ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Phosphinic Tripeptides as Dual Angiotensin-Converting Enzyme C-Domain and Endothelin-Converting Enzyme-1 Inhibitors

View Author Information
CEA, DSV, Service d’Ingénierie Moléculaire des Protéines (SIMOPRO), Bat 152, CE-Saclay, Gif/Yvette 91191 Cedex, France
Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zografou 15771, Athens, Greece
*To whom correspondence should be addressed. Phone: 330169082603. Fax: 330169089071. E-mail: [email protected]
§Present address: Institut de Radioprotection et de Sureté Nucléaire (IRSN), DRPH/SRBE/LRPAT, Bat 05, BP17, Fontenay-aux-roses 92262, France.
Cite this: J. Med. Chem. 2010, 53, 1, 208–220
Publication Date (Web):November 9, 2009
https://doi.org/10.1021/jm9010803
Copyright © 2009 American Chemical Society

    Article Views

    2032

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    A new series of phosphinic inhibitors able to interact with both angiotensin-converting enzyme (ACE) C-domain and endothelin-converting enzyme-1 (ECE-1), while sparing neprilysin (NEP), has been developed. The most potent and selective inhibitor in this series (compound 8F2) displays Ki values of 0.65 nM, 150 nM, 14 nM and 6.7 μM toward somatic ACE C-domain, ACE N-domain, ECE-1, and NEP, respectively. Remarkably, in this series, the inhibitor’s ability to discriminate between ECE-1 and NEP was observed to depend on the stereochemistry of the residue present in the inhibitor’s P1′ position. After iv administration, compound 8F2 (10 mg/kg) lowered mean arterial blood pressure by 24 ± 2 mmHg in spontaneously hypertensive rats, as compared with controls. Mixed ACE/ECE-1 inhibitor may lead to a new generation of vasopeptide inhibitors that should reduce the levels of angiotensin-II and endothelin-1, without interfering with bradykinin cleavage.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    NMR characterization of compounds 5F1, 5F2, 7F1, 7F2, 8F1, and 8F2. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 59 publications.

    1. Ohud Alzaidi, Thomas Wirth. Continuous Flow Electroselenocyclization of Allylamides and Unsaturated Oximes to Selenofunctionalized Oxazolines and Isoxazolines. ACS Organic & Inorganic Au 2024, Article ASAP.
    2. Angelos Lelis, Nikolaos Skoulikas, Mirto Papathanasopoulou, Kostas Voreakos, Dimitris Georgiadis. Diastereoselective Synthesis of Phosphinic Dipeptide Isosteres: Domino Chirality Transfer during a Stereocontrolled P-Michael Reaction. Organic Letters 2023, 25 (36) , 6623-6627. https://doi.org/10.1021/acs.orglett.3c02335
    3. Alexander Yu. Mitrofanov, Irina P. Beletskaya. Regiodivergent Metal-Controlled Synthesis of Multiply Substituted Quinolin-2-yl- and Quinolin-3-ylphosphonates. The Journal of Organic Chemistry 2023, 88 (4) , 2367-2376. https://doi.org/10.1021/acs.joc.2c02780
    4. Dimitris Georgiadis, Nikolaos Skoulikas, Athanasios Papakyriakou, Efstratios Stratikos. Phosphinic Peptides as Tool Compounds for the Study of Pharmacologically Relevant Zn-Metalloproteases. ACS Pharmacology & Translational Science 2022, 5 (12) , 1228-1253. https://doi.org/10.1021/acsptsci.2c00183
    5. Xianghong Xu, Lingzi Peng, Xihao Chang, Chang Guo. Ni/Chiral Sodium Carboxylate Dual Catalyzed Asymmetric O-Propargylation. Journal of the American Chemical Society 2021, 143 (49) , 21048-21055. https://doi.org/10.1021/jacs.1c11044
    6. Arun Yadav, Dileep Kumar, Manish Kumar Mishra, Deeksha, Chandra Bhushan Tripathi. Catalytic Enantioselective Synthesis of Aryl–Methyl Organophosphorus Compounds. The Journal of Organic Chemistry 2021, 86 (2) , 2000-2011. https://doi.org/10.1021/acs.joc.0c02675
    7. Alexander Yu. Mitrofanov, Valentina A. Bychkova, Sergey E. Nefedov, Irina P. Beletskaya. Selective Metal-Controlled Synthesis of Trifluoromethylated (Indolin-2-ylidene)methyl- and Quinolin-3-ylphosphonates. The Journal of Organic Chemistry 2020, 85 (22) , 14507-14515. https://doi.org/10.1021/acs.joc.0c00913
    8. Urvashi Sharma, Gyles E. Cozier, Edward D. Sturrock, K. Ravi Acharya. Molecular Basis for Omapatrilat and Sampatrilat Binding to Neprilysin—Implications for Dual Inhibitor Design with Angiotensin-Converting Enzyme. Journal of Medicinal Chemistry 2020, 63 (10) , 5488-5500. https://doi.org/10.1021/acs.jmedchem.0c00441
    9. Barry M. Trost, Anand H. Shinde, Youliang Wang, Zhijun Zuo, Chang Min. Palladium-Catalyzed Regio-, Enantio-, and Diastereoselective Asymmetric [3 + 2] Cycloaddition Reactions: Synthesis of Chiral Cyclopentyl Phosphonates. ACS Catalysis 2020, 10 (3) , 1969-1975. https://doi.org/10.1021/acscatal.9b05073
    10. Kostas Voreakos, Laurent Devel, Dimitris Georgiadis. Late-Stage Diversification of Phosphinic Dehydroalanine Pseudopeptides Based on a Giese-Type Radical C-Alkylation Strategy. Organic Letters 2019, 21 (12) , 4397-4401. https://doi.org/10.1021/acs.orglett.9b00857
    11. Giovanni Covaleda, Pablo Gallego, Josep Vendrell, Dimitris Georgiadis, Julia Lorenzo, Vincent Dive, Francesc Xavier Aviles, David Reverter, Laurent Devel. Synthesis and Structural/Functional Characterization of Selective M14 Metallocarboxypeptidase Inhibitors Based on Phosphinic Pseudopeptide Scaffold: Implications on the Design of Specific Optical Probes. Journal of Medicinal Chemistry 2019, 62 (4) , 1917-1931. https://doi.org/10.1021/acs.jmedchem.8b01465
    12. Allie Y. Chen, Rebecca N. Adamek, Benjamin L. Dick, Cy V. Credille, Christine N. Morrison, Seth M. Cohen. Targeting Metalloenzymes for Therapeutic Intervention. Chemical Reviews 2019, 119 (2) , 1323-1455. https://doi.org/10.1021/acs.chemrev.8b00201
    13. Tomáš David, Veronika Hlinová, Vojtěch Kubíček, Ralf Bergmann, Franziska Striese, Nicole Berndt, Dávid Szöllősi, Tibor Kovács, Domokos Máthé, Michael Bachmann, Hans-Jürgen Pietzsch, Petr Hermann. Improved Conjugation, 64-Cu Radiolabeling, in Vivo Stability, and Imaging Using Nonprotected Bifunctional Macrocyclic Ligands: Bis(Phosphinate) Cyclam (BPC) Chelators. Journal of Medicinal Chemistry 2018, 61 (19) , 8774-8796. https://doi.org/10.1021/acs.jmedchem.8b00932
    14. Weigang Zhang, Yingpeng Su, Ke-Hu Wang, Lili Wu, Bingbing Chang, Ya Shi, Danfeng Huang, and Yulai Hu . Trichloroisocyanuric Acid Promoted Cascade Cyclization/Trifluoromethylation of Allylic Oximes: Synthesis of Trifluoromethylated Isoxazolines. Organic Letters 2017, 19 (2) , 376-379. https://doi.org/10.1021/acs.orglett.6b03582
    15. Paraskevi Kokkala, Anastasia Mpakali, Francois-Xavier Mauvais, Athanasios Papakyriakou, Ira Daskalaki, Ioanna Petropoulou, Sofia Kavvalou, Mirto Papathanasopoulou, Stefanos Agrotis, Theodora-Markisia Fonsou, Peter van Endert, Efstratios Stratikos, and Dimitris Georgiadis . Optimization and Structure–Activity Relationships of Phosphinic Pseudotripeptide Inhibitors of Aminopeptidases That Generate Antigenic Peptides. Journal of Medicinal Chemistry 2016, 59 (19) , 9107-9123. https://doi.org/10.1021/acs.jmedchem.6b01031
    16. Stamatia Vassiliou, Ewelina Węglarz-Tomczak, Łukasz Berlicki, Małgorzata Pawełczak, Bogusław Nocek, Rory Mulligan, Andrzej Joachimiak, and Artur Mucha . Structure-Guided, Single-Point Modifications in the Phosphinic Dipeptide Structure Yield Highly Potent and Selective Inhibitors of Neutral Aminopeptidases. Journal of Medicinal Chemistry 2014, 57 (19) , 8140-8151. https://doi.org/10.1021/jm501071f
    17. Bertrand Czarny, Enrico A. Stura, Laurent Devel, Laura Vera, Evelyne Cassar-Lajeunesse, Fabrice Beau, Vito Calderone, Marco Fragai, Claudio Luchinat, and Vincent Dive . Molecular Determinants of a Selective Matrix Metalloprotease-12 Inhibitor: Insights from Crystallography and Thermodynamic Studies. Journal of Medicinal Chemistry 2013, 56 (3) , 1149-1159. https://doi.org/10.1021/jm301574d
    18. Artur Mucha, Paweł Kafarski, and Łukasz Berlicki . Remarkable Potential of the α-Aminophosphonate/Phosphinate Structural Motif in Medicinal Chemistry. Journal of Medicinal Chemistry 2011, 54 (17) , 5955-5980. https://doi.org/10.1021/jm200587f
    19. Akram Ranjbar Derranji, Mohammad Anary-Abbasinejad. An efficient synthesis of phosphonated cyclopentenones by NaN3-catalyzed three-component reaction between trialkyl phosphites, ethyl arylmethylidenecyanoacetates and dialkyl acetylenedicarboxylates. Molecular Diversity 2024, 28 (1) , 209-216. https://doi.org/10.1007/s11030-023-10744-1
    20. Ram Singh Jat, Raveendrababu Kothapalli, M. Bhanuchandra. K2CO3-Mediated Intramolecular Oxa-Michael Cyclization of α,β-Unsaturated Ketoximes: Synthesis of Densely Arene-Substituted 2-Isoxazolines Bearing a Quaternary Center. Synthesis 2024, 77 https://doi.org/10.1055/a-2242-6435
    21. Cangzhu Hu, Shiji Xu, Qiang Wang, Jing Sun, Ying Han, Chao-Guo Yan, Lei Wang. The synthesis of isoxazolines and dihydrooxazines by Pd-catalyzed oxyalkynylation alkenyl oximes with alkynyl bromides. Organic Chemistry Frontiers 2024, 138 https://doi.org/10.1039/D4QO00263F
    22. Alexey V. Rayevsky, Andrii S. Poturai, Iryna O. Kravets, Alexander E. Pashenko, Tatiana A. Borisova, Ganna M. Tolstanova, Dmitriy M. Volochnyuk, Petro O. Borysko, Olga B. Vadzyuk, Diana O. Alieksieieva, Yuliana Zabolotna, Olga Klimchuk, Dragos Horvath, Gilles Marcou, Sergey V. Ryabukhin, Alexandre Varnek. In Vitro Evaluation of In Silico Screening Approaches in Search for Selective ACE2 Binding Chemical Probes. Molecules 2022, 27 (17) , 5400. https://doi.org/10.3390/molecules27175400
    23. Magdalena Mizerska-Kowalska, Sylwia Sowa, Beata Donarska, Wojciech Płaziński, Adrianna Sławińska-Brych, Aleksandra Tomasik, Anna Ziarkowska, Krzysztof Z. Łączkowski, Barbara Zdzisińska. New Borane-Protected Derivatives of α-Aminophosphonous Acid as Anti-Osteosarcoma Agents: ADME Analysis and Molecular Modeling, In Vitro Studies on Anti-Cancer Activities, and NEP Inhibition as a Possible Mechanism of Anti-Proliferative Activity. International Journal of Molecular Sciences 2022, 23 (12) , 6716. https://doi.org/10.3390/ijms23126716
    24. Lucas Caruso, Nathalia Fonseca Nadur, Marina Brandão da Fonseca, Larissa de Almeida Peixoto Ferreira, Renata Barbosa Lacerda, Cedric Stephan Graebin, Arthur Eugen Kümmerle. The Design of Multi-target Drugs to Treat Cardiovascular Diseases: Two (or more) Birds on One Stone. Current Topics in Medicinal Chemistry 2022, 22 (5) , 366-394. https://doi.org/10.2174/1568026622666220201151248
    25. Paraskevi Kokkala, Kostas Voreakos, Angelos Lelis, Konstantinos Patiniotis, Nikolaos Skoulikas, Laurent Devel, Angeliki Ziotopoulou, Eleni Kaloumenou, Dimitris Georgiadis. Practical Synthesis of Phosphinic Dipeptides by Tandem Esterification of Aminophosphinic and Acrylic Acids under Silylating Conditions. Molecules 2022, 27 (4) , 1242. https://doi.org/10.3390/molecules27041242
    26. Kajal Chakraborty, Shubhajit Dhara. Conoidecyclics A-C from marine macroalga Turbinaria conoides: Newly described natural macrolides with prospective bioactive properties. Phytochemistry 2021, 191 , 112909. https://doi.org/10.1016/j.phytochem.2021.112909
    27. Wenchao Gao, Beibei Li, Luyi Zong, Lintao Yu, Xuyang Li, Qiyang Li, Xu Zhang, Sheng Zhang, Kun Xu. Electrochemical Tandem Cyclization of Unsaturated Oximes with Diselenides: A General Approach to Seleno Isoxazolines Derivatives with Quaternary Carbon Center. European Journal of Organic Chemistry 2021, 2021 (17) , 2431-2435. https://doi.org/10.1002/ejoc.202100294
    28. Wei Yu, Pei‐Long Wang, Ke Xu, Hongji Li. Iron‐Promoted Radical Cyclization of β, γ‐Unsaturated Oximes: Dual Role of Iron(III) Nitrate as a Promoter and Nitrooxy Source. Asian Journal of Organic Chemistry 2021, 10 (4) , 831-837. https://doi.org/10.1002/ajoc.202100040
    29. Moaz M. Abdou. Synopsis of recent synthetic methods and biological applications of phosphinic acid derivatives. Tetrahedron 2020, 137 , 131251. https://doi.org/10.1016/j.tet.2020.131251
    30. Lei Wang, Kenan Zhang, Yuzhuo Wang, Wenbo Li, Mingjie Chen, Junliang Zhang. Enantioselective Synthesis of Isoxazolines Enabled by Palladium‐Catalyzed Carboetherification of Alkenyl Oximes. Angewandte Chemie 2020, 132 (11) , 4451-4457. https://doi.org/10.1002/ange.201912408
    31. Lei Wang, Kenan Zhang, Yuzhuo Wang, Wenbo Li, Mingjie Chen, Junliang Zhang. Enantioselective Synthesis of Isoxazolines Enabled by Palladium‐Catalyzed Carboetherification of Alkenyl Oximes. Angewandte Chemie International Edition 2020, 59 (11) , 4421-4427. https://doi.org/10.1002/anie.201912408
    32. Lauren B. Arendse, A. H. Jan Danser, Marko Poglitsch, Rhian M. Touyz, John C. Burnett, Catherine Llorens-Cortes, Mario R. Ehlers, Edward D. Sturrock, . Novel Therapeutic Approaches Targeting the Renin-Angiotensin System and Associated Peptides in Hypertension and Heart Failure. Pharmacological Reviews 2019, 71 (4) , 539-570. https://doi.org/10.1124/pr.118.017129
    33. Mája Polakovičová, Josef Jampílek. Advances in Structural Biology of ACE and Development of Domain Selective ACE-inhibitors. Medicinal Chemistry 2019, 15 (6) , 574-587. https://doi.org/10.2174/1573406415666190514081132
    34. Michał Talma, Marta Maślanka, Artur Mucha. Recent developments in the synthesis and applications of phosphinic peptide analogs. Bioorganic & Medicinal Chemistry Letters 2019, 29 (9) , 1031-1042. https://doi.org/10.1016/j.bmcl.2019.02.034
    35. Kajal Chakraborty, Soumya Krishnan, Minju Joy. Macrocyclic lactones from seafood Amphioctopus neglectus: Newly described natural leads to attenuate angiotensin-II induced cardiac hypertrophy. Biomedicine & Pharmacotherapy 2019, 110 , 155-167. https://doi.org/10.1016/j.biopha.2018.11.034
    36. Zhong-Qi Xu, Lin-Chuang Zheng, Lin Li, Lili Duan, Yue-Ming Li. Metal-free oxysulfonylation and aminosulfonylation of alkenyl oximes: synthesis of sulfonylated isoxazolines and cyclic nitrones. Organic & Biomolecular Chemistry 2019, 17 (4) , 898-907. https://doi.org/10.1039/C8OB02879F
    37. Alexios N. Matralis, Dimitrios Xanthopoulos, Geneviève Huot, Stéphane Lopes-Paciencia, Charles Cole, Hugo de Vries, Gerardo Ferbeyre, Youla S. Tsantrizos. Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration. Bioorganic & Medicinal Chemistry 2018, 26 (20) , 5547-5554. https://doi.org/10.1016/j.bmc.2018.10.001
    38. Xinye Shang, Kun Liu, Zhongyin Zhang, Xianhong Xu, Pengfei Li, Wenjun Li. Direct access to spirobiisoxazoline via the double 1,3-dipolar cycloaddition of nitrile oxide with allenoate. Organic & Biomolecular Chemistry 2018, 16 (6) , 895-898. https://doi.org/10.1039/C7OB03040A
    39. José Viveros-Ceballos, Mario Ordóñez, Francisco Sayago, Carlos Cativiela. Stereoselective Synthesis of α-Amino-C-phosphinic Acids and Derivatives. Molecules 2016, 21 (9) , 1141. https://doi.org/10.3390/molecules21091141
    40. David Ramírez, Julio Caballero. Is It Reliable to Use Common Molecular Docking Methods for Comparing the Binding Affinities of Enantiomer Pairs for Their Protein Target?. International Journal of Molecular Sciences 2016, 17 (4) , 525. https://doi.org/10.3390/ijms17040525
    41. Wenjun Li, Xiao Zhou, Zhenyan Shi, Yang Liu, Zhantao Liu, Hua Gao. Enolate-mediated 1,3-dipolar cycloaddition reactions of allyl ketones with nitrile oxides: direct access to 3,5-disubstituted isoxazolines. Organic & Biomolecular Chemistry 2016, 14 (42) , 9985-9988. https://doi.org/10.1039/C6OB02025A
    42. A V Galenko, A F Khlebnikov, M S Novikov, V V Pakalnis, N V Rostovskii. Recent advances in isoxazole chemistry. Russian Chemical Reviews 2015, 84 (4) , 335-377. https://doi.org/10.1070/RCR4503
    43. Stéphane Laurent, Ulrike M. Steckelings. New Drugs Under Development for Cardiovascular Prevention. 2015, 323-334. https://doi.org/10.1016/B978-0-12-801387-8.00030-2
    44. Sagar H. Barage, Chidambar B. Jalkute, Maruti J. Dhanavade, Kailas D. Sonawane. Simulated Interactions between Endothelin Converting Enzyme and Aβ Peptide: Insights into Subsite Recognition and Cleavage Mechanism. International Journal of Peptide Research and Therapeutics 2014, 20 (4) , 409-420. https://doi.org/10.1007/s10989-014-9403-2
    45. Yan‐Yun Liu, Ji Yang, Ren‐Jie Song, Jin‐Heng Li. Synthesis of 5‐(Fluoromethyl)‐4,5‐dihydroisoxazoles by Silver‐ Catalyzed Oxyfluorination of Unactivated Alkenes. Advanced Synthesis & Catalysis 2014, 356 (14-15) , 2913-2918. https://doi.org/10.1002/adsc.201400242
    46. Geoffrey Masuyer, Mohd Akif, Bertrand Czarny, Fabrice Beau, Sylva L. U. Schwager, Edward D. Sturrock, R. Elwyn Isaac, Vincent Dive, K. Ravi Acharya. Crystal structures of highly specific phosphinic tripeptide enantiomers in complex with the angiotensin‐ I converting enzyme. The FEBS Journal 2014, 281 (3) , 943-956. https://doi.org/10.1111/febs.12660
    47. Dimitris Georgiadis, Vincent Dive. Phosphinic Peptides as Potent Inhibitors of Zinc-Metalloproteases. 2014, 1-38. https://doi.org/10.1007/128_2014_571
    48. Yan-Yun Liu, Xu-Heng Yang, Ji Yang, Ren-Jie Song, Jin-Heng Li. Silver-mediated radical cyclization: construction of Δ2-isoxazolines from α-halo ketoximes and 1,3-dicarbonyl compounds. Chemical Communications 2014, 50 (52) , 6906. https://doi.org/10.1039/c4cc02084g
    49. Subhasis Samai, Tanmoy Chanda, Hiriyakkanavar Ila, Maya Shankar Singh. One‐Pot Three‐Component Heteroannulation of β‐Oxo Dithioesters, Amines and Hydroxylamine: Regioselective, Facile and Straightforward Entry to 5‐Substituted 3‐Aminoisoxazoles. European Journal of Organic Chemistry 2013, 2013 (19) , 4026-4031. https://doi.org/10.1002/ejoc.201300038
    50. Xing Wang, Yuhong Xiang, Zhenzhen Ren, Yanling Zhang, Yanjiang Qiao. Rational questing for inhibitors of endothelin converting enzyme-1 from Salvia miltiorrhiza by combining ligand- and structure-based virtual screening. Canadian Journal of Chemistry 2013, 91 (6) , 448-456. https://doi.org/10.1139/cjc-2012-0523
    51. Mario R Ehlers, J Albert Abrie, Edward D Sturrock. C domain-selective inhibition of angiotensin-converting enzyme. Journal of the Renin-Angiotensin-Aldosterone System 2013, 14 (2) , 189-192. https://doi.org/10.1177/1470320313489206
    52. Catherine Nury, Sarah Bregant, Bertrand Czarny, Fannely Berthon, Evelyne Cassar-Lajeunesse, Vincent Dive. Detection of Endogenous Matrix Metalloprotease-12 Active Form with a Novel Broad Spectrum Activity-based Probe*. Journal of Biological Chemistry 2013, 288 (8) , 5636-5644. https://doi.org/10.1074/jbc.M112.419499
    53. Takehiro Yamagishi, Atsushi Kinbara, Noriko Okubo, Shunpei Sato, Haruhiko Fukaya. Diastereoselective synthesis of Pro-Phe phosphinyl dipeptide isosteres. Tetrahedron: Asymmetry 2012, 23 (24) , 1633-1639. https://doi.org/10.1016/j.tetasy.2012.10.019
    54. Artur Mucha. Synthesis and Modifications of Phosphinic Dipeptide Analogues. Molecules 2012, 17 (11) , 13530-13568. https://doi.org/10.3390/molecules171113530
    55. Elena Trogu, Claudia Vinattieri, Francesco De Sarlo, Fabrizio Machetti. Acid–Base‐Catalysed Condensation Reaction in Water: Isoxazolines and Isoxazoles from Nitroacetates and Dipolarophiles. Chemistry – A European Journal 2012, 18 (7) , 2081-2093. https://doi.org/10.1002/chem.201102264
    56. Ross G. Douglas, Edward D. Sturrock. Structure-Based Design of Domain-Selective Angiotensin-Converting Enzyme Inhibitors. 2012, 355-377. https://doi.org/10.1007/978-3-642-28175-4_15
    57. Ulrike Muscha Steckelings, Ludovit Paulis, Thomas Unger, Michael Bader. Emerging drugs which target the renin–angiotensin–aldosterone system. Expert Opinion on Emerging Drugs 2011, 16 (4) , 619-630. https://doi.org/10.1517/14728214.2011.618495
    58. Mohd Akif, Sylva L. Schwager, Colin S. Anthony, Bertrand Czarny, Fabrice Beau, Vincent Dive, Edward D. Sturrock, K. Ravi Acharya. Novel mechanism of inhibition of human angiotensin-I-converting enzyme (ACE) by a highly specific phosphinic tripeptide. Biochemical Journal 2011, 436 (1) , 53-59. https://doi.org/10.1042/BJ20102123
    59. Laurent Devel, Sandra Garcia, Bertrand Czarny, Fabrice Beau, Evelyne Lajeunesse, Laura Vera, Dimitris Georgiadis, Enrico Stura, Vincent Dive. Insights from Selective Non-phosphinic Inhibitors of MMP-12 Tailored to Fit with an S1′ Loop Canonical Conformation. Journal of Biological Chemistry 2010, 285 (46) , 35900-35909. https://doi.org/10.1074/jbc.M110.139634

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect