Found 53 structures.
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1. Compound ID: 1480
Structure type: oligomer
Compound class: N-glycan
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 468
Schäffer C, Messner P "Surface-layer glycoproteins: an example for the diversity of bacterial glycosylation with promising impacts on nanobiotechnology" -
Glycobiology 14(8) (2004) 31R-42R
Bacterial cell surface layers, referred to simply as S-layers, have been described for all major phylogenetic groups of bacteria, which may indicate their pivotal role for a bacterium in its natural habitat. They have the unique ability to assemble into two-dimensional crystalline arrays that completely cover the bacterial cells. Glycosylation represents the most frequent modification of S-layer proteins. S-layer glycoproteins constitute a class of glycoconjugates first isolated in the mid-1970s, but S-layer glycoprotein research is still being regarded as an 'exotic field of glycobiology,' possibly because of its 'noneukaryotic' character. Extensive work over the past 30 years provided evidence of an enormous diversity of S-layer glycoproteins that have been created in nature over 3 billion years of prokaryotic evolution. These glycoconjugates are substantially different from eukaryotic glycoproteins, with regard to both composition and structure; nevertheless, some general structural concepts may be deduced. The awareness of the high application potential of S-layer glycoproteins, especially in combination with their intrinsic cell surface display feature, in the field of modern nanobiotechnology as a base for glycoengineering has recently led to the investigation of the S-layer protein glycosylation process at the molecular level, which has lagged behind the structural studies due to the lack of suitable molecular tools. From that work an even more interesting picture of this class of glycoconjugates is emerging. The availability of purified enzymes from S-layer glycan biosynthesis pathways exhibiting increased stabilities and/or rare sugar specificities in conjunction with preliminary genomic data on S-layer glycan biosynthesis clusters will pave the way for the rational design of S-layer neoglycoproteins.
LPS, bacterial glycosylation, genomic glycosylation loci, glycan diversity, glycoengineering, S-layer nanoglycobiology
NCBI PubMed ID: 15044388Publication DOI: 10.1093/glycob/cwh064Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: paul.messner@boka.ac.at
Institutions: Center for NanoBiotechnology, University of Applied Life Sciences and Natural Resources, Gregor-Mendel-Strasse 33, A-1180 Wien, Austria
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2. Compound ID: 9800
|
S-3)-+ S-3)-+
| |
S-3)-GlcpA-(1-4)-GlcpA-(1-4)-GlcpA-(1-4)-b-D-Glcp1N-(1-4)-Asn-(?--/S-layer protein/ |
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Structure type: oligomer
Aglycon: S-layer protein
Trivial name: cell-surface glycoprotein
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 4100
Raedts J, Kengen SW, van der OJ "Occurrence of L-iduronic acid and putative D-glucuronyl C5-epimerases in prokaryotes" -
Glycoconjugate Journal 28(2) (2011) 57-66
Glycosaminoglycans (GAGs) are polysaccharides that are typically present in a wide diversity of animal tissue. Most common GAGs are well-characterized and pharmaceutical applications exist for many of these compounds, e.g. heparin and hyaluronan. In addition, also bacterial glycosaminoglycan-like structures exist. Some of these bacterial GAGs have been characterized, but until now no bacterial GAG has been found that possesses the modifications that are characteristic for many of the animal GAGs such as sulfation and C5-epimerization. Nevertheless, the latter conversion may also occur in bacterial and archaeal GAGs, as some prokaryotic polysaccharides have been demonstrated to contain L-iduronic acid. However, experimental evidence for the enzymatic synthesis of L-iduronic acid in prokaryotes is as yet lacking. We therefore performed an in silico screen for D-glucuronyl C5-epimerases in prokaryotes. Multiple candidate C5-epimerases were found, suggesting that many more microorganisms are likely to exist possessing an L-iduronic acid residue as constituent of their cell wall polysaccharides.
Lipopolysaccharide, glycosaminoglycans, capsule polysaccharide, L-iduronic acid, D-glucuronyl C5-epimerase
NCBI PubMed ID: 21347714Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: John.Raedts@wur.nl
Institutions: Laboratory of Microbiology, Wageningen University, Dreijenplein 10, 6703 HB Wageningen, The Netherlands
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3. Compound ID: 10214
|
S-3)-+ S-3)-+
| |
S-3)-b-D-GlcpA-(1-4)-b-D-GlcpA-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp1N-(1-4)-Asn |
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Structure type: oligomer
Compound class: N-glycan
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 4240
Mengele R, Sumper M "Drastic differences in glycosylation of related S-layer glycoproteins from moderate and extreme halophiles" -
Journal of Biological Chemistry 267 (1992) 8182-8185
The outer surface of the moderate halophilic archaebacterium Haloferax volcanii (formerly named Halobacterium volcanii) is covered with a hexagonally packed surface (S) layer glycoprotein. The polypeptide (794 amino acid residues) contains 7 N-glycosylation sites. Four of these sites were isolated as glycopeptides and the structure of one of the corresponding saccharides was determined. Oligosaccharides consisting of β-1,4-linked glucose residues are attached to the protein via the linkage unit asparaginyl-glucose. In the related glycoprotein from the extreme halophile Halobacterium halobium, the glucose residues are replaced by sulfated glucuronic acid residues, causing a drastic increase in surface charge density. This is discussed in terms of a recent model explaining the stability of halophilic proteins.
NCBI PubMed ID: 1569073Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Lehrstuhl Biochemie I, Universität Regensburg, Federal Republic of Germany
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4. Compound ID: 10215
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp1N-(1-4)-Asn |
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Structure type: oligomer
Compound class: N-glycan
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4240
Mengele R, Sumper M "Drastic differences in glycosylation of related S-layer glycoproteins from moderate and extreme halophiles" -
Journal of Biological Chemistry 267 (1992) 8182-8185
The outer surface of the moderate halophilic archaebacterium Haloferax volcanii (formerly named Halobacterium volcanii) is covered with a hexagonally packed surface (S) layer glycoprotein. The polypeptide (794 amino acid residues) contains 7 N-glycosylation sites. Four of these sites were isolated as glycopeptides and the structure of one of the corresponding saccharides was determined. Oligosaccharides consisting of β-1,4-linked glucose residues are attached to the protein via the linkage unit asparaginyl-glucose. In the related glycoprotein from the extreme halophile Halobacterium halobium, the glucose residues are replaced by sulfated glucuronic acid residues, causing a drastic increase in surface charge density. This is discussed in terms of a recent model explaining the stability of halophilic proteins.
NCBI PubMed ID: 1569073Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Lehrstuhl Biochemie I, Universität Regensburg, Federal Republic of Germany
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5. Compound ID: 10261
Structure type: oligomer
Compound class: N-glycan
The structure is contained in the following publication(s):
- Article ID: 4250
Hayes BK, Hart GW "Novel forms of protein glycosylation" -
Current Opinion in Structural Biology 4 (1994) 692-696
Journal NLM ID: 9107784Publisher: Elsevier
- Article ID: 4251
Schreiner R, Schnabel E, Wieland F "Novel N-glycosylation in eukaryotes: Laminin contains the linkage unit β-glucosylasparagine" -
Journal of Cell Biology 124 (1994) 1071-1081
The linkage unit to protein of N-linked carbohydrate in eukaryotic glycoproteins consists of N-acetylglucosamine, coupled to the amido nitrogen of asparagine. Additional N-glycosyl linkage units have been unequivocally proven to exist only in the cell surface glycoproteins of various bacteria. Based on immunological analyses, isolation and chemical characterization, we report that one of these units, namely glucose linked to asparagine, exists in the mammalian protein laminin, an extracellular basement membrane component. This finding and the occurrence of identical disaccharide structures in archaebacterial cell surface glycoproteins and mammalian basement membrane protein complexes points towards a conserved and distinct function of these extracellular structural elements. In addition, a method is described to uncover a masked epitope in fixed tissues by chemical O-deglycosylation. This has allowed to morphologically localize the antigen β-Glc-Asn by immunofluorescence to the basement membranes of kidney glomeruli.
NCBI PubMed ID: 8132707Journal NLM ID: 0375356Publisher: New York: Rockefeller University Press
Institutions: Baylor Research Institute, Dallas, Texas 75226
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6. Compound ID: 10414
|
S-2)-+
|
a-Legp5Fo7Ac-(2-4)-b-D-GlcpA-(1-2)-a-D-Manp-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp1N |
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Structure type: oligomer
Trivial name: VP4 glycan
Compound class: N-glycan, S-layer glycan
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_140630,IEDB_144983,IEDB_152206,IEDB_423153,IEDB_983930,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 4325
Kandiba L, Aitio O, Helin J, Guan Z, Permi P, Bamford DH, Eichler J, Roine E "Diversity in prokaryotic glycosylation: an archaeal-derived N-linked glycan contains legionaminic acid" -
Molecular Microbiology 84(3) (2012) 578-593
VP4, the major structural protein of the haloarchaeal pleomorphic virus, HRPV-1, is glycosylated. To define the glycan structure attached to this protein, oligosaccharides released by beta-elimination were analysed by mass spectrometry and nuclear magnetic resonance spectroscopy. Such analyses showed that the major VP4-derived glycan is a pentasaccharide comprising glucose, glucuronic acid, mannose, sulphated glucuronic acid and a terminal 5-N-formyl-legionaminic acid residue. This is the first observation of legionaminic acid, a sialic acid-like sugar, in an archaeal-derived glycan structure. The importance of this residue for viral infection was demonstrated upon incubation with N-acetylneuraminic acid, a similar monosaccharide. Such treatment reduced progeny virus production by half 4 h post infection. LC-ESI/MS analysis confirmed the presence of pentasaccharide precursors on two different VP4-derived peptides bearing the N-glycosylation signal, NTT. The same sites modified by the native host, Halorubrum sp. strain PV6, were also recognized by the Haloferax volcanii N-glycosylation apparatus, as determined by LC-ESI/MS of heterologously expressed VP4. Here, however, the N-linked pentasaccharide was the same as shown to decorate the S-layer glycoprotein in this species. Hence, N-glycosylation of the haloarchaeal viral protein, VP4, is host-specific. These results thus present additional examples of archaeal N-glycosylation diversity and show the ability of Archaea to modify heterologously expressed proteins.
glycosylation, N-acetylneuraminic acid, N-linked, glycoprotein, virus, S-layer glycan, archaea, Haloferax volcanii
NCBI PubMed ID: 22435790Publication DOI: 10.1111/j.1365-2958.2012.08045.xJournal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: elina.roine@helsinki.fi
Institutions: Department of Life Sciences, Ben Gurion University of the Negev, Beersheva 84105, Israel
Methods: 13C NMR, 1H NMR, NMR-2D, b-elimination, MALDI-TOF MS, NMR-1D, LC-ESI-MS
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7. Compound ID: 14181
|
a-L-2dthrPenp4NMe-(1-6)-b-D-Glcp1N4Me-(1-12)-Subst
Subst = 11-chloroarcyriaflavin A = SMILES O=c1{6}[nH]c(=O)c6c1c3c2ccccc2[nH]c3c5{12}[nH]c4c(Cl)cccc4c56;
aL2dthrPenp4N = 4-amino-2,4-dideoxy-threo-pentose |
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Structure type: oligomer
; 665.2008 [M+H]+, 663.1846 [M-H]-
C33H33ClN4O9
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5589
Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS "Cytotoxic indolocarbazoles from Actinomadura melliaura ATCC 39691" -
Journal of Natural Products 78(7) (2015) 1723-1729
Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the isolation and structure elucidation of the four new analogues, AT2433-A3, A4, A5, and B3 (1-4). The availability of this broader set of compounds enabled a subsequent small antibacterial/fungal/cancer SAR study that revealed disaccharyl substitution, N-6 methylation, and C-11 chlorination as key modulators of bioactivity. The slightly improved anticancer potency of the newly reported N-6-desmethyl 1 (compared to 6) contrasts extensive SAR of monoglycosylated rebeccamycin-type topoisomerase I inhibitors where N-6 alkylation has contributed to improved potency and ADME. Complete 2D NMR assignments for the known metabolite BMY-41219 (5) and (13)C NMR spectroscopic data for the known analogue AT2433-B1 (7) are also provided for the first time
cytotoxicity, indolocarbazoles, Actinomadura melliaura
NCBI PubMed ID: 26091285Publication DOI: 10.1021/acs.jnatprod.5b00429Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: jsthorson@uky.edu
Institutions: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, USA, Center for Pharmaceutical Research and Innovation, University of Kentucky, Lexington, USA, School of Pharmacy, University of Maryland Eastern Shore, Princess Anne, USA
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, SEC, CC, cell growth, HPLC-MS, HR-ESI-MS, cell viability assay, evaporation, antimicrobial assay
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8. Compound ID: 14182
|
b-D-Glcp1N4Me-(1-12)-Subst6Me
Subst = 11-chloroarcyriaflavin A = SMILES O=c1{6}[nH]c(=O)c6c1c3c2ccccc2[nH]c3c5{12}[nH]c4c(Cl)cccc4c56 |
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Structure type: monomer
; 550.1381 [M+H]+, 548.1222 [M-H]-
C28H24ClN3O7
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5589
Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS "Cytotoxic indolocarbazoles from Actinomadura melliaura ATCC 39691" -
Journal of Natural Products 78(7) (2015) 1723-1729
Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the isolation and structure elucidation of the four new analogues, AT2433-A3, A4, A5, and B3 (1-4). The availability of this broader set of compounds enabled a subsequent small antibacterial/fungal/cancer SAR study that revealed disaccharyl substitution, N-6 methylation, and C-11 chlorination as key modulators of bioactivity. The slightly improved anticancer potency of the newly reported N-6-desmethyl 1 (compared to 6) contrasts extensive SAR of monoglycosylated rebeccamycin-type topoisomerase I inhibitors where N-6 alkylation has contributed to improved potency and ADME. Complete 2D NMR assignments for the known metabolite BMY-41219 (5) and (13)C NMR spectroscopic data for the known analogue AT2433-B1 (7) are also provided for the first time
cytotoxicity, indolocarbazoles, Actinomadura melliaura
NCBI PubMed ID: 26091285Publication DOI: 10.1021/acs.jnatprod.5b00429Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: jsthorson@uky.edu
Institutions: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, USA, Center for Pharmaceutical Research and Innovation, University of Kentucky, Lexington, USA, School of Pharmacy, University of Maryland Eastern Shore, Princess Anne, USA
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, SEC, CC, cell growth, HPLC-MS, HR-ESI-MS, cell viability assay, evaporation, antimicrobial assay
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9. Compound ID: 14183
|
b-D-Glcp1N4Me-(1-12)-Subst6Me
Subst = arcyriaflavin A = SMILES O=c1{6}[nH]c(=O)c6c1c3c2ccccc2[nH]c3c5{12}[nH]c4ccccc4c56 |
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Structure type: monomer
; 516.1769 [M+H]+, 514.1611 [M-H]-
C28H25N3O7
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5589
Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS "Cytotoxic indolocarbazoles from Actinomadura melliaura ATCC 39691" -
Journal of Natural Products 78(7) (2015) 1723-1729
Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the isolation and structure elucidation of the four new analogues, AT2433-A3, A4, A5, and B3 (1-4). The availability of this broader set of compounds enabled a subsequent small antibacterial/fungal/cancer SAR study that revealed disaccharyl substitution, N-6 methylation, and C-11 chlorination as key modulators of bioactivity. The slightly improved anticancer potency of the newly reported N-6-desmethyl 1 (compared to 6) contrasts extensive SAR of monoglycosylated rebeccamycin-type topoisomerase I inhibitors where N-6 alkylation has contributed to improved potency and ADME. Complete 2D NMR assignments for the known metabolite BMY-41219 (5) and (13)C NMR spectroscopic data for the known analogue AT2433-B1 (7) are also provided for the first time
cytotoxicity, indolocarbazoles, Actinomadura melliaura
NCBI PubMed ID: 26091285Publication DOI: 10.1021/acs.jnatprod.5b00429Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: jsthorson@uky.edu
Institutions: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, USA, Center for Pharmaceutical Research and Innovation, University of Kentucky, Lexington, USA, School of Pharmacy, University of Maryland Eastern Shore, Princess Anne, USA
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, SEC, CC, cell growth, HPLC-MS, HR-ESI-MS, cell viability assay, evaporation, antimicrobial assay
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10. Compound ID: 14184
|
b-D-Glcp1N-(1-12)-Subst
Subst = arcyriaflavin A = SMILES O=c1{6}[nH]c(=O)c6c1c3c2ccccc2[nH]c3c5{12}[nH]c4ccccc4c56 |
Show graphically |
Structure type: monomer
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5589
Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS "Cytotoxic indolocarbazoles from Actinomadura melliaura ATCC 39691" -
Journal of Natural Products 78(7) (2015) 1723-1729
Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the isolation and structure elucidation of the four new analogues, AT2433-A3, A4, A5, and B3 (1-4). The availability of this broader set of compounds enabled a subsequent small antibacterial/fungal/cancer SAR study that revealed disaccharyl substitution, N-6 methylation, and C-11 chlorination as key modulators of bioactivity. The slightly improved anticancer potency of the newly reported N-6-desmethyl 1 (compared to 6) contrasts extensive SAR of monoglycosylated rebeccamycin-type topoisomerase I inhibitors where N-6 alkylation has contributed to improved potency and ADME. Complete 2D NMR assignments for the known metabolite BMY-41219 (5) and (13)C NMR spectroscopic data for the known analogue AT2433-B1 (7) are also provided for the first time
cytotoxicity, indolocarbazoles, Actinomadura melliaura
NCBI PubMed ID: 26091285Publication DOI: 10.1021/acs.jnatprod.5b00429Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: jsthorson@uky.edu
Institutions: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, USA, Center for Pharmaceutical Research and Innovation, University of Kentucky, Lexington, USA, School of Pharmacy, University of Maryland Eastern Shore, Princess Anne, USA
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, SEC, CC, cell growth, HPLC-MS, HR-ESI-MS, cell viability assay, evaporation, antimicrobial assay
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11. Compound ID: 14185
|
a-L-2dthrPenp4NMe-(1-6)-b-D-Glcp1N4Me-(1-12)-Subst6Me
Subst = 11-chloroarcyriaflavin A = SMILES O=c1{6}[nH]c(=O)c6c1c3c2ccccc2[nH]c3c5{12}[nH]c4c(Cl)cccc4c56;
aL2dthrPenp4N = 4-amino-2,4-dideoxy-threo-pentose |
Show graphically |
Structure type: oligomer
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5589
Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS "Cytotoxic indolocarbazoles from Actinomadura melliaura ATCC 39691" -
Journal of Natural Products 78(7) (2015) 1723-1729
Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the isolation and structure elucidation of the four new analogues, AT2433-A3, A4, A5, and B3 (1-4). The availability of this broader set of compounds enabled a subsequent small antibacterial/fungal/cancer SAR study that revealed disaccharyl substitution, N-6 methylation, and C-11 chlorination as key modulators of bioactivity. The slightly improved anticancer potency of the newly reported N-6-desmethyl 1 (compared to 6) contrasts extensive SAR of monoglycosylated rebeccamycin-type topoisomerase I inhibitors where N-6 alkylation has contributed to improved potency and ADME. Complete 2D NMR assignments for the known metabolite BMY-41219 (5) and (13)C NMR spectroscopic data for the known analogue AT2433-B1 (7) are also provided for the first time
cytotoxicity, indolocarbazoles, Actinomadura melliaura
NCBI PubMed ID: 26091285Publication DOI: 10.1021/acs.jnatprod.5b00429Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: jsthorson@uky.edu
Institutions: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, USA, Center for Pharmaceutical Research and Innovation, University of Kentucky, Lexington, USA, School of Pharmacy, University of Maryland Eastern Shore, Princess Anne, USA
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, SEC, CC, cell growth, HPLC-MS, HR-ESI-MS, cell viability assay, evaporation, antimicrobial assay
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12. Compound ID: 14186
|
a-L-2dthrPenp4NMe-(1-6)-b-D-Glcp1N4Me-(1-12)-Subst6Me
Subst = arcyriaflavin A = SMILES O=c1{6}[nH]c(=O)c6c1c3c2ccccc2[nH]c3c5{12}[nH]c4ccccc4c56;
aL2dthrPenp4N = 4-amino-2,4-dideoxy-threo-pentose |
Show graphically |
Structure type: oligomer
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5589
Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS "Cytotoxic indolocarbazoles from Actinomadura melliaura ATCC 39691" -
Journal of Natural Products 78(7) (2015) 1723-1729
Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the isolation and structure elucidation of the four new analogues, AT2433-A3, A4, A5, and B3 (1-4). The availability of this broader set of compounds enabled a subsequent small antibacterial/fungal/cancer SAR study that revealed disaccharyl substitution, N-6 methylation, and C-11 chlorination as key modulators of bioactivity. The slightly improved anticancer potency of the newly reported N-6-desmethyl 1 (compared to 6) contrasts extensive SAR of monoglycosylated rebeccamycin-type topoisomerase I inhibitors where N-6 alkylation has contributed to improved potency and ADME. Complete 2D NMR assignments for the known metabolite BMY-41219 (5) and (13)C NMR spectroscopic data for the known analogue AT2433-B1 (7) are also provided for the first time
cytotoxicity, indolocarbazoles, Actinomadura melliaura
NCBI PubMed ID: 26091285Publication DOI: 10.1021/acs.jnatprod.5b00429Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: jsthorson@uky.edu
Institutions: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, USA, Center for Pharmaceutical Research and Innovation, University of Kentucky, Lexington, USA, School of Pharmacy, University of Maryland Eastern Shore, Princess Anne, USA
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, SEC, CC, cell growth, HPLC-MS, HR-ESI-MS, cell viability assay, evaporation, antimicrobial assay
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13. Compound ID: 14187
|
a-L-2dthrPenp4N-(1-6)-b-D-Glcp1N4Me-(1-12)-Subst6Me
Subst = 11-chloroarcyriaflavin A = SMILES O=c1{6}[nH]c(=O)c6c1c3c2ccccc2[nH]c3c5{12}[nH]c4c(Cl)cccc4c56;
aL2dthrPenp4N = 4-amino-2,4-dideoxy-threo-pentose |
Show graphically |
Structure type: oligomer
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5589
Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS "Cytotoxic indolocarbazoles from Actinomadura melliaura ATCC 39691" -
Journal of Natural Products 78(7) (2015) 1723-1729
Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the isolation and structure elucidation of the four new analogues, AT2433-A3, A4, A5, and B3 (1-4). The availability of this broader set of compounds enabled a subsequent small antibacterial/fungal/cancer SAR study that revealed disaccharyl substitution, N-6 methylation, and C-11 chlorination as key modulators of bioactivity. The slightly improved anticancer potency of the newly reported N-6-desmethyl 1 (compared to 6) contrasts extensive SAR of monoglycosylated rebeccamycin-type topoisomerase I inhibitors where N-6 alkylation has contributed to improved potency and ADME. Complete 2D NMR assignments for the known metabolite BMY-41219 (5) and (13)C NMR spectroscopic data for the known analogue AT2433-B1 (7) are also provided for the first time
cytotoxicity, indolocarbazoles, Actinomadura melliaura
NCBI PubMed ID: 26091285Publication DOI: 10.1021/acs.jnatprod.5b00429Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: jsthorson@uky.edu
Institutions: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, USA, Center for Pharmaceutical Research and Innovation, University of Kentucky, Lexington, USA, School of Pharmacy, University of Maryland Eastern Shore, Princess Anne, USA
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, SEC, CC, cell growth, HPLC-MS, HR-ESI-MS, cell viability assay, evaporation, antimicrobial assay
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14. Compound ID: 14188
|
a-L-2dthrPenp4N-(1-6)-b-D-Glcp1N4Me-(1-12)-Subst6Me
Subst = arcyriaflavin A = SMILES O=c1{6}[nH]c(=O)c6c1c3c2ccccc2[nH]c3c5{12}[nH]c4ccccc4c56;
aL2dthrPenp4N = 4-amino-2,4-dideoxy-threo-pentose |
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Structure type: oligomer
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5589
Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS "Cytotoxic indolocarbazoles from Actinomadura melliaura ATCC 39691" -
Journal of Natural Products 78(7) (2015) 1723-1729
Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the isolation and structure elucidation of the four new analogues, AT2433-A3, A4, A5, and B3 (1-4). The availability of this broader set of compounds enabled a subsequent small antibacterial/fungal/cancer SAR study that revealed disaccharyl substitution, N-6 methylation, and C-11 chlorination as key modulators of bioactivity. The slightly improved anticancer potency of the newly reported N-6-desmethyl 1 (compared to 6) contrasts extensive SAR of monoglycosylated rebeccamycin-type topoisomerase I inhibitors where N-6 alkylation has contributed to improved potency and ADME. Complete 2D NMR assignments for the known metabolite BMY-41219 (5) and (13)C NMR spectroscopic data for the known analogue AT2433-B1 (7) are also provided for the first time
cytotoxicity, indolocarbazoles, Actinomadura melliaura
NCBI PubMed ID: 26091285Publication DOI: 10.1021/acs.jnatprod.5b00429Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: jsthorson@uky.edu
Institutions: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, USA, Center for Pharmaceutical Research and Innovation, University of Kentucky, Lexington, USA, School of Pharmacy, University of Maryland Eastern Shore, Princess Anne, USA
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, SEC, CC, cell growth, HPLC-MS, HR-ESI-MS, cell viability assay, evaporation, antimicrobial assay
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15. Compound ID: 14189
|
b-D-Glcp1N4Me-(1-12)-Subst
Subst = 1,11-dichloroarcyriaflavin A = SMILES O=c1[nH]c(=O)c6c1c3c2cccc(Cl)c2{12}[nH]c3c5[nH]c4c(Cl)cccc4c56 |
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Structure type: monomer
Trivial name: rebeccamycin
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5589
Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS "Cytotoxic indolocarbazoles from Actinomadura melliaura ATCC 39691" -
Journal of Natural Products 78(7) (2015) 1723-1729
Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the isolation and structure elucidation of the four new analogues, AT2433-A3, A4, A5, and B3 (1-4). The availability of this broader set of compounds enabled a subsequent small antibacterial/fungal/cancer SAR study that revealed disaccharyl substitution, N-6 methylation, and C-11 chlorination as key modulators of bioactivity. The slightly improved anticancer potency of the newly reported N-6-desmethyl 1 (compared to 6) contrasts extensive SAR of monoglycosylated rebeccamycin-type topoisomerase I inhibitors where N-6 alkylation has contributed to improved potency and ADME. Complete 2D NMR assignments for the known metabolite BMY-41219 (5) and (13)C NMR spectroscopic data for the known analogue AT2433-B1 (7) are also provided for the first time
cytotoxicity, indolocarbazoles, Actinomadura melliaura
NCBI PubMed ID: 26091285Publication DOI: 10.1021/acs.jnatprod.5b00429Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: jsthorson@uky.edu
Institutions: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, USA, Center for Pharmaceutical Research and Innovation, University of Kentucky, Lexington, USA, School of Pharmacy, University of Maryland Eastern Shore, Princess Anne, USA
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, UV, extraction, SEC, CC, cell growth, HPLC-MS, HR-ESI-MS, cell viability assay, evaporation, antimicrobial assay
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