Quaternized Cellulose Based Self-Assembled Micelles

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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