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  1. Article ; Online: Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography.

    Chatziorfanou, Eleftheria / Romero, Atilio Reyes / Chouchane, Lotfi / Dömling, Alexander

    The Journal of organic chemistry

    2024  Volume 89, Issue 2, Page(s) 957–974

    Abstract: The isocyanide group is the chameleon among the functional groups in organic chemistry. Unlike other multiatom functional groups, where the electrophilic and nucleophilic moieties are typically separated, isocyanides combine both functionalities in the ... ...

    Abstract The isocyanide group is the chameleon among the functional groups in organic chemistry. Unlike other multiatom functional groups, where the electrophilic and nucleophilic moieties are typically separated, isocyanides combine both functionalities in the terminal carbon. This unique feature can be rationalized using the frontier orbital concept and has significant implications for its intermolecular interactions and the reactivity of the functional group. In this study, we perform a Cambridge Crystallographic Database-supported analysis of isocyanide intramolecular interactions to investigate the intramolecular interactions of isocyanides in the solid state, excluding isocyanide-metal complexes. We discuss examples of different interaction classes, including the isocyanide as a hydrogen bond acceptor (RNC···HX), halogen bonding (RNC···X), and interactions involving the isocyanide and carbon atoms (RNC···C). The latter interaction serves as an intriguing illustration of a Bürgi-Dunitz trajectory and represents a crucial experimental detail in the well-known multicomponent reactions such as the Ugi- and Passerini-type mechanisms. Understanding the spectrum of intramolecular interactions that isocyanides can undergo holds significant implications in fields such as medicinal chemistry, materials science, and asymmetric catalysis.
    Language English
    Publishing date 2024-01-04
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.3c02038
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  2. Article ; Online: Comprehensive Characterization of Protein Turnover by Comparative SILAC Labeling Analysis in 3T3-L1.

    Choi, Sunkyu / Romero, Atilio Reyes / Mashood, Fathima / Goswami, Neha / Chouchane, Lotfi / Schmidt, Frank

    Journal of proteome research

    2023  Volume 22, Issue 6, Page(s) 1723–1733

    Abstract: A balance between the synthesis and degradation of proteins is referred to as protein turnover, which is crucial for cellular protein homeostasis. Proteome-wide analysis of protein turnover in adipocytes, which are well-known for their role in energy ... ...

    Abstract A balance between the synthesis and degradation of proteins is referred to as protein turnover, which is crucial for cellular protein homeostasis. Proteome-wide analysis of protein turnover in adipocytes, which are well-known for their role in energy storage and their link to obesity and metabolism disorders, is yet to be conducted. Thus, with this objective in mind, our investigation utilized a comparative analysis of time-dependent SILAC labeling to assess protein turnover in 3T3-L1 adipocytes, spanning a period of 0 to 144 h. We observed that relatively faster or slower protein half-lives in several protein groups were associated with the PPARγ signaling pathway, energy metabolism, extracellular matrix, ubiquitin-proteasome system, RNA splicing, Golgi complex, and lysosome. It is anticipated that these protein half-life profiles will provide greater clarity on the life cycle of adipocyte proteome and shed light on how they maintain protein homeostasis.
    MeSH term(s) Animals ; Mice ; Proteome/genetics ; Proteome/metabolism ; 3T3-L1 Cells ; Adipocytes/metabolism ; Proteolysis ; Proteasome Endopeptidase Complex/metabolism ; Cell Differentiation
    Chemical Substances Proteome ; Proteasome Endopeptidase Complex (EC 3.4.25.1)
    Language English
    Publishing date 2023-04-14
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2078618-9
    ISSN 1535-3907 ; 1535-3893
    ISSN (online) 1535-3907
    ISSN 1535-3893
    DOI 10.1021/acs.jproteome.2c00763
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 6189: Show issues Location:
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  3. Article ; Online: Production of "biobetter" variants of glucarpidase with enhanced enzyme activity.

    Al-Qahtani, Alanod D / Bashraheel, Sara S / Rashidi, Fatma B / O'Connor, C David / Romero, Atilio Reyes / Domling, Alexander / Goda, Sayed K

    Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie

    2019  Volume 112, Page(s) 108725

    Abstract: Glucarpidase, also known as carboxypeptidase ... ...

    Abstract Glucarpidase, also known as carboxypeptidase G
    MeSH term(s) Antimetabolites, Antineoplastic/adverse effects ; Antimetabolites, Antineoplastic/pharmacokinetics ; Cloning, Molecular ; Drug Design ; Enzyme Stability ; Enzyme Therapy/methods ; Methotrexate/adverse effects ; Methotrexate/pharmacokinetics ; Models, Molecular ; Neoplasms/drug therapy ; Neoplasms/immunology ; Point Mutation ; Prodrugs/administration & dosage ; Prodrugs/therapeutic use ; Pseudomonas putida/genetics ; Recombinant Proteins/genetics ; Recombinant Proteins/immunology ; Recombinant Proteins/therapeutic use ; gamma-Glutamyl Hydrolase/genetics ; gamma-Glutamyl Hydrolase/immunology ; gamma-Glutamyl Hydrolase/therapeutic use
    Chemical Substances Antimetabolites, Antineoplastic ; Prodrugs ; Recombinant Proteins ; glucarpidase (2GFP9BJD79) ; gamma-Glutamyl Hydrolase (EC 3.4.19.9) ; Methotrexate (YL5FZ2Y5U1)
    Language English
    Publishing date 2019-02-28
    Publishing country France
    Document type Journal Article
    ZDB-ID 392415-4
    ISSN 1950-6007 ; 0753-3322 ; 0300-0893
    ISSN (online) 1950-6007
    ISSN 0753-3322 ; 0300-0893
    DOI 10.1016/j.biopha.2019.108725
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    In stock of ZB MED Cologne/Königswinter

    Ud II Zs.198: Show issues Location:
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  4. Article ; Online: Genetic predisposition to porto-sinusoidal vascular disorder: A functional genomic-based, multigenerational family study.

    Shan, Jingxuan / Megarbane, André / Chouchane, Aziz / Karthik, Deepak / Temanni, Ramzi / Romero, Atilio Reyes / Hua, Huiying / Pan, Chun / Chen, Xixi / Subramanian, Murugan / Saad, Chadi / Mbarek, Hamdi / Mehawej, Cybel / Chouery, Eliane / Abuaqel, Sirin W / Dömling, Alexander / Remadi, Sami / Yaghi, Cesar / Li, Pu /
    Chouchane, Lotfi

    Hepatology (Baltimore, Md.)

    2022  Volume 77, Issue 2, Page(s) 501–511

    Abstract: Background and aims: Porto-sinusoidal vascular disorder (PSVD) is a group of liver vascular diseases featuring lesions encompassing the portal venules and sinusoids unaccompanied by cirrhosis, irrespective of the presence/absence of portal hypertension. ...

    Abstract Background and aims: Porto-sinusoidal vascular disorder (PSVD) is a group of liver vascular diseases featuring lesions encompassing the portal venules and sinusoids unaccompanied by cirrhosis, irrespective of the presence/absence of portal hypertension. It can occur secondary to coagulation disorders or insult by toxic agents. However, the cause of PSVD remains unknown in most cases. Hereditary cases of PSVD are exceptionally rare, but they are of particular interest and may unveil genetic alterations and molecular mechanisms associated with the disease.
    Approach and results: We performed genome sequencing of four patients and two healthy individuals of a large multigenerational Lebanese family with PSVD and identified a heterozygous deleterious variant (c.547C>T, p.R183W) of FCH and double SH3 domains 1 ( FCHSD1 ), an uncharacterized gene, in patients. This variant segregated with the disease, and its pattern of inheritance was suggestive of autosomal dominant with variable expressivity. RNA structural modelling of human FCHSD1 suggests that the C-to-T substitution at position 547, corresponding to FCHSD1R183W , may increase both messenger RNA (mRNA) and protein stability and its interaction with MTOR-associated protein, LST8 homolog, a key protein of the mechanistic target of rapamycin (mTOR pathway). These predictions were substantiated by biochemical analyses, which showed that FCHSD1R183W induced high FCHSD1 mRNA stability, overexpression of FCHSD1 protein, and an increase in mTORC1 activation. This human FCHSD1 variant was introduced into mice through CRISPR/Cas9 genome editing. Nine out of the 15 mice carrying the human FCHSD1R183W variant mimicked the phenotype of human PSVD, including splenomegaly and enlarged portal vein.
    Conclusions: Aberrant FCHSD1 structure and function leads to mTOR pathway overactivation and may cause PSVD.
    MeSH term(s) Humans ; Mice ; Animals ; Genetic Predisposition to Disease ; Extended Family ; TOR Serine-Threonine Kinases/genetics ; TOR Serine-Threonine Kinases/metabolism ; Hypertension, Portal/metabolism ; Genomics ; Vascular Diseases
    Chemical Substances TOR Serine-Threonine Kinases (EC 2.7.11.1)
    Language English
    Publishing date 2022-09-03
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 604603-4
    ISSN 1527-3350 ; 0270-9139
    ISSN (online) 1527-3350
    ISSN 0270-9139
    DOI 10.1002/hep.32735
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 1660: 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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  5. Book ; Online: Gliptin Repurposing for COVID-19

    Groves, Matthew / Domling, Alexander / Moreno, Angel Jonathan Ruiz / Romero, Atilio Reyes / Neochoritis, Constantinos / Velasco-Velázquez, Marco

    2020  

    Abstract: ... De novo ... drug discovery of any therapeutic modality (e.g. antibodies, vaccines or small molecules) historically takes years from idea/preclinic to the market and it is therefore not a short-term solution for the current SARS-CoV-2 pandemic. ... ...

    Abstract De novo drug discovery of any therapeutic modality (e.g. antibodies, vaccines or small molecules) historically takes years from idea/preclinic to the market and it is therefore not a short-term solution for the current SARS-CoV-2 pandemic. Therefore, drug repurposing – the discovery novel indication areas for already approved drugs - is perhaps the only approach able to yield a short term relieve. Here we describe computational screening results suggesting that certain members of the drug class of gliptins are inhibitors of the two SARS-CoV-2 proteases 3CLpro and PLpro. The oral bioavailable antidiabetic drug class of gliptins are safe and have been introduced clinically since 2006 and used by millions of patients since then. Based on our repurposing hypothesis the nitrile containing gliptins deserve further investigation as potential anti-COVID19 drugs.
    Keywords covid19
    Publisher American Chemical Society (ACS)
    Publishing country us
    Document type Book ; Online
    DOI 10.26434/chemrxiv.12110760
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  6. Book ; Online: Gliptin Repurposing for COVID-19

    Groves, Matthew / Domling, Alexander / Moreno, Angel Jonathan Ruiz / Romero, Atilio Reyes / Neochoritis, Constantinos / Velasco-Velázquez, Marco

    2020  

    Abstract: ... De novo ... drug discovery of any therapeutic modality (e.g. antibodies, vaccines or small molecules) historically takes years from idea/preclinic to the market and it is therefore not a short-term solution for the current SARS-CoV-2 pandemic. ... ...

    Abstract De novo drug discovery of any therapeutic modality (e.g. antibodies, vaccines or small molecules) historically takes years from idea/preclinic to the market and it is therefore not a short-term solution for the current SARS-CoV-2 pandemic. Therefore, drug repurposing – the discovery novel indication areas for already approved drugs - is perhaps the only approach able to yield a short term relieve. Here we describe computational screening results suggesting that certain members of the drug class of gliptins are inhibitors of the two SARS-CoV-2 proteases 3CLpro and PLpro. The oral bioavailable antidiabetic drug class of gliptins are safe and have been introduced clinically since 2006 and used by millions of patients since then. Based on our repurposing hypothesis the nitrile containing gliptins deserve further investigation as potential anti-COVID19 drugs.
    Keywords covid19
    Publisher American Chemical Society (ACS)
    Publishing country us
    Document type Book ; Online
    DOI 10.26434/chemrxiv.12110760.v1
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  7. Article ; Online: Rapid approach to complex boronic acids.

    Neochoritis, Constantinos G / Shaabani, Shabnam / Ahmadianmoghaddam, Maryam / Zarganes-Tzitzikas, Tryfon / Gao, Li / Novotná, Michaela / Mitríková, Tatiana / Romero, Atilio Reyes / Irianti, Marina Ika / Xu, Ruixue / Olechno, Joe / Ellson, Richard / Helan, Victoria / Kossenjans, Michael / Groves, Matthew R / Dömling, Alexander

    Science advances

    2019  Volume 5, Issue 7, Page(s) eaaw4607

    Abstract: The compatibility of free boronic acid building blocks in multicomponent reactions to readily create large libraries of diverse and complex small molecules was investigated. Traditionally, boronic acid synthesis is sequential, synthetically demanding, ... ...

    Abstract The compatibility of free boronic acid building blocks in multicomponent reactions to readily create large libraries of diverse and complex small molecules was investigated. Traditionally, boronic acid synthesis is sequential, synthetically demanding, and time-consuming, which leads to high target synthesis times and low coverage of the boronic acid chemical space. We have performed the synthesis of large libraries of boronic acid derivatives based on multiple chemistries and building blocks using acoustic dispensing technology. The synthesis was performed on a nanomole scale with high synthesis success rates. The discovery of a protease inhibitor underscores the usefulness of the approach. Our acoustic dispensing-enabled chemistry paves the way to highly accelerated synthesis and miniaturized reaction scouting, allowing access to unprecedented boronic acid libraries.
    MeSH term(s) Boronic Acids/chemical synthesis ; Boronic Acids/chemistry ; Boronic Acids/classification ; Cyanides/chemical synthesis ; Cyanides/chemistry ; Mass Spectrometry/methods ; Microwaves ; Molecular Structure ; Small Molecule Libraries/chemical synthesis ; Small Molecule Libraries/chemistry ; Small Molecule Libraries/classification
    Chemical Substances Boronic Acids ; Cyanides ; Small Molecule Libraries
    Language English
    Publishing date 2019-07-05
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 2810933-8
    ISSN 2375-2548 ; 2375-2548
    ISSN (online) 2375-2548
    ISSN 2375-2548
    DOI 10.1126/sciadv.aaw4607
    Database MEDical Literature Analysis and Retrieval System OnLINE

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