- Prop-2-ynyloxybenzyloxy substituted phthalocyanine-based polymeric nanoparticles: synthesis, photophysical properties and in?vitro PDT efficacy
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Two prop-2-ynyloxybenzyloxy axially/peripherally substituted zinc/silicon phthalocyanines (YSiPc and YZnPc) were synthesized. They were encapsulated into an amphiphilic block copolymeric micelle polyethylene glycol monomethyl ether-polycaprolactone (MPEG5000–PCL2000) to form polymeric nanoparticles YSiPc@MPEG5000–PCL2000 and YZnPc@MPEG5000–PCL2000. The photophysical and photochemical properties of these polymeric nanoparticles were studied by UV/Vis and fluorescence spectroscopy. The cellular uptake and reactive oxygen species (ROS) production abilities of two polymeric nanoparticles in MCF-7 breast cancer cells were evaluated by confocal laser scanning imaging. YSiPc@MPEG5000–PCL2000 exhibited a higher cellular uptake, higher ROS generation ability as well as higher photodynamic efficacy against MCF-7 cells. YSiPc@MPEG5000–PCL2000 is a promising photosensitizer for photodynamic therapy.
- Xiao, Shuanghuang,Chen, Xiuqin,Ye, Qiuhao,Chen, Kuizhi,Xiao, Wenling,Guan, Xinqiao,Huang, Bingcheng,Liu, Guowei,Wei, Hui,Peng, Yiru
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- Sequence Control of Macromers via Iterative Sequential and Exponential Growth
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A general strategy through the use of direct azidation of alcohols allowed the sequence control of macromers via both the iterative sequential growth and iterative exponential growth methods. The chemistry was highly efficient in building polymers from a
- Amir, Faheem,Jia, Zhongfan,Monteiro, Michael J.
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- Clicked (AB)2C-type miktoarm terpolymers: Synthesis, thermal and self-assembly properties, and preparation of nanoporous materials
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A well-defined (PEO-PS)2-PLA miktoarm terpolymer (1) was synthesized by stepwise click reactions of individually prepared poly(ethylene oxide) (PEO), polystyrene (PS, polymerized by atom transfer radical polymerization), and polylactide (PLA, p
- Song, Jie,Lee, Eunji,Cho, Byoung-Ki
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Read Online
- An expeditious click approach towards the synthesis of galactose coated novel glyco-dendrimers and dentromers utilizing a double stage convergent method
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The primary motive behind this article is to bring to the forefront a unique kind of dendrimer which has remained a dark horse since its discovery, namely dentromer. We herein report the synthesis of glycodendrimers and glycodentromers crowned with galactose units by harnessing an expeditious synthesis of dendrimer core 18 and dentromer core 19, divergently with branching directionality (1 → 2) and (1 → 3), respectively. A competent, double stage convergent synthetic path was chosen to facilitate ease of refining and spectroscopic elucidations. By exploiting a Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction strategy, we successfully developed a new series of galactosylated dendrimers 20, 21, 22, and 24 containing 6, 12, 18, and 18 peripheral galactose units, respectively. We are first to report the practical synthesis of 9-peripheral galactose coated glycodentromer 23 (0th generation) and 27-peripheral galactose coated glycodentromer 25 (1st generation). These synthesized scaffolds were characterized by spectral studies such as 1H, 13C NMR, FT-IR, MALDI-TOF MS, HRMS and SEC analysis. Additionally, gel permeation chromatography depicted the regular progression in size from 6 to 27-peripheral galactose coated glycodendrimers along with glycodentromers, with their high monodispersity. Also, the glyco-dendrimers and dentromers synthesized from two different hypercore units i.e. dendrimers core (18) and dentromer core (19), have been supported by their UV-visible absorbance and emission spectroscopy. This journal is
- Agrahari, Anand K.,Mukherjee, Rishav,Singh., Anoop S.,Tiwari, Vinod K.
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p. 31553 - 31562
(2020/09/21)
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- Supramolecular redox-responsive substrate carrier activity of a ferrocenyl Janus device
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Supramolecular Janus compounds have recently attracted increasing attention owing to their dynamic reversible properties, distinct topological structures, and remarkable physicochemical characteristics, e.g., amphiphilicity, heterofunctionality, and high-
- Mu, Shengdong,Ling, Qiangjun,Liu, Xiong,Ruiz, Jaime,Astruc, Didier,Gu, Haibin
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- Self-assembly of tetraphenylethylene-based dendron into blue fluorescent nanoparticles with aggregation induced enhanced emission §
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Abstract: Luminescent organic nanoassemblies have received great attention in recent years due to their potential applications in material science and bioimaging. Since most of the fluorophores undergo aggregation-caused quenching in the solid state, thei
- Krishnan, Nithiyanandan,Ameena, M A Hanna,Atchimnaidu, Siriki,Perumal, Devanathan,Golla, Murali,Krishna, Jithu,Varghese, Reji
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- Enhanced electro-optic activity of two novel bichromophores which are synthesized by Cu(I) catalyzed click-reaction
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Two novel bichromophores YL1 and YL2 based on traditional aniline chromophore YL were synthesized by Cu(I) catalyzed click-reaction and systematically investigated in this paper. The UV–Vis, electrochemical property, thermal stability and EO activity of t
- He, Yanling,Chen, Lu,Liu, Fenggang,Zhang, Hua,Huo, Fuyang,Chen, Zhuo,Liu, Jialei,Zhen, Zhen,Liu, Xinhou,Bo, Shuhui
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p. 756 - 763
(2017/01/17)
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- Direct Enzymatic Branch-End Extension of Glycocluster-Presented Glycans: An Effective Strategy for Programming Glycan Bioactivity
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The sequence of a glycan and its topology of presentation team up to determine the specificity and selectivity of recognition by saccharide receptors (lectins). Structure–activity analysis would be furthered if the glycan part of a glycocluster could be efficiently elaborated in situ while keeping all other parameters constant. By using a bacterial α2,6-sialyltransferase and a small library of bi- to tetravalent glycoclusters, we illustrate the complete conversion of scaffold-presented lactoside units into two different sialylated ligands based on N-acetyl/glycolyl-neuraminic acid incorporation. We assess the ensuing effect on their bioactivity for a plant toxin, and present an analysis of the noncovalent substrate binding contacts that the added sialic acid moiety makes to the lectin. Enzymatic diversification of a scaffold-presented glycan can thus be brought to completion in situ, offering a versatile perspective for rational glycocluster engineering.
- Bayón, Carlos,He, Ning,Deir-Kaspar, Mario,Blasco, Pilar,André, Sabine,Gabius, Hans-Joachim,Rumbero, ángel,Jiménez-Barbero, Jesús,Fessner, Wolf-Dieter,Hernáiz, María J.
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p. 1623 - 1633
(2017/02/10)
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- π-Conjugated polymers with pendant coumarins: Design, synthesis, characterization, and interactions with carbon nanotubes
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A series of new fluorene-based π-conjugated polymers having coumarin derivatives as part of dendritic side chains were designed and prepared using the Suzuki-Miyaura cross-coupling reaction. A new coumarin derivative bearing a heptyl side chain for solubility was utilized to ensure solubility of the final polymers. It was found that fluorescence resonance energy transfer (FRET) from the coumrains to the polyfluorene backbone was efficient, especially for the polymers decorated with lower-generation dendrons. Each of the polymers was found to interact strongly with the surface of single-walled carbon nanotubes (SWNTs) in THF, and their ability to selectively disperse specific SWNT chiralities was investigated. Photoluminescence studies revealed that the strong polymer emission is efficiently quenched in the corresponding supramolecular complexes with SWNTs. This high quenching efficiency indicates that the coumarin-polymer FRET system can be supramolecularly bound to the surface of (SWNTs to produce an energy transfer system in which the energy absorbed by the donor coumarin chromophores is channeled to the SWNTs.
- Imit, Mokhtar,Imin, Patigul,Adronov, Alex
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p. 759 - 768
(2016/10/12)
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- Synthesis and characterization of novel dendritic compounds bearing a porphyrin core and cholic acid units using "click chemistry"
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Four novel dendritic molecules bearing a porphyrin core and peripheral cholic acid units (TPPh(Zn) Tetra-CA, TPPh(2H) Tetra-CA, TPPh(Zn) Octa-CA and TPPh(2H) Octa-CA) have been synthesized by the "click chemistry" approach, using azide-alkyne couplings. These compounds are fully characterized by 1H and 13C NMR spectroscopy and MALDI-TOF. The optical properties of the dendronized porphyrins are studied by absorption and fluorescence spectroscopy in different solvents, in order to study the amphiphilic properties of the cholic acid units in combination with the optical response of the porphyrin unit. After complexation with Zn, the metallated porphyrins (TPPh(Zn) tetra-CA and TPPh(Zn) octa-CA) tend to form J-aggregates in solvents of different polarity, whereas the free base porphyrins TPPh(2H) tetra-CA and TPPh(2H) octa-CA behaved differently. The aggregation phenomenon has been investigated by varying the polarity of the environment, temperature and metallation.
- Aguilar-Ortíz, Edgar,Lévaray, Nicolas,Vonlanthen, Mireille,Morales-Espinoza, Eric G.,Rojas-Aguirre, Yareli,Zhu, Xiao Xia,Rivera, Ernesto
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p. 110 - 120
(2016/05/19)
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- Synthesis, photophysical, electrochemical, and DSSC application of novel donor-acceptor triazole bridged dendrimers with a triphenylamine core and benzoheterazole as a surface unit
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Triazole bridged novel donor-acceptor dendrimers with triphenylamine as the core and benzoheterazole as the surface unit have been synthesized by click chemistry via a convergent approach. All the dendrimers exhibited excellent optical and electrochemical
- Rajavelu, Kannan,Rajakumar, Perumal,Sudip, Mandal,Kothandaraman, Ramanujam
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p. 10246 - 10258
(2016/12/07)
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- Click chemistry inspired synthesis of glycoporphyrin dendrimers
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A series of porphyrin-cored glycodendrimers containing 8, 12, 16, and 24 β-d-glucopyranose units at the periphery, have been synthesized by convergent methodology using click chemistry. The structure of developed dendrimers is established by 1H
- Kushwaha, Divya,Tiwari, Vinod K.
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p. 8184 - 8190
(2013/09/12)
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- Triazole-based ferrocenyl dendrimers as a medium for encapsulated palladium nanoparticles
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Novel ferrocenyl dendrimers with 1,3,5-tris(aminothiophenol)benzeneamide core has been synthesized through click chemistry under microwave-assisted solid-support technique. The higher-generation ferrocenyl dendrimers can 'sense' and bind palladium nanopar
- Rajakumar, Perumal,Anandhan, Ramasamy,Malathi, Sampath,Balasubramanian, Sengottuvelan
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p. 575 - 580
(2013/04/10)
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- Dye-incorporated water-soluble polymer via click triazole formation
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A click triazole-polymerization is proposed for the synthesis of a water-soluble polymer dye. 4,4′-Diazidostilbene-2,2′-disulfonate (DASS) sodium salt reacted with a diacetylenic derivative of para-methyl red (PMR) in water, which was catalyzed by copper
- Jang, Byungkwon,Kim, Sung Yoon,Do, Jung Yun
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p. 217 - 223
(2012/05/05)
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- "Click" chemistry-mediated phenylene-cored carborane dendrimers
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Phenylene-cored small dendrimers containing three to nine peripheral o-carborane clusters were synthesized via Cu(I)-catalyzed Huisgen-type azide alkyne cycloaddition reactions. The resulting dendrimers have been characterized by IR and NMR spectroscopy a
- Dash, Barada Prasanna,Satapathy, Rashmirekha,Bode, Barrie P.,Reidl, Cory T.,Sawicki, James W.,Mason, Allen J.,Maguire, John A.,Hosmane, Narayan S.
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p. 2931 - 2935
(2012/06/15)
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- Effects of dendron generation and salt concentration on phase structures of dendritic-linear block copolymers with a semirigid dendron containing PEG tails
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We prepared a series of dendritic-linear block copolymers (DLBCPs) bearing a semirigid Percec-type dendron with ionophilic poly(ethylene glycol) (PEG) tails and a polystyrene (PS) linear polymer by nitroxide-mediated living radical polymerization (NMRP).
- Cai, Huanhuan,Jiang, Guoliang,Shen, Zhihao,Fan, Xinghe
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p. 6176 - 6184
(2012/10/18)
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- Towards unimolecular luminescent solar concentrators: Bodipy-based dendritic energy-transfer cascade with panchromatic absorption and monochromatized emission
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A polymer-embedded dendritic, bodipy-based panchromatic absorber with a built-in energy gradient concentrates incident solar radiation at a terminal chromophore, resulting in a monochromatized emission directed to the sides of the polymer waveguide (see p
- Altan Bozdemir,Erbas-Cakmak, Sundus,Ekiz, O. Oner,Dana, Aykutlu,Akkaya, Engin U.
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supporting information; experimental part
p. 10907 - 10912
(2012/01/02)
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- Synthesis and DSSC application of novel dendrimers with benzothiazole and triazole units
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Synthesis of novel dendrimers with benzothiazole as surface group and triazole as branching unit is achieved through click chemistry. The presence of more number of benzothiazole and triazole units increases the molar absorption coefficient and alters the
- Rajakumar, Perumal,Kalpana, Venkatesan,Ganesan, Shanmugam,Maruthamuthu, Pichai
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p. 5812 - 5816
(2011/12/14)
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- CLICK CHEMISTRY ROUTE TO TRIAZOLE DENDRIMERS
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The high efficiency and fidelity of click chemistry permits a large number of diverse dendrimers encompassing a wide variety of functionalities at the chain ends, repeat units, and/or core to be prepared. Almost quantitative yields were obtained during the synthesis. In some cases, filtration or solvent extraction was the only method required for purification. These features represent a significant advancement in dendrimer chemistry and demonstrate an evolving synergy between organic chemistry and functional materials.
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Page/Page column 6
(2009/04/24)
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- Click chemistry approach for the synthesis of water-soluble glycodendrimer with triazole as building unit
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A new family of chiral glycodendrimers scaffolds containing di-, tetra- and octavalent glucose residues as peripheral unit and with 1,2,3-triazole as building unit has been synthesized through Cu(I)-catalyzed click chemistry by convergent approach. Georg
- Rajakumar, Perumal,Anandhan, Ramasamy,Kalpana, Venkatesan
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body text
p. 1417 - 1422
(2009/12/04)
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- Glycosylated Carboranylporphyrins and Uses Thereof
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The present invention is directed to low toxicity boronated compounds and methods for their use in the treatment, visualization, and diagnosis of tumors. More specifically, the present invention is directed to low toxicity glycosylated carborane-containin
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- Symmetric and Asymmetric Halogen-Containing Metallocarboranylporphyrins and Uses Thereof
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The present invention is directed to low toxicity boronated compounds and methods for their use in the treatment, visualization, and diagnosis of tumors. More specifically, the present invention is directed to low toxicity halogenated, carborane-containin
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Page/Page column 10
(2008/12/08)
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- A chemoselective approach for the accelerated synthesis of well-defined dendritic architectures
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A chemoselective and layered growth approach has been developed for the synthesis of dendrimers, combining Click chemistry with traditional esterification/etherification reactions, without the need for activation steps and with excellent overall yields. T
- Antoni, Per,Nystroem, Daniel,Hawker, Craig J.,Hult, Anders,Malkoch, Michael
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p. 2249 - 2251
(2007/12/27)
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- METHOD OF USING CLICK CHEMISTRY TO FUNCTIONALIZE DENDRIMERS
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A library of functionalized dendritic macromolecules was prepared in extremely high yields using no protecting group strategies and with only minimal purification steps through the use of copper(l)-catalyzed 1 ,3-dipolar cycloaddition of azides and termin
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(2008/06/13)
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- Total syntheses of three copper (II) tetracarboranylphenylporphyrins containing 40 or 80 boron atoms and their biological properties in EMT-6 tumor-bearing mice
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Three carboranyltetraphenylporphyrins containing 40 or 80 boron atoms were synthesized and evaluated for their biodistribution and toxicity in EMT-6 tumor-bearing mice. Copper (II) meso-5,10,15,20-tetrakis[3-methoxy-4-(o-carboranylmethoxy)phenyl]porphyrin
- Wu, Haitao,Micca, Peggy L.,Makar, Michael S.,Miura, Michiko
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p. 5083 - 5092
(2008/02/05)
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- Structurally diverse dendritic libraries: A highly efficient functionalization approach using click chemistry
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The high fidelity and efficiency of Click chemistry are exploited in the synthesis of a library of chain end functionalized dendritic macromolecules. In this example, the selectivity of the Cu-catalyzed [3 + 2π] cycloaddition reaction of azides with termi
- Malkoch, Michael,Schleicher, Kristin,Drockenmuller, Eric,Hawker, Craig J.,Russell, Thomas P.,Wu, Peng,Fokin, Valery V.
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p. 3663 - 3678
(2008/02/01)
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- CARBORANYLPORPHYRINS AND USES THEREOF
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The present invention is directed to low toxicity boronated compounds and methods for their use in the treatment, visualization, and diagnosis of tumors. More specifically, the present invention is directed to low toxicity carborane-containing 5,10,15,20-
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Page/Page column 13
(2008/06/13)
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- Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes
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Components that click: A large number of diverse dendrimers (see scheme) was prepared in almost quantitative yield by the click-chemistry transformation described in the title. In some cases filtration or solvent extraction was the only method required for purification in this highly efficient construction of the triazole units of the dendrimers.
- Wu, Peng,Feldman, Alina K.,Nugent, Anne K.,Hawker, Craig J.,Scheel, Arnulf,Voit, Brigitte,Pyun, Jeffrey,Frechet, Jean M. J.,Sharpless, K. Barry,Fokin, Valery V.
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p. 3928 - 3932
(2007/10/03)
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- Selective upper rim functionalization and lower rim bridge building with calix[4]arenes and calix[6]arenes
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Selective upper rim functionalization of calix[6]arenes has been achieved by selective lower rim benzoylation at the 1,2,4,5 positions followed by AlCl3-induced removal of the tert-butyl groups of the unesterified aryl residues and introduction of various functionalities into the vacated para positions, including bromo (5), dialkylamino, (7-11) cyanomethyl (12), and (propargyloxy)methyl (13) groups. Lower rim bridge building has been achieved via oxidative coupling reactions between the aryne moieties of calix[4]arenes and calix[6]arenes in which O-benzyl groups carry one (from 23 and 24) or two (from 25) propargyloxy residues. In the calix[4]arene series both a single-spanned (32) and a double-spanned (33) double-cavity calixarene were obtained. In the calix[6]arene series only a single-spanned double cavity calixarene (36) could be characterized.
- Kanamathareddy, Suseela,Gutsche, C. David
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p. 2511 - 2516
(2007/10/03)
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