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Article ; Online: Drugging the Folate Pathway in Mycobacterium tuberculosis: The Role of Multi-targeting Agents.

Hajian, Behnoush / Scocchera, Eric / Shoen, Carolyn / Krucinska, Jolanta / Viswanathan, Kishore / G-Dayanandan, Narendran / Erlandsen, Heidi / Estrada, Alexavier / Mikušová, Katarína / Korduláková, Jana / Cynamon, Michael / Wright, Dennis

Cell chemical biology

2019 Volume 26, Issue 6, Page(s) 781–791.e6

Abstract: The folate biosynthetic pathway offers many druggable targets that have yet to be exploited in tuberculosis therapy. Herein, we have identified a series of small molecules that interrupt Mycobacterium tuberculosis (Mtb) folate metabolism by dual ... ...

Abstract	The folate biosynthetic pathway offers many druggable targets that have yet to be exploited in tuberculosis therapy. Herein, we have identified a series of small molecules that interrupt Mycobacterium tuberculosis (Mtb) folate metabolism by dual targeting of dihydrofolate reductase (DHFR), a key enzyme in the folate pathway, and its functional analog, Rv2671. We have also compared the antifolate activity of these compounds with that of para-aminosalicylic acid (PAS). We found that the bioactive metabolite of PAS, in addition to previously reported activity against DHFR, inhibits flavin-dependent thymidylate synthase in Mtb, suggesting a multi-targeted mechanism of action for this drug. Finally, we have shown that antifolate treatment in Mtb decreases the production of mycolic acids, most likely due to perturbation of the activated methyl cycle. We conclude that multi-targeting of the folate pathway in Mtb is associated with highly potent anti-mycobacterial activity.
MeSH term(s)	4-Aminobenzoic Acid/chemistry ; 4-Aminobenzoic Acid/metabolism ; 4-Aminobenzoic Acid/pharmacology ; Antitubercular Agents/chemistry ; Antitubercular Agents/metabolism ; Antitubercular Agents/pharmacology ; Folic Acid/metabolism ; Microbial Sensitivity Tests ; Molecular Structure ; Mycobacterium tuberculosis/chemistry ; Mycobacterium tuberculosis/metabolism ; Small Molecule Libraries/chemistry ; Small Molecule Libraries/metabolism ; Small Molecule Libraries/pharmacology ; Tetrahydrofolate Dehydrogenase/metabolism
Chemical Substances	Antitubercular Agents ; Small Molecule Libraries ; Folic Acid (935E97BOY8) ; Tetrahydrofolate Dehydrogenase (EC 1.5.1.3) ; 4-Aminobenzoic Acid (TL2TJE8QTX)
Language	English
Publishing date	2019-03-28
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ISSN	2451-9448
ISSN (online)	2451-9448
DOI	10.1016/j.chembiol.2019.02.013
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Direct Substitution of Arylalkynyl Carbinols Provides Access to Diverse Terminal Acetylene Building Blocks.

G-Dayanandan, Narendran / Scocchera, Eric W / Keshipeddy, Santosh / Jones, Heather F / Anderson, Amy C / Wright, Dennis L

Organic letters

2016 Volume 19, Issue 1, Page(s) 142–145

Abstract: To develop next generation antifolates for the treatment of trimethoprim-resistant bacteria, synthetic methods were needed to prepare a diverse array of 3-aryl-propynes with various substitutions at the propargyl position. A direct route was sought ... ...

Abstract	To develop next generation antifolates for the treatment of trimethoprim-resistant bacteria, synthetic methods were needed to prepare a diverse array of 3-aryl-propynes with various substitutions at the propargyl position. A direct route was sought whereby nucleophilic addition of acetylene to aryl carboxaldehydes would be followed by reduction or substitution of the resulting propargyl alcohol. The direct reduction, methylation, and dimethylation of these readily available alcohols provide efficient access to this uncommon functional array. In addition, an unusual silane exchange reaction was observed in the reduction of the propargylic alcohols.
MeSH term(s)	Alcohols/chemical synthesis ; Aldehydes/chemistry ; Alkynes/chemical synthesis ; Alkynes/chemistry ; Anti-Bacterial Agents/chemical synthesis ; Anti-Bacterial Agents/chemistry ; Drug Design ; Drug Resistance, Bacterial ; Folic Acid Antagonists/chemical synthesis ; Folic Acid Antagonists/chemistry ; Folic Acid Antagonists/pharmacology ; Humans ; Methylation ; Molecular Structure ; Oxidation-Reduction ; Stereoisomerism ; Structure-Activity Relationship ; Trimethoprim/pharmacology
Chemical Substances	Alcohols ; Aldehydes ; Alkynes ; Anti-Bacterial Agents ; Folic Acid Antagonists ; Trimethoprim (AN164J8Y0X)
Language	English
Publishing date	2016-12-13
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.6b03438
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Charged Propargyl-Linked Antifolates Reveal Mechanisms of Antifolate Resistance and Inhibit Trimethoprim-Resistant MRSA Strains Possessing Clinically Relevant Mutations.

Reeve, Stephanie M / Scocchera, Eric / Ferreira, Jacob J / G-Dayanandan, Narendran / Keshipeddy, Santosh / Wright, Dennis L / Anderson, Amy C

Journal of medicinal chemistry

2016 Volume 59, Issue 13, Page(s) 6493–6500

Abstract: Drug-resistant enzymes must balance catalytic function with inhibitor destabilization to provide a fitness advantage. This sensitive balance, often involving very subtle structural changes, must be achieved through a selection process involving a minimal ...

Abstract	Drug-resistant enzymes must balance catalytic function with inhibitor destabilization to provide a fitness advantage. This sensitive balance, often involving very subtle structural changes, must be achieved through a selection process involving a minimal number of eligible point mutations. As part of a program to design propargyl-linked antifolates (PLAs) against trimethoprim-resistant dihydrofolate reductase (DHFR) from Staphylococcus aureus, we have conducted a thorough study of several clinically observed chromosomal mutations in the enzyme at the cellular, biochemical, and structural levels. Through this work, we have identified a promising lead series that displays significantly greater activity against these mutant enzymes and strains than TMP. The best inhibitors have enzyme inhibition and MIC values near or below that of trimethoprim against wild-type S. aureus. Moreover, these studies employ a series of crystal structures of several mutant enzymes bound to the same inhibitor; analysis of the structures reveals a more detailed molecular understanding of drug resistance in this important enzyme.
MeSH term(s)	Anti-Bacterial Agents/chemical synthesis ; Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Dose-Response Relationship, Drug ; Drug Design ; Folic Acid/metabolism ; Folic Acid Antagonists/chemical synthesis ; Folic Acid Antagonists/chemistry ; Folic Acid Antagonists/pharmacology ; Methicillin-Resistant Staphylococcus aureus/drug effects ; Methicillin-Resistant Staphylococcus aureus/genetics ; Methicillin-Resistant Staphylococcus aureus/metabolism ; Microbial Sensitivity Tests ; Models, Molecular ; Molecular Structure ; Structure-Activity Relationship ; Trimethoprim/pharmacology
Chemical Substances	Anti-Bacterial Agents ; Folic Acid Antagonists ; Folic Acid (935E97BOY8) ; Trimethoprim (AN164J8Y0X)
Language	English
Publishing date	2016-07-14
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.6b00688
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Article ; Online: Spindle Assembly Disruption and Cancer Cell Apoptosis with a CLTC-Binding Compound.

Bond, Michael J / Bleiler, Marina / Harrison, Lauren E / Scocchera, Eric W / Nakanishi, Masako / G-Dayanan, Narendran / Keshipeddy, Santosh / Rosenberg, Daniel W / Wright, Dennis L / Giardina, Charles

Molecular cancer research : MCR

2018 Volume 16, Issue 9, Page(s) 1361–1372

Abstract: AK3 compounds are mitotic arrest agents that induce high levels of γH2AX during mitosis and apoptosis following release from arrest. We synthesized a potent AK3 derivative, AK306, that induced arrest and apoptosis of the HCT116 colon cancer cell line ... ...

Abstract	AK3 compounds are mitotic arrest agents that induce high levels of γH2AX during mitosis and apoptosis following release from arrest. We synthesized a potent AK3 derivative, AK306, that induced arrest and apoptosis of the HCT116 colon cancer cell line with an EC
MeSH term(s)	Animals ; Apoptosis/drug effects ; Apoptosis/physiology ; Clathrin Heavy Chains/genetics ; Clathrin Heavy Chains/metabolism ; Colonic Neoplasms/drug therapy ; Colonic Neoplasms/genetics ; Colonic Neoplasms/metabolism ; Gene Knockdown Techniques ; HCT116 Cells ; Humans ; Male ; Mice ; Mitosis/drug effects ; Molecular Targeted Therapy ; Piperazines/chemistry ; Piperazines/pharmacology ; Spindle Apparatus/drug effects ; Spindle Apparatus/genetics ; Spindle Apparatus/metabolism ; Structure-Activity Relationship ; Transfection
Chemical Substances	(4-(3-chlorophenyl)piperazin-1-yl)(2-ethoxyphenyl)methanone ; CLTC protein, human ; Piperazines ; Clathrin Heavy Chains (114899-12-6)
Language	English
Publishing date	2018-05-16
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	2098788-2
ISSN	1557-3125 ; 1541-7786
ISSN (online)	1557-3125
ISSN	1541-7786
DOI	10.1158/1541-7786.MCR-18-0178
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Article ; Online: Identification of novel compounds that enhance colon cancer cell sensitivity to inflammatory apoptotic ligands.

Chopra, Avijeet S / Kuratnik, Anton / Scocchera, Eric W / Wright, Dennis L / Giardina, Charles

Cancer biology & therapy

2013 Volume 14, Issue 5, Page(s) 436–449

Abstract: Immune and inflammatory death ligands expressed within neoplastic tissue could potentially target apoptosis to transformed cells. To develop approaches that accentuate the anti-cancer potential of the inflammatory response, the Chembridge DIVERSet (TM) ... ...

Abstract	Immune and inflammatory death ligands expressed within neoplastic tissue could potentially target apoptosis to transformed cells. To develop approaches that accentuate the anti-cancer potential of the inflammatory response, the Chembridge DIVERSet (TM) library was screened for compounds that accentuated apoptosis in a strictly TNF-dependent manner. We identified a number of novel compounds with this activity, the most active of these, AK3 and AK10, sensitized colon cancer cells to TNF at 0.5 μM and 2 μM, respectively, without inducing apoptosis on their own. The activity of these compounds was structure-dependent and general, as they accentuated cell death by TNF or Fas ligation in multiple colon cancer cell lines. Both AK3 and AK10 arrested cells in mitosis, with live cell imaging indicating that mitotically arrested cells were the source of apoptotic bodies. AK3 accentuated caspase-8 and caspase-9 activation with little effect on NFκB target gene activation. Enhanced caspase activation corresponded to an increased expression of TNFR1 on the cell surface. To determine the general interplay between mitotic arrest and TNF sensitivity, Aurora kinase (MLN8054 and MLN8237) and PLK1 (BI2536) inhibitors were tested for their ability to sensitize cells to TNF. PLK1 inhibition was particularly effective and influenced TNFR1 surface presentation and caspase cleavage like AK3, even though it arrested mitosis at an earlier stage. We propose that AK3 and AK10 represent a new class of mitotic inhibitor and that selected mitotic inhibitors may be useful for treating colon cancers or earlier lesions that have a high level of inflammatory cell infiltrate.
MeSH term(s)	Antineoplastic Agents/pharmacology ; Apoptosis/drug effects ; Cell Death/drug effects ; Cell Extracts/pharmacology ; Cell Line, Tumor ; Cell Survival/drug effects ; Colonic Neoplasms/drug therapy ; Colonic Neoplasms/immunology ; Colonic Neoplasms/pathology ; Drug Synergism ; HCT116 Cells ; HT29 Cells ; Humans ; Inflammation/immunology ; Inflammation/pathology ; Ligands ; Signal Transduction ; Tumor Cells, Cultured ; Tumor Necrosis Factor-alpha/pharmacology
Chemical Substances	Antineoplastic Agents ; Cell Extracts ; Ligands ; Tumor Necrosis Factor-alpha
Language	English
Publishing date	2013-02-01
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2146305-0
ISSN	1555-8576 ; 1538-4047
ISSN (online)	1555-8576
ISSN	1538-4047
DOI	10.4161/cbt.23787
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Zs.A 5887: Show issues

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Article: Direct Substitution of Arylalkynyl Carbinols Provides Access to Diverse Terminal Acetylene Building Blocks

G-Dayanandan, Narendran / Scocchera Eric W / Keshipeddy Santosh / Jones Heather F / Anderson Amy C / Wright Dennis L

Organic letters. 2017 Jan. 06, v. 19, no. 1

2017

Abstract	To develop next generation antifolates for the treatment of trimethoprim-resistant bacteria, synthetic methods were needed to prepare a diverse array of 3-aryl-propynes with various substitutions at the propargyl position. A direct route was sought whereby nucleophilic addition of acetylene to aryl carboxaldehydes would be followed by reduction or substitution of the resulting propargyl alcohol. The direct reduction, methylation, and dimethylation of these readily available alcohols provide efficient access to this uncommon functional array. In addition, an unusual silane exchange reaction was observed in the reduction of the propargylic alcohols.
Keywords	Lewis bases ; acetylene ; alcohols ; bacteria ; chemical structure ; methylation ; silane
Language	English
Dates of publication	2017-0106
Size	p. 142-145.
Publishing place	American Chemical Society
Document type	Article
ISSN	1523-7052
DOI	10.1021%2Facs.orglett.6b03438
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: MRSA Isolates from United States Hospitals Carry dfrG and dfrK Resistance Genes and Succumb to Propargyl-Linked Antifolates.

Reeve, Stephanie M / Scocchera, Eric W / G-Dayanadan, Narendran / Keshipeddy, Santosh / Krucinska, Jolanta / Hajian, Behnoush / Ferreira, Jacob / Nailor, Michael / Aeschlimann, Jeffrey / Wright, Dennis L / Anderson, Amy C

Cell chemical biology

2016 Volume 23, Issue 12, Page(s) 1458–1467

Abstract: Antibiotic resistance is a rapidly evolving health concern that requires a sustained effort to understand mechanisms of resistance and to develop new agents that overcome those mechanisms. The dihydrofolate reductase (DHFR) inhibitor, trimethoprim (TMP), ...

Abstract	Antibiotic resistance is a rapidly evolving health concern that requires a sustained effort to understand mechanisms of resistance and to develop new agents that overcome those mechanisms. The dihydrofolate reductase (DHFR) inhibitor, trimethoprim (TMP), remains one of the most important orally administered antibiotics. However, resistance through chromosomal mutations and mobile, plasmid-encoded insensitive DHFRs threatens the continued use of this agent. We are pursuing the development of new propargyl-linked antifolate (PLA) DHFR inhibitors designed to evade these mechanisms. While analyzing contemporary TMP-resistant clinical isolates of methicillin-resistant and sensitive Staphylococcus aureus, we discovered two mobile resistance elements, dfrG and dfrK. This is the first identification of these resistance mechanisms in the United States. These resistant organisms were isolated from a variety of infection sites, show clonal diversity, and each contain distinct resistance genotypes for common antibiotics. Several PLAs showed significant activity against these resistant strains by direct inhibition of the TMP resistance elements.
Language	English
Publishing date	2016-12-22
Publishing country	United States
Document type	Journal Article
ISSN	2451-9456
ISSN (online)	2451-9456
DOI	10.1016/j.chembiol.2016.11.007
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: Charged Nonclassical Antifolates with Activity Against Gram-Positive and Gram-Negative Pathogens.

Scocchera, Eric / Reeve, Stephanie M / Keshipeddy, Santosh / Lombardo, Michael N / Hajian, Behnoush / Sochia, Adrienne E / Alverson, Jeremy B / Priestley, Nigel D / Anderson, Amy C / Wright, Dennis L

ACS medicinal chemistry letters

2016 Volume 7, Issue 7, Page(s) 692–696

Abstract: Although classical, negatively charged antifolates such as methotrexate possess high affinity for the dihydrofolate reductase (DHFR) enzyme, they are unable to penetrate the bacterial cell wall, rendering them poor antibacterial agents. Herein, we report ...

Abstract	Although classical, negatively charged antifolates such as methotrexate possess high affinity for the dihydrofolate reductase (DHFR) enzyme, they are unable to penetrate the bacterial cell wall, rendering them poor antibacterial agents. Herein, we report a new class of charged propargyl-linked antifolates that capture some of the key contacts common to the classical antifolates while maintaining the ability to passively diffuse across the bacterial cell wall. Eight synthesized compounds exhibit extraordinary potency against Gram-positive S. aureus with limited toxicity against mammalian cells and good metabolic profile. High resolution crystal structures of two of the compounds reveal extensive interactions between the carboxylate and active site residues through a highly organized water network.
Language	English
Publishing date	2016-05-05
Publishing country	United States
Document type	Journal Article
ISSN	1948-5875
ISSN	1948-5875
DOI	10.1021/acsmedchemlett.6b00120
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Article ; Online: Propargyl-Linked Antifolates Are Potent Inhibitors of Drug-Sensitive and Drug-Resistant Mycobacterium tuberculosis.

Hajian, Behnoush / Scocchera, Eric / Keshipeddy, Santosh / G-Dayanandan, Narendran / Shoen, Carolyn / Krucinska, Jolanta / Reeve, Stephanie / Cynamon, Michael / Anderson, Amy C / Wright, Dennis L

PloS one

2016 Volume 11, Issue 8, Page(s) e0161740

Abstract: Mycobacterium tuberculosis continues to cause widespread, life-threatening disease. In the last decade, this threat has grown dramatically as multi- and extensively-drug resistant (MDR and XDR) bacteria have spread globally and the number of agents that ... ...

Abstract	Mycobacterium tuberculosis continues to cause widespread, life-threatening disease. In the last decade, this threat has grown dramatically as multi- and extensively-drug resistant (MDR and XDR) bacteria have spread globally and the number of agents that effectively treat these infections is significantly reduced. We have been developing the propargyl-linked antifolates (PLAs) as potent inhibitors of the essential enzyme dihydrofolate reductase (DHFR) from bacteria and recently found that charged PLAs with partial zwitterionic character showed improved mycobacterial cell permeability. Building on a hypothesis that these PLAs may penetrate the outer membrane of M. tuberculosis and inhibit the essential cytoplasmic DHFR, we screened a group of PLAs for antitubercular activity. In this work, we identified several PLAs as potent inhibitors of the growth of M. tuberculosis with several of the compounds exhibiting minimum inhibition concentrations equal to or less than 1 μg/mL. Furthermore, two of the compounds were very potent inhibitors of MDR and XDR strains. A high resolution crystal structure of one PLA bound to DHFR from M. tuberculosis reveals the interactions of the ligands with the target enzyme.
MeSH term(s)	Antitubercular Agents/chemistry ; Bacterial Proteins/antagonists & inhibitors ; Bacterial Proteins/metabolism ; Drug Resistance, Multiple, Bacterial/drug effects ; Folic Acid Antagonists/chemistry ; Humans ; Mycobacterium tuberculosis/enzymology ; Tetrahydrofolate Dehydrogenase/metabolism
Chemical Substances	Antitubercular Agents ; Bacterial Proteins ; Folic Acid Antagonists ; Tetrahydrofolate Dehydrogenase (EC 1.5.1.3)
Language	English
Publishing date	2016-08-31
Publishing country	United States
Document type	Journal Article
ISSN	1932-6203
ISSN (online)	1932-6203
DOI	10.1371/journal.pone.0161740
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Propargyl-Linked Antifolates Are Potent Inhibitors of Drug-Sensitive and Drug-Resistant Mycobacterium tuberculosis.

Behnoush Hajian / Eric Scocchera / Santosh Keshipeddy / Narendran G-Dayanandan / Carolyn Shoen / Jolanta Krucinska / Stephanie Reeve / Michael Cynamon / Amy C Anderson / Dennis L Wright

PLoS ONE, Vol 11, Iss 8, p e

2016 Volume 0161740

Abstract	Mycobacterium tuberculosis continues to cause widespread, life-threatening disease. In the last decade, this threat has grown dramatically as multi- and extensively-drug resistant (MDR and XDR) bacteria have spread globally and the number of agents that effectively treat these infections is significantly reduced. We have been developing the propargyl-linked antifolates (PLAs) as potent inhibitors of the essential enzyme dihydrofolate reductase (DHFR) from bacteria and recently found that charged PLAs with partial zwitterionic character showed improved mycobacterial cell permeability. Building on a hypothesis that these PLAs may penetrate the outer membrane of M. tuberculosis and inhibit the essential cytoplasmic DHFR, we screened a group of PLAs for antitubercular activity. In this work, we identified several PLAs as potent inhibitors of the growth of M. tuberculosis with several of the compounds exhibiting minimum inhibition concentrations equal to or less than 1 μg/mL. Furthermore, two of the compounds were very potent inhibitors of MDR and XDR strains. A high resolution crystal structure of one PLA bound to DHFR from M. tuberculosis reveals the interactions of the ligands with the target enzyme.
Keywords	Medicine ; R ; Science ; Q
Subject code	540
Language	English
Publishing date	2016-01-01T00:00:00Z
Publisher	Public Library of Science (PLoS)
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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