Recent Progress in Combinatorial Solid Phase Synthesis: Techniques, Characterization and its Application in Drug Development

Kumar, Parveen; Yadav, Nalini; Chhikara, Aruna; Chopra, Madhu

doi:10.2174/2212711903666160622085741

Cited by 6 publications

(5 citation statements)

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“…Eugenia Nogueira et al [100] utilized the bifunctional SP-D peptide-containing neck-domain, which acted as an anchor and a linker for FA to the liposomes. Neck-domain peptides constructed from SP-D were fabricated by covalent conjugation of FA with the N-terminal of peptides via pteroic acid and glutamic acid using an Fmoc-based solid-phase synthetic procedure [101,102], and C-terminal was covalently bound with Oregon Green 488 [103,104]. The peptide was deeply inserted into the lipid bilayer of the liposomes without affecting their integrity.…”

Section: Design and Fabrication Of Folate-conjugated Liposomesmentioning

confidence: 99%

Formulation Strategies for Folate-Targeted Liposomes and Their Biomedical Applications

2019

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The folate receptor (FR) is a tumor-associated antigen that can bind with folic acid (FA) and its conjugates with high affinity and ingests the bound molecules inside the cell via the endocytic mechanism. A wide variety of payloads can be delivered to FR-overexpressed cells using folate as the ligand, ranging from small drug molecules to large DNA-containing macromolecules. A broad range of folate attached liposomes have been proven to be highly effective as the targeted delivery system. For the rational design of folate-targeted liposomes, an intense conceptual understanding combining chemical and biomedical points of view is necessary because of the interdisciplinary nature of the field. The fabrication of the folate-conjugated liposomes basically involves the attachment of FA with phospholipids, cholesterol or peptides before liposomal formulation. The present review aims to provide detailed information about the design and fabrication of folate-conjugated liposomes using FA attached uncleavable/cleavable phospholipids, cholesterol or peptides. Advances in the area of folate-targeted liposomes and their biomedical applications have also been discussed.

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Section: Design and Fabrication Of Folate-conjugated Liposomesmentioning

confidence: 99%

Formulation Strategies for Folate-Targeted Liposomes and Their Biomedical Applications

2019

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“…22 4-Hydroxy-5,6-dihydropyridin-2(1H)-one ( 2) is considered a six-membered homologue of tetramic acid. A similar structural motif can be found in the structure of natural bioactive alkaloid piperlongumine (3) 23 and other piperamides (4, 24 5 25 ) or as a subunit of fused compounds, 2-quinolones (6). 2-Quinolones, also referred to as 1-azacoumarins (formal substitution of the ring nitrogen with oxygen leads to coumarin 7) or carbostyrils, are often found in quinoline alkaloids.…”

Section: ■ Introductionmentioning

confidence: 71%

“…In 1963, Merrifield introduced solid-phase peptide synthesis (SPPS) . In the 1990s, SPPS was applied in combinatorial chemistry, , was later extended to heterocyclic chemistry, and found its application in drug discovery. , This technique is time-efficient and straightforward in comparison to the solution-phase approach. Typically, it is a multistep synthesis on resin-bound intermediates, and only after the final synthetic step, the product is released from the insoluble support, isolated, purified, and fully characterized.…”

Section: Introductionmentioning

confidence: 99%

Greening Solid-Phase Organic Synthesis: Environmentally Conscious Synthesis of Pharmaceutically Relevant Privileged Structures 5,6-Dihydropyridin-2(1H)-ones and Quinolin-2(1H)-ones

et al. 2020

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Solid-phase organic synthesis (SPOS) is a very efficient methodology for the synthesis of diverse organic molecules, particularly exploited in drug discovery. Here, we present the transformation of the traditional SPOS to an ecofriendlier methodology on examples of pharmacologically relevant privileged structures 5,6-dihydropyridin-2(1H)-ones and quinolin-2(1H)-ones. The green approach is primarily based on the utilization of environmentally friendly solvent 2-MeTHF in all steps of the synthesis. Target heterocycles were synthesized by extending our previously published synthesis of five-membered tetramic acid analogues to six-membered cycles. The crucial step of the synthesis is cyclization via nonclassical Wittig olefination of resin-bound esters. Traditional and green protocols provided comparable results with respect to purity and yield of products, thus opening the way for greener access to a variety of diverse heterocycles.

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“…Parallel library synthesis, long established in small-molecule drug discovery as a means of generating rapid diversity and enabling data-rich design cycles, 22 well micromole-scale parallel peptide synthesizer modules. 23 The success of the latter approach relies in large part on the robustness and generality of amide coupling and selective deprotection protocols. Introducing nonstandard chemistries, such as Pd-catalyzed cross-coupling methods, into this sequence would require similarly high levels of method robustness and substrate scope to enable the synthesis of diverse libraries with acceptable success rates.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Parallel library synthesis, long established in small-molecule drug discovery as a means of generating rapid diversity and enabling data-rich design cycles, is also gaining increasing prominence in peptide drug discovery with the advent of 96-well micromole-scale parallel peptide synthesizer modules . The success of the latter approach relies in large part on the robustness and generality of amide coupling and selective deprotection protocols.…”

Section: Introductionmentioning

confidence: 99%

Merging Late-Stage Diversification with Solid-Phase Peptide Synthesis Enabled by High-Throughput On-Resin Reaction Screening

Pissarnitski

Nowak

et al. 2022

ACS Catal.

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An integrated workflow is described that combines micromole-scale high-throughput experimentation (HTE) reaction screening and solid-phase peptide synthesis (SPPS) to enable rapid synthetic method development for on-resin peptide diversification. Using this new approach, we have identified several sets of robust Suzuki–Miyaura coupling conditions with complementary scope that collectively display broad coverage with respect to both resin-bound peptide substrates containing aryl halide side chains and (hetero)arylboronic acid coupling partners. We have also demonstrated the utility of this integrated SPPS/chemical diversification method by synthesizing a multidimensional library of diverse peptides in high yields.

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Recent Progress in Combinatorial Solid Phase Synthesis: Techniques, Characterization and its Application in Drug Development

Cited by 6 publications

References 0 publications

Formulation Strategies for Folate-Targeted Liposomes and Their Biomedical Applications

Formulation Strategies for Folate-Targeted Liposomes and Their Biomedical Applications

Greening Solid-Phase Organic Synthesis: Environmentally Conscious Synthesis of Pharmaceutically Relevant Privileged Structures 5,6-Dihydropyridin-2(1H)-ones and Quinolin-2(1H)-ones

Merging Late-Stage Diversification with Solid-Phase Peptide Synthesis Enabled by High-Throughput On-Resin Reaction Screening

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