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Journal articles on the topic 'N-butyl deoxynojirimycin'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Matos, Carlos R. R., Rosangela S. C. Lopes, and Claudio C. Lopes. "Synthesis of 1-Deoxynojirimycin and N-Butyl-1-deoxynojirimycin." Synthesis 1999, no. 04 (1999): 571–73. http://dx.doi.org/10.1055/s-1999-3430.

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2

Matos, Carlos R. R., Rosangela S. C. Lopes, and Claudio C. Lopes. "ChemInform Abstract: Synthesis of 1-Deoxynojirimycin and N-Butyl-1-deoxynojirimycin." ChemInform 30, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199931249.

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3

Wang, Jiajia, Yunyan Zhao, Wei Zhao, Peng Wang, and Jing Li. "Total synthesis of N-butyl-1-deoxynojirimycin." Journal of Carbohydrate Chemistry 35, no. 8-9 (2016): 445–54. http://dx.doi.org/10.1080/07328303.2017.1330415.

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4

Mehta, Anand, Serguey Ouzounov, Robert Jordan, et al. "Imino Sugars That are Less Toxic but More Potent as Antivirals, In Vitro, Compared with N-n-Nonyl DNJ." Antiviral Chemistry and Chemotherapy 13, no. 5 (2002): 299–304. http://dx.doi.org/10.1177/095632020201300505.

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Imino sugar glucosidase inhibitors have selective antiviral activity against certain enveloped, mammalian viruses. Deoxynojirimycins (DNJs) modified by N-alkylation to contain a nine carbon atom side chain (N-n-nonyl-deoxynojirimycin; N-nonyl-DNJ, NN-DNJ) were shown to be, for example, at least 20 times more potent in inhibiting hepatitis B virus (HBV) and bovine viral diarrhoea virus (BVDV) in cell based assays than the non-alkylated DNJ. These data suggested that modification of the alkyl side chain could influence antiviral activity. Previous work has focused on varying side chain length. I

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5

Boudewyn, Lauren C., Jakub Sikora, Ladislav Kuchar, Jana Ledvinova, and Steven U. Walkley. "Assessment of n-butyl-deoxynojirimycin as a therapeutic option for mucolipidosis type IV." Molecular Genetics and Metabolism 117, no. 2 (2016): S29. http://dx.doi.org/10.1016/j.ymgme.2015.12.204.

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6

Woodhouse, Stephen D., Caroline Smith, Maud Michelet, et al. "Iminosugars in Combination with Interferon and Ribavirin Permanently Eradicate Noncytopathic Bovine Viral Diarrhea Virus from Persistently Infected Cells." Antimicrobial Agents and Chemotherapy 52, no. 5 (2008): 1820–28. http://dx.doi.org/10.1128/aac.01181-07.

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ABSTRACT We evaluated interferon (IFN) and ribavirin (RBV) as dual therapy and as part of triple-combination therapies with the iminosugars N-butyl-deoxynojirimycin (NB-DNJ), N-nonyl-deoxynojirimycin, and N-7-oxanonyl-6-deoxymethyl-galactonojirimycin. The ability of these compounds to clear bovine viral diarrhea virus (BVDV), a surrogate model for hepatitis C virus (HCV), from a persistently infected Madin-Darby bovine kidney cells cell line was determined by monitoring the secretion of viral RNA and the infectivity of secreted virions. In the BVDV system, after treatment with IFN-RBV alone, v

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7

Chang, Jinhong, Lijuan Wang, Dongling Ma, et al. "Novel Imino Sugar Derivatives Demonstrate Potent Antiviral Activity against Flaviviruses." Antimicrobial Agents and Chemotherapy 53, no. 4 (2009): 1501–8. http://dx.doi.org/10.1128/aac.01457-08.

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ABSTRACT Imino sugars, such as N-butyl-deoxynojirimycin and N-nonyl-deoxynojirimycin (NNDNJ), are glucose analogues that selectively inhibit cellular α-glucosidase I and II in the endoplasmic reticulum and exhibit antiviral activities against many types of enveloped viruses. Although these molecules have broad-spectrum antiviral activity, their development has been limited by a lack of efficacy and/or selectivity. We have previously reported that a DNJ derivative with a hydroxylated cyclohexyl side chain, called OSL-95II, has an antiviral efficacy similar to that of NNDNJ but significantly les

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8

Tierney, M., J. Pottage, H. Kessler, et al. "The Tolerability and Pharmacokinetics of N-Butyl-deoxynojirimycin in Patients with Advanced HIV Disease (ACTG 100)." Journal of Acquired Immune Deficiency Syndromes & Human Retrovirology 10, no. 5 (1995): 549–53. http://dx.doi.org/10.1097/00042560-199510050-00008.

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9

Tierney, M., J. Pottage, H. Kessler, et al. "The Tolerability and Pharmacokinetics of N-Butyl-deoxynojirimycin in Patients with Advanced HIV Disease (ACTG 100)." Journal of Acquired Immune Deficiency Syndromes & Human Retrovirology 10, no. 5 (1995): 549–53. http://dx.doi.org/10.1097/00042560-199512050-00008.

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10

Ribas, Graziela S., Ricardo Pires, Janice Carneiro Coelho, et al. "Oxidative stress in Niemann‐Pick type C patients: a protective role of N‐butyl‐deoxynojirimycin therapy." International Journal of Developmental Neuroscience 30, no. 6 (2012): 439–44. http://dx.doi.org/10.1016/j.ijdevneu.2012.07.002.

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11

MELLOR, Howard R., David C. A. NEVILLE, David J. HARVEY, Frances M. PLATT, Raymond A. DWEK, and Terry D. BUTTERS. "Cellular effects of deoxynojirimycin analogues: inhibition of N-linked oligosaccharide processing and generation of free glucosylated oligosaccharides." Biochemical Journal 381, no. 3 (2004): 867–75. http://dx.doi.org/10.1042/bj20031824.

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In the accompanying paper [Mellor, Neville, Harvey, Platt, Dwek and Butters (2004) Biochem. J. 381, 861–866] we treated HL60 cells with N-alk(en)yl-deoxynojirimycin (DNJ) compounds to inhibit glucosphingolipid (GSL) biosynthesis and identified a number of non-GSL-derived, small, free oligosaccharides (FOS) most likely produced due to inhibition of the oligosaccharide-processing enzymes α-glucosidases I and II. When HL60 cells were treated with concentrations of N-alk(en)ylated DNJ analogues that inhibited GSL biosynthesis completely, N-butyl- and N-nonyl-DNJ inhibited endoplasmic reticulum (ER

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12

MELLOR, Howard R., David C. A. NEVILLE, David J. HARVEY, Frances M. PLATT, Raymond A. DWEK, and Terry D. BUTTERS. "Cellular effects of deoxynojirimycin analogues: uptake, retention and inhibition of glycosphingolipid biosynthesis." Biochemical Journal 381, no. 3 (2004): 861–66. http://dx.doi.org/10.1042/bj20031822.

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Deoxynojirimycin (DNJ) analogues are inhibitors of ceramide glucosyltransferase (CGT), which catalyses the first step in the glucosphingolipid (GSL) biosynthetic pathway. We have synthesized a series of DNJ analogues to study the contribution of N-alk(en)yl side chains (C4, C9 or C18) to the behaviour of these analogues in cultured HL60 cells. When cells were treated for 16 h at non-cytotoxic concentrations of inhibitor, a 40–50% decrease in GSL levels was measured by HPLC analysis of GSL-derived oligosaccharides following ceramide glycanase digestion of GSL and 2-aminobenzamide labelling of t

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13

MELLOR, Howard R., Frances M. PLATT, Raymond A. DWEK, and Terry D. BUTTERS. "Membrane disruption and cytotoxicity of hydrophobic N-alkylated imino sugars is independent of the inhibition of protein and lipid glycosylation." Biochemical Journal 374, no. 2 (2003): 307–14. http://dx.doi.org/10.1042/bj20030348.

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The N-alkyl moiety of N-alkylated imino sugars is crucial for therapeutic activities of these compounds as inhibitors of glycosphingolipid (GSL) biosynthesis and as antivirals. The improved potency afforded by a long N-alkyl moiety is coincident with increased compound-induced cytotoxicity. Therefore, in the present study, we examined the mechanism of this cytotoxicity in detail. Despite N-butyl-deoxynojirimycin and N-butyl-deoxygalactonojirimycin inhibiting the glycosylation of ceramide to glucosylceramide, ceramide levels did not increase in HL60 cells treated with these compounds. Long-chai

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14

Miller, Joanna L., Ruben Lachica, Andrew C. Sayce, et al. "Liposome-Mediated Delivery of Iminosugars Enhances Efficacy against Dengue VirusIn Vivo." Antimicrobial Agents and Chemotherapy 56, no. 12 (2012): 6379–86. http://dx.doi.org/10.1128/aac.01554-12.

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ABSTRACTA key challenge faced by promising antiviral drugs, such as iminosugars, isin vivodelivery to achieve effective levels of drug without toxicity. Four iminosugars, all deoxynojirimycin (DNJ) derivatives—N-butyl DNJ (NB-DNJ),N-nonyl DNJ,N-(9-methoxynonyl) DNJ, andN-(6′-[4″-azido-2″-nitrophenylamino]hexyl)-1-DNJ (NAP-DNJ)—potently inhibited both the percentage of cells infected with dengue virus and release of infectious virus from primary human monocyte-derived macrophages, demonstrating their efficacy in primary cells. In a lethal antibody-dependent enhancement mouse model of dengue pat

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15

D’Alonzo, Daniele, Maria De Fenza, Caterina Porto та ін. "N-Butyl-l-deoxynojirimycin (l-NBDNJ): Synthesis of an Allosteric Enhancer of α-Glucosidase Activity for the Treatment of Pompe Disease". Journal of Medicinal Chemistry 60, № 23 (2017): 9462–69. http://dx.doi.org/10.1021/acs.jmedchem.7b00646.

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16

Zamoner, Luís O. B., Valquiria Aragão-Leoneti, and Ivone Carvalho. "Iminosugars: Effects of Stereochemistry, Ring Size, and N-Substituents on Glucosidase Activities." Pharmaceuticals 12, no. 3 (2019): 108. http://dx.doi.org/10.3390/ph12030108.

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N-substituted iminosugar analogues are potent inhibitors of glucosidases and glycosyltransferases with broad therapeutic applications, such as treatment of diabetes and Gaucher disease, immunosuppressive activities, and antibacterial and antiviral effects against HIV, HPV, hepatitis C, bovine diarrhea (BVDV), Ebola (EBOV) and Marburg viruses (MARV), influenza, Zika, and dengue virus. Based on our previous work on functionalized isomeric 1,5-dideoxy-1,5-imino-D-gulitol (L-gulo-piperidines, with inverted configuration at C-2 and C-5 in respect to glucose or deoxynojirimycin (DNJ)) and 1,6-dideox

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17

Esposito, Anna, Daniele D’Alonzo, Maria De Fenza, et al. "Synthesis and Therapeutic Applications of Iminosugars in Cystic Fibrosis." International Journal of Molecular Sciences 21, no. 9 (2020): 3353. http://dx.doi.org/10.3390/ijms21093353.

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Iminosugars are sugar analogues endowed with a high pharmacological potential. The wide range of biological activities exhibited by these glycomimetics associated with their excellent drug profile make them attractive therapeutic candidates for several medical interventions. The ability of iminosugars to act as inhibitors or enhancers of carbohydrate-processing enzymes suggests their potential use as therapeutics for the treatment of cystic fibrosis (CF). Herein we review the most relevant advances in the field, paying attention to both the chemical synthesis of the iminosugars and their biolo

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18

Alonzi, Dominic S., David C. A. Neville, Robin H. Lachmann, Raymond A. Dwek та Terry D. Butters. "Glucosylated free oligosaccharides are biomarkers of endoplasmic- reticulum α-glucosidase inhibition". Biochemical Journal 409, № 2 (2007): 571–80. http://dx.doi.org/10.1042/bj20070748.

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The inhibition of ER (endoplasmic reticulum) α-glucosidases I and II by imino sugars, including NB-DNJ (N-butyl-deoxynojirimycin), causes the retention of glucose residues on N-linked oligosaccharides. Therefore, normal glycoprotein trafficking and processing through the glycosylation pathway is abrogated and glycoproteins are directed to undergo ERAD (ER-associated degradation), a consequence of which is the production of cytosolic FOS (free oligosaccharides). Following treatment with NB-DNJ, FOS were extracted from cells, murine tissues and human plasma and urine. Improved protocols for anal

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19

Scanlan, Christopher N., Ralph Pantophlet, Mark R. Wormald та ін. "The Broadly Neutralizing Anti-Human Immunodeficiency Virus Type 1 Antibody 2G12 Recognizes a Cluster of α1→2 Mannose Residues on the Outer Face of gp120". Journal of Virology 76, № 14 (2002): 7306–21. http://dx.doi.org/10.1128/jvi.76.14.7306-7321.2002.

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ABSTRACT 2G12 is a broadly neutralizing human monoclonal antibody against human immunodeficiency virus type-1 (HIV-1) that has previously been shown to bind to a carbohydrate-dependent epitope on gp120. Here, site-directed mutagenesis and carbohydrate analysis were used to define further the 2G12 epitope. Extensive alanine scanning mutagenesis showed that elimination of the N-linked carbohydrate attachment sequences associated with residues N295, N332, N339, N386, and N392 by N→A substitution produced significant decreases in 2G12 binding affinity to gp120JR-CSF. Further mutagenesis suggested

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20

Durantel, David, Norica Branza-Nichita, Sandra Carrouée-Durantel, Terry D. Butters, Raymond A. Dwek, and Nicole Zitzmann. "Study of the Mechanism of Antiviral Action of Iminosugar Derivatives against Bovine Viral Diarrhea Virus." Journal of Virology 75, no. 19 (2001): 8987–98. http://dx.doi.org/10.1128/jvi.75.19.8987-8998.2001.

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ABSTRACT The glucose-derived iminosugar derivatives N-butyl- andN-nonyl-deoxynojirimycin (DNJ) have an antiviral effect against a broad spectrum of viruses including Bovine viral diarrhea virus (BVDV). For BVDV, this effect has been attributed to the reduction of viral secretion due to an impairment of viral morphogenesis caused by the ability of DNJ-based iminosugar derivatives to inhibit ER α-glucosidases (N. Zitzmann, A. S. Mehta, S. Carrouée, T. D. Butters, F. M. Platt, J. McCauley, B. S. Blumberg, R. A. Dwek, and T. M. Block, Proc. Natl. Acad. Sci. USA 96:11878–11882, 1999). Here we pres

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21

Ouzounov, Serguey, Anand Mehta, Raymond A. Dwek, Timothy M. Block та Robert Jordan. "The combination of interferon α-2b and n-butyl deoxynojirimycin has a greater than additive antiviral effect upon production of infectious bovine viral diarrhea virus (BVDV) in vitro: implications for hepatitis C virus (HCV) therapy". Antiviral Research 55, № 3 (2002): 425–35. http://dx.doi.org/10.1016/s0166-3542(02)00075-x.

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22

Leng, Houfu, Adel Ersek, Emma Morris, Beatriz Gamez Molina, Claire M. Edwards, and Nicole Horwood. "Altering Glycosphingolipid Composition to Improve Multiple Myeloma Bone Complication." Blood 132, Supplement 1 (2018): 1942. http://dx.doi.org/10.1182/blood-2018-99-112237.

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Abstract Multiple myeloma (MM) is an incurable cancer of plasma cells (PC), with a median survival of 5-7 years. Osteolytic bone disease and skeletal complications occur in more than 80% of MM patients and significantly contribute to the morbidity and mortality of these patients. Glycosphingolipid (GSL), an essential constituent of the outer leaflet of the cellular membrane, is altered in MM and other hematological cancers. We previously reported that GM3, a subtype of GSL promotes osteoclastogenesis. On the other hand, the GSL synthase inhibitor N-butyl-deoxynojirimycin (NB-DNJ) reduces myelo

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23

Wang, Jiajia, and Yunyan Zhao. "An Improved Synthetic Method for N-Butyl-1-Deoxynojirimycin." Medicinal chemistry 6, no. 7 (2016). http://dx.doi.org/10.4172/2161-0444.1000388.

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24

Amiri, Mahdi, and Hassan Y. Naim. "The effect of N‐butyl‐deoxynojirimycin on the structure, function and trafficking of intestinal glycoproteins." FASEB Journal 27, S1 (2013). http://dx.doi.org/10.1096/fasebj.27.1_supplement.553.16.

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