臺灣博碩士論文加值系統

Functional silica-based nanomaterials have recently received much attention due to their unique physiochemical properties. Studies on functionalized mesoporous silica nanoparticle (MSN) for various applications in the field of biomedicine have seen a significant increase, with an ultimate goal to extend these functionalized nanomaterials for therapeutic and diagnostic applications. Herein, the synthesis and characterization of MSN-based nanomaterials for stimuli responsive drug delivery and phototherapeutic applications are described.
First the study was focused on devising a functional pH responsive drug delivery system for the controlled release of silver, a widely used antibacterial agent. The nanoparticles (NPs) were immobilized with silver-indole-3 acetic acid hydrazide (IAAH-Ag) complexes via a pH-sensitive hydrazone bond via surface silanol groups. When the transitional metal complexes with IBN-4-IAAH-Ag were exposed to acidic pH (near pH 5.0), the silver ions were preferentially released (70%) in a controlled manner up to 12 hours by pH sensitive denial of hydrazone bonds. In contrary a low drug release (about 25%) was seen in physiological buffer (pH 7.4) demonstrating the pH sensitive release of this drug. This result is advantageous for selective release of drugs at bacterial sites, as most disease foci have lower extracellular pH than the healthy tissues.
Then photo responsive MSNs are developed in order to investigate the possibilities of using mesoporous nanomaterials as carriers for photo-triggered drug activation. The immobilization of curcumin-metal complexes inside the mesoporous silicate framework was extensively evaluated by monitoring the ability of diamine functionalized mesoporous silica nanomaterials to adsorb and deliver phototherapeutics. The ability of Vanadium metal in potentiating the activity of spice curcumin against bacteria and cells is investigated.
IBN-4 nanoparticles loaded with photoactivable Vanadium curcumin [VO (cur) (dppz) Cl)] metal complex was prepared and tested for their photodynamic therapy efficacy on planktonic cells and biofilms of S.aureus.
Finally, Copper substituted Mesoporous silicates were synthesized with Curcumin adsorbed inside the pores in combination with silver nanoparticles decorated to the exterior surface show a strong Photodynamic inactivation (PDI) of antibiotic-resistant E.coli, significantly much higher than that expected from the combination of the independent effects of both phototherapeutics. We demonstrated that silver is capable of sensitizing Gram-negative bacteria E.coli to the Gram-positive specific phototherapeutic agent, curcumin thereby expanding the phototherapeutic spectrum of this drug. Under light irradiation curcumin produced reactive oxygen which directly affected the release of silver ions from the surface decorated silver nanoparticles. Additionally silver nanoparticles were shown to improve antimicrobial response by imparting a positive charge on the nanoparticle surface improving the electrostatic attractions towards bacterial membranes. The antibacterial action of the synthesized materials is activated through various mechanisms, including, the transmission of the excited state from curcumin to silver, the synergistic effect of reactive oxygen species (ROS) along with the coexisting copper and silver ions. In dark conditions, nanoparticles exhibited very low antimicrobial response. However, up on light irradiation, they showed a strong antibacterial effects. Thus the employed synergistic strategy can significantly reduce the dosage of silver, copper and curcumin necessary to treat gram negative bacterial diseases there by reducing the cytotoxic effects of metal ions on human cells and also preventing the chances multi-drug resistance in bacterial cells.

Functional silica-based nanomaterials have recently received much attention due to their unique physiochemical properties. Studies on functionalized mesoporous silica nanoparticle (MSN) for various applications in the field of biomedicine have seen a significant increase, with an ultimate goal to extend these functionalized nanomaterials for therapeutic and diagnostic applications. Herein, the synthesis and characterization of MSN-based nanomaterials for stimuli responsive drug delivery and phototherapeutic applications are described.
First the study was focused on devising a functional pH responsive drug delivery system for the controlled release of silver, a widely used antibacterial agent. The nanoparticles (NPs) were immobilized with silver-indole-3 acetic acid hydrazide (IAAH-Ag) complexes via a pH-sensitive hydrazone bond via surface silanol groups. When the transitional metal complexes with IBN-4-IAAH-Ag were exposed to acidic pH (near pH 5.0), the silver ions were preferentially released (70%) in a controlled manner up to 12 hours by pH sensitive denial of hydrazone bonds. In contrary a low drug release (about 25%) was seen in physiological buffer (pH 7.4) demonstrating the pH sensitive release of this drug. This result is advantageous for selective release of drugs at bacterial sites, as most disease foci have lower extracellular pH than the healthy tissues.
Then photo responsive MSNs are developed in order to investigate the possibilities of using mesoporous nanomaterials as carriers for photo-triggered drug activation. The immobilization of curcumin-metal complexes inside the mesoporous silicate framework was extensively evaluated by monitoring the ability of diamine functionalized mesoporous silica nanomaterials to adsorb and deliver phototherapeutics. The ability of Vanadium metal in potentiating the activity of spice curcumin against bacteria and cells is investigated.
IBN-4 nanoparticles loaded with photoactivable Vanadium curcumin [VO (cur) (dppz) Cl)] metal complex was prepared and tested for their photodynamic therapy efficacy on planktonic cells and biofilms of S.aureus.
Finally, Copper substituted Mesoporous silicates were synthesized with Curcumin adsorbed inside the pores in combination with silver nanoparticles decorated to the exterior surface show a strong Photodynamic inactivation (PDI) of antibiotic-resistant E.coli, significantly much higher than that expected from the combination of the independent effects of both phototherapeutics. We demonstrated that silver is capable of sensitizing Gram-negative bacteria E.coli to the Gram-positive specific phototherapeutic agent, curcumin thereby expanding the phototherapeutic spectrum of this drug. Under light irradiation curcumin produced reactive oxygen which directly affected the release of silver ions from the surface decorated silver nanoparticles. Additionally silver nanoparticles were shown to improve antimicrobial response by imparting a positive charge on the nanoparticle surface improving the electrostatic attractions towards bacterial membranes. The antibacterial action of the synthesized materials is activated through various mechanisms, including, the transmission of the excited state from curcumin to silver, the synergistic effect of reactive oxygen species (ROS) along with the coexisting copper and silver ions. In dark conditions, nanoparticles exhibited very low antimicrobial response. However, up on light irradiation, they showed a strong antibacterial effects. Thus the employed synergistic strategy can significantly reduce the dosage of silver, copper and curcumin necessary to treat gram negative bacterial diseases there by reducing the cytotoxic effects of metal ions on human cells and also preventing the chances multi-drug resistance in bacterial cells.

Table of Contents
1. The emergence of antibiotic resistance & Importance of nanodrug delivery systems 1
1.1 Introduction to Mesoporous Silica Nanomaterials 1
1.1.1 Brief description of Mesoporous Silica Nanoparticles 2
1.1.2 Biological Applications of Mesoporous Silica Nanoparticles 6
1.2 References 12
2. pH Controlled Drug Release of Silver-Indole-3 Acetic Acid Complexes From Mesoporous Silica Nanoparticles (IBN-4) For Targeted Antibacterial Therapy 17
2.1 Abstract 18
2.2 Introduction 19
2.3 Experimental Section 26
2.3.1 Materials 26
2.3.2 Characterization 26
2.3.3 Synthesis Procedure 27
2.3.4 Biological activity Assessment 29
2.4 Results and Discussion 37
2.5 Conclusions 62
2.6 References 63
2.7 Appendixes 72
3. Synthesis, Characterization and Photoinduced Antibacterial activity of Vanadium-Curcumin Metal Complex loaded IBN-4 Nanoparticles 81
3.1 Abstract 81
3.2 Introduction 82
3.3 Experimental Section 86
3.3.1 Materials 86
3.3.2 Characterization 86
3.3.3 Synthesis Procedure: 87
3.3.4 Biological activity Assessment 89
3.4 Results and Discussion 93
3.5 Conclusions 107
3.6 References 108
4. Copper Substituted Mesoporous Silica Nanoparticles Decorated with Curcumin and Well Dispersed Silver Nanoparticles as a Three Component, Highly Efficient Photo Bacterial Agent 115
4.1 Abstract 115
4.2 Introduction 116
4.3 Experimental Section 121
4.3.1 Materials 121
4.3.2 Characterization 121
4.3.3 Synthesis Procedure 122
4.3.4 Biological activity Assessment 124
4.4 Results and Discussion 128
4.5 Conclusions 146
4.6 References 147
4.7 Appendixes 156
5. General Conclusions 159









Figure index
Fig 1. 1 A representation of organo-functionalized MSN by using one step co-condensation by employing sol-gel process. 4
Fig 1. 2 A representation of post-synthesis modification of MSN surfaces. 5
Fig 1. 3 Functionalization of mesoporous silica nanoparticles for biomedical applications 7
Fig 1. 4 Representation of Cu–MSN–AT framework and mechanistic illustration of delivery in a cancer cell environment 8
Fig 1. 5 Schematic representation of enzyme prodrug therapy using IBN-4-HRP nanocomposites in the presence of indole-3-acetic acid and the resultant cell apoptosis (1. skatolyl radical and 2. peroxyl radical). 9
Fig 1. 6 Schematic representation of MSNS⊂VAN for selective recognition and killing pathogenic gram-positive bacteria over macrophage-like cells. 10
Fig 1. 7 (A) Design: The drug is entrapped within the mesoporous silica particle, protected by a lipid coating. (B) Delivery: Particle system is robust for oral delivery for treatment of salmonella (STM) infection. (C) Mechanism: The particle enters into the infected gastrointestinal cell and releases the antibiotic cargo to eliminate the pathogen. 10
Fig 1. 8 (A) Synthesis of aldehyde-functionalized msns, yielding msn – cho (leftmost reaction); attachment of isoniazid (INH) onto the surface of the aldehyde-modified nanoparticles, yielding MSN– CHO –INH (middle reaction); and release of the INH from MSN – CHO – INH by hydrolysis at acid pH (rightmost reaction). (B) Assembly of copolymer PEI–PEG on the pH-responsive INH-loaded msns, yielding MSN –CHO – INH – PEIi–PEG. 11
Fig 2.1 Schematic illustration of method for the synthesis of hydrazone bond based pH-responsive drug delivery system. The IBN-4 particles were selectively functionalized with aldehyde groups on the mesopore surface via post-synthesis method. The coordination bond based Ald-Hydrazide-Ag architecture can be easily formed. Ag can be released under mildly acidic pH conditions by the cleavage of either side of the Aldehyde-Hydrazide or Hydrazide–Ag coordination bond by pH reduction. 22
Fig 2.2 Percentage of drug release as a function of time, for IBN-4-IAAH-Ag nanocomposites at different pH. The same mass of silver is used in each sample. 41
Fig 2.3 FT-IR spectra of (a) IBN-4 particles after calcination (b) IBN-4 particles modified with aldehyde groups, (c) the IBN-4-aldehyde sample after formation of hydrazone bond (d) Silver conjugated IBN-4 nanoparticles. 42
Fig 2.4 Nitrogen adsorption–desorption isotherms of (a) IBN-4, (b) IBN-4-ald, (c) IBN-4-IAAH, (d) IBN-4-IAAH-Ag (e) IBN-4 nanoparticles after drug release. Corresponding surface area and pore size. 43
Fig 2. 5 TGA weight loss curves of (a) IBN-4, (b) IBN-4-ald, (c) IBN-4-IAAH and (d) IBN-4-IAAH-Ag complexes. 45
Fig 2. 6 Effect of nanoparticles on bacterial growth with various individual and drug loaded nanoconjugates of IBN-4-IAAH-Ag nps at various concentrations. 48
Fig 2. 7 Petri dishes with lb-agar inoculated with lb-agar inoculated with drug resistant strains of a) S. aureus and b) E. coli, showing variable number of colonies when supplemented with differents amounts of nanoparticles. 49
Fig 2. 8 Intracellular ros levels measured using fluorescent probe H2DCF-DA for bacterial cells (B. subtilis and E. coli) treated with nanoparticles at 50 μg/mL for 3 h.. 53
Fig 2. 9 Effect of IBN-4 nanoparticles on the inhibition of biofilm formation at different drug concentrations against drug resistant strains of E. coli, B. subtilis, S. aureus, and S. epidermis). .55
Fig 2. 10 Effect of IBN-4 nanoparticles in inhibiting the activity of matured biofilms treated with different drug concentrations against drug resistant strains of E. coli, B. subtilis, S. aureus and S. epidermidis determined through MTT cell viability assay… 56
Fig 2. 11 Fluorescence micrograph of (a,c) control S. aureus cells of the biofilm and (b,d) biofilms treated with 30 μg/ml of nanoparticles. (a, b) magnification of control cells at 60x and (c, d) magnification of drug treated cells at 10x. Biofilm were stained with fluorescein isothiocyanate (FITC) and propidium iodide (PI) dyes: green fluorescence is characteristic of the live cells, whereas red fluorescence is due to dead cells. 59
Fig 2. 12 Representative fe-sem images of E. coli. (a) and S. aureus (c) without nanoparticle treatment; (b) and (d) images of E. coli and S. aureus treated by a 30 μg/ml concentration of IBN-4-IAAH-Ag nanocomposites. 60
Fig 2. 13 Kill curves of E.coli within the peritoneal cavity of mice after no treatment or treatment with bare IBN-4 (10 mg/kg), IBN-4-IAAH-Ag (0.5 mg/kg) and IBN-4-IAAH-Ag nps (2.0 mg/kg). 60
Fig 3. 1 The TEM images of (a) Calcined IBN-4 nanoparticles 100 nm (b) IBN-4-V-curcumin (200 nm), and (d) IBN-4-V-curcumin (50 nm). 94
Fig 3. 2 (a) FT-IR spectra of (a) IBN-4 particles after calcination (b) IBN-4 particles modified with diamine groups, (c) Pure curcumin vanadium complex (d) IBN-4-curcumin-vanadium complex. (b) EPR spectra of vanadium-curcumin immobilized in IBN-4 95
Fig 3. 3 (A) Nitrogen adsorption–desorption isotherms of (a) IBN-4, (b) IBN-4-diamine, (c) IBN-4-V-Cur corresponding surface area and pore size. (B) Photographic image of curcumin metal complex loading onto the IBN-4 nanoparticles (a) Template extracted IBN-4 nanoparticles (b) Vanadium metal ion loaded IBN-4 nanoparticles (c) Dppz loaded on to the surface of metal ion loaded IBN-4 nanoparticles (d) Conjugation of curcumin on to the metal Dppz modified IBN nanoparticles 96
Fig 3. 4 (A) Uv-visible spectra of (a) Curcumin (434) (b) Curcumin vanadium complex (256, 440) and (c) IBN-4 adsorbed curcumin vanadium complex. (273,382,460) in 70% aq. Ethanol. (B) TGA thermograms of (a) IBN-4, (b) IBN-4-diamine, (c) IBN-4 diamine-vanadium (d) IBN-4 diamine-vanadium Dppz and (e) IBN4-diamine-vandium curcumin complex. 98
Fig 3. 5 Instability of free curcumin from plots showing the time dependence of the absorbance of (a) curcumin and (b) vanadium curcumin complex immobilized IBN-4. 100
Fig 3. 6 Mean values of cfu/mL for all experimental conditions and reduction (%) in the number of viable cells for experimental groups compared to dark control group. (+): samples treated with led; (-) samples in dark conditions. Statistical significance at 0.05 in comparison to control 101
Fig 3. 7 Membrane permeability of S.aureus was measured using flow cytometry with PI staining on treatment using various concentrations drug loaded nanoparticles (a) Without phototherapy and (b) With phototherapy, (a) 50 μg/mL (b) 10 μg/mL and (c) control (0 μg/mL). 102
Fig 3. 8 (A) The ROS level in s.aureus was analyzed using FCM with DCFH-DA staining after nanoparticle treatment and blue light irradiation (72 J/cm2). (a) Light control; (b) Dark control (c) IBN-4-vanadium-curcumin-dark; (d) IBN-4-vanadium-curcumin-light. (B) Singlet oxygen detection after light irradiation of IBN-v-cur samples using DPBF at various time points. 103
Fig 3. 9 (A) Flow-cytometric assessment of IBN-v-cur uptake in s.aureus (a) Control (b) 10 μg/mL (c) 50 μg/mL (B) Representative FE-SEM images of S.aureus (a) Dark control; (b) Light control (c) Treatment with 30 μg/mL concentration of IBN-v-cur nano composites in the absence of light and (d) Treatment with 30 μg/ml concentration of IBN-v-cur nano composites exposed to light irradiation. 104
Fig 3. 10 Confocal fluorescence micrograph of S.aureus biofilms (a) control in the presence of light (b) Treated with 25 μg/ml concentration of IBN-v-cur nano composites in the absence of light (c) Treated with 25 μg/ml concentration of IBN-v-cur nano composites and exposed to light irradiation. Biofilm were stained with fluorescein isothiocyanate (FITC) and propidium iodide (PI) dyes: green fluorescence is characteristic of the live cells, whereas red fluorescence is due to dead cells 105
Fig 3. 11 Flow cytometric analyses of cellular uptake of iIBN-v curcumin samples in HT-29 cells 106
Fig 3. 12 Drug uptake imaging of IBN-v-cur nanoparticles in HT29 cells after 4 hours of incubation (a) DAPI stained nucleus (b) Autofluorosence of curcumin (c) Merge of DAPI and curcumin treated samples 107
Fig 4. 1 (A) Schematic illustration of diamine modification, snp and curcumin loading in to cumsn. (B) TEM image of (a) SNP adsorbed in diamine modified cumsn with curcumin loading at 100nm. (b) SNP diameter distribution at 10 nm (c) Curcumin loaded cumsn at 50nm and (d) Curcumin and snp loaded cumsn at 1 µm. (e) SEM image of CuMSN at 1 µm and (f) SNP-CuMSN at 400nm. 129
Fig 4. 2 UV-visible spectra of (a) Curcumin (434nm) (b) CuMSN-Curcumin (425nm) (c) CuMSN-SNP (410nm) and (d) CuMSN-SNP-Curcumin (428nm). 130
Fig 4. 3 (A) FT-IR spectra of (a) Extracted cumsn (b) Diamine modified CuMSN (c) CuMSN-SNP (d) CuMSN-SNP-Curcumin (e) CuMSN-Curcumin (f) Curcumin (B) Nitrogen adsorption–desorption isotherms of (a) Diamine modified cumsn after template extraction (b) Curcumin loaded cumsn (c) SNP & Curcumin loaded CuMSN. 132
Fig 4. 4 EPR spectrum of solid (a) CuMSN and (b) CuMSN-Curcumin complex, (c) CuMSN-SNP (d) CuMSN-SNP-Curcumin at 77k. 135
Fig 4. 5 Optical images of (a) Extracted cumsn (b) Silver nitrate adsorbed cumsn (c) After reduction of silver nitrate to snp with formaldehyde (d) CuMSN-SNP-Curcumin (e) CuMSN-Curcumin 136
Fig 4. 6 13C cp/mas solid-state NMR spectra of (A) (a) Msn and (b) CuMSN (B) (a) Diamine modified CuMSN (b) SNP modified CuMSN and (c) SNP and Curcumin conjugated CuMSN 139
Fig 4. 7 Membrane permeability of E. coli was measured using flow cytometry with PI staining either in (A) Dark or (B) Light with (a) CuMSN (b) CuMSN-Curcumin (c) CuMSN-SNP and (d) CuMSN-SNP-Curcumin 142
Fig 4. 8 The ROS level in E. coli was analyzed using fcm with DCFH-DA staining after nanoparticle treatment (A) In dark and (B) With blue light irradiation (72 J/cm2). (a) control; (b) CuMSN curcumin (c) CuMSN-SNP (d) CuMSN-SNP- Curcumin 142
Fig 4. 9 Viability of E. coli in the absence or presence of blue light. Bacteria were incubated with different concentrations of curcumin (1.5, 3 and 6

Chapter 1: 1.2 References

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9. I. I. Slowing, J. L. Vivero-Escoto, C.-W. Wu and V. S. Y. Lin, Advanced Drug Delivery Reviews, 2008, 60, 1278-1288.
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13. M. Manzano, V. Aina, C. O. Areán, F. Balas, V. Cauda, M. Colilla, M. R. Delgado and M. Vallet-Regí, Chemical Engineering Journal, 2008, 137, 30-37.
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