4.0 Review

Cyclic peptide drugs approved in the last two decades (2001-2021)

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Review Biochemistry & Molecular Biology

Site-Selective Peptide Macrocyclization

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Summary: Research on site-selective chemistry for cyclized peptides can reduce the generation of side products and increase the yield of desired products. The latest CyClick strategy achieves N-terminal site-selective cyclization through imine formation and nucleophilic attack.

CHEMBIOCHEM (2021)

Review Biotechnology & Applied Microbiology

Echinocandins: structural diversity, biosynthesis, and development of antimycotics

Wolfgang Huettel

Summary: Echinocandins, a class of non-ribosomal antifungal lipopeptides, are semisynthetically manufactured due to their complex structure containing numerous hydroxylated non-proteinogenic amino acids. Industrial research efforts have led to the development of active ingredients like caspofungin, micafungin, and anidulafungin, which are now commonly used as first-line treatments against invasive mycosis. The identification of echinocandin biosynthetic gene clusters has further advanced the understanding and potential engineering of echinocandin biosynthesis on a molecular level.

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY (2021)

Article Biotechnology & Applied Microbiology

Identification of highly selective covalent inhibitors by phage display

Shiyu Chen et al.

Summary: A phage display method was developed to screen for covalent inhibitors that bind to protein targets by introducing a reactive linker to form cyclic peptides and an electrophilic 'warhead' to react with target nucleophiles. This approach identified cyclic peptides that irreversibly inhibited cysteine protease and serine hydrolase with high specificity and potency. It enables rapid, unbiased screening to identify new classes of highly selective covalent inhibitors for diverse molecular targets.

NATURE BIOTECHNOLOGY (2021)

Article Chemistry, Organic

Construction of Peptide Macrocycles via Radical-Mediated Intramolecular C-H Alkylations

Xiafei Hu et al.

Summary: New methods have been developed in this study to construct peptide macrocycles via radical-mediated intramolecular C-H alkylation reactions under photoredox catalysis, providing a new strategy for the synthesis of complex peptide macrocycles.

ORGANIC LETTERS (2021)

Review Nanoscience & Nanotechnology

Internalization mechanisms of cell-penetrating peptides

Ivana Ruseska et al.

BEILSTEIN JOURNAL OF NANOTECHNOLOGY (2020)

Review Chemistry, Multidisciplinary

Methods for generating and screening libraries of genetically encoded cyclic peptides in drug discovery

Catrin Sohrabi et al.

NATURE REVIEWS CHEMISTRY (2020)

Review Critical Care Medicine

Vasopressin and its analogues in shock states: a review

Julien Demiselle et al.

ANNALS OF INTENSIVE CARE (2020)

Review Biochemistry & Molecular Biology

Antifungal Drugs

Jiri Houst et al.

METABOLITES (2020)

Review Chemistry, Multidisciplinary

Methodologies for Backbone Macrocyclic Peptide Synthesis Compatible With Screening Technologies

Koki Shinbara et al.

FRONTIERS IN CHEMISTRY (2020)

Review Biochemistry & Molecular Biology

Harnessing cyclotides to design and develop novel peptide GPCR ligands

Edin Muratspahic et al.

RSC CHEMICAL BIOLOGY (2020)

Review Chemistry, Multidisciplinary

Macrocyclic Peptides as Drug Candidates: Recent Progress and Remaining Challenges

Alexander A. Vinogradov et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Multidisciplinary

Understanding Cell Penetration of Cyclic Peptides

Patrick G. Dougherty et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

Construction of Natural-Product-Like Cyclophane-Braced Peptide Macrocycles via sp3 C-H Arylation

Bo Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Pharmacology & Pharmacy

Nature-Derived Peptides: A Growing Niche for GPCR Ligand Discovery

Edin Muratspahic et al.

TRENDS IN PHARMACOLOGICAL SCIENCES (2019)

Review Chemistry, Multidisciplinary

Ligation Technologies for the Synthesis of Cyclic Peptides

Hoi Yee Chow et al.

CHEMICAL REVIEWS (2019)

Review Chemistry, Multidisciplinary

Conformational Control of Macrocycles by Remote Structural Modification

Solomon D. Appavoo et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

CyClick Chemistry for the Synthesis of Cyclic Peptides

Victor Adebomi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Microbiology

Diversity, Ecology, and Prevalence of Antimicrobials in Nature

Megan M. Mullis et al.

FRONTIERS IN MICROBIOLOGY (2019)

Article Chemistry, Multidisciplinary

Ribosomal Synthesis of Backbone-Cyclic Peptides Compatible with In Vitro Display

Ryo Takatsuji et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Endocrinology & Metabolism

Pharmacotherapy of obesity: Available medications and drugs under investigation

Eleni Pilitsi et al.

METABOLISM-CLINICAL AND EXPERIMENTAL (2019)

Article Pharmacology & Pharmacy

Battle of GLP-1 delivery technologies

Minzhi Yu et al.

ADVANCED DRUG DELIVERY REVIEWS (2018)

Review Pharmacology & Pharmacy

Clinical Pharmacokinetics and Pharmacodynamics of Telavancin Compared with the Other Glycopeptides

Valentin al Jalali et al.

CLINICAL PHARMACOKINETICS (2018)

Article Gastroenterology & Hepatology

Linaclotide in irritable bowel syndrome with constipation: A Phase 3 randomized trial in China and other regions

Yunsheng Yang et al.

JOURNAL OF GASTROENTEROLOGY AND HEPATOLOGY (2018)

Article Biochemistry & Molecular Biology

MC4R agonism promotes durable weight loss in patients with leptin receptor deficiency

Karine Clement et al.

NATURE MEDICINE (2018)

Review Endocrinology & Metabolism

Novel Somatostatin Receptor Ligands Therapies for Acromegaly

Rosa Maria Paragliola et al.

FRONTIERS IN ENDOCRINOLOGY (2018)

Review Biochemistry & Molecular Biology

DNA-Encoded Chemical Libraries: A Selection System Based on Endowing Organic Compounds with Amplifiable Information

Dario Neri et al.

ANNUAL REVIEW OF BIOCHEMISTRY, VOL 87 (2018)

Article Chemistry, Multidisciplinary

Display Selection of Exotic Macrocyclic Peptides Expressed under a Radically Reprogrammed 23 Amino Acid Genetic Code

Toby Passioura et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Biochemistry & Molecular Biology

Natural Cyclic Peptides as an Attractive Modality for Therapeutics: A Mini Review

Muna Ali Abdalla et al.

MOLECULES (2018)

Review Genetics & Heredity

Cyclic Peptides: Promising Scaffolds for Biopharmaceuticals

Donghyeok Gang et al.

Review Pharmacology & Pharmacy

Clinical Pharmacokinetics and Pharmacodynamics of Micafungin

Roeland E. Wasmann et al.

CLINICAL PHARMACOKINETICS (2018)

Review Biochemistry & Molecular Biology

Cyclic Peptides as Novel Therapeutic Microbicides: Engineering of Human Defensin Mimetics

Annarita Falanga et al.

MOLECULES (2017)

Article Biotechnology & Applied Microbiology

Trends in GPCR drug discovery: new agents, targets and indications

Alexander S. Hauser et al.

NATURE REVIEWS DRUG DISCOVERY (2017)

Article Multidisciplinary Sciences

Acylated heptapeptide binds albumin with high affinity and application as tag furnishes long-acting peptides

Alessandro Zorzi et al.

NATURE COMMUNICATIONS (2017)

Article Endocrinology & Metabolism

Evaluation of a melanocortin-4 receptor (MC4R) agonist (Setmelanotide) in MC4R deficiency

Tinh-Hai Collet et al.

MOLECULAR METABOLISM (2017)

Article Multidisciplinary Sciences

THPdb: Database of FDA-approved peptide and protein therapeutics

Salman Sadullah Usmani et al.

PLOS ONE (2017)

Review Biochemistry & Molecular Biology

Cyclic peptide therapeutics: past, present and future

Alessandro Zorzi et al.

CURRENT OPINION IN CHEMICAL BIOLOGY (2017)

Article Pharmacology & Pharmacy

Plecanatide: First Global Approval

Zaina T. Al-Salama et al.

Article Pharmacology & Pharmacy

Therapeutically targeting guanylate cyclase-C: computational modeling of plecanatide, a uroguanylin analog

Andrea Brancale et al.

PHARMACOLOGY RESEARCH & PERSPECTIVES (2017)

Article Chemistry, Multidisciplinary

A RaPID way to discover nonstandard macrocyclic peptide modulators of drug targets

Toby Passioura et al.

CHEMICAL COMMUNICATIONS (2017)

Review Biotechnology & Applied Microbiology

Half-life extended biotherapeutics

Roland E. Kontermann

EXPERT OPINION ON BIOLOGICAL THERAPY (2016)

Review Pharmacology & Pharmacy

Peginesatide for the treatment of anemia due to chronic kidney disease - an unfulfilled promise

Terhi Hermanson et al.

EXPERT OPINION ON DRUG SAFETY (2016)

Review Biochemistry & Molecular Biology

Applications and Challenges for Use of Cell-Penetrating Peptides as Delivery Vectors for Peptide and Protein Cargos

Mie Kristensen et al.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2016)

Article Medicine, General & Internal

Proopiomelanocortin Deficiency Treated with a Melanocortin-4 Receptor Agonist

Peter Kuehnen et al.

NEW ENGLAND JOURNAL OF MEDICINE (2016)

Article Microbiology

Antifungal Drugs: The Current Armamentarium and Development of New Agents

Nicole Robbins et al.

MICROBIOLOGY SPECTRUM (2016)

Review Biochemistry & Molecular Biology

Biosynthesis of cyclosporins and other natural peptidyl prolyl cis/trans isomerase inhibitors

Alfons Lawen

BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS (2015)

Article Biochemical Research Methods

GLASS: a comprehensive database for experimentally validated GPCR-ligand associations

Wallace K. B. Chan et al.

BIOINFORMATICS (2015)

Article Immunology

Oritavancin: A Long-Half-Life Lipoglycopeptide

Louis D. Saravolatz et al.

CLINICAL INFECTIOUS DISEASES (2015)

Article Endocrinology & Metabolism

RM-493, a Melanocortin-4 Receptor (MC4R) Agonist, Increases Resting Energy Expenditure in Obese Individuals

Kong Y. Chen et al.

JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM (2015)

Article Chemistry, Multidisciplinary

Cell-Permeable Cyclic Peptides from Synthetic Libraries Inspired by Natural Products

William M. Hewitt et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Biochemistry & Molecular Biology

A biomimetic approach for enhancing the in vivo half-life of peptides

Sravan C. Penchala et al.

NATURE CHEMICAL BIOLOGY (2015)

Article Neurosciences

A neural basis for melanocortin-4 receptor-regulated appetite

Alastair S. Garfield et al.

NATURE NEUROSCIENCE (2015)

Article Oncology

Romidepsin targets multiple survival signaling pathways in malignant T cells

B. C. Valdez et al.

BLOOD CANCER JOURNAL (2015)

Review Pharmacology & Pharmacy

Drugs in early clinical development for the treatment of female sexual dysfunction

Zoe R. Belkin et al.

EXPERT OPINION ON INVESTIGATIONAL DRUGS (2015)

Article Chemistry, Multidisciplinary

Peptide Ligands Stabilized by Small Molecules

Shiyu Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Constrained Peptides with Target-Adapted Cross-Links as Inhibitors of a Pathogenic Protein-Protein Interaction**

Adrian Glas et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Biochemistry & Molecular Biology

Early Endosomal Escape of a Cyclic Cell-Penetrating Peptide Allows Effective Cytosolic Cargo Delivery

Ziqing Qian et al.

BIOCHEMISTRY (2014)

Letter Gastroenterology & Hepatology

Clarification of Linaclotide Pharmacology Presented in a Recent Clinical Study of Plecanatide

Robert W. Busby et al.

DIGESTIVE DISEASES AND SCIENCES (2014)

Review Biochemistry & Molecular Biology

Discovery and development of first in class antifungal caspofungin (CANCIDAS®)-A case study

James M. Balkovec et al.

NATURAL PRODUCT REPORTS (2014)

Letter Medicine, General & Internal

Anaphylaxis and Hypotension after Administration of Peginesatide

Charles L. Bennett et al.

NEW ENGLAND JOURNAL OF MEDICINE (2014)

Article Biotechnology & Applied Microbiology

Efficient Bioconversion of Echinocandin B to Its Nucleus by Overexpression of Deacylase Genes in Different Host Strains

Lei Shao et al.

APPLIED AND ENVIRONMENTAL MICROBIOLOGY (2013)

Article Pharmacology & Pharmacy

Telavancin: A Review of Its Use in Patients with Nosocomial Pneumonia

Lesley J. Scott

Review Biochemistry & Molecular Biology

Cell-penetrating peptides: 20 years later, where do we stand?

Cherine Bechara et al.

FEBS LETTERS (2013)

Article Biochemistry & Molecular Biology

Bicyclic Peptide Inhibitor Reveals Large Contact Interface with a Protease Target

Alessandro Angelini et al.

ACS CHEMICAL BIOLOGY (2012)

Article Immunology

Oritavancin: Mechanism of Action

George G. Zhanel et al.

CLINICAL INFECTIOUS DISEASES (2012)

Article Biochemical Research Methods

Structural basis for the cyclophilin A binding affinity and immunosuppressive potency of E-ISA247 (voclosporin)

Andreas Kuglstatter et al.

ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY (2011)

Article Infectious Diseases

Update on the telavancin activity tested against European staphylococcal clinical isolates (2009-2010)

Rodrigo E. Mendes et al.

DIAGNOSTIC MICROBIOLOGY AND INFECTIOUS DISEASE (2011)

Article Chemistry, Medicinal

New, Potent, Selective, and Short-Acting Peptidic V1a Receptor Agonists

Kazimierz Wisniewski et al.

JOURNAL OF MEDICINAL CHEMISTRY (2011)

Review Chemistry, Multidisciplinary

Contemporary strategies for peptide macrocyclization

ChHstcpher J. White et al.

NATURE CHEMISTRY (2011)

Article Gastroenterology & Hepatology

Linaclotide, a synthetic guanylate cyclase C agonist, for the treatment of functional gastrointestinal disorders associated with constipation

Maria Vazquez Roque et al.

EXPERT REVIEW OF GASTROENTEROLOGY & HEPATOLOGY (2011)

Article Pharmacology & Pharmacy

Regulation of appetite to treat obesity

Gilbert W Kim et al.

Expert Review of Clinical Pharmacology (2011)

Article Pharmacology & Pharmacy

Ligand-Based Peptide Design and Combinatorial Peptide Libraries to Target G Protein-Coupled Receptors

Christian W. Gruber et al.

CURRENT PHARMACEUTICAL DESIGN (2010)

Article Microbiology

Oritavancin Kills Stationary-Phase and Biofilm Staphylococcus aureus Cells In Vitro

Adam Belley et al.

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY (2009)

Article Biochemistry & Molecular Biology

Synthesis and screening of a cyclic peptide library: Discovery of small-molecule ligands against human prolactin receptor

Tao Liu et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2009)

Review Biotechnology & Applied Microbiology

Micafungin: a sulfated echinocandin

Seiji Hashimoto

JOURNAL OF ANTIBIOTICS (2009)

Article Biochemistry & Molecular Biology

Vancomycin and Oritavancin Have Different Modes of Action in Enterococcus faecium

Gary J. Patti et al.

JOURNAL OF MOLECULAR BIOLOGY (2009)

Article Biochemistry & Molecular Biology

Phage-encoded combinatorial chemical libraries based on bicyclic peptides

Christian Heinis et al.

NATURE CHEMICAL BIOLOGY (2009)

Article Biochemical Research Methods

RGD-Human Serum Albumin Conjugates as Efficient Tumor Targeting Probes

Kai Chen et al.

MOLECULAR IMAGING (2009)

Article Chemistry, Multidisciplinary

Improving oral bioavailability of peptides by multiple N-methylation: Somatostatin analogues

Eric Biron et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Article Biochemistry & Molecular Biology

Oritavancin exhibits dual mode of action to inhibit cell-wall biosynthesis, in Staphylococcus aureus

Sung Joon Kim et al.

JOURNAL OF MOLECULAR BIOLOGY (2008)

Article Urology & Nephrology

Bremelanotide: An overview of preclinical CNS effects on female sexual function

James Pfaus et al.

JOURNAL OF SEXUAL MEDICINE (2007)

Article Biochemistry & Molecular Biology

Synthesis of cyclic peptides and peptide libraries on a new disulfide linker

Werner Tegge et al.

JOURNAL OF PEPTIDE SCIENCE (2007)

Article Medicine, General & Internal

Dalbavancin: a novel antimicrobial

A. Y. Chen et al.

INTERNATIONAL JOURNAL OF CLINICAL PRACTICE (2007)

Article Pharmacology & Pharmacy

Telavancin: a novel lipoglycopeptide for serious Gram-positive infections

Somvadee Laohavaleeson et al.

EXPERT OPINION ON INVESTIGATIONAL DRUGS (2007)

Review Endocrinology & Metabolism

Studies on the physiological functions of the melanocortin system

Roger D. Cone

ENDOCRINE REVIEWS (2006)

Article Infectious Diseases

Daptomycin: a lipopeptide antibiotic for the treatment of serious Gram-positive infections

JN Steenbergen et al.

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY (2005)

Article Infectious Diseases

Origin, structure, and activity in vitro and in vivo of dalbavancin

A Malabarba et al.

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY (2005)

Article Microbiology

Pharmacodynamics of telavancin (TD-6424), a novel bactericidal agent, against gram-positive bacteria

SS Hegde et al.

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY (2004)

Review Medicine, General & Internal

Echinocandin antifungal drugs

DW Denning

LANCET (2003)

Review Microbiology

Mechanism of action of oritavancin and related glycopeptide antibiotics

NE Allen et al.

FEMS MICROBIOLOGY REVIEWS (2003)

Article Infectious Diseases

Echinocandins: a new class of antifungal

DW Denning

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY (2002)

Review Biochemistry & Molecular Biology

Glycopeptide derivatives

A Malabarba et al.

CURRENT MEDICINAL CHEMISTRY (2001)

Review Chemistry, Organic

The synthesis of cyclic peptides

JN Lambert et al.

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (2001)