Dendrimers Terminated with Dichlorotriazine Groups Provide a Route to Compositional Diversity

Patra, Subrata; Kozura, Brittany; Huang, Adela Ya-Ting; Enciso, Alan E.; Sun, Xiankai; Hsieh, Jer Tsong; Kao, Ching Huei; Chen, Hui Ting; Simanek, Eric E.

doi:10.1021/ol400811h

Cited by 21 publications

(22 citation statements)

References 42 publications

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“… Well‐defined, better characterized soft/hard nanoparticles that may be synthesized reproducibly by standardized methodologies. Stealthier nanoparticle surface chemistry beyond PEGylation to present fewer side effects and avoid complement activation . Well‐defined, size‐controlled, monodispersed hard and soft nanoparticle categories, with well understood aggregation and protein corona features. Nanoparticles with suitable surface chemistry for reproducible stochastic or quantized attachment of drugs, targeting groups, imaging moieties or stealth coatings . Smaller nanoparticles sizes (<10 nm) or degradation features that enable desirable kidney excretion modes (versus liver, etc.) and more effective tumour penetration properties. Shelf stable, water‐soluble, single‐component nanomedicine formulations with simple administration protocols. Noninvasive patient‐friendly administration modes (e.g.…”

Section: Emergence Of Dendrimer‐based Products/therapeutics In the Pamentioning

confidence: 99%

“…• Stealthier nanoparticle surface chemistry beyond PEGylation to present fewer side effects and avoid complement activation [224].…”

Section: Opto-electronicsmentioning

confidence: 99%

“…• Nanoparticles with suitable surface chemistry for reproducible stochastic or quantized attachment of drugs, targeting groups, imaging moieties or stealth coatings [224].…”

Section: Opto-electronicsmentioning

confidence: 99%

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Emerging concepts in dendrimer‐based nanomedicine: from design principles to clinical applications

Kannan¹,

et al. 2014

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Abstract. Kannan RM, Nance E, Kannan S, Tomalia DA (Center for Nanomedicine; Johns Hopkins University School of Medicine, Baltimore, MD; NanoSynthons LLC, Mt. Pleasant, MI; University of Pennsylvania, Philadelphia, PA; and Virginia Commonwealth University, VA, USA). Emerging concepts in dendrimer-based nanomedicine: from design principles to clinical applications (Review). J Intern Med 2014; 276: 579-617.Dendrimers are discrete nanostructures/nanoparticles with 'onion skin-like' branched layers. Beginning with a core, these nanostructures grow in concentric layers to produce stepwise increases in size that are similar to the dimensions of many in vivo globular proteins. These branched tree-like concentric layers are referred to as 'generations'. The outer generation of each dendrimer presents a precise number of functional groups that may act as a monodispersed platform for engineering favourable nanoparticle-drug and nanoparticletissue interactions. These features have attracted significant attention in medicine as nanocarriers for traditional small drugs, proteins, DNA/RNA and in some instances as intrinsically active nanoscale drugs. Dendrimer-based drugs, as well as diagnostic and imaging agents, are emerging as promising candidates for many nanomedicine applications. First, we will provide a brief survey of recent nanomedicines that are either approved or in the clinical approval process. This will be followed by an introduction to a new 'nanoperiodic' concept which proposes nanoparticle structure control and the engineering of 'critical nanoscale design parameters' (CNDPs) as a strategy for optimizing pharmocokinetics, pharmocodynamics and site-specific targeting of disease. This paradigm has led to the emergence of CNDP-directed nanoperiodic property patterns relating nanoparticle behaviour to critical in vivo clinical translation issues such as cellular uptake, transport, elimination, biodistribution, accumulation and nanotoxicology. With a focus on dendrimers, these CNDPdirected nanoperiodic patterns are used as a strategy for designing and optimizing nanoparticles for a variety of drug delivery and imaging applications, including a recent dendrimer-based theranostic nanodevice for imaging and treating cancer. Several emerging preclinical dendrimer-based nanotherapy concepts related to inflammation, neuro-inflammatory disorders, oncology and infectious and ocular diseases are reviewed. Finally we will consider challenges and opportunities anticipated for future clinical translation, nanotoxicology and the commercialization of nanomedicine.

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Section: Emergence Of Dendrimer‐based Products/therapeutics In the Pamentioning

confidence: 99%

“…• Stealthier nanoparticle surface chemistry beyond PEGylation to present fewer side effects and avoid complement activation [224].…”

Section: Opto-electronicsmentioning

confidence: 99%

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Emerging concepts in dendrimer‐based nanomedicine: from design principles to clinical applications

Kannan¹,

et al. 2014

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“…The crude product was puried by column chromatography (DCM : MeOH 97 : 3 to DCM : MeOH 9 : 1; to give 14 as a white wax (132 mg, 81%). 1 H NMR (400 MHz, CDCl 3 ) d 7.13 (s, 1H, from triazole), 6.79-6.77 (d, J ¼ 7.2, 2H, HO-C-CH]CH-C), 6.72-6.7 (d, J ¼ 8.0, 2H, HO-C-CH]CH-C), 4.48-4.47 (t, J ¼ 6.1, 2H, NH-CH 2 -triazole), 3.65-3.43 (m, 88H, CH 2 OCH 2 CH 2 OCH 2-CH 2 OCH 2 , C 3 N 3 -NHCH 2 CH 2 CH 2 O), 3.21 (br, m, 8H, BocNHCH 2 ), 3.04 (m, 2H, triazole-N-CH 2 -CH 2 -phenol),1.83-1.70 (m, 24H, OCH 2 CH 2 CH 2 ), 1.44 (s, 36H, C(CH 3 ) 3 ); 13 …”

Section: Compound 14mentioning

confidence: 99%

“…12 To accommodate the dual roles, we have begun to incorporate alkynes at the focus of these dendrimers. 13 With click chemistry, Scheme 1 Iterative cycle for convergent dendrimer synthesis. these groups could ultimately host uorescent dyes or imaging agents.…”

Section: Introductionmentioning

confidence: 99%

Rapid, semi-automated convergent synthesis of low generation triazine dendrimers using microwave assisted reactions

2014

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Microwave assisted synthesis allows for the rapid access of low generation triazine dendrimers in high yields. Products include a macromonomer and alkyne functionalized dendrimers from generation one to three. Using a microwave assisted, convergent synthetic approach, two nucleophilic aromatic substitution reactions are executed on cyanuric chloride in 10 min at 60 C using primary amines. Substitution of the resulting monochlorotriazine with a diamine requires 95 C for 30 min. Purifications are accomplished using an automated chromatography system such that the generation three dendrimer can be prepared from the starting materials in less than one day.

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p‐Substituted Tris(2‐pyridylmethyl)amines as Ligands for Highly Active ATRP Catalysts: Facile Synthesis and Characterization

et al. 2020

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A facile and efficient two‐step synthesis of p‐substituted tris(2‐pyridylmethyl)amine (TPMA) ligands to form Cu complexes with the highest activity to date in atom transfer radical polymerization (ATRP) is presented. In the divergent synthesis, p‐Cl substituents in tris(4‐chloro‐2‐pyridylmethyl)amine (TPMA3Cl) were replaced in one step and high yield by electron‐donating cyclic amines (pyrrolidine (TPMAPYR), piperidine (TPMAPIP), and morpholine (TPMAMOR)) by nucleophilic aromatic substitution. The [CuII(TPMANR2)Br]+ complexes exhibited larger energy gaps between frontier molecular orbitals and >0.2 V more negative reduction potentials than [CuII(TPMA)Br]+, indicating >3 orders of magnitude higher ATRP activity. [CuI(TPMAPYR)]+ exhibited the highest reported activity for Br‐capped acrylate chain ends in DMF, and moderate activity toward C−F bonds at room temperature. ATRP of n‐butyl acrylate using only 10–25 part per million loadings of [CuII(TPMANR2)Br]+ exhibited excellent control.

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Dendrimers Terminated with Dichlorotriazine Groups Provide a Route to Compositional Diversity

Cited by 21 publications

References 42 publications

Emerging concepts in dendrimer‐based nanomedicine: from design principles to clinical applications

Emerging concepts in dendrimer‐based nanomedicine: from design principles to clinical applications

Rapid, semi-automated convergent synthesis of low generation triazine dendrimers using microwave assisted reactions

p‐Substituted Tris(2‐pyridylmethyl)amines as Ligands for Highly Active ATRP Catalysts: Facile Synthesis and Characterization

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