Fabrication of an Electrochemical E. coli Biosensor in Biowells Using Bimetallic Nanoparticle‐Labelled Antibodies

An electrochemical biosensor was developed for the determination of Escherichia coli (E. coli) in water. For this purpose, silver‐gold core‐shell (Ag@Au) bioconjugates and anti‐E. coli modified PS‐microwells were designed in a sandwich‐type format in order to obtain higher sensitivity and selectivity. Ag@Au bimetallic nanoparticles were synthesized by co‐reduction method. The core‐shell formation was analyzed by using UV‐Vis spectroscopy and transmission electron microscopy. Biotin labeled anti‐E. coli antibodies were coupled with Ag@Au nanoparticles to form bioconjugates. The electrochemical immunosensor was prepared by immobilizing anti‐E. coli on polystyrene (PS)‐microwells via chemical bonding. These modified microwells were identified with X‐ray photoelectron spectroscopy and surface enhanced Raman spectroscopy. E. coli was sandwiched between Ag@Au bioconjugates and anti‐E. coli on PS‐microwells at different concentrations. The relationship between the E. coli concentration and stripping current of gold ions (Au³⁺) were investigated by square wave anodic stripping voltammetry at pencil graphite electrode. The proposed method can provide some advantages such as lower detection limit and shorter detection time. The electrochemical response for the immunosensor was linear with the concentration of the E. coli in the range of 10¹ and 10⁵ cfu/mL with a limit of detection 3 cfu/mL. The procedure maintains good sensitivity and repeatability and also offers utility in the fields of environmental monitoring and clinical diagnosis.     

Synthesis and characterization of chiral polymer complexes incorporating polybinaphthyls,bipyridine, and Eu(III)

Chiral conjugated polymers P‐1 and P‐2 were synthesized by the polymerization of (S)‐3,3′‐diiodo‐2,2′‐bisbutoxy‐1,1′‐binaphthyl and (S)‐6,6′‐dibromo‐2,2′‐bisbutoxy‐1,1′‐binaphthyl, respectively, with 5,5′‐divinyl‐2,2′‐bipyridine through a Heck cross‐coupling reaction. Chiral polymer complexes P‐C‐1 and P‐C‐2 were obtained by the bipyridine chelating coordination of P‐1 and P‐2 with Eu(TTA)₃·2H₂O (where TTA is 2‐thenoyltrifluoroacetonate). Polymers P‐1 and P‐2 and polymer complexes P‐C‐1 and P‐C‐2 exhibited intense circular dichroism signals, with negative and positive Cotton effects in their circular dichroism spectra. The chiral polymers showed strong green‐blue fluorescence because of the efficient energy migration from the extended π‐electronic structure of the conjugated polymer main to the chiral binaphthyl core. The chiral polymer complexes could have not only polymer fluorescence but also the characteristic fluorescence of Eu(III) (⁵D₀→⁷F₂) at a different excited wavelength. These kinds of chiral polymer complexes incorporating polybinaphthyls, bipyridine, and Eu(III) moieties are expected to provide an understanding of the relationship between the structure and properties of chiral polymer complexes. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 650–660, 2007     

Chromatographic Resolution of α‐Amino Acids by (R)‐(3,3'‐Halogen Substituted‐1,1'‐binaphthyl)‐20‐crown‐6 Stationary Phase in HPLC

Three new chiral stationary phases (CSPs ) for high‐performance liquid chromatography were prepared from R ‐(3,3'‐halogen substituted‐1,1'‐binaphthyl)‐20‐crown‐6 (halogen = Cl, Br and I). The experimental results showed that R ‐(3,3'‐dibromo‐1,1'‐binaphthyl)‐20‐crown‐6 ( CSP ‐1 ) possesses more prominent enantioselectivity than the two other halogen‐substituted crown ether derivatives. All twenty‐one α ‐amino acids have different degrees of separation on R ‐(3,3'‐dibromo‐1,1'‐binaphthyl)‐20‐crown‐6‐based CSP ‐1 at room temperature. The enantioselectivity of CSP ‐1 is also better than those of some commercial R ‐(1,1'‐binaphthyl)‐20‐crown‐6 derivatives. Both the separation factors (α ) and the resolution (R _s) are better than those of commercial crown ether‐based CSPs [CROWNPAK CR (+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by commercial CR (+). This study proves the commercial usefulness of the R ‐(3,3'‐dibromo‐1,1'‐binaphthyl)‐20‐crown‐6 chiral stationary phase.     

Reversal Circularly Polarized Luminescence of AIE‐Active Chiral Binaphthyl Molecules from Solution to Aggregation

Four aggregation‐induced emission (AIE)‐active chiral binaphthyl‐based molecules, (R/S)‐ 1 and (R/S)‐ 2 , were designed and synthesized. Interestingly, all of them can exhibit reversal circularly polarized luminescence (CPL) signals from solution to aggregation, which could be attributed to the different dihedral angle of binaphthyl units from cis‐conformation in pure THF solution to trans‐conformation in THF/water mixtures.     

In situ synthesis of ABA triblock copolymer nanoparticles by seeded RAFT polymerization: Effect of the chain length of the third a block on the triblock copolymer morphology

Synthesis of the ABA triblock copolymer nanoparticles of poly(N,N‐dimethylacrylamide)‐block‐polystyrene‐block‐poly(N,N‐dimethylacrylamide) (PDMA‐b‐PS‐b‐PDMA) by seeded RAFT polymerization is performed, and the effect of the introduced third poly(N,N‐dimethylacrylamide) (PDMA) block on the size and morphology of the PDMA‐b‐PS‐b‐PDMA triblock copolymer nanoparticles is investigated. This seeded RAFT polymerization affords the in situ synthesis of the PDMA‐b‐PS‐b‐PDMA core‐corona nanoparticles, in which the middle solvophobic PS block forms the compacted core, and the first solvophilic PDMA block and the introduced third PDMA block form the solvated complex corona. During the seeded RAFT polymerization, the introduced third PDMA block extends, and the molecular weight of the PDMA‐b‐PS‐b‐PDMA triblock copolymer linearly increases with the monomer conversion. It is found that, the size of the PS core in the PDMA‐b‐PS‐b‐PDMA triblock copolymer core‐corona nanoparticles is almost equal to that in the precursor of the poly(N,N‐dimethylacrylamide)‐block‐polystyrene diblock copolymer core‐corona nanoparticles and it keeps constant during the seeded RAFT polymerization, and whereas the introduction of the third PDMA block leads to a crowded complex corona on the PS core. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015 , 53, 1777–1784     

Chiral Crystal Structure of Racemic Binaphthyl Poly(ether ketone) Macrocycles

Summary: The crystal structure of rigid, hollow, racemic binaphthyl poly(ether ketone) macrocycles has been elucidated by single crystal X‐ray analysis. Multitudinal interactions were identified within the chiral space group P2₁2₁2₁. The structural analysis revealed that this macrocyclic compound contains an elliptic chiral cavity with a size of 9.80 × 5.18 Å, which is similar to that of cyclodextrins. The knowledge about the interaction sites and the structure of the binaphthyl‐based macrocycle provides a unique opportunity to understand its molecular or chiral recognition properties.

Space‐filling representation of the single (R)‐macrocycle.     

Asymmetric Epoxidation of Terminal Olefins with Binaphthyl Strapped Porphyrin Catalysts: (‐( Stacking Interaction and Steric Effects on the Enantioselectivities

将两种具有相似手性联萘空腔的手性卟啉1b和2b作为催化剂,对苯乙烯衍生物及非芳香烯烃底物进行了催化不对称环氧化反应。应用理论计算方法研究了底物同两种催化剂之间的作用机理;应用1H NMR探讨了催化剂的手性空腔结构;结果表明芳香烯烃同催化剂的手性联萘基团之间的p-p相互作用是决定该类催化剂对映选择性的重要因素,同时催化剂手性结构的立体位阻效应使该类催化剂具有良好的ee值。     

A Chiral Hemiporphyrazine Derivative: Synthesis and Chiroptical Properties

The synthesis of an optically active hemiporphyrazine with chiral binaphthyl substituents ( 1 ) is reported, providing the first example of the incorporation of an intrinsically chiral moiety into the macrocyclic core of a hemiporphyrazine analogue. A negative circular dichroism (CD) signal is observed in the 325–450 nm region of the CD spectrum of (S,S)‐ 1 , while mainly positive bands are observed in the 220–325 nm region. Mirror symmetry is observed across the entire wavelength range of the CD spectra of (R,R)‐ 1 and (S,S)‐ 1 . An irreversible one‐electron oxidation wave with an onset potential at 1.07 V is observed by cyclic voltammetry, along with a reversible one‐electron reduction wave at ?0.85 V. Density functional calculations reproduce the experimentally observed data and trends, and provide further insight into the nature of the electronic transitions.     

“Click” synthesis of thermally stable au nanoparticles with highly grafted polymer shell and control of their behavior in polymer matrix

Thermally stable core–shell gold nanoparticles (Au NPs) with highly grafted polymer shells were synthesized by combining reversible addition‐fragmentation transfer (RAFT) polymerization and click chemistry of copper‐catalyzed azide‐alkyne cycloaddition (CuAAC). First, alkyne‐terminated poly(4‐benzylchloride‐b‐styrene) (alkyne‐PSCl‐b‐PS) was prepared from the alkyne‐terminated RAFT agent. Then, an alkyne‐PSCl‐b‐PS chain was coupled to azide‐functionalized Au NPs via the CuAAC reaction. Careful characterization using FT‐IR, UV–Vis, and TGA showed that PSCl‐b‐PS chains were successfully grafted onto the Au NP surface with high grafting density. Finally, azide groups were introduced to PSCl‐b‐PS chains on the Au NP surface to produce thermally stable Au NPs with crosslinkable polymer shell ( Au‐PSN₃‐b‐PS 1 ). As the control sample, PS‐b‐PSN₃‐coated Au NPs ( Au‐PSN₃‐b‐PS 2 ) were made by the conventional “grafting to” approach. The grafting density of polymer chains on Au‐PSN₃‐b‐PS 1 was found to be much higher than that on Au‐PSN₃‐b‐PS 2 . To demonstrate the importance of having the highly packed polymer shell on the nanoparticles, Au‐PSN₃‐b‐PS 1 particles were added into the PS and PS‐b‐poly(2‐vinylpyridine) matrix, respectively. Consequently, it was found that Au‐PSN₃‐b‐PS 1 nanoparticles were well dispersed in the PS matrix and PS‐b‐P2VP matrix without any aggregation even after annealing at 220 °C for 2 days. Our simple and powerful approach could be easily extended to design other core–shell inorganic nanoparticles. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011     

Preparation and characterization of a polystyrene/bovine serum albumin nanoparticle‐coated capillary for chiral separation using open‐tubular capillary electrochromatography

Polystyrene (PS) nanoparticles coated by BSA, hereafter denoted as PS/BSA, were prepared and chemically immobilized for the first time onto a capillary inner wall for open‐tubular CEC (OTCEC). EOF and scanning electron micrography were used to characterize the prepared nanoparticle‐coated capillaries. To investigate the performance of the prepared columns in OTCEC, chiral separation of d ,l ‐tryptophan (dl ‐Trp) was performed in monolayer BSA‐modified capillary and PS/BSA nanoparticle‐coated columns. The results indicated that the nanoparticle‐modified column afforded a higher resolution compared with the monolayer type. Rapid enantioseparation of dl ‐Trp (within 3 min) was achieved with the PS/BSA‐immobilized column using an electroosmotic pump‐assisted CEC. Enantiomer separations of other compounds like dl ‐tyrosine and warfarin were also achieved with the column. Besides, run‐to‐run and column‐to‐column repeatabilities of the PS/BSA‐coated column in the chiral separation were systematically introduced.     

Synthesis and chiroptical properties of chiral binaphthyl‐containing polyfluorene derivatives

New chiral binaphthyl‐containing polyfluorene (PF) derivatives, PFOH , PFMOM , and PFP , bearing different binaphthyl units ((S)‐2,2′‐bis(methoxymethoxy)‐1,1′‐binaphthyl for PFMOM , (S)‐1,1′‐binaphthyl‐2,2′‐diol for PFOH , and (S)‐2,2′‐bis(diphenylphosphinyl)‐1,1′‐binaphthyl for PFP ) in the backbone have been designed and synthesized through Pd‐catalyzed Suzuki polycondensation. Their properties have been investigated in detail by ¹H NMR, ¹³C NMR, TGA, DSC, UV–vis, photoluminescence (in solutions, in thin films before and after annealing), and circular dichroism (CD) spectroscopic methods compared with poly(9,9‐dihexylfluorene‐2,7‐diyl) ( PF ). The resulting copolymers possessed excellent solubility in organic solvents and emitted strong blue light. The phosphine oxide‐containing copolymers PFP and PFMOM exhibited higher quantum yields and better thermal spectral stability in comparison with PF . All the copolymers exhibited obviously the linearly polarized photoluminescent properties both in solutions and in solid states. High emission polarization ratios (R_PL) of PFP were observed with no obvious decrease upon thermal annealing. In addition, investigation of the CD spectroscopic properties of these copolymers in THF solutions indicated that the chirality of the binaphthyls could be transferred to the whole PF backbone. All these results demonstrated that introduction of the chiral binaphthyls, particularly BINAPO, into the backbone could effectively improve the performances of the copolymers. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011     

Biosynthesis of Zinc Oxide Nanoparticles Using Leaf Extract of Passiflora subpeltata: Characterization and Antibacterial Activity Against Escherichia coli Isolated from Poultry Faeces

The current study was undertaken to investigate the antibacterial (against molecular characterized E. coli isolated from poultry faeces) potential of biosynthesized zinc oxide nanoparticles (ZnO-NPs) from Passiflora subpeltata Ortega aqueous leaf extract. The biosynthesized nanoparticles were subjected to physico-chemical characterization to study shape, size and purity by UV–Vis spectroscopy, X-Ray diffraction (XRD), Fourier Transform Infrared Spectroscopy (FT-IR), Scanning Electron Microscopy (SEM), Energy Dispersive Spectroscopy (EDS) and Transmission Electron Microscopy (TEM). The molecular identification of isolated E. coli from faeces samples was carried out by using 16–23s rRNA primers. The results of the physico-chemical characterization revealed that the biosynthesized nanoparticles were of 93.7% purity with an average size between 45 and 50 nm. The ZnO-NPs offered significant inhibition against the isolated Gram-negative E. coli with MIC at 62.5 µg mL^?1 concentration. The antibacterial potential of ZnO NPs against E. coli has also been investigated by the cell viability test, and further the effects of ZnO NPs on bacterial morphological structures was analysed by SEM and TEM.

     

Hybrid Compound Block Copolymer Micelles Encapsulating Gold Nanoparticles

We report here on the formation of hybrid compound block copolymer micelles encapsulating gold nanoparticles, utilizing a direct and general preparation method. The giant hybrid compound micelles are structured with micelles of PS‐b‐P2VP with gold nanoparticles in their P2VP core and PI‐b‐PS chains as the outer part of the compound micelles. The gold nanoparticles were produced using gold ion‐loaded PS‐b‐P2VP micelles as a nanoreactor, in a PS selective solvent (toluene), by the subsequent reduction of gold ions. The synthesis of the gold nanoparticles was monitored by UV‐vis spectroscopy. The gold containing micelles were then encapsulated in larger micelles of PI‐b‐PS copolymer, by successive utilization of toluene and heptane with the intermediate evaporation of toluene. The nanoassembly of the compound materials comprised a PI corona and a PS compound core, with P2VP/Au⁰ domains, and was characterized using UV‐vis spectroscopy, dynamic light scattering and transmission electron microscopy.

     

Comparison of HPLC enantioseparation of substituted binaphthyls on CD‐, polysaccharide‐ and synthetic polymer‐based chiral stationary phases

Retention and enantioseparation behavior of ten 2,2′‐disubstituted or 2,3,2′‐trisubstituted 1,1′‐binaphthyls and 8,3′‐disubstituted 1,2′‐binaphthyls, which are used as catalysts in asymmetric synthesis, was investigated on eight chiral stationary phases (CSPs) based on β‐CD, polysaccharides (tris(3,5‐dimethylphenylcarbamate) cellulose or amylose CSPs) and new synthetic polymers (trans‐1,2‐diamino‐cyclohexane, trans‐1,2‐diphenylethylenediamine and trans‐9,10‐dihydro‐9,10‐ethanoanthracene‐(11S,12S)‐11,12‐dicarboxylic acid CSPs). Normal‐, reversed‐phase and polar‐organic separation modes were employed. The effect of the mobile phase composition was examined. The enantiomeric separation of binaphthyl derivatives, which possess quite similar structures, was possible in different enantioselective environments. The substituents and their positions on the binaphthyl skeleton affect their properties and, as a consequence, the separation system suitable for their enantioseparation. In general, the presence of ionizable groups on the binaphthyl skeleton, substitution with non‐identical groups and a chiral axis in the 1,2′ position had the greatest impact on the enantiomeric discrimination. The 8,3′‐disubstituted 1,2′‐binaphthyl derivatives were the most easily separated compounds in several separation systems. From all the chiral stationary phases tested, cellulose‐based columns were shown to be the most convenient for enantioseparation of the studied analytes. However, the polymeric CSPs with their complementary behavior provided good enantioselective environments for some derivatives that could be hardly separated in any other chromatographic system.     

Design of Binaphthyl‐Modified Symmetrical Chiral Phase‐Transfer Catalysts: Substituent Effect of 4,4′,6,6′‐Positions of Binaphthyl Rings in the Asymmetric Alkylation of a Glycine Derivative

A series of symmetrical chiral phase‐transfer catalysts with 4,4′,6,6′‐tetrasubstituted binaphthyl units have been designed, and these aryl‐ and trialkylsilyl‐substituted phase‐transfer catalysts, which included a highly fluorinated catalyst, were prepared. The chiral efficiency of these chiral phase‐transfer catalysts was investigated in the asymmetric alkylation of tert‐butylglycinate–benzophenone Schiff base under mild phase‐transfer conditions, and the eminent substituent effect of the 4,4′,6,6′‐positions of the binaphthyl units on enantioselection was observed. In particular, the OctMe₂Si‐substituted catalyst was found to be highly efficient for the phase‐transfer alkylation of tert‐butylglycinate–benzophenone Schiff base with various alkyl halides, including sec‐alkyl halides. The highly fluorinated catalyst was also utilized as a recyclable chiral phase‐transfer catalyst by simple extraction with fluorous solvents.     

Facile synthesis of core‐surface crosslinked nanoparticles by interblock RAFT polymerization

A new, efficient method for synthesizing stable nanoparticles with poly(ethylene oxide) (PEO) functionalities on the core surface, in which the micellization and crosslinking reactions occur in one pot, has been developed. First, amphiphilic PEO‐b‐PS copolymers were synthesized by reversible addition fragmentation chain transfer (RAFT) radical polymerization of styrene using (PEO)‐based trithiocarbonate as a macro‐RAFT agent. The low molecular weight PEO‐b‐PS copolymer was dissolved in isopropyl alcohol where the block copolymer self‐assembled as core‐shell micelles, and then the core‐shell interface crosslink was performed using divinylbenzene as a crosslinking agent and 2,2′‐azobisisobutyronitrile as an initiator. The design of the amphiphilic RAFT agent is critical for the successful preparation of core‐shell interface crosslinked micellar nanoparticles, because of RAFT functional groups interconnect PEO and polystyrene blocks. The PEO functionality of the nanoparticles surface was confirmed by ¹H NMR and FTIR. The size and morphology of the nanoparticles was confirmed by scanning electron microscopy, transmission electron microscopy, and dynamic laser light scattering analysis. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010     

Norvancomycin-capped silver nanoparticles: Synthesis and antibacterial activities against E. coli

The synthesis of norvancomycin (NVan)-capped silver nanoparticles (Ag@NVan) and their notable in vitro antibacterial activities against E. coli, a Gram-negative bacterial strain (GNB), are reported here. Mercaptoacetic acid-stabilized spherical silver nanoparticles with a diameter of 16±4 nm are prepared by a simple chemical reaction. The formation process of the silver nanoparticles is investigated by UV-visible (UV-vis) spectroscopy and transmission electron microscopy (TEM). NVan is then grafted to the terminal carboxyl of the mercaptoacetic acid in the presence of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC). The TEM images of single bacteria treated with Ag@NVan show that plenty of Ag@NVan aggregate in the cell wall of E. coli. A possible antibacterial mechanism is proposed that silver nanoparticles may help destroy the stability of the outer membrane of E. coli, which makes NVan easier to bind to the nether part of the peptidoglycan structure. The antibacterial activities of silver nanoparticles on their own, together with the rigid polyvalent interaction between Ag@NVan and cell wall, enables Ag@NVan to be an effective inhibitor of GNB. This kind of bionanocomposites might be used as novel bactericidal materials and we also provide an effective synthesis method for preparing functional bioconjugated nanoparticles here. Supported by the National Natural Science Foundation of China (Grant No. 50373036) and Fok Ying Tung Education Foundation (Grant No. J20040212)     

Phase‐Transfer‐Catalyzed Asymmetric Synthesis of Axially Chiral Anilides

Catalytic asymmetric synthesis of axially chiral o‐iodoanilides and o‐tert‐butylanilides as useful chiral building blocks was achieved by means of binaphthyl‐modified chiral quaternary ammonium‐salt‐catalyzed N‐alkylations under phase‐transfer conditions. The synthetic utility of axially chiral products was demonstrated in various transformations. For example, axially chiral N‐allyl‐o‐iodoanilide was transformed to 3‐methylindoline by means of radical cyclization with high chirality transfer from axial chirality to C‐centered chirality. Furthermore, stereochemical information on axial chirality in o‐tert‐butylanilides could be used as a template to control the stereochemistry of subsequent transformations. The transition‐state structure of the present phase‐transfer reaction was discussed on the basis of the X‐ray crystal structure of ammonium anilide, which was prepared from binaphthyl‐modified chiral ammonium bromide and o‐iodoanilide. The chiral tetraalkylammonium bromide as a phase‐transfer catalyst recognized the steric difference between the ortho substituents on anilide to obtain high enantioselectivity. The size and structural effects of the ortho substituents on anilide were investigated, and a wide variety of axially chiral anilides that possess various functional groups could be synthesized with high enantioselectivities. This method is the only general way to access a variety of axially chiral anilides in a highly enantioselective fashion reported to date.     

Circularly Polarized Luminescence of a Stereogenic Curved Paraphenylene Anchoring a Chiral Binaphthyl in Solution and Solid State

A curved stereogenic [6]paraphenylene ([6]PP), anchoring a chiral binaphthyl scaffold at 7,7’-positions, was prepared and investigated for its properties as a solid-state circularly polarized luminescence (CPL) dye. X-ray analysis revealed a helically twisted structure of PP units induced by axial chirality of binaphthyl framework. The curved [6]PP exhibits fluorescence in powder and polymethyl methacrylate (PMMA) film as well as solution. A significant increase in quantum yield was observed for a non-fluid PMMA film owing the suppression of the molecular motion. The g_CPL values of the dye in solution and as PMMA film were almost the same (4.3–4.4×10⁻³) and lager than that in powder. TD-DFT calculations in the excited state suggest that the exciton can be delocalized into a twisted PP unit to produce a larger magnetic transition dipole moment.     

Human Calcitonin Delivered Orally by Means of Nanoparticles Composed of Novel Graft Copolymers

Abstract

The ability of nanoparticles having surface hydrophilic polymeric chains to enhance the oral absorption of human calcitonin was examined in rats. The oral relative bioavailability of calcitonin against its subcutaneous administration was 0.01% without nanoparticles, but increased significantly when it was administered with nanoparticles. Nanoparticles having cationic poly(vinylamine) (PVAm) chains on their surfaces had a relatively stronger enhancing effect than did other nanoparticles. When divinylbenzene was added to the nanoparticle preparation, PVAm nanoparticles with a crosslinked hydrophobic polystyrene core were synthesized. The addition of divinylbenzene resulted in nanoparticles with larger zeta potential through the efficient accumulation of hydrophilic PVAm chains on their surfaces; however, inadequate amounts decreased the zeta potential. Changes in the bioavailability proportional to the zeta potential indicated that the cationic moiety is indispensable for inducing the significant enhancement of calcitonin absorption. The chemical structure of nanoparticles could be optimized by introducing nonionic poly(N‐isopropylacrylamide) (PNIPAAm) or anionic poly(methacrylic acid) chains onto the PVAm nanoparticle surface to effectively further improve the absorption‐enhancing function of PVAm nanoparticles. Finally, the maximum bioavailability of 1.1% was achieved after oral administration of calcitonin with PVAm–PNIPAAm nanoparticles whose components, VAm macromonomer, N‐isopropylacrylamine (NIPAAm) macromonomer, and styrene were copolymerized in the molar ratio of 1.5:0.5:10.