Linear and Cyclic Depsipeptidomimetics with β‐Lactam Cores: A Class of New α<sub>v</sub>β<sub>3</sub> Integrin Receptor Inhibitors

Zabala-Uncilla, Nerea; Miranda, José I.; Laso, António; Fernández, Xavier; Ganboa, José Ignacio; Palomo, Claudio

doi:10.1002/cbic.201600642

Cited by 4 publications

(1 citation statement)

References 64 publications

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“…69a In this regard, the work carried out by researchers such as L. Gentilucci and C. Palomo must be pinpointed. 136 Pseudopeptidic macrocycles have also opened a new window of opportunities in building up dynamic combinatorial libraries (DCLs). In fact, DCLs have served as simplified minimalistic models of complex evolutionary biological processes, proposing the generation of dynamic mixtures of components that can rapidly exchange and interconvert.…”

Section: Pseudopeptidic Macrocyclesmentioning

confidence: 99%

Pseudopeptidic Macrocyclic Systems with Preorganized Cavities

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6.1.2. Introduction 6.1.3. Experimental section 6.1.4. Results and discussion 6.1.4.1.Synthesis of the pseudopeptidic macrocycles 6.1.4.2.Evaluation of the macrocyclic systems as catalysts under homogenous conditions 6.1.4.3.Immobilization of the macrocycles on hydrophobic supports 6.1.4.4.Heterogenous catalysis experiments 6.1.5. Conclusions 6.1.6. References 6.2. Supporting information 7. Chapter 7 -Highly Active and Enantioselective Multifunctional One-Component Supramolecular Catalysts for the Cycloaddition of CO2 to Epoxides 7.1. Main text 7.1.1. Abstract 7.1.2. Introduction 7.1.3. Experimental section 7.1.4. Results and discussion 7.1.5. Conclusions 7.1.6. References 7.2. Supporting information 8. Chapter 8 -Doubly Chiral Pseudopeptidic Macrobicyclic Molecular cages: Water-assisted Dynamic Covalent Self-Assembly and Chiral Self-sorting 8.1. Main text 8.1.1. Abstract 8.1.2. Introduction Pseudopeptidic Macrocyclic Systems with Preorganized Cavities 36 8.1.3. Experimental section 8.1.4. Results and discussion 8.1.4.1. Synthesis and characterisation of the pseudopeptidic cryptands 8.1.4.2. Competition studies with the parent achiral component TREN 8.1.4.3. Effect of the sidechain in the self-sorting between components 8.1.4.4. Effect of component chirality in the self-sorting processes 8.1.5. Conclusions 8.1.6. References 8.2. Supporting information 9. Chapter 9 -Unravelling the Supramolecular Driving Forces in the Formation of CO2-Responsive Pseudopeptidic Low Molecular Weight Hydrogelators 9.1. Main text 9.1.1. Abstract 9.1.2. Introduction 9.1.3. Experimental section 9.1.4. Results and discussion 9.1.4.1. Synthesis of the pseudopeptidic compounds and gelation properties as LMWGs 9.1.4.2. Supramolecular driving forces 9.1.4.3. CO2 stimulus responsiveness 9.1.5. Conclusions 9.1.6. References 9.2. Supporting information 10. Chapter 10 -Conclusions Chapter 1 General Introduction Chapter 1 38 1.1. Supramolecular chemistry Supramolecular chemistry is a relatively recent domain of chemistry, frequently defined as the "non-covalent chemistry" or the "chemistry beyond molecules". 1 These non-covalent interactions are comparatively weaker than covalent bonds, although they have been proved to be essential in a wide range of fundamental biological functions. 2 Supramolecular interactions include, among others, electrostatic interactions, hydrogen bonding, van der Waals forces, π-interactions, hydrophobic interactions or halogen bonding. 3However, before delving further into this topic, it is important to set the discovery of these interactions in their historical background. At the end of the nineteenth century, the forces between molecules were being studied by authors such as J. D. van der Waals (Nobel Prize in Physics in 1910) and H. E. Fischer (Nobel Prize in Chemistry in 1902). In 1894, Fischer postulated the fundamental roots of supramolecular chemistry when he suggested that substrate-enzyme interactions could be defined in terms of the "lock and key" principle, paving the way for understanding host-guest chemist...

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Section: Pseudopeptidic Macrocyclesmentioning

confidence: 99%

Pseudopeptidic Macrocyclic Systems with Preorganized Cavities

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Gold Nanoparticles Functionalized with RGD‐Semipeptides: A Simple yet Highly Effective Targeting System for α_Vβ₃ Integrins

Maggi

Bianchini

Portioli

et al. 2018

Chemistry A European J

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Effective and selective targeting of the α β integrin subtype is of high relevance in cancer research for the development of therapeutic systems with improved efficacy and of diagnostic imaging probes. We report here a new class of highly selective, α β -targeted gold nanoparticles (AuNPs), which carry cyclic 4-aminoproline-RGD semipeptides (cAmpRGD) as the targeting moiety immobilized at low surface density on the poly(ethylene glycol) (PEG)-based nanoparticle coating. We show that these nanoparticles are potent inhibitors of the integrin-mediated melanoma tumor cell adhesion to vitronectin and are selectively internalized via receptor-mediated endocytosis. Furthermore, we have developed bifunctional cAmpRGD-functionalized AuNPs by conjugation of a fluorophore (FAM or TAMRA) to a separate set of reactive groups on the PEG-based coating. These bifunctional AuNPs not only recapitulate the binding properties of cAmpRGD-AuNPs but also can be visualized via confocal laser microscopy, allowing direct observation of nanoparticle internalization. The peculiar molecular design of these nanoparticles and their precisely defined architecture at the molecular level accounts for their selective integrin binding with very low nonspecific background.

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Antiangiogenic activity of the penicillin derivative TAP7f in melanoma

et al. 2023

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Linear and Cyclic Depsipeptidomimetics with β‐Lactam Cores: A Class of New α_vβ₃ Integrin Receptor Inhibitors

Cited by 4 publications

References 64 publications

Pseudopeptidic Macrocyclic Systems with Preorganized Cavities

Pseudopeptidic Macrocyclic Systems with Preorganized Cavities

Gold Nanoparticles Functionalized with RGD‐Semipeptides: A Simple yet Highly Effective Targeting System for α_Vβ₃ Integrins

Antiangiogenic activity of the penicillin derivative TAP7f in melanoma

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Linear and Cyclic Depsipeptidomimetics with β‐Lactam Cores: A Class of New αvβ3 Integrin Receptor Inhibitors

Cited by 4 publications

References 64 publications

Pseudopeptidic Macrocyclic Systems with Preorganized Cavities

Pseudopeptidic Macrocyclic Systems with Preorganized Cavities

Gold Nanoparticles Functionalized with RGD‐Semipeptides: A Simple yet Highly Effective Targeting System for αVβ3 Integrins

Antiangiogenic activity of the penicillin derivative TAP7f in melanoma

Contact Info

Product

Resources

About

Linear and Cyclic Depsipeptidomimetics with β‐Lactam Cores: A Class of New α_vβ₃ Integrin Receptor Inhibitors

Gold Nanoparticles Functionalized with RGD‐Semipeptides: A Simple yet Highly Effective Targeting System for α_Vβ₃ Integrins