antifungal agents. [23][24][25][26] Attachment of aryl and acyl group(s) to the sugar molecules enhances the biological activities many times than that of the parent sugar 27,28 .…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents

Matin¹,

Bhuiyan²,

Azad³

et al. 2017

10.5267/j.ccl

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Regioselective synthesis and biological profiling of butyric and phenylalkylcarboxylic esters derivated from D-mannose and xylitol: influence of alkyl chain length on acute toxicity

Cited by 23 publications

References 25 publications

Characterization of the prepolymer and gel of biocompatible poly(xylitol sebacate) in comparison with poly(glycerol sebacate) using a combination of mass spectrometry and nuclear magnetic resonance

Characterization of the prepolymer and gel of biocompatible poly(xylitol sebacate) in comparison with poly(glycerol sebacate) using a combination of mass spectrometry and nuclear magnetic resonance

Butyrate‐stable monosaccharide derivatives induce maturation and apoptosis in human acute myeloid leukaemia cells

Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents

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