quaternized cellulose based self-assembled micelles
TRANSCRIPT
Self-assembled micelles based on hydrophobically modified quaternized
cellulose for drug deliveryYongbo Song, Lingzhi Zhang, Weiping Gan, Jinping Zhou, Lina Zhang
Colloids and Surfaces B: Biointerfaces 83 (2011) 313-320
Presented by : Mr. Wasin KoosomsuanStudent ID : 5437822
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Self-assembly micelles
Fig. 1. Formation of polymeric micelles from different types of amphiphilic block co-polymers (Extracted from Torchillin, 2001).
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Naturally occurring polymers as drug carrier
Scheme 1. Synthesis of HM-DEX and HM-hydroxypropylcellulose copolymers (extracted from Mira F, 2004).
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Naturally occurring polymers as drug carrier
Advantages
Natural abundant Cheap Biocompatibility Biodegradability Nontoxicity
Fig. 2. Synthesis of N,N,N-trimethyl chitosan
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Fig.3. Epoxidation of 3-Chloro-2-hydroxypropyl trimethylammonium chloride (CHPTAC)
Cellulose-based polymer micelle preparation
Cl N+CH3
CH3
CH3OH
Cl- N aO H O
N+CH3
CH3
CH3
Cl-
+ NaCl + H2O
3-Chloro-2-hydroxypropyl trimethylammonium
chloride (CHPTAC)
Cl N+CH3
CH3
CH3O
H
Cl-
OH-
Cl N+CH3
CH3
CH3O-
Cl-
-H 2O
ON
+CH3
CH3
CH3
Cl-
+ Cl-
Mechanism
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Cellulose-based polymer micelle preparation (cont.)
Scheme 2. Synthesis of hydrophobically modified quaternized cellulose (HMQC).
Mechanism
O O
OH
OH
O
H OH-
OO
OH
OH
O-
-H 2O
CH3 CH2 CH2 Br
14
O O
OH
OH
O
CH2 CH3
15
nn n
+ Br-
Hexadecyl bromide
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Scheme 3. Schematic representation of self-assembled micelles based on hydrophobically modified quaternized cellulose.
Drug + HMQC in DMSO/H2O
solution
Dialysis against distilled water Filtration
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Fig. 4. FT-IR spectra of QC and HMQC samples.
C-N stretching
-CH3 of substituted ammonium
C-H stretching
C-O stretching of ether
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Fig. 5. The drug loading capacity (LC) and loading efficiency (LE) of HMQC micelles.Data are shown as mean±SD (n = 3).
Fig. 6. Drug release behavior of prednisone acetate from HMQC micelles in PBS (pH7.4) at 37 ◦C. Data are shown as mean±SD (n = 3).
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Loading efficiency and capacity as well as drug release
Nucleophilic substitution
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Applications of quaternized Chitosan or cellulose
- Antimicrobials : by disrupting the cell membrane
- Ion exchange membrane
- Intercalation of silicate layer
- Improved drug delivery : by mucoadhesion ability
- Enhanced dyeability : lower electrolyte concentration
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Properties obtained from etherification of cellulose
- Water solubility : (Increase or decrease)*
- Amphiphilic : can serve as a surfactant
- Viscosity : (depends on softening point)
- Thermoplastic : lower softening point
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Thank You
for your attention
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