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Article ; Online: Identification of global inhibitors of cellular glycosylation.

2023 Volume 14, Issue 1, Page(s) 948

Abstract: Small molecule inhibitors of glycosylation enzymes are valuable tools for dissecting glycan functions and potential drug candidates. Screening for inhibitors of glycosyltransferases are mainly performed by in vitro enzyme assays with difficulties moving ... ...

Abstract	Small molecule inhibitors of glycosylation enzymes are valuable tools for dissecting glycan functions and potential drug candidates. Screening for inhibitors of glycosyltransferases are mainly performed by in vitro enzyme assays with difficulties moving candidates to cells and animals. Here, we circumvent this by employing a cell-based screening assay using glycoengineered cells expressing tailored reporter glycoproteins. We focused on GalNAc-type O-glycosylation and selected the GalNAc-T11 isoenzyme that selectively glycosylates endocytic low-density lipoprotein receptor (LDLR)-related proteins as targets. Our screen of a limited small molecule compound library did not identify selective inhibitors of GalNAc-T11, however, we identify two compounds that broadly inhibited Golgi-localized glycosylation processes. These compounds mediate the reversible fragmentation of the Golgi system without affecting secretion. We demonstrate how these inhibitors can be used to manipulate glycosylation in cells to induce expression of truncated O-glycans and augment binding of cancer-specific Tn-glycoprotein antibodies and to inhibit expression of heparan sulfate and binding and infection of SARS-CoV-2.
MeSH term(s)	Animals ; Glycosylation ; SARS-CoV-2/metabolism ; COVID-19 ; Glycoproteins/metabolism ; Polysaccharides/metabolism
Chemical Substances	Glycoproteins ; Polysaccharides
Language	English
Publishing date	2023-02-20
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2553671-0
ISSN	2041-1723 ; 2041-1723
ISSN (online)	2041-1723
ISSN	2041-1723
DOI	10.1038/s41467-023-36598-7
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Article ; Online: Beware, commercial chondroitinases vary in activity and substrate specificity.

Spliid, Charlotte B / Toledo, Alejandro Gomez / Salanti, Ali / Esko, Jeffrey D / Clausen, Thomas Mandel

Glycobiology

2020 Volume 31, Issue 2, Page(s) 103–115

Abstract: Chondroitin sulfate (CS)and dermatan sulfate (DS) are negatively charged polysaccharides found abundantly in animal tissue and have been extensively described to play key roles in health and disease. The most common method to analyze their structure is ... ...

Abstract	Chondroitin sulfate (CS)and dermatan sulfate (DS) are negatively charged polysaccharides found abundantly in animal tissue and have been extensively described to play key roles in health and disease. The most common method to analyze their structure is by digestion into disaccharides with bacterial chondroitinases, followed by chromatography and/or mass spectrometry. While studying the structure of oncofetal CS, we noted a large variation in the activity and specificity of commercially available chondroitinases. Here studied the kinetics of the enzymes and used high-performance liquid chromatography-mass spectrometry to determine the di- and oligosaccharide products resulting from the digestion of commercially available bovine CS A, shark CS C and porcine DS, focusing on chondroitinases ABC, AC and B from different vendors. Application of a standardized assay setup demonstrated large variations in the enzyme-specific activity compared to the values provided by vendors, large variation in enzyme specific activity of similar enzymes from different vendors and differences in the extent of cleavage of the substrates and the generated products. The high variability of different chondroitinases highlights the importance of testing enzyme activity and monitoring product formation in assessing the content and composition of chondroitin and DSs in cells and tissues.
MeSH term(s)	Animals ; Carbohydrate Conformation ; Cattle ; Chondroitin Sulfates/metabolism ; Chondroitinases and Chondroitin Lyases/metabolism ; Dermatan Sulfate/metabolism ; Disaccharides/metabolism ; Substrate Specificity ; Swine
Chemical Substances	Disaccharides ; Dermatan Sulfate (24967-94-0) ; Chondroitin Sulfates (9007-28-7) ; Chondroitinases and Chondroitin Lyases (EC 4.2.2.-)
Language	English
Publishing date	2020-06-22
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1067689-2
ISSN	1460-2423 ; 0959-6658
ISSN (online)	1460-2423
ISSN	0959-6658
DOI	10.1093/glycob/cwaa056
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Article ; Online: Erratum to: Molecular dissection of placental malaria protein VAR2CSA interaction with a chemo-enzymatically synthesized chondroitin sulfate library.

Sugiura, Nobuo / Clausen, Thomas Mandel / Shioiri, Tatsumasa / Gustavsson, Tobias / Watanabe, Hideto / Salanti, Ali

Glycoconjugate journal

2016 Volume 33, Issue 6, Page(s) 995

Language	English
Publishing date	2016-12
Publishing country	United States
Document type	Published Erratum
ZDB-ID	283770-5
ISSN	1573-4986 ; 0282-0080
ISSN (online)	1573-4986
ISSN	0282-0080
DOI	10.1007/s10719-016-9752-5
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Article ; Online: Dissecting structure-function of 3-O-sulfated heparin and engineered heparan sulfates.

Karlsson, Richard / Chopra, Pradeep / Joshi, Apoorva / Yang, Zhang / Vakhrushev, Sergey Y / Clausen, Thomas Mandel / Painter, Chelsea D / Szekeres, Gergo P / Chen, Yen-Hsi / Sandoval, Daniel R / Hansen, Lars / Esko, Jeffrey D / Pagel, Kevin / Dyer, Douglas P / Turnbull, Jeremy E / Clausen, Henrik / Boons, Geert-Jan / Miller, Rebecca L

Science advances

2021 Volume 7, Issue 52, Page(s) eabl6026

Abstract: Heparan sulfate (HS) polysaccharides are master regulators of diverse biological processes via sulfated motifs that can recruit specific proteins. 3-O-sulfation of HS/heparin is crucial for anticoagulant activity, but despite emerging evidence for roles ... ...

Abstract	Heparan sulfate (HS) polysaccharides are master regulators of diverse biological processes via sulfated motifs that can recruit specific proteins. 3-O-sulfation of HS/heparin is crucial for anticoagulant activity, but despite emerging evidence for roles in many other functions, a lack of tools for deciphering structure-function relationships has hampered advances. Here, we describe an approach integrating synthesis of 3-O-sulfated standards, comprehensive HS disaccharide profiling, and cell engineering to address this deficiency. Its application revealed previously unseen differences in 3-O-sulfated profiles of clinical heparins and 3-
Language	English
Publishing date	2021-12-22
Publishing country	United States
Document type	Journal Article
ZDB-ID	2810933-8
ISSN	2375-2548 ; 2375-2548
ISSN (online)	2375-2548
ISSN	2375-2548
DOI	10.1126/sciadv.abl6026
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Article ; Online: Noninvasive detection of any-stage cancer using free glycosaminoglycans.

Bratulic, Sinisa / Limeta, Angelo / Dabestani, Saeed / Birgisson, Helgi / Enblad, Gunilla / Stålberg, Karin / Hesselager, Göran / Häggman, Michael / Höglund, Martin / Simonson, Oscar E / Stålberg, Peter / Lindman, Henrik / Bång-Rudenstam, Anna / Ekstrand, Matias / Kumar, Gunjan / Cavarretta, Ilaria / Alfano, Massimo / Pellegrino, Francesco / Mandel-Clausen, Thomas /

Salanti, Ali / Maccari, Francesca / Galeotti, Fabio / Volpi, Nicola / Daugaard, Mads / Belting, Mattias / Lundstam, Sven / Stierner, Ulrika / Nyman, Jan / Bergman, Bengt / Edqvist, Per-Henrik / Levin, Max / Salonia, Andrea / Kjölhede, Henrik / Jonasch, Eric / Nielsen, Jens / Gatto, Francesco

Proceedings of the National Academy of Sciences of the United States of America

2022 Volume 119, Issue 50, Page(s) e2115328119

Abstract: Cancer mortality is exacerbated by late-stage diagnosis. Liquid biopsies based on genomic biomarkers can noninvasively diagnose cancers. However, validation studies have reported ~10% sensitivity to detect stage I cancer in a screening population and ... ...

Abstract	Cancer mortality is exacerbated by late-stage diagnosis. Liquid biopsies based on genomic biomarkers can noninvasively diagnose cancers. However, validation studies have reported ~10% sensitivity to detect stage I cancer in a screening population and specific types, such as brain or genitourinary tumors, remain undetectable. We investigated urine and plasma free glycosaminoglycan profiles (GAGomes) as tumor metabolism biomarkers for multi-cancer early detection (MCED) of 14 cancer types using 2,064 samples from 1,260 cancer or healthy subjects. We observed widespread cancer-specific changes in biofluidic GAGomes recapitulated in an in vivo cancer progression model. We developed three machine learning models based on urine (
MeSH term(s)	Humans ; Glycosaminoglycans ; Biomarkers, Tumor/genetics ; Liquid Biopsy ; Early Detection of Cancer ; Neoplasms/diagnosis
Chemical Substances	Glycosaminoglycans ; Biomarkers, Tumor
Language	English
Publishing date	2022-12-05
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	209104-5
ISSN	1091-6490 ; 0027-8424
ISSN (online)	1091-6490
ISSN	0027-8424
DOI	10.1073/pnas.2115328119
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Article ; Online: Reformation of the chondroitin sulfate glycocalyx enables progression of AR-independent prostate cancer.

Al-Nakouzi, Nader / Wang, Chris Kedong / Oo, Htoo Zarni / Nelepcu, Irina / Lallous, Nada / Spliid, Charlotte B / Khazamipour, Nastaran / Lo, Joey / Truong, Sarah / Collins, Colin / Hui, Desmond / Esfandnia, Shaghayegh / Adomat, Hans / Clausen, Thomas Mandel / Gustavsson, Tobias / Choudhary, Swati / Dagil, Robert / Corey, Eva / Wang, Yuzhuo /

Chauchereau, Anne / Fazli, Ladan / Esko, Jeffrey D / Salanti, Ali / Nelson, Peter S / Gleave, Martin E / Daugaard, Mads

Nature communications

2022 Volume 13, Issue 1, Page(s) 4760

Abstract: Lineage plasticity of prostate cancer is associated with resistance to androgen receptor (AR) pathway inhibition (ARPI) and supported by a reactive tumor microenvironment. Here we show that changes in chondroitin sulfate (CS), a major glycosaminoglycan ... ...

Abstract	Lineage plasticity of prostate cancer is associated with resistance to androgen receptor (AR) pathway inhibition (ARPI) and supported by a reactive tumor microenvironment. Here we show that changes in chondroitin sulfate (CS), a major glycosaminoglycan component of the tumor cell glycocalyx and extracellular matrix, is AR-regulated and promotes the adaptive progression of castration-resistant prostate cancer (CRPC) after ARPI. AR directly represses transcription of the 4-O-sulfotransferase gene CHST11 under basal androgen conditions, maintaining steady-state CS in prostate adenocarcinomas. When AR signaling is inhibited by ARPI or lost during progression to non-AR-driven CRPC as a consequence of lineage plasticity, CHST11 expression is unleashed, leading to elevated 4-O-sulfated chondroitin levels. Inhibition of the tumor cell CS glycocalyx delays CRPC progression, and impairs growth and motility of prostate cancer after ARPI. Thus, a reactive CS glycocalyx supports adaptive survival and treatment resistance after ARPI, representing a therapeutic opportunity in patients with advanced prostate cancer.
MeSH term(s)	Androgens ; Chondroitin Sulfates ; Glycocalyx/metabolism ; Humans ; Male ; Prostatic Neoplasms, Castration-Resistant/drug therapy ; Signal Transduction ; Tumor Microenvironment
Chemical Substances	Androgens ; Chondroitin Sulfates (9007-28-7)
Language	English
Publishing date	2022-08-13
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, N.I.H., Extramural
ZDB-ID	2553671-0
ISSN	2041-1723 ; 2041-1723
ISSN (online)	2041-1723
ISSN	2041-1723
DOI	10.1038/s41467-022-32530-7
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Article ; Online: Cryo-EM reveals the architecture of placental malaria VAR2CSA and provides molecular insight into chondroitin sulfate binding

Kaituo Wang / Robert Dagil / Thomas Lavstsen / Sandeep K. Misra / Charlotte B. Spliid / Yong Wang / Tobias Gustavsson / Daniel R. Sandoval / Elena Ethel Vidal-Calvo / Swati Choudhary / Mette Ø Agerbaek / Kresten Lindorff-Larsen / Morten A. Nielsen / Thor G. Theander / Joshua S. Sharp / Thomas Mandel Clausen / Pontus Gourdon / Ali Salanti

Nature Communications, Vol 12, Iss 1, Pp 1-

2021 Volume 10

Abstract: In placental malaria, interactions between parasite protein VAR2CSA and human glycosaminoglycan chondroitin sulfate A (CS) sequesters infected red blood cells in the placenta. Here, the authors provide cryo-EM structures of VAR2CSA and placental CS, ... ...

Abstract	In placental malaria, interactions between parasite protein VAR2CSA and human glycosaminoglycan chondroitin sulfate A (CS) sequesters infected red blood cells in the placenta. Here, the authors provide cryo-EM structures of VAR2CSA and placental CS, identifying molecular interactions that could guide design of placental malaria vaccines.
Keywords	Science ; Q
Language	English
Publishing date	2021-05-01T00:00:00Z
Publisher	Nature Portfolio
Document type	Article ; Online
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Article ; Online: The specificity of the malarial VAR2CSA protein for chondroitin sulfate depends on 4-O-sulfation and ligand accessibility.

Spliid, Charlotte B / Toledo, Alejandro Gomez / Sanderson, Patience / Mao, Yang / Gatto, Francesco / Gustavsson, Tobias / Choudhary, Swati / Saldanha, Ana L / Vogelsang, Rasmus P / Gögenur, Ismail / Theander, Thor G / Leach, Franklin E / Amster, I Jonathan / Esko, Jeffrey D / Salanti, Ali / Clausen, Thomas Mandel

The Journal of biological chemistry

2021 Volume 297, Issue 6, Page(s) 101391

Abstract: Placental malaria infection is mediated by the binding of the malarial VAR2CSA protein to the placental glycosaminoglycan, chondroitin sulfate. Recombinant subfragments of VAR2CSA (rVAR2) have also been shown to bind specifically and with high affinity ... ...

Abstract	Placental malaria infection is mediated by the binding of the malarial VAR2CSA protein to the placental glycosaminoglycan, chondroitin sulfate. Recombinant subfragments of VAR2CSA (rVAR2) have also been shown to bind specifically and with high affinity to cancer cells and tissues, suggesting the presence of a shared type of oncofetal chondroitin sulfate (ofCS) in the placenta and in tumors. However, the exact structure of ofCS and what determines the selective tropism of VAR2CSA remains poorly understood. In this study, ofCS was purified by affinity chromatography using rVAR2 and subjected to detailed structural analysis. We found high levels of N-acetylgalactosamine 4-O-sulfation (∼80-85%) in placenta- and tumor-derived ofCS. This level of 4-O-sulfation was also found in other tissues that do not support parasite sequestration, suggesting that VAR2CSA tropism is not exclusively determined by placenta- and tumor-specific sulfation. Here, we show that both placenta and tumors contain significantly more chondroitin sulfate moieties of higher molecular weight than other tissues. In line with this, CHPF and CHPF2, which encode proteins required for chondroitin polymerization, are significantly upregulated in most cancer types. CRISPR/Cas9 targeting of CHPF and CHPF2 in tumor cells reduced the average molecular weight of cell-surface chondroitin sulfate and resulted in a marked reduction of rVAR2 binding. Finally, utilizing a cell-based glycocalyx model, we showed that rVAR2 binding correlates with the length of the chondroitin sulfate chains in the cellular glycocalyx. These data demonstrate that the total amount and cellular accessibility of chondroitin sulfate chains impact rVAR2 binding and thus malaria infection.
MeSH term(s)	Antigens, Protozoan/chemistry ; Antigens, Protozoan/genetics ; Antigens, Protozoan/metabolism ; Chondroitin Sulfates/chemistry ; Chondroitin Sulfates/genetics ; Chondroitin Sulfates/metabolism ; Female ; Glycocalyx/chemistry ; Glycocalyx/genetics ; Glycocalyx/metabolism ; HEK293 Cells ; HeLa Cells ; Humans ; Malaria, Falciparum/genetics ; Malaria, Falciparum/metabolism ; N-Acetylgalactosaminyltransferases/genetics ; N-Acetylgalactosaminyltransferases/metabolism ; Placenta/metabolism ; Plasmodium falciparum/genetics ; Plasmodium falciparum/metabolism ; Pregnancy ; Protozoan Proteins/chemistry ; Protozoan Proteins/genetics ; Protozoan Proteins/metabolism
Chemical Substances	Antigens, Protozoan ; Protozoan Proteins ; VAR2CSA protein, Plasmodium falciparum ; Chondroitin Sulfates (9007-28-7) ; N-Acetylgalactosaminyltransferases (EC 2.4.1.-) ; chondroitin synthase (EC 2.4.1.175)
Language	English
Publishing date	2021-11-08
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	2997-x
ISSN	1083-351X ; 0021-9258
ISSN (online)	1083-351X
ISSN	0021-9258
DOI	10.1016/j.jbc.2021.101391
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Article ; Online: Reformation of the chondroitin sulfate glycocalyx enables progression of AR-independent prostate cancer

Nader Al-Nakouzi / Chris Kedong Wang / Htoo Zarni Oo / Irina Nelepcu / Nada Lallous / Charlotte B. Spliid / Nastaran Khazamipour / Joey Lo / Sarah Truong / Colin Collins / Desmond Hui / Shaghayegh Esfandnia / Hans Adomat / Thomas Mandel Clausen / Tobias Gustavsson / Swati Choudhary / Robert Dagil / Eva Corey / Yuzhuo Wang /

Anne Chauchereau / Ladan Fazli / Jeffrey D. Esko / Ali Salanti / Peter S. Nelson / Martin E. Gleave / Mads Daugaard

Nature Communications, Vol 13, Iss 1, Pp 1-

2022 Volume 14

Abstract: Chondroitin sulfate (CS) is one of the most abundant glycosaminoglycans in prostate cancers. Here the authors show that inhibition of the androgen receptor pathway leads to the upregulation of CS, which promotes prostate cancer growth and metastasis. ...

Abstract	Chondroitin sulfate (CS) is one of the most abundant glycosaminoglycans in prostate cancers. Here the authors show that inhibition of the androgen receptor pathway leads to the upregulation of CS, which promotes prostate cancer growth and metastasis.
Keywords	Science ; Q
Language	English
Publishing date	2022-08-01T00:00:00Z
Publisher	Nature Portfolio
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Molecular dissection of placental malaria protein VAR2CSA interaction with a chemo-enzymatically synthesized chondroitin sulfate library.

Sugiura, Nobuo / Clausen, Thomas Mandel / Shioiri, Tatsumasa / Gustavsson, Tobias / Watanabe, Hideto / Salanti, Ali

Glycoconjugate journal

2016 Volume 33, Issue 6, Page(s) 985–994

Abstract: Placental malaria, a serious infection caused by the parasite Plasmodium falciparum, is characterized by the selective accumulation of infected erythrocytes (IEs) in the placentas of the pregnant women. Placental adherence is mediated by the malarial ... ...

Abstract	Placental malaria, a serious infection caused by the parasite Plasmodium falciparum, is characterized by the selective accumulation of infected erythrocytes (IEs) in the placentas of the pregnant women. Placental adherence is mediated by the malarial VAR2CSA protein, which interacts with chondroitin sulfate (CS) proteoglycans present in the placental tissue. CS is a linear acidic polysaccharide composed of repeating disaccharide units of D-glucuronic acid and N-acetyl-D-galactosamine that are modified by sulfate groups at different positions. Previous reports have shown that placental-adhering IEs were associated with an unusually low sulfated form of chondroitin sulfate A (CSA) and that a partially sulfated dodecasaccharide is the minimal motif for the interaction. However, the fine molecular structure of this CS chain remains unclear. In this study, we have characterized the CS chain that interacts with a recombinant minimal CS-binding region of VAR2CSA (rVAR2) using a CS library of various defined lengths and sulfate compositions. The CS library was chemo-enzymatically synthesized with bacterial chondroitin polymerase and recombinant CS sulfotransferases. We found that C-4 sulfation of the N-acetyl-D-galactosamine residue is critical for supporting rVAR2 binding, whereas no other sulfate modifications showed effects. Interaction of rVAR2 with CS is highly correlated with the degree of C-4 sulfation and CS chain length. We confirmed that the minimum structure binding to rVAR2 is a tri-sulfated CSA dodecasaccharide, and found that a highly sulfated CSA eicosasaccharide is a more potent inhibitor of rVAR2 binding than the dodecasaccharides. These results suggest that CSA derivatives may potentially serve as targets in therapeutic strategies against placental malaria.
Language	English
Publishing date	2016-12
Publishing country	United States
Document type	Journal Article
ZDB-ID	283770-5
ISSN	1573-4986 ; 0282-0080
ISSN (online)	1573-4986
ISSN	0282-0080
DOI	10.1007/s10719-016-9685-z
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