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Article: Protecting-Group-Mediated Diastereoselective Synthesis of C4′-Methylated Uridine Analogs and Their Activity against the Human Respiratory Syncytial Virus

Köllmann, Christoph / Sake, Svenja M / Jones, Peter G / Pietschmann, Thomas / Werz, Daniel B

Journal of organic chemistry. 2020 Feb. 10, v. 85, no. 6

2020

Abstract: Adjusting the protecting group strategy, from an alkyl ether to a bidentate ketal at the carbohydrate backbone of uridine, facilitates a switchable diastereoselective α- or β-C4′/C5′-spirocyclopropanation. Using these spirocyclopropanated nucleosides as ... ...

Abstract	Adjusting the protecting group strategy, from an alkyl ether to a bidentate ketal at the carbohydrate backbone of uridine, facilitates a switchable diastereoselective α- or β-C4′/C5′-spirocyclopropanation. Using these spirocyclopropanated nucleosides as key intermediates, we synthesized a variety of C4′-methylated d-ribose and l-lyxose-configured uridine derivatives by a base-mediated ring-opening of the spirocyclopropanol moiety. Investigations of antiviral activity against the human respiratory syncytial virus were carried out for selected derivatives, showing moderate activity.
Keywords	antiviral properties ; carbohydrates ; chemical reactions ; diastereoselective synthesis ; diastereoselectivity ; moieties ; organic compounds ; uridine
Language	English
Dates of publication	2020-0210
Size	p. 4267-4278.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.9b03425
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Protecting-Group-Mediated Diastereoselective Synthesis of C4'-Methylated Uridine Analogs and Their Activity against the Human Respiratory Syncytial Virus.

Köllmann, Christoph / Sake, Svenja M / Jones, Peter G / Pietschmann, Thomas / Werz, Daniel B

The Journal of organic chemistry

2020 Volume 85, Issue 6, Page(s) 4267–4278

Abstract: Adjusting the protecting group strategy, from an alkyl ether to a bidentate ketal at the carbohydrate backbone of uridine, facilitates a switchable diastereoselective α- or β-C4'/C5'-spirocyclopropanation. Using these spirocyclopropanated nucleosides as ... ...

Abstract	Adjusting the protecting group strategy, from an alkyl ether to a bidentate ketal at the carbohydrate backbone of uridine, facilitates a switchable diastereoselective α- or β-C4'/C5'-spirocyclopropanation. Using these spirocyclopropanated nucleosides as key intermediates, we synthesized a variety of C4'-methylated d-ribose and l-lyxose-configured uridine derivatives by a base-mediated ring-opening of the spirocyclopropanol moiety. Investigations of antiviral activity against the human respiratory syncytial virus were carried out for selected derivatives, showing moderate activity.
MeSH term(s)	Antiviral Agents/pharmacology ; Humans ; Nucleosides ; Respiratory Syncytial Virus, Human ; Uridine/pharmacology
Chemical Substances	Antiviral Agents ; Nucleosides ; Uridine (WHI7HQ7H85)
Language	English
Publishing date	2020-02-26
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.9b03425
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Article ; Online: Repurposing screen identifies novel candidates for broad-spectrum coronavirus antivirals and druggable host targets.

Antimicrobial agents and chemotherapy

2024 Volume 68, Issue 3, Page(s) e0121023

Abstract: Libraries composed of licensed drugs represent a vast repertoire of molecules modulating physiological processes in humans, providing unique opportunities for the discovery of host-targeting antivirals. We screened the Repurposing, Focused Rescue, and ... ...

Abstract	Libraries composed of licensed drugs represent a vast repertoire of molecules modulating physiological processes in humans, providing unique opportunities for the discovery of host-targeting antivirals. We screened the Repurposing, Focused Rescue, and Accelerated Medchem (ReFRAME) repurposing library with approximately 12,000 molecules for broad-spectrum coronavirus antivirals and discovered 134 compounds inhibiting an alphacoronavirus and mapping to 58 molecular target categories. Dominant targets included the 5-hydroxytryptamine receptor, the dopamine receptor, and cyclin-dependent kinases. Gene knock-out of the drugs' host targets including cathepsin B and L (CTSB/L; VBY-825), the aryl hydrocarbon receptor (AHR; Phortress), the farnesyl-diphosphate farnesyltransferase 1 (FDFT1; P-3622), and the kelch-like ECH-associated protein 1 (KEAP1; Omaveloxolone), significantly modulated HCoV-229E infection, providing evidence that these compounds inhibited the virus through acting on their respective host targets. Counter-screening of all 134 primary compound candidates with SARS-CoV-2 and validation in primary cells identified Phortress, an AHR activating ligand, P-3622-targeting FDFT1, and Omaveloxolone, which activates the NFE2-like bZIP transcription factor 2 (NFE2L2) by liberating it from its endogenous inhibitor KEAP1, as antiviral candidates for both an
MeSH term(s)	Humans ; Kelch-Like ECH-Associated Protein 1/metabolism ; Drug Repositioning ; NF-E2-Related Factor 2/metabolism ; Coronavirus 229E, Human/metabolism ; Antiviral Agents/pharmacology ; Antiviral Agents/therapeutic use ; Coronavirus Infections ; Thiazoles ; Triterpenes
Chemical Substances	Phortress (AXR52N9SMF) ; omaveloxolone (G69Z98951Q) ; Kelch-Like ECH-Associated Protein 1 ; NF-E2-Related Factor 2 ; Antiviral Agents ; Thiazoles ; Triterpenes
Language	English
Publishing date	2024-02-06
Publishing country	United States
Document type	Journal Article
ZDB-ID	217602-6
ISSN	1098-6596 ; 0066-4804
ISSN (online)	1098-6596
ISSN	0066-4804
DOI	10.1128/aac.01210-23
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Zs.A 809: Show issues			Location: Je nach Verfügbarkeit (siehe Angabe bei Bestand) bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular Jg. 1995 - 2021: Lesesall (1.OG) ab Jg. 2022: Lesesaal (EG)
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Article ; Online: Protecting-Group-Mediated Diastereoselective Synthesis of C4'-Methylated Uridine Analogs and Their Activity against the Human Respiratory Syncytial Virus.

Köllmann, Christoph / Sake, Svenja M / Jones, Peter G / Pietschmann, Thomas / Werz, Daniel B

85 ; 6 ; 4267 ; 4278 ; The Journal of organic chemistry ; United States

2020

Abstract: Adjusting the protecting group strategy, from an alkyl ether to a bidentate ketal at the carbohydrate backbone of uridine, facilitates a switchable diastereoselective α- or β-C4'/C5'-spirocyclopropanation. Using these spirocyclopropanated nucleosides as ... ...

Abstract	Adjusting the protecting group strategy, from an alkyl ether to a bidentate ketal at the carbohydrate backbone of uridine, facilitates a switchable diastereoselective α- or β-C4'/C5'-spirocyclopropanation. Using these spirocyclopropanated nucleosides as key intermediates, we synthesized a variety of C4'-methylated d-ribose and l-lyxose-configured uridine derivatives by a base-mediated ring-opening of the spirocyclopropanol moiety. Investigations of antiviral activity against the human respiratory syncytial virus were carried out for selected derivatives, showing moderate activity.
Language	English
Publishing date	2020-02-26
Publisher	American Chemical Society
Publishing country	de
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Drug repurposing screen identifies lonafarnib as respiratory syncytial virus fusion protein inhibitor.

Sake, Svenja M / Zhang, Xiaoyu / Rajak, Manoj Kumar / Urbanek-Quaing, Melanie / Carpentier, Arnaud / Gunesch, Antonia P / Grethe, Christina / Matthaei, Alina / Rückert, Jessica / Galloux, Marie / Larcher, Thibaut / Le Goffic, Ronan / Hontonnou, Fortune / Chatterjee, Arnab K / Johnson, Kristen / Morwood, Kaycie / Rox, Katharina / Elgaher, Walid A M / Huang, Jiabin /

Wetzke, Martin / Hansen, Gesine / Fischer, Nicole / Eléouët, Jean-Francois / Rameix-Welti, Marie-Anne / Hirsch, Anna K H / Herold, Elisabeth / Empting, Martin / Lauber, Chris / Schulz, Thomas F / Krey, Thomas / Haid, Sibylle / Pietschmann, Thomas

Nature communications

2024 Volume 15, Issue 1, Page(s) 1173

Abstract: Respiratory syncytial virus (RSV) is a common cause of acute lower respiratory tract infection in infants, older adults and the immunocompromised. Effective directly acting antivirals are not yet available for clinical use. To address this, we screen the ...

Abstract	Respiratory syncytial virus (RSV) is a common cause of acute lower respiratory tract infection in infants, older adults and the immunocompromised. Effective directly acting antivirals are not yet available for clinical use. To address this, we screen the ReFRAME drug-repurposing library consisting of 12,000 small molecules against RSV. We identify 21 primary candidates including RSV F and N protein inhibitors, five HSP90 and four IMPDH inhibitors. We select lonafarnib, a licensed farnesyltransferase inhibitor, and phase III candidate for hepatitis delta virus (HDV) therapy, for further follow-up. Dose-response analyses and plaque assays confirm the antiviral activity (IC
MeSH term(s)	Animals ; Female ; Mice ; Dibenzocycloheptenes ; Drug Repositioning ; Piperidines/pharmacology ; Piperidines/therapeutic use ; Pyridines ; Respiratory Syncytial Virus Infections/drug therapy ; Viral Fusion Proteins/genetics ; Viral Fusion Proteins/chemistry
Chemical Substances	Dibenzocycloheptenes ; lonafarnib (IOW153004F) ; Piperidines ; Pyridines ; Viral Fusion Proteins
Language	English
Publishing date	2024-02-08
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	2553671-0
ISSN	2041-1723 ; 2041-1723
ISSN (online)	2041-1723
ISSN	2041-1723
DOI	10.1038/s41467-024-45241-y
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Respiratory Syncytial Virus Two-Step Infection Screen Reveals Inhibitors of Early and Late Life Cycle Stages.

Sake, Svenja M / Kosch, Christina / Blockus, Sebastian / Haid, Sibylle / Gunesch, Antonia P / Zhang, Xiaoyu / Friesland, Martina / Trummer, Sofie B / Grethe, Christina / Kühnel, Anne / Rückert, Jessica / Duprex, W Paul / Huang, Jiabin / Rameix-Welti, Marie-Anne / Empting, Martin / Fischer, Nicole / Hirsch, Anna K H / Schulz, Thomas F / Pietschmann, Thomas

Antimicrobial agents and chemotherapy

2022 , Page(s) e0103222

Abstract: Human respiratory syncytial virus (hRSV) infection is a leading cause of severe respiratory tract infections. Effective, directly acting antivirals against hRSV are not available. We aimed to discover new and chemically diverse candidates to enrich the ... ...

Abstract	Human respiratory syncytial virus (hRSV) infection is a leading cause of severe respiratory tract infections. Effective, directly acting antivirals against hRSV are not available. We aimed to discover new and chemically diverse candidates to enrich the hRSV drug development pipeline. We used a two-step screen that interrogates compound efficacy after primary infection and a consecutive virus passaging. We resynthesized selected hit molecules and profiled their activities with hRSV lentiviral pseudotype cell entry, replicon, and time-of-addition assays. The breadth of antiviral activity was tested against recent RSV clinical strains and human coronavirus (hCoV-229E), and in pseudotype-based entry assays with non-RSV viruses. Screening 6,048 molecules, we identified 23 primary candidates, of which 13 preferentially scored in the first and 10 in the second rounds of infection, respectively. Two of these molecules inhibited hRSV cell entry and selected for F protein resistance within the fusion peptide. One molecule inhibited transcription/replication in hRSV replicon assays, did not select for phenotypic hRSV resistance and was active against non-hRSV viruses, including hCoV-229E. One compound, identified in the second round of infection, did not measurably inhibit hRSV cell entry or replication/transcription. It selected for two coding mutations in the G protein and was highly active in differentiated BCi-NS1.1 lung cells. In conclusion, we identified four new hRSV inhibitor candidates with different modes of action. Our findings build an interesting platform for medicinal chemistry-guided derivatization approaches followed by deeper phenotypical characterization
Language	English
Publishing date	2022-11-08
Publishing country	United States
Document type	Journal Article
ZDB-ID	217602-6
ISSN	1098-6596 ; 0066-4804
ISSN (online)	1098-6596
ISSN	0066-4804
DOI	10.1128/aac.01032-22
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Zs.A 809: Show issues			Location: Je nach Verfügbarkeit (siehe Angabe bei Bestand) bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular Jg. 1995 - 2021: Lesesall (1.OG) ab Jg. 2022: Lesesaal (EG)
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Article ; Online: A condensate-hardening drug blocks RSV replication in vivo.

Risso-Ballester, Jennifer / Galloux, Marie / Cao, Jingjing / Le Goffic, Ronan / Hontonnou, Fortune / Jobart-Malfait, Aude / Desquesnes, Aurore / Sake, Svenja M / Haid, Sibylle / Du, Miaomiao / Zhang, Xiumei / Zhang, Huanyun / Wang, Zhaoguo / Rincheval, Vincent / Zhang, Youming / Pietschmann, Thomas / Eléouët, Jean-François / Rameix-Welti, Marie-Anne / Altmeyer, Ralf

Nature

2021 Volume 595, Issue 7868, Page(s) 596–599

Abstract: Biomolecular condensates have emerged as an important subcellular organizing ... ...

Abstract	Biomolecular condensates have emerged as an important subcellular organizing principle
MeSH term(s)	Animals ; Antiviral Agents/pharmacology ; Biomolecular Condensates/virology ; Cell Line ; Female ; Humans ; Inclusion Bodies ; Lung/virology ; Mice ; Mice, Inbred BALB C ; Respiratory Syncytial Virus, Human/drug effects ; Respiratory Syncytial Virus, Human/physiology ; Transcription Factors ; Veratrum Alkaloids/pharmacology ; Viral Proteins ; Virus Replication/drug effects
Chemical Substances	Antiviral Agents ; Transcription Factors ; Veratrum Alkaloids ; Viral Proteins ; human respiratory syncytial virus M2-1 protein ; cyclopamine (ZH658AJ192)
Language	English
Publishing date	2021-07-07
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	120714-3
ISSN	1476-4687 ; 0028-0836
ISSN (online)	1476-4687
ISSN	0028-0836
DOI	10.1038/s41586-021-03703-z
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Repurposing screen highlights broad-spectrum coronavirus antivirals and their host targets

Haid, Sibylle / Matthaei, Alina / Winkler, Melina / Sake, Svenja M / Gunesch, Antonia P / Rueckert, Jessica / Vieyres, Gabrielle / Kuehl, David / Nguyen, Tu-Trinh / Lasswitz, Lisa / Zapatero, Francisco / Brogden, Graham / Gerold, Gisa / Wiegmann, Bettina / Bilitewski, Ursula / Broenstrup, Mark / Schulz, Thomas / Pietschmann, Thomas

bioRxiv

Abstract: Libraries composed of licensed drugs represent a vast repertoire of molecules modulating physiologic processes in humans, thus providing unique opportunities for discovery of host targeting antivirals. We interrogated the ReFRAME repurposing library with ...

Abstract	Libraries composed of licensed drugs represent a vast repertoire of molecules modulating physiologic processes in humans, thus providing unique opportunities for discovery of host targeting antivirals. We interrogated the ReFRAME repurposing library with 12,993 molecules for broad-spectrum coronavirus antivirals and discovered 134 compounds inhibiting an alphacoronavirus, mapping to 59 molecular target categories. Dominant targets included the 5-hydroxytryptamine receptor and dopamine receptor and cyclin-dependent kinase inhibitors. Counter-screening with SARS-CoV-2 and validation in primary cells identified Phortress, an aryl hydrocarbon receptor (AHR) ligand, Bardoxolone and Omaveloxolone, two nuclear factor, erythroid 2 like 2 (NFE2L2) activators as inhibitors of both alpha- and betacoronaviruses. The landscape of coronavirus targeting molecules provides important information for the development of broad-spectrum antivirals reinforcing pandemic preparedness.
Keywords	covid19
Language	English
Publishing date	2021-07-14
Publisher	Cold Spring Harbor Laboratory
Document type	Article ; Online
DOI	10.1101/2021.07.14.452343
Database	COVID19

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Article ; Online: Labyrinthopeptins as virolytic inhibitors of respiratory syncytial virus cell entry.

Antiviral research

2020 Volume 177, Page(s) 104774

Abstract: Acute lower respiratory tract infections (ALRI) caused by respiratory syncytial virus (RSV) are associated with a severe disease burden among infants and elderly patients. Treatment options are limited. While numerous drug candidates with different viral ...

Abstract	Acute lower respiratory tract infections (ALRI) caused by respiratory syncytial virus (RSV) are associated with a severe disease burden among infants and elderly patients. Treatment options are limited. While numerous drug candidates with different viral targets are under development, the utility of RSV entry inhibitors is challenged by a low resistance barrier and by single mutations causing cross-resistance against a wide spectrum of fusion inhibitor chemotypes. We developed a cell-based screening assay for discovery of compounds inhibiting infection with primary RSV isolates. Using this system, we identified labyrinthopeptin A1 and A2 (Laby A1/A2), lantibiotics isolated from Actinomadura namibiensis, as effective RSV cell entry inhibitors with IC
MeSH term(s)	Animals ; Antiviral Agents/pharmacology ; Bacteriocins/pharmacology ; Cell Line ; Cells, Cultured ; Female ; Humans ; Lung/cytology ; Mice ; Mice, Inbred BALB C ; Respiratory Syncytial Virus Infections/drug therapy ; Respiratory Syncytial Virus, Human/drug effects ; Respiratory Syncytial Virus, Human/physiology ; Virus Internalization/drug effects
Chemical Substances	Antiviral Agents ; Bacteriocins ; labyrinthopeptin A1, Actinomadura namibiensis ; labyrinthopeptin A2
Language	English
Publishing date	2020-03-18
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	306628-9
ISSN	1872-9096 ; 0166-3542
ISSN (online)	1872-9096
ISSN	0166-3542
DOI	10.1016/j.antiviral.2020.104774
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Zs.A 1627: Show issues

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Article ; Online: Labyrinthopeptins as virolytic inhibitors of respiratory syncytial virus cell entry.

177 ; 104774 ; Antiviral research ; Netherlands

2020

Abstract	Acute lower respiratory tract infections (ALRI) caused by respiratory syncytial virus (RSV) are associated with a severe disease burden among infants and elderly patients. Treatment options are limited. While numerous drug candidates with different viral targets are under development, the utility of RSV entry inhibitors is challenged by a low resistance barrier and by single mutations causing cross-resistance against a wide spectrum of fusion inhibitor chemotypes. We developed a cell-based screening assay for discovery of compounds inhibiting infection with primary RSV isolates. Using this system, we identified labyrinthopeptin A1 and A2 (Laby A1/A2), lantibiotics isolated from Actinomadura namibiensis, as effective RSV cell entry inhibitors with IC50s of 0.39 μM and 4.97 μM, respectively, and with favourable therapeutic index (>200 and > 20, respectively). Both molecules were active against multiple RSV strains including primary isolates and their antiviral activity against RSV was confirmed in primary human airway cells ex vivo and a murine model in vivo. Laby A1/A2 were antiviral in prophylactic and therapeutic treatment regimens and displayed synergistic activity when applied in combination with each other. Mechanistic studies showed that Laby A1/A2 exert virolytic activity likely by binding to phosphatidylethanolamine moieties within the viral membrane and by disrupting virus particle membrane integrity. Probably due to its specific mode of action, Laby A1/A2 antiviral activity was not affected by common resistance mutations to known RSV entry inhibitors. Taken together, Laby A1/A2 represent promising candidates for development as RSV inhibitors. Moreover, the cell-based screening system with primary RSV isolates described here should be useful to identify further antiviral agents.
Keywords	Antiviral activity ; Human respiratory syncytial virus (hRSV) ; Labyrinthopeptin ; Lanthipeptide ; Virolytic ; Virus entry
Language	English
Publishing date	2020-03-18
Publisher	Elsevier
Publishing country	de
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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