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Johnson, Renjith P.,Jeong, Young−,Il,John, Johnson V.,Chung, Chung-Wook,Kang, Dae Hwan,Selvaraj, Manickam,Suh, Hongsuk,Kim, Il American Chemical Society 2013 Biomacromolecules Vol.14 No.5
<P>A series of dual stimuli responsive synthetic polymer bioconjugate chimeric materials, poly(<I>N</I>-isopropylacrylamide)<SUB>55</SUB>-<I>block</I>-poly(<SMALL>l</SMALL>-histidine)<SUB><I>n</I></SUB> [p(NIPAM)<SUB>55</SUB>-<I>b</I>-p(His)<SUB><I>n</I></SUB>] (<I>n</I> = 50, 75, 100, 125), have been synthesized by employing reversible addition–fragmentation chain transfer polymerization of NIPAM, followed by ring–opening polymerization of α-amino acid <I>N</I>-carboxyanhydrides. The dual stimuli responsive properties of the resulting biocompatiable and membrenolytic p(NIPAM)<SUB>55</SUB>-<I>b</I>-p(His)<SUB><I>n</I></SUB> polymers are investigated for their use as a stimuli responsive drug carrier for tumor targeting. Highly uniform self-assembled micelles (∼55 nm) fabricated by p(NIPAM)<SUB>55</SUB>-<I>b</I>-p(His)<SUB><I>n</I></SUB> polymers display sharp thermal and pH responses in aqueous media. An anticancer drug, doxorubicin (Dox), is effectively encapsulated in the micelles and the controlled Dox release is investigated in different temperature and pH conditions. Antitumor effect of the released Dox is also assessed using the HepG2 human hepatocellular carcinoma cell lines. Dox molecules released from the [p(NIPAM)<SUB>55</SUB>-<I>b</I>-p(His)<SUB><I>n</I></SUB>] micelles remain biologically active and have stimuli responsive capability to kill cancer cells. The self-assembling ability of these hybrid materials into uniform micelles and their efficiency to encapsulate Dox makes them a promising drug carrier to cancer cells. The new chimeric materials thus display tunable properties that can make them useful for a molecular switching device and controlled drug delivery applications needing responses to temperature and pH for the improvement of cancer chemotherapy.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/bomaf6/2013/bomaf6.2013.14.issue-5/bm400089m/production/images/medium/bm-2013-00089m_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/bm400089m'>ACS Electronic Supporting Info</A></P>
Johnson, Renjith P.,Jeong, Young‐,Il,Choi, Eunji,Chung, Chung‐,Wook,Kang, Dae Hwan,Oh, Sae‐,Ock,Suh, Hongsuk,Kim, Il WILEY‐VCH Verlag 2012 Advanced Functional Materials Vol.22 No.5
<P><B>Abstract</B></P><P>A series of synthetic polymer bioconjugate hybrid materials consisting of poly(2‐hydroxyethyl methacrylate) (p(HEMA)) and poly(<SMALL>l‐</SMALL>histidine) (p(His)) are synthesized by combining atom transfer radical polymerization of HEMA with ring opening polymerization of benzyl‐<I>N</I>‐carboxy‐<SMALL>L</SMALL>‐histidine anhydride. The resulting biocompatible and membranolytic p(HEMA)<SUB>25</SUB>‐<I>b</I>‐p(His)<SUB><I>n</I></SUB> (<I>n</I> = 15, 25, 35, and 45) polymers are investigated for their use as pH‐sensitive drug‐carrier for tumor targeting. Doxorubicin (Dox) is encapsulated in nanosized micelles fabricated by a self‐assembly process and delivered under different pH conditions. Micelle size is characterized by dynamic light scattering (DLS) and transmission electron microscopy (TEM) observations. Dox release is investigated according to pH, demonstrating the release is sensitive to pH. Antitumor activity of the released Dox is assessed using the HCT 116 human colon carcinoma cell line. Dox released from the p(HEMA)‐<I>b</I>‐p(His) micelles remains biologically active and has the dose‐dependent capability to kill cancer cells at acidic pH. The p(HEMA)‐<I>b</I>‐p(His) hybrid materials are capable of self‐assembling into nanomicelles and effectively encapsulating the chemotherapeutic agent Dox, which allows them to serve as suitable carriers of drug molecules for tumor targeting.</P>
Johnson, Renjith P,Chung, Chung-Wook,Jeong, Young-Il,Kang, Dae Hwan,Suh, Hongsuk,Kim, Il Dove Medical Press 2012 INTERNATIONAL JOURNAL OF NANOMEDICINE Vol.7 No.-
<P><B>Background</B></P><P>5-Aminolevulinic acid (ALA) and its derivatives have been widely used in photodynamic therapy. The main drawback associated with ALA-based photodynamic therapy (ALA-PDT) and ALA fluorescence diagnosis results from the hydrophilic nature of ALA and lack of selectivity for tumor versus nontumor cells. The application of certain triggers, such as pH, into conventional sensitizers for controllable <SUP>1</SUP>O<SUB>2</SUB> release is a promising strategy for tumor-targeted treatment.</P><P><B>Methods</B></P><P>A series of pH-sensitive ALA-poly(L-histidine) [p(L-His)<SUB>n</SUB>] prodrugs were synthesized via ring opening polymerization of 1-benzyl-<I>N</I>-carboxy-L-histidine anhydride initiated by the amine hydrochloride group of ALA itself. As an alternative to ALA for PDT, the synthesized prodrugs were used to treat a cultured human colon cancer HCT116 cell line under different pH conditions. The effect of ALA-p(L-His)<SUB>n</SUB> derivatives was evaluated by monitoring the fluorescence intensity of protoporphyrin IX, and measuring the cell survival rate after suitable light irradiation.</P><P><B>Results</B></P><P>The cytotoxicity and dark toxicity of ALA and synthesized ALA-p(L-His) derivatives in HEK293T and HCT116 cells in the absence of light at pH 7.4 and 6.8 shows that the cell viability was relatively higher than 100%. ALA-p(L-His)<SUB>n</SUB> showed high phototoxicity and selectivity in different pH conditions compared with ALA alone. Because the length of the histidine chain increases in the ALA-p(L-His)<SUB>n</SUB> prodrugs, the PDT effect was found to be more powerful. In particular, high phototoxicity was observed when the cells were treated with ALA-p(L-His)<SUP>15</SUP>, compared with treatment using ALA alone.</P><P><B>Conclusion</B></P><P>The newly synthesized ALA-p(L-His)<SUB>n</SUB> derivatives are an effective alternative to ALA for enhancing protoporphyrin IX production and the selectivity of the phototoxic effect in tumor cells.</P>
Johnson, Renjith P,Uthaman, Saji,John, Johnson V,Lee, Hye Ri,Lee, Sang Joon,Park, Huiju,Park, In-Kyu,Suh, Hongsuk,Kim, Il American Chemical Society 2015 ACS APPLIED MATERIALS & INTERFACES Vol.7 No.39
<P>A series of poly(ethylene glycol) methyl ether acrylate-block-poly(l-lysine)-block-poly(l-histidine) [p(PEGA)30-b-p(Lys)25-b-p(His)n] (n = 25, 50, 75, 100) triblock copolypeptides were designed and synthesized for tumoral pH-responsive intracellular release of anticancer drug doxorubicin hydrochloride (Dox). The tumoral acidic pH-responsive hybrid vesicles fabricated were stable at physiological pH 7.4 and could gradually destabilize in acidic pH as a result of pH-induced swelling of the p(His) block. The blank vesicles were nontoxic over a wide concentration range (0.01-100 관g/mL) in normal cell lines. The tumor acidic pH responsiveness of these vesicles was exploited for intracellular delivery of Dox. Vesicles efficiently encapsulated Dox, and pH-induced destabilization resulted in the controlled and sustained release of Dox in CT26 murine cancer cells, and dose-dependent cytotoxicity. The tumor-specific controlled release Dox from vesicles demonstrates this system represents a promising theranostic agent for tumor-targeted delivery.</P>
Li, Haiqing,Bahuleyan, Bijal K.,Johnson, Renjith P.,Shchipunov, Yury A.,Suh, Hongsuk,Ha, Chang-Sik,Kim, Il Royal Society of Chemistry 2011 Journal of materials chemistry Vol.21 No.44
<P>An α-diimine compound (DC) bearing multiple hydroxyl and amine groups presents excellent self-assembly behavior, yielding DC self-assemblies with tunable morphologies ranging from solid spheres, nanotubes and capsules <I>via</I> hydrogen bonds and π–π stacking interactions. These DC self-assemblies provide promising multifunctional hosts for varied metal species. As a typical example, Au nanoparticles are <I>in situ</I> generated and accommodated into both solid and hollow DC self-assemblies by one-pot and two-step fabrication processes, respectively, resulting in the formation of solid and hollow DC/Au hybrid nanostructures. Both solid and hollow DC self-assemblies also enable host Ni(<SMALL>II</SMALL>) ions to generate DC/Ni(<SMALL>II</SMALL>) catalysts for the efficient production of porous polyethylene (PE) beads consisting of numerous PE microspheres. Moreover, the yielded PE beads replicate the textural morphologies of the original DC/Ni(<SMALL>II</SMALL>) catalysts. These DC self-assemblies also might be further utilized to host varied metal species to fabricate versatile DC/metal nanoparticle (Ag, Pt, Pd, <I>etc.</I>) hybrids and porous polyolefin beads with desired morphologies.</P> <P>Graphic Abstract</P><P>Supramolecular self-assemblies of a α-diimine complex are presented together with their applications as multifunctional host systems. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c1jm13081a'> </P>
John, Johnson V.,Chung, Chung-Wook,Johnson, Renjith P.,Jeong, Young-Il,Chung, Kyu-Don,Kang, Dae Hwan,Suh, Hongsuk,Chen, Hongyu,Kim, Il American Chemical Society 2016 Biomacromolecules Vol.17 No.1
<P>Smart delivery system of photosensitizer chlorin e6 (Ce6) has been developed for targeted photodynamic therapy (PDT). Simple self-assemblies of the mixtures comprising soybean lecithin derived phosphatidylcholine (PC), phosphatidylethanolamine-poly(L-histidine)(40) (PE-p-(His)(40)), and folic acid (FA) conjugated phosphatidylethanolamine-poly(N-isopropylacrylamide)(40) (PE-p(NIPAM)(40)-FA) in different ratios yield smart nanospheres characterized by (i) stable and uniform particle size (similar to 100 nm), (ii) positive surface charge, (iii) high hydrophobic drug (Ce6) loading efficiency up to 45%, (iv) covalently linked targeting moiety, (v) low cytotoxicity, and (vi) smartness showing p(His) block oriented pH and p(NIPAM) oriented temperature responsiveness. The Ce6-encapsulated vesicular nanospheres (Ce6@VNS) were used to confirm the efficiency of cellular uptake, intracellular distribution, and phototoxicity against KB tumor cells compared to free Ce6 at different temperature and pH conditions. The Ce6@VNS system showed significant photodynamic therapeutic efficiency on KB cells than free Ce6. A receptor-mediated inhibition study proved the site-specific delivery of Ce6 in targeted tumor cells.</P>