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Article ; Online: Novel β-Glucocerebrosidase Activators That Bind to a New Pocket at a Dimer Interface and Induce Dimerization.

Benz, Joerg / Rufer, Arne C / Huber, Sylwia / Ehler, Andreas / Hug, Melanie / Topp, Andreas / Guba, Wolfgang / Hofmann, Eva Carolina / Jagasia, Ravi / Rodríguez Sarmiento, Rosa María

Angewandte Chemie (International ed. in English)

2021 Volume 60, Issue 10, Page(s) 5436–5442

Abstract: Genetic, preclinical and clinical data link Parkinson's disease and Gaucher's disease and provide a rational entry point to disease modification therapy via enhancement of β-Glucocerebrosidase (GCase) activity. We discovered a new class of pyrrolo[2,3-b] ... ...

Abstract	Genetic, preclinical and clinical data link Parkinson's disease and Gaucher's disease and provide a rational entry point to disease modification therapy via enhancement of β-Glucocerebrosidase (GCase) activity. We discovered a new class of pyrrolo[2,3-b]pyrazine activators effecting both Vmax and Km. They bind to human GCase and increase substrate metabolism in the lysosome in a cellular assay. We obtained the first crystal structure for an activator and identified a novel non-inhibitory binding mode at the interface of a dimer, rationalizing the observed structure-activity relationship (SAR). The compound binds GCase inducing formation of a dimeric state at both endoplasmic reticulum (ER) and lysosomal pHs, as confirmed by analytical ultracentrifugation. Importantly, the pyrrolo[2,3-b]pyrazines have central nervous system (CNS) drug-like properties. Our findings are important for future drug discovery efforts in the field of GCase activation and provide a deeper mechanistic understanding of the requirements for enzymatic activation, pointing to the relevance of dimerization.
MeSH term(s)	Binding Sites ; Crystallography, X-Ray ; Enzyme Activators/chemistry ; Enzyme Activators/metabolism ; Glucosylceramidase/chemistry ; Glucosylceramidase/metabolism ; Humans ; Kinetics ; Molecular Structure ; Protein Binding ; Protein Multimerization/drug effects ; Pyrazines/chemistry ; Pyrazines/metabolism ; Pyrroles/chemistry ; Pyrroles/metabolism ; Structure-Activity Relationship
Chemical Substances	Enzyme Activators ; Pyrazines ; Pyrroles ; Glucosylceramidase (EC 3.2.1.45)
Language	English
Publishing date	2021-01-19
Publishing country	Germany
Document type	Journal Article
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.202013890
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Article ; Online: Discovery of Novel Allosteric EGFR L858R Inhibitors for the Treatment of Non-Small-Cell Lung Cancer as a Single Agent or in Combination with Osimertinib.

Obst-Sander, Ulrike / Ricci, Antonio / Kuhn, Bernd / Friess, Thomas / Koldewey, Philipp / Kuglstatter, Andreas / Hewings, David / Goergler, Annick / Steiner, Sandra / Rueher, Daniel / Imhoff, Marie-Paule / Raschetti, Noemi / Marty, Hans-Peter / Dietzig, Aline / Rynn, Caroline / Ehler, Andreas / Burger, Dominique / Kornacker, Martin / Schaffland, Jeannine Petrig /

Herting, Frank / Pao, William / Bischoff, James R / Martoglio, Bruno / Alice Nagel, Yvonne / Jaeschke, Georg

Journal of medicinal chemistry

2022 Volume 65, Issue 19, Page(s) 13052–13073

Abstract: Addressing resistance to third-generation EGFR TKIs such as osimertinib via the ... ...

Abstract	Addressing resistance to third-generation EGFR TKIs such as osimertinib via the EGFR
MeSH term(s)	Acrylamides ; Aniline Compounds/pharmacology ; Aniline Compounds/therapeutic use ; Carcinoma, Non-Small-Cell Lung/pathology ; Drug Resistance, Neoplasm ; ErbB Receptors/genetics ; Humans ; Indoles ; Lung Neoplasms/pathology ; Mutation ; Protein Kinase Inhibitors/pharmacology ; Protein Kinase Inhibitors/therapeutic use ; Pyrimidines
Chemical Substances	Acrylamides ; Aniline Compounds ; Indoles ; Protein Kinase Inhibitors ; Pyrimidines ; osimertinib (3C06JJ0Z2O) ; EGFR protein, human (EC 2.7.10.1) ; ErbB Receptors (EC 2.7.10.1)
Language	English
Publishing date	2022-09-30
Publishing country	United States
Document type	Journal Article
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.2c00893
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Article ; Online: Prodrug-Activating Chain Exchange (PACE) converts targeted prodrug derivatives to functional bi- or multispecific antibodies.

Dickopf, Steffen / Buldun, Can / Vasic, Vedran / Georges, Guy / Hage, Carina / Mayer, Klaus / Forster, Matthias / Wessels, Uwe / Stubenrauch, Kay-Gunnar / Benz, Jörg / Ehler, Andreas / Lauer, Matthias E / Ringler, Philippe / Kobold, Sebastian / Endres, Stefan / Klein, Christian / Brinkmann, Ulrich

Biological chemistry

2022 Volume 403, Issue 5-6, Page(s) 495–508

Abstract: Driven by the potential to broaden the target space of conventional monospecific antibodies, the field of multi-specific antibody derivatives is growing rapidly. The production and screening of these artificial proteins entails a high combinatorial ... ...

Abstract	Driven by the potential to broaden the target space of conventional monospecific antibodies, the field of multi-specific antibody derivatives is growing rapidly. The production and screening of these artificial proteins entails a high combinatorial complexity. Antibody-domain exchange was previously shown to be a versatile strategy to produce bispecific antibodies in a robust and efficient manner. Here, we show that the domain exchange reaction to generate hybrid antibodies also functions under physiological conditions. Accordingly, we modified the exchange partners for use in therapeutic applications, in which two inactive prodrugs convert into a product with additional functionalities. We exemplarily show the feasibility for generating active T cell bispecific antibodies from two inactive prodrugs, which per se do not activate T cells alone. The two complementary prodrugs harbor antigen-targeting Fabs and non-functional anti-CD3 Fvs fused to IgG-CH3 domains engineered to drive chain-exchange reactions between them. Importantly, Prodrug-Activating Chain Exchange (PACE) could be an attractive option to conditionally activate therapeutics at the target site. Several examples are provided that demonstrate the efficacy of PACE as a new principle of cancer immunotherapy
MeSH term(s)	Antibodies, Bispecific ; Humans ; Immunotherapy ; Prodrugs/pharmacology ; T-Lymphocytes
Chemical Substances	Antibodies, Bispecific ; Prodrugs
Language	English
Publishing date	2022-01-20
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1334659-3
ISSN	1437-4315 ; 1431-6730 ; 1432-0355
ISSN (online)	1437-4315
ISSN	1431-6730 ; 1432-0355
DOI	10.1515/hsz-2021-0401
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Article ; Online: Mapping the conformational space accessible to catechol-O-methyltransferase.

Ehler, Andreas / Benz, Jörg / Schlatter, Daniel / Rudolph, Markus G

Acta crystallographica. Section D, Biological crystallography

2014 Volume 70, Issue Pt 8, Page(s) 2163–2174

Abstract: Methylation catalysed by catechol-O-methyltransferase (COMT) is the main pathway of catechol neurotransmitter deactivation in the prefrontal cortex. Low levels of this class of neurotransmitters are held to be causative of diseases such as schizophrenia, ...

Abstract	Methylation catalysed by catechol-O-methyltransferase (COMT) is the main pathway of catechol neurotransmitter deactivation in the prefrontal cortex. Low levels of this class of neurotransmitters are held to be causative of diseases such as schizophrenia, depression and Parkinson's disease. Inhibition of COMT may increase neurotransmitter levels, thus offering a route for treatment. Structure-based drug design hitherto seems to be based on the closed enzyme conformation. Here, a set of apo, semi-holo, holo and Michaelis form crystal structures are described that define the conformational space available to COMT and that include likely intermediates along the catalytic pathway. Domain swaps and sizeable loop movements around the active site testify to the flexibility of this enzyme, rendering COMT a difficult drug target. The low affinity of the co-substrate S-adenosylmethionine and the large conformational changes involved during catalysis highlight significant energetic investment to achieve the closed conformation. Since each conformation of COMT is a bona fide target for inhibitors, other states than the closed conformation may be promising to address. Crystallographic data for an alternative avenue of COMT inhibition, i.e. locking of the apo state by an inhibitor, are presented. The set of COMT structures may prove to be useful for the development of novel classes of inhibitors.
MeSH term(s)	Amino Acid Sequence ; Animals ; Catalytic Domain ; Catechol O-Methyltransferase/chemistry ; Crystallography, X-Ray ; Humans ; Mice ; Models, Molecular ; Molecular Sequence Data ; Protein Conformation ; Rats ; Sequence Homology, Amino Acid
Chemical Substances	Catechol O-Methyltransferase (EC 2.1.1.6)
Language	English
Publishing date	2014-07-25
Publishing country	United States
Document type	Journal Article
ZDB-ID	2020492-9
ISSN	1399-0047 ; 0907-4449
ISSN (online)	1399-0047
ISSN	0907-4449
DOI	10.1107/S1399004714012917
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Article ; Online: Variable heavy-variable light domain and Fab-arm CrossMabs with charged residue exchanges to enforce correct light chain assembly.

Regula, Joerg Thomas / Imhof-Jung, Sabine / Mølhøj, Michael / Benz, Joerg / Ehler, Andreas / Bujotzek, Alexander / Schaefer, Wolfgang / Klein, Christian

Protein engineering, design & selection : PEDS

2018 Volume 31, Issue 7-8, Page(s) 289–299

Abstract: Technologies for the production of bispecific antibodies need to overcome two major challenges. The first one is correct heavy chain assembly, which was solved by knobs-into-holes technology or charge interactions in the CH3 domains. The second challenge ...

Abstract	Technologies for the production of bispecific antibodies need to overcome two major challenges. The first one is correct heavy chain assembly, which was solved by knobs-into-holes technology or charge interactions in the CH3 domains. The second challenge is correct light chain assembly. This can be solved by engineering the Fab-arm interfaces or applying the immunoglobulin domain crossover approach. There are three different crossovers possible, namely Fab-arm, constant domain and variable domain crossovers. The CrossMabCH1-CL exchange does not lead to the formation of unexpected side products, whereas the CrossMabFab and the CrossMabVH-VL formats result in the formation of typical side products. Thus, CrossMabCH1-CL was initially favored for therapeutic antibody development. Here, we report a novel improved CrossMab design principle making use of site-specific positional exchanges of charged amino acid pairs in the constant domain of these CrossMabs to enable the correct light chain assembly in the CrossMabVH-VL and improvements for the CrossMabFab design.
MeSH term(s)	Amino Acid Sequence ; Immunoglobulin Heavy Chains/chemistry ; Immunoglobulin Heavy Chains/immunology ; Immunoglobulin Light Chains/chemistry ; Immunoglobulin Light Chains/immunology ; Immunoglobulin Variable Region/chemistry ; Immunoglobulin Variable Region/immunology ; Models, Molecular ; Protein Conformation
Chemical Substances	Immunoglobulin Heavy Chains ; Immunoglobulin Light Chains ; Immunoglobulin Variable Region
Language	English
Publishing date	2018-09-01
Publishing country	England
Document type	Journal Article
ZDB-ID	1466729-0
ISSN	1741-0134 ; 1741-0126
ISSN (online)	1741-0134
ISSN	1741-0126
DOI	10.1093/protein/gzy021
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Article ; Online: Acute Disseminated Encephalomyelitis with Seizures and Myocarditis: A Fatal Triad.

Lademann, Hanne / Bertsche, Astrid / Petzold, Axel / Zack, Fred / Büttner, Andreas / Däbritz, Jan / Hauenstein, Christina / Bahn, Erik / Spang, Christian / Reuter, Daniel / Warnke, Philipp / Ehler, Johannes

Medicina (Kaunas, Lithuania)

2020 Volume 56, Issue 6

Abstract: Autoimmune pathology of acute disseminated encephalomyelitis (ADEM) is generally restricted to the brain. Our objective is to expand the phenotype of ADEM. A four-year-old girl was admitted to the pediatric emergency room of a university medical center ... ...

Abstract	Autoimmune pathology of acute disseminated encephalomyelitis (ADEM) is generally restricted to the brain. Our objective is to expand the phenotype of ADEM. A four-year-old girl was admitted to the pediatric emergency room of a university medical center five days after a common upper respiratory tract infection. Acute symptoms were fever, leg pain, and headaches. She developed meningeal signs, and her level of consciousness dropped rapidly. Epileptic seizure activity started, and she became comatose, requiring intubation and mechanical ventilation. Serial brain magnetic resonance imaging (MRI) illustrated the fulminant development of ADEM. Treatment escalation with high-dose corticosteroids, immunoglobulins, and plasma exchange did not lead to clinical improvement. On day ten, the patient developed treatment-refractory cardiogenic shock and passed away. The postmortem assessment confirmed ADEM and revealed acute lymphocytic myocarditis, likely explaining the acute cardiac failure. Human metapneumovirus and picornavirus were detected in the tracheal secrete by PCR. Data sources-medical chart of the patient. This case is consistent with evidence from experimental findings of an association of ADEM with myocarditis as a postinfectious systemic autoimmune response, with life-threatening involvement of the brain and heart.
MeSH term(s)	Brain/pathology ; Child, Preschool ; Encephalomyelitis, Acute Disseminated/complications ; Encephalomyelitis, Acute Disseminated/pathology ; Encephalomyelitis, Acute Disseminated/physiopathology ; Female ; Humans ; Magnetic Resonance Imaging/methods ; Myocarditis/etiology ; Respiratory Tract Infections/complications ; Seizures/etiology
Keywords	covid19
Language	English
Publishing date	2020-06-04
Publishing country	Switzerland
Document type	Case Reports
ZDB-ID	2188113-3
ISSN	1648-9144 ; 1010-660X
ISSN (online)	1648-9144
ISSN	1010-660X
DOI	10.3390/medicina56060277
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Article ; Online: Correction to Design of Potent and Druglike Nonphenolic Inhibitors for Catechol O-Methyltransferase Derived from a Fragment Screening Approach Targeting the S-Adenosyl-l-methionine Pocket.

Lerner, Christian / Jakob-Roetne, Roland / Buettelmann, Bernd / Ehler, Andreas / Rudolph, Markus G / Rodríguez Sarmiento, Rosa María

Journal of medicinal chemistry

2017 Volume 60, Issue 9, Page(s) 4099

Language	English
Publishing date	2017-04-27
Publishing country	United States
Document type	Journal Article ; Published Erratum
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.7b00613
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Article ; Online: P329G-CAR-J: a novel Jurkat-NFAT-based CAR-T reporter system recognizing the P329G Fc mutation.

Darowski, Diana / Jost, Christian / Stubenrauch, Kay / Wessels, Uwe / Benz, Jörg / Ehler, Andreas / Freimoser-Grundschober, Anne / Brünker, Peter / Mössner, Ekkehard / Umaña, Pablo / Kobold, Sebastian / Klein, Christian

Protein engineering, design & selection : PEDS

2019 Volume 32, Issue 5, Page(s) 207–218

Abstract: Monoclonal antibody-based therapeutics are an integral part of treatment of different human diseases, and the selection of suitable antibody candidates during the discovery phase is essential. Here, we describe a novel, cellular screening approach for ... ...

Abstract	Monoclonal antibody-based therapeutics are an integral part of treatment of different human diseases, and the selection of suitable antibody candidates during the discovery phase is essential. Here, we describe a novel, cellular screening approach for the identification and characterization of therapeutic antibodies suitable for conversion into T cell bispecific antibodies using chimeric antigen receptor (CAR) transduced Jurkat-NFAT-luciferase reporter cells (CAR-J). For that purpose, we equipped a Jurkat-NFAT reporter cell line with a universal CAR, based on a monoclonal antibody recognizing the P329G mutation in the Fc-part of effector-silenced human IgG1-antibodies. In addition to scFv-based second generation CARs, Fab-based CARs employing the P329G-binder were generated. Using these anti-P329G-CAR-J cells together with the respective P329G-mutated IgG1-antibodies, we established a system, which facilitates the rapid testing of therapeutic antibody candidates in a flexible, high throughput setting during early stage discovery. We show that both, scFv- and Fab-based anti-P329G-CAR-J cells elicit a robust and dose-dependent luciferase signal if the respective antibody acts as an adaptor between tumor target and P329G-CAR-J cells. Importantly, we could demonstrate that functional characteristics of the antibody candidates, derived from the anti-P329G-CAR-J screening assay, are predictive for the functionality of these antibodies in the T cell bispecific antibody format.
MeSH term(s)	Amino Acid Substitution ; Antibodies, Bispecific/genetics ; Antibodies, Bispecific/immunology ; Humans ; Immunoglobulin G/genetics ; Immunoglobulin G/immunology ; Jurkat Cells ; Mutation, Missense ; Receptors, Chimeric Antigen/genetics ; Receptors, Chimeric Antigen/immunology
Chemical Substances	Antibodies, Bispecific ; Immunoglobulin G ; Receptors, Chimeric Antigen
Language	English
Publishing date	2019-09-10
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1466729-0
ISSN	1741-0134 ; 1741-0126
ISSN (online)	1741-0134
ISSN	1741-0126
DOI	10.1093/protein/gzz027
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Article ; Online: Acute Disseminated Encephalomyelitis with Seizures and Myocarditis

Hanne Lademann / Astrid Bertsche / Axel Petzold / Fred Zack / Andreas Büttner / Jan Däbritz / Christina Hauenstein / Erik Bahn / Christian Spang / Daniel Reuter / Philipp Warnke / Johannes Ehler

Medicina, Vol 56, Iss 277, p

A Fatal Triad

2020 Volume 277

Abstract	Autoimmune pathology of acute disseminated encephalomyelitis (ADEM) is generally restricted to the brain. Our objective is to expand the phenotype of ADEM. A four-year-old girl was admitted to the pediatric emergency room of a university medical center five days after a common upper respiratory tract infection. Acute symptoms were fever, leg pain, and headaches. She developed meningeal signs, and her level of consciousness dropped rapidly. Epileptic seizure activity started, and she became comatose, requiring intubation and mechanical ventilation. Serial brain magnetic resonance imaging (MRI) illustrated the fulminant development of ADEM. Treatment escalation with high-dose corticosteroids, immunoglobulins, and plasma exchange did not lead to clinical improvement. On day ten, the patient developed treatment-refractory cardiogenic shock and passed away. The postmortem assessment confirmed ADEM and revealed acute lymphocytic myocarditis, likely explaining the acute cardiac failure. Human metapneumovirus and picornavirus were detected in the tracheal secrete by PCR. Data sources–medical chart of the patient. This case is consistent with evidence from experimental findings of an association of ADEM with myocarditis as a postinfectious systemic autoimmune response, with life-threatening involvement of the brain and heart.
Keywords	delirium ; critical ill patient ; critical illness ; ADEM ; Medicine (General) ; R5-920
Subject code	610
Language	English
Publishing date	2020-06-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
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Article ; Online: Design of Potent and Druglike Nonphenolic Inhibitors for Catechol O-Methyltransferase Derived from a Fragment Screening Approach Targeting the S-Adenosyl-l-methionine Pocket.

Lerner, Christian / Jakob-Roetne, Roland / Buettelmann, Bernd / Ehler, Andreas / Rudolph, Markus / Rodríguez Sarmiento, Rosa María

Journal of medicinal chemistry

2016 Volume 59, Issue 22, Page(s) 10163–10175

Abstract: A fragment screening approach designed to target specifically the S-adenosyl-l-methionine pocket of catechol O-methyl transferase allowed the identification of structurally related fragments of high ligand efficiency and with activity on the described ... ...

Abstract	A fragment screening approach designed to target specifically the S-adenosyl-l-methionine pocket of catechol O-methyl transferase allowed the identification of structurally related fragments of high ligand efficiency and with activity on the described orthogonal assays. By use of a reliable enzymatic assay together with X-ray crystallography as guidance, a series of fragment modifications revealed an SAR and, after several expansions, potent lead compounds could be obtained. For the first time nonphenolic and small low nanomolar potent, SAM competitive COMT inhibitors are reported. These compounds represent a novel series of potent COMT inhibitors that might be further optimized to new drugs useful for the treatment of Parkinson's disease, as adjuncts in levodopa based therapy, or for the treatment of schizophrenia.
MeSH term(s)	Catechol O-Methyltransferase/metabolism ; Catechol O-Methyltransferase Inhibitors/chemical synthesis ; Catechol O-Methyltransferase Inhibitors/chemistry ; Catechol O-Methyltransferase Inhibitors/pharmacology ; Dose-Response Relationship, Drug ; Drug Design ; Drug Evaluation, Preclinical ; Humans ; Models, Molecular ; Molecular Structure ; S-Adenosylmethionine/chemical synthesis ; S-Adenosylmethionine/chemistry ; S-Adenosylmethionine/pharmacology ; Structure-Activity Relationship
Chemical Substances	Catechol O-Methyltransferase Inhibitors ; S-Adenosylmethionine (7LP2MPO46S) ; Catechol O-Methyltransferase (EC 2.1.1.6)
Language	English
Publishing date	2016-10-14
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.6b00927
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