Novel Arylhydrazone-Conjugated Gold Nanoparticles with DNA-Cleaving Ability: The First DNA-Nicking Nanomaterial

Hsu, Ming-Ying; Josephrajan, T.; Yeh, Chen-Sheng; Shieh, Dar‐Bin; Su, Wu‐Chou; Hwu, Jih Ru

doi:10.1021/bc700222n

Cited by 14 publications

(19 citation statements)

References 36 publications

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“…This effect was attributed to cooperativity due to confinement on the GNP surface. [125] Catalysis of DNA nicking was reported by Hsu et al [127]. The ability of GNPs to confine ligands to locally high concentrations on their surface was again exploited.…”

Section: Biological Catalysis By the Ligandmentioning

confidence: 94%

Gold Nanoparticle-Biological Molecule Interactions and Catalysis

Heddle

2013

Catalysts

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This review gives a brief summary of the field of gold nanoparticle interactions with biological molecules, particularly those with possible catalytic relevance. Gold nanoparticles are well known as catalysts in organic chemistry but much is unknown regarding their potential as catalysts of reactions involving biological molecules such as protein and nucleic acids. Biological molecules may be the substrate for catalysis or, if they are the ligand coating the gold particle, may be the catalyst itself. In other cases biological molecules may form a template upon which gold nanoparticles can be precisely arrayed. As relatively little is currently known about the catalytic capabilities of gold nanoparticles in this area, this review will consider templating in general (including, but not restricted to, those which result in structures having potential as catalysts) before going on to consider firstly catalysis by the gold nanoparticle itself followed by catalysis by ligands attached to gold nanoparticles, all considered with a focus on biological molecules.

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Section: Biological Catalysis By the Ligandmentioning

confidence: 94%

Gold Nanoparticle-Biological Molecule Interactions and Catalysis

Heddle

2013

Catalysts

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“…Pt II complex 5 does not have a functional group available for attachment to recognition carriers, such as proteins and genes. However, empowerment of the carboxylic functional group in Pt II complex 6 with a moiety, such as the N ‐succinimidyl ester terminal in Pt II complex 7 , allows it to attach to a protein carrier through a nucleophilic attack . Hence, the carboxylic group in 6 was first activated by use of 1‐ethyl‐3‐[3‐dimethylaminopropyl]carbodiimide (EDCI) and N ‐methylmorpholine in CH 2 Cl 2 .…”

Section: Methodsmentioning

confidence: 99%

“…The N ‐succinimidyl ester functionality in the entity Pt–sulindac 7 could undergo a nucleophilic attack by targeting protein carriers to form protein‐conjugated drugs. After reaching the cancer target, anticancer entity 6 could be liberated from the conjugated drug .…”

Section: Methodsmentioning

confidence: 99%

“…However,e mpowerment of the carboxylic functional group in Pt II complex 6 with am oiety,s uch as the N-succinimidyl ester terminal in Pt II complex 7,a llows it to attach to ap rotein carrier through an ucleophilic attack. [12] Hence, the carboxylic group in 6 was first activated by use of 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide (EDCI) and N-methylmorpholine in CH 2 Cl 2 .T ot he reactionm ixture was then added N-hydroxysuccinimide( 1.2 equiv). After 24 ha tr oom temperature, the desired Pt II complex 7 was produced as yellow solid in 67 %y ield.…”

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confidence: 99%

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Syntheses of Platinum–Sulindac Complexes and Their Nanoparticles as Targeted Anticancer Drugs

Hwu

Tsay

Chuang

et al. 2016

Chemistry A European J

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Platinum(II)-sulindac complexes [{η -C H SN(O)}Pt(DMSO){O(C=O)Sulindac}], [{η -C H SN(O)}PtCl{(S=O)Sulindac}], [{η -C H SN(O)}PtCl{(S=O)Sulindac-succinimide}], and [{η -C H SN(O)}PtCl{(S=O)Sulindac-thymidine}] were synthesized that exhibited IC values of 2.9-4.8 μm against human oral cancer cells OECM1. The poly(lactic-co-glycolic acid) (PLGA) encapsulated [{η -C H SN(O)}PtCl{(S=O)Sulindac}] also showed cytotoxic activity although less potent than the pristine species.

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“…As a result, imine compounds could be better candidates for use in light-responsive systems. Since gold nanoparticles stabilized by SAMs containing C=N bonds have hitherto rarely been investigated, [19,20] we decided to react benzaldehyde with diethylene glycol monomethyl ether at the para-position, DEGBA with 4'-aminobiphenyl-4-methanethiol (ABPMT). Afterwards, a new type of gold nanoparticle (AuNP, Scheme 1) fabricated by functionalized thiol-imine ABPMT-DEGBA was introduced, including its synthesis, characterization, and photoswitching tests.…”

mentioning

confidence: 99%

Effective Reversible Photoinduced Switching of Self‐Assembled Monolayers of Functional Imines on Gold Nanoparticles

et al. 2010

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In the past decade, surface-functionalized gold nanoparticles have received increasing attention from scientists due to their potential application in areas such as biology, electronics, catalysis, and materials science. [1][2][3][4] Usually, self-assembled monolayers (SAMs) of different thiol compounds modify bare gold colloids by strong Au-S interaction to form particles of reduced polydispersity with controlled size. [5,6] When capped by azobenzene [7][8][9][10][11][12] or stilbene [8,13] compounds, some of these functional nanoparticles can reversibly change the degree of solvation by light stimuli, an effect resulting from photoisomerization of these groups.The molecular structures of azobenzene and stilbene derivatives are susceptible to cis-trans isomerization by irradiation. In solution, illumination with UV light effectively results in isomerization from the trans-to the cis-isomer, while back isomerization can be done either by irradiation with visible light or thermal relaxation.[14] In 1998, Evans et al. [7] detected reversible photoswitching of azobenzene between the cis and trans states in the mixed monolayers on colloidal gold, but it was not observed in single-component monolayers. Three years later, Whitesell et al.[8] studied the influence of chain length upon the photoisomerization quantum yields of azobenzenederived, alkanethiol-capped gold nanoparticles. It was found that the quantum yields of isomerization markedly increased with increased linker length, but were still much lower than for the corresponding thiol in solution. These earlier reports conclude that more free volume for every chromophore unit is necessary to achieve photoswitching on the surfaces. Further, optimized systems with mixed SAMs, [11] SAMs of asymmetric disulfides, [9] or suprarmolecular complexes with cyclodextrin (CD) [10] were designed and exhibited improved photoswitching.Besides azobenzene and stilbene, the imine functional group is also photoisomerizable. The imine group undergoes photoinduced trans!cis isomerization with half the energy barrier of the corresponding azobenzene. Moreover, the activation energy in the thermal relaxation process is about 16-17 kcal mol À1 , which is appreciably lower than for azobenzene (23 kcal mol À1) and stilbene (42 kcal mol À1 ), and results in a far shorter half-life of the cis isomer of only 1 second at 25 8C.[15]Low energy barriers allow the extremely rapid, reversible geometrical change under light stimuli, which is the key feature for light-driven devices. [16][17][18] Furthermore, various conjugated imine compounds can be modularly synthesized by one-step condensation reactions of different aldehydes with a particular surface-mounted substrate amine. This provides the chance to prepare a series of imine derivatives for functionalizing gold surfaces. As a result, imine compounds could be better candidates for use in light-responsive systems. Since gold nanoparticles stabilized by SAMs containing C=N bonds have hitherto rarely been investigated, [19,20] we decided to react b...

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Novel Arylhydrazone-Conjugated Gold Nanoparticles with DNA-Cleaving Ability: The First DNA-Nicking Nanomaterial

Abstract: Arylhydrazones were linked onto gold nanoparticles through the poly(ethylene glycol) spacer to produce a new type of photoinduced DNA-cleaving nanomaterials with great potency.

Cited by 14 publications

References 36 publications

Gold Nanoparticle-Biological Molecule Interactions and Catalysis

Gold Nanoparticle-Biological Molecule Interactions and Catalysis

Syntheses of Platinum–Sulindac Complexes and Their Nanoparticles as Targeted Anticancer Drugs

Effective Reversible Photoinduced Switching of Self‐Assembled Monolayers of Functional Imines on Gold Nanoparticles

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