Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives

Robertson, Mark J.; Bremner, John B.; Coates, Jonathan; Deadman, John; Keller, P. A.; Pyne, Stephen G.; Somphol, Kittiya; Rhodes, David

doi:10.1016/j.ejmech.2011.06.024

Cited by 8 publications

(8 citation statements)

References 23 publications

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“…The ester moiety of 3 was then removed by alkaline hydrolysis, and after acidic treatment carboxy ZnPc 4 was obtained. To introduce a pendent azido group, compound 7 was prepared by removing the tert ‐butyloxycarbonyl (Boc) protecting group of the previously reported N ‐Boc‐ N ′‐Fmoc‐ l ‐lysine methyl ester 5 (Fmoc=9‐fluorenylmethyloxycarbonyl) with a 1:1 mixture of trifluoroacetic acid and CH 2 Cl 2 , followed by coupling with N ‐hydroxysuccinimide (NHS)‐activated 2‐azidoacetyl ester 6 in tetrahydrofuran (THF). The Fmoc protecting group of 7 was then removed upon treatment with 20 % piperidine in THF.…”

Section: Resultsmentioning

confidence: 99%

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Encapsulating pH‐Responsive Doxorubicin–Phthalocyanine Conjugates in Mesoporous Silica Nanoparticles for Combined Photodynamic Therapy and Controlled Chemotherapy

Wong

Fong

et al. 2017

Chemistry A European J

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Doxorubicin (Dox) was conjugated to a zinc(II) phthalocyanine (ZnPc) through an acid-cleavable hydrazone linker. This azido-containing conjugate was then anchored to the nanochannels of an alkyne-modified mesoporous silica nanoparticle (MSN) system via copper(I)-catalyzed azide-alkyne cycloaddition. An analogous nanosystem was also prepared by immobilization of a hydrazine-substituted ZnPc to the MSN followed by coupling with Dox. The release of Dox under acidic conditions was studied in phosphate-buffered saline. After internalization into human hepatocellular carcinoma HepG2 cells, these nanoparticles showed fluorescence not only for ZnPc, but also for Dox, suggesting that release of Dox was triggered by the acidic intracellular environment. The chemocytotoxic Dox together with singlet oxygen generated upon irradiation on the encapsulated ZnPc in these MSNs could kill the cells effectively. A synergistic cytotoxicity was suggested by a less-than-unity combination index. These nanoparticles function as both nanophotosensitizers for photodynamic therapy and as nanoplatforms for pH-controlled drug release.

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Section: Resultsmentioning

confidence: 99%

“…All other solvents and reagents were of reagent grade and used as received. Compounds 1 , 5 , and 6 were prepared as described previously.…”

Section: Methodsmentioning

confidence: 99%

Encapsulating pH‐Responsive Doxorubicin–Phthalocyanine Conjugates in Mesoporous Silica Nanoparticles for Combined Photodynamic Therapy and Controlled Chemotherapy

Wong

Fong

et al. 2017

Chemistry A European J

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“…Binaphthyl [89] hydrophobic scaffolds with cationic amino group substitutions on both 2,2′-oxy positions were further investigated. The SAR was developed by positioning the amino acids sequentially pendant from one of the naphthyl unit hydrophobic scaffold.…”

Section: Development Of Peptidomimeticsmentioning

confidence: 99%

Short Cationic Peptidomimetic Antimicrobials

et al. 2019

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The rapid growth of antimicrobial resistance against several frontline antibiotics has encouraged scientists worldwide to develop new alternatives with unique mechanisms of action. Antimicrobial peptides (AMPs) have attracted considerable interest due to their rapid killing and broad-spectrum activity. Peptidomimetics overcome some of the obstacles of AMPs such as high cost of synthesis, short half-life in vivo due to their susceptibility to proteolytic degradation, and issues with toxicity. This review will examine the development of short cationic peptidomimetics as antimicrobials.

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“…[15, 16] The synthesis of peptidomimetics that also possess well-defined amphiphilic structure is therefore a logical step in the pursuit of new antibacterial agents and a number of research groups are currently active in this field. [17–20]…”

Section: Introductionmentioning

confidence: 99%

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

Hickey

Ashton

Boer

et al. 2018

European Journal of Medicinal Chemistry

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The design, synthesis and evaluation of a small series of potent amphiphilic norbornane antibacterial agents has been performed (compound 10 MIC = 0.25 μg/mL against MRSA). Molecular modelling indicates rapid aggregation of this class of antibacterial agent prior to membrane association and insertion. Two fluorescent analogues (compound 29 with 4-amino-naphthalimide and 34 with 4-nitrobenz-2-oxa-1,3-diazole fluorophores) with good activity (MIC = 0.5 μg/mL against MRSA) were also constructed and confocal microscopy studies indicate that the primary site of interaction for this family of compounds is the bacterial membrane.

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Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives

Cited by 8 publications

References 23 publications

Encapsulating pH‐Responsive Doxorubicin–Phthalocyanine Conjugates in Mesoporous Silica Nanoparticles for Combined Photodynamic Therapy and Controlled Chemotherapy

Encapsulating pH‐Responsive Doxorubicin–Phthalocyanine Conjugates in Mesoporous Silica Nanoparticles for Combined Photodynamic Therapy and Controlled Chemotherapy

Short Cationic Peptidomimetic Antimicrobials

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

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