An easy stereospecific synthesis of 1-amino-2,5-anhydro-1-deoxy-d-mannitol and arylamino derivatives

Claustre, Samantha; Bringaud, Frédéric; Azéma, Laurent; Baron, Rudi; Périé, Jacques; Willson, Michèle

doi:10.1016/s0008-6215(99)00040-3

Cited by 27 publications

(19 citation statements)

References 12 publications

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“…On the basis of these findings, we suggest that Holman's observations of inhibition of fructose uptake by mannitolamine derivatives were the result of competitive uptake as opposed to merely binding. It is noteworthy that the ratio of NBDG/NBDF uptake correlates with the ratio measured previously for 14 C-labeled analogues of glucose and fructose, [18] thus underlining that NBD conjugates are reliable probes for evaluating carbohydrate uptake.…”

Section: Synthesis Of Fluorescent Conjugatessupporting

confidence: 77%

“…Fructosamine was synthesized from glucose by the procedure reported by Auger et al [13] 1-Amino-2,5-anhydro-d-mannitol was synthesized from glucosamine by a modified procedure. [14] Claustre et al used an acidic resin to produce HONO in situ, and carried out a subsequent neutralization with basic ion-exchange resin. Our modifications to the method include exchanging the chloride ion of the glucosamine·HCl salt with nitrite, which then allows the reaction to occur without excess acid.…”

Section: Synthesis Of Fluorescent Conjugatesmentioning

confidence: 99%

“…The synthesis was completed by forming the oxime 5, followed by hydrogenolysis. [14] 1-Amino-1-deoxyfructose was synthesized through Amadori rearrangement of d-glucose with dibenzylamine, followed by hydrogenolysis of the benzyl groups. [13] Competitive uptake of NBDM as a fructose uptake inhibitory mechanism Transport of each analogue (NBDM, NBDF, and NBDG) was evaluated with breast cancer MCF7 cells, which have previously been observed to exhibit enhanced fructose uptake.…”

Section: Synthesis Of Fluorescent Conjugatesmentioning

confidence: 99%

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Fluorescent THF‐Based Fructose Analogue Exhibits Fructose‐Dependent Uptake

et al. 2013

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Recent publications suggest that high dietary fructose might play a significant role in cancer metabolism and can exacerbate a number of aspects of metabolic syndrome. Addressing the role that fructose plays in human health is a controversial question and requires a detailed understanding of many factors including the mechanism of fructose transport into healthy and diseased cells. Fructose transport into cells is thought to be largely mediated by the passive hexose transporters Glut2 and Glut5. To date, no probes that can be selectively transported by one of these enzymes but not by the other have been identified. The data presented here indicate that, in MCF-7 cells, a 1-amino-2,5-anhydro-D-mannitol-based fluorescent NBDM probe is transported twice as efficiently as fructose and that this takes place with the aid of Glut5. Its Glut5 specificity and differential uptake in cancer cells and in normal cells suggest this NBDM probe as a potentially useful tool for cross-cell-line correlation of Glut5 transport activity.

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Section: Synthesis Of Fluorescent Conjugatessupporting

confidence: 77%

Section: Synthesis Of Fluorescent Conjugatesmentioning

confidence: 99%

Section: Synthesis Of Fluorescent Conjugatesmentioning

confidence: 99%

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Fluorescent THF‐Based Fructose Analogue Exhibits Fructose‐Dependent Uptake

et al. 2013

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“…2 -structure 4), namely the triskelion. The detailed protocols of the triskelion synthesis and characterization ( 1 H, 13 protocol 34 and then derivatized with 5-20 equivalents of molecules bearing a thiol-hook (ethanedithiol -EDT and triskelion linker). The detailed protocols of this transformation, as well as the complete characterization of the nal products are available in ESI -Section 2.1; † Briey, the previously described thioacetylation conditions were used (10-20 mM M-Unit aldehyde at pH 1, 4-72 h at 50 C (ref.…”

Section: 32mentioning

confidence: 99%

Regioselective chitosan end-group activation: the triskelion approach

et al. 2017

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Chitosan (CS) end-group conjugation methods are rarely reported in the literature, mainly since the CS terminal aldehyde moiety produced by nitrous acid depolymerization is only present in trace amounts in its reactive form. In a previous study, our group proposed an intermolecular thioacetylation process that allowed terminal conjugation of thiol-reactive species to chitosan with 50% efficiency. However, this reaction is incompatible with acid-labile substituents and the conversion efficiency of CS end-groups could be limited by the size of the thiol-reactive species engaged in the reaction, mainly by steric hindrance since two substituents are required to obtain the stabilized thioacetal derivative. In the present study, we developed a novel CS end-group thioacetylation approach relying on a new regioselective linker that bears three thiol moieties. This trivalent linker, referred to as triskelion here, was specifically designed for activation of the CS 2,5-anhydro-D-mannose (M-Unit) end-group and consists of a thiolhook for efficient aldehyde conjugation through an intramolecular reaction and a thiol-tail that remains available for subsequent end-group functionalization with any thiol-reactive species. The chemical synthesis of this linker provided the desired material with high yields over three steps. The in situ intramolecular thioacetylation process between the triskelion linker and 2,5-anhydro-D-mannose (MUnit, monomeric) was assessed by semi-quantitative LC-MS studies, revealing that the corresponding intramolecular thioacetal largely predominated ($90%). This regioselective derivatization was also performed onto M-Unit CS aldehydes and the desired CS-b-triskelion conjugates were obtained with functionalization degrees over 85%, as confirmed by NMR spectroscopy ( 1 H and DOSY). As a final assessment of the CS-b-triskelion thiol-tail reactivity, these conjugates were successfully engaged with thiol-reactive magnetic beads into disulfide bond displacement with 50% efficiency. The proposed CS terminal activation with the triskelion linker opens new perspectives for biomedical applications, especially brush-like surface modifications and other copolymer formation through disulfide linkages or Michael-type additions.

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“…In each case, inhibition was noncompetitive, and the observed inhibition was partially reversible for phloretin and completely reversible for cytochalasin B. Interestingly, glucosamine derivatives related to compound 47 (Fig. 14) [136] were effective inhibitors of trypanosomal glucose transport, and K i values as low as 200 mM were reported [140]. Various triazine dyes also inhibit glucose transport in mammalian cell lines, and these were subsequently found to inhibitor trypanosomal glucose transport as well [129].…”

Section: Inhibitors Of Parasitic Glucose Metabolism and Glycosomal Trmentioning

confidence: 99%

Antiprotozoal/Antiparasitic Agents

Woster

2010

Burger's Medicinal Chemistry and Drug Discovery

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Collectively, diseases caused by parasitic protozoa, including human African trypanosomiasis ( HAT ), Chagas' disease and leishmaniasis, threaten more than 550 million people worldwide and cause nearly 150,000 deaths annually. The causative organisms for these diseases are unicellular trypanosomatid parasites of the genera Trypanosoma brucei , Trypanosoma cruzi , and Leishmania sp., respectively. Drug therapies available for these diseases have not changed significantly in the past 50 years, and currently used agents are far less than satisfactory due to extreme toxicity, and because resistant parasitic strains are becoming more prevalent. These diseases are confined to impoverished or rural areas of Mexico, Central America, South America, sub‐Saharan Africa, the Middle East, Indonesia, and India. As such, drug discovery efforts against trypanosomatid diseases are limited because patients in underdeveloped areas cannot afford therapy, and because the infected population is too small to justify the required research expenditures. In addition, antiparasitic research in Third World nations is often hampered by economic issues and political turmoil, virtually assuring that the world's most impoverished people will continue to bear the major burden of parasitic disease. Clearly, there is a need for new anti‐infective agents that are potent, nontoxic and inexpensive to manufacture. In this chapter, the etiology of these diseases and their current treatment are described. The chapter also deals with medicinal chemistry aspects of efforts to identify new drug targets for parasitic diseases, and to produce novel inhibitors of trypanosomatid growth for use as antiparasitic agents.

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An easy stereospecific synthesis of 1-amino-2,5-anhydro-1-deoxy-d-mannitol and arylamino derivatives

Cited by 27 publications

References 12 publications

Fluorescent THF‐Based Fructose Analogue Exhibits Fructose‐Dependent Uptake

Fluorescent THF‐Based Fructose Analogue Exhibits Fructose‐Dependent Uptake

Regioselective chitosan end-group activation: the triskelion approach

Antiprotozoal/Antiparasitic Agents

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