Sodium cellulose sulfate: A promising biomaterial used for microcarriers’ designing
Qing-Xi Wu1,2, Yi-Xin Guan1, Shan-Jing Yao1()
1. Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China 2. School of Life Sciences, Anhui University; Anhui Key Laboratory of Modern Biomanufacturing; Key Laboratory of Eco-engineering and Biotechnology of Anhui Province, Hefei 230601, China
Due to a worldwide focus on sustainable materials for human health and economy services, more and more natural renewable biomass are regarded as promising materials that could replace synthetic polymers and reduce global dependence on petroleum resources. Cellulose is known as the most abundant renewable polymer in nature, varieties of cellulose-based products have been developed and have gained growing interest in recent years. In this review, a kind of water-soluble cellulose derivative, i.e., sodium cellulose sulfate (NaCS) is introduced. Details about NaCS’s physicochemical properties like solubility, biocompatibility, biodegradability, degree of substitution, etc. are systematically elaborated. And promising applications of NaCS used as biomaterials for microcarriers’ designing, such as micro-cell-carriers, micro-drug-carriers, etc., are presented.
Substitution uniformly; little molecular weight reduction; no using of anhydrous sulfuric acid
Difficulty in handling of SO3; reaction violently
[15]
DMF and N2O4
Preparation and handling easily; substitution uniformly; using less sulfuric acid; no acetylation of cellulose; preferably reaction at room temperature
Toxicity of N2O4; high production cost
[16]
Chlorosulfuric acid and pyridine
Substitution uniformly; a high degree of substitution; no significant degradation
Highly toxicity of chlorosulfuric acid; serious environmental pollution
[17]
Tab.1
Fig.2
Measurement methods
Principle
Advantages
Disadvantages
Ref.
Polyelectrolytes titration
Reacting and forming particles that having a UV absorption peak at 290 nm, using spectrophotometer to judge the end of titration
A simple and rapid method
Difficult to judge the end of titration accurately
[39]
Barium sulfate turbidimetrya)
Hydrolyze NaCS with 1 mol·L−1 HCl to release SO3− groups, adding BaCl2 to form BaSO4 precipitate, drawing the standard curve with K2SO4 and BaCl2 at 360 nm
A rapid and convenient method
Existing some experimental errors due to the turbid liquid of BaSO4 particles distributed non-uniformly with time
[53]
Element analysisb)
Contents of carbon, hydrogen, nitrogen and sulfur can be determined via Elemental Analyser
Precise, reducing the manual measurement errors
High cost relatively
[18]
13C-NMR spectroscopy
Based on 13C-NMR spectroscopy by means of NMR spectrometer
Good accuracy and credibility
High analysis cost
[18]
FT Raman spectroscopy
Record FT Raman spectra with a spectrometer via a liquid-nitrogen cooled Ge diode as detector
A rapid method of quantifying the total DS of NaCS
Need high-end equipments, high analysis costs and a certain level of operational technology
DKlemm, B Heublein, H PFink, ABohn. Cellulose: Fascinating biopolymer and sustainable raw material. Angewandte Chemie International Edition, 2005, 44(22): 3358–3393 https://doi.org/10.1002/anie.200460587
2
C SGoh, K T Tan, K T Lee, S Bhatia. Bio-ethanol from lignocellulose: Status, perspectives and challenges in Malaysia. Bioresource Technology, 2010, 101(13): 4834–4841 https://doi.org/10.1016/j.biortech.2009.08.080
3
BKoo, H Kim, YCho, K TLee, N SChoi, JCho. A highly cross-linked polymeric binder for high-performance silicon negative electrodes in lithium ion batteries. Angewandte Chemie International Edition, 2012, 51(35): 8762–8767 https://doi.org/10.1002/anie.201201568
JKadokawa. Precision polysaccharide synthesis catalyzed by enzymes. Chemical Reviews, 2011, 111(7): 4308–4345 https://doi.org/10.1021/cr100285v
8
DAndrade, M H Mendonca, C V Helm, W Magalhaes, Gde Muniz, S GKestur. Assessment of nano cellulose from peach palm residue as potential food additive: Part II: Preliminary studies. Journal of Food Science and Technology-Mysore, 2015, 52(9): 5641–5650 https://doi.org/10.1007/s13197-014-1684-0
9
H CGomez, A Serpa, JVelasquez-Cock, PGanan, CCastro, LVelez, RZuluaga. Vegetable nanocellulose in food science: A review. Food Hydrocolloids, 2016, 57: 178–186 https://doi.org/10.1016/j.foodhyd.2016.01.023
10
L AGarcia-Zapateiro, CValencia, J MFranco. Formulation of lubricating greases from renewable basestocks and thickener agents: A rheological approach. Industrial Crops and Products, 2014, 54: 115–121 https://doi.org/10.1016/j.indcrop.2014.01.020
11
ZAl-Ibraheemi, M S Anuar, F S Taip, M Amin, S MTahir, A BMahdi. Deformation and mechanical characteristics of compacted binary mixtures of plastic (microcrystalline cellulose), elastic (sodium starch glycolate), and brittle (lactose monohydrate) pharmaceutical excipients. Particulate Science and Technology, 2013, 31(6): 561–567 https://doi.org/10.1080/02726351.2013.785451
12
JOjala, J A Sirvio, H Liimatainen. Nanoparticle emulsifiers based on bifunctionalized cellulose nanocrystals as marine diesel oil-water emulsion stabilizers. Chemical Engineering Journal, 2016, 288: 312–320 https://doi.org/10.1016/j.cej.2015.10.113
13
A AOun, J W Rhim. Isolation of cellulose nanocrystals from grain straws and their use for the preparation of carboxymethyl cellulose-based nanocomposite films. Carbohydrate Polymers, 2016, 150: 187–200 https://doi.org/10.1016/j.carbpol.2016.05.020
14
XMa, M Lv, D PAnderson, P RChang. Natural polysaccharide composites based on modified cellulose spheres and plasticized chitosan matrix. Food Hydrocolloids, 2017, 66: 276–285 https://doi.org/10.1016/j.foodhyd.2016.11.038
15
R GSchweiger. Polysaccharide sulfates. I. Cellulose sulfate with a high degree of substitution. Carbohydrate Research, 1972, 21(2): 219–228 https://doi.org/10.1016/S0008-6215(00)82148-5
16
R JBrewer, K Tenn. US Patent, 4480091, 1984-10-30
17
T CUsher, N Patel, C GTele. US Patent, 5378828, 1995-01-03
18
KHettrich, W Wagenknecht, BVolkert, SFischer. New possibilities of the acetosulfation of cellulose. Macromolecular Symposia, 2008, 262(1): 162–169 https://doi.org/10.1002/masy.200850216
19
D BSparrow, W R Powers. US Patent, 2862922, 1958-12-02
S JYao, D Q Lin, L. CN Fang Patent, 101274964B, 2010-11-03
22
S JYao. Verfahrenstechnische auslegung einer anlage fuer die natrium-cellulosesulfatherstellung zur immobiliserung von biokatalysatoren. Dissertation for the Doctoral Degree. Berlin: Technical University of Berlin, 1996, 57–90
23
R AAnderson, L J D Zaneveld, T C Usher. US Patent, 6063773, 2000-05-16
24
KOkajima, K Kamide, T. EPMatsui Patent, 0053473A1, 1981-11-25
TYoshida, B W Kang, K Hattori, TMimura, YKaneko, HNakashima, MPremanathan, RAragaki, NYamamoto, TUryu. Anti-HIV activity of sulfonated arabinofuranan and xylofuranan. Carbohydrate Polymers, 2001, 42(2): 141–150 https://doi.org/10.1016/S0144-8617(00)00210-1
27
R AAnderson, K A Feathergill, X H Diao, M D Cooper, R Kirkpatrick, B CHerold, G FDoncel, C JChany, D PWaller, W FRencher, et al. Preclinical evaluation of sodium cellulose sulfate (Ushercell) as a contraceptive antimicrobial agent. Journal of Andrology, 2002, 23(3): 426–438
28
R AAnderson, K Feathergill, X HDiao, C IIChany, W FRencher, LZaneveld, D PWaller. Contraception by Ushercell (TM) (cellulose sulfate) in formulation: Duration of effect and dose effectiveness. Contraception, 2004, 70(5): 415–422 https://doi.org/10.1016/j.contraception.2004.05.014
29
L J DZaneveld, R AAnderson, T CUsher. US Patent, 7078392B2, 2006-07-18
WTao, C Richards, DHamer. Short communication—enhancement of HIV infection by cellulose sulfate. AIDS Research and Human Retroviruses, 2008, 24(7): 925–929 https://doi.org/10.1089/aid.2008.0043
32
VPirrone, S Passic, BWigdahl, FKrebs. Clinical failures of select polyanionic microbicide candidates may be predicted by in vitro enhancement of HIV-1 infection. Antiviral Research, 2009, 82(2): A65–A66 https://doi.org/10.1016/j.antiviral.2009.02.159
33
VPirrone, B Wigdahl, F CKrebs. The rise and fall of polyanionic inhibitors of the human immunodeficiency virus type 1. Antiviral Research, 2011, 90(3): 168–182 https://doi.org/10.1016/j.antiviral.2011.03.176
34
H KAgarwal, A Kumar, G FDoncel, KParang. Synthesis, antiviral and contraceptive activities of nucleoside-sodium cellulose sulfate acetate and succinate conjugates. Bioorganic & Medicinal Chemistry Letters, 2010, 20(23): 6993–6997 https://doi.org/10.1016/j.bmcl.2010.09.133
35
M JWang, Y L Xie, Q D Zheng, S J Yao. A novel, potential microflora-activated carrier for a colon-specific drug delivery system and its characteristics. Industrial & Engineering Chemistry Research, 2009, 48(11): 5276–5284 https://doi.org/10.1021/ie801295y
36
L YZhu, D Q Lin, S J Yao. Biodegradation of polyelectrolyte complex films composed of chitosan and sodium cellulose sulfate as the controllable release carrier. Carbohydrate Polymers, 2010, 82(2): 323–328 https://doi.org/10.1016/j.carbpol.2010.04.062
37
JRohowsky, K Heise, SFischer, KHettrich. Synthesis and characterization of novel cellulose ether sulfates. Carbohydrate Polymers, 2016, 142: 56–62 https://doi.org/10.1016/j.carbpol.2015.12.060
38
MGericke, T Liebert, THeinze. Interaction of ionic liquids with polysaccharides, 8-synthesis of cellulose sulfates suitable for polyelectrolyte complex formation. Macromolecular Bioscience, 2009, 9(4): 343–353 https://doi.org/10.1002/mabi.200800329
39
M JWang. Study on NaCS used for vegetable capsule and colon-targeted drug delivery capsule. Dissertation for the Doctoral Degree. Hangzhou: Zhejiang University, 2010, 29–38 (in Chinese)
40
KZhang, D Peschel, EBaeucker, TGroth, SFischer. Synthesis and characterisation of cellulose sulfates regarding the degrees of substitution, degrees of polymerisation and morphology. Carbohydrate Polymers, 2011, 83(4): 1659–1664 https://doi.org/10.1016/j.carbpol.2010.10.029
41
GChen, B Zhang, JZhao, HChen. Improved process for the production of cellulose sulfate using sulfuric acid/ethanol solution. Carbohydrate Polymers, 2013, 95(1): 332–337 https://doi.org/10.1016/j.carbpol.2013.03.003
42
A AJohn, A P Subramanian, M V Vellayappan, A Balaji, S KJaganathan, HMohandas, TParamalinggam, ESupriyanto, MYusof. Review: Physico-chemical modification as a versatile strategy for the biocompatibility enhancement of biomaterials. RSC Advances, 2015, 5(49): 39232–39244 https://doi.org/10.1039/C5RA03018H
43
L HMei, S J Yao. Cultivation and modelling of encapsulated Saccharomyces cerevisiae in NaCS-PDMDAAC polyelectrolyte complexes. Journal of Microencapsulation, 2002, 19(4): 397–405 https://doi.org/10.1080/02652040210141101
44
L HMei, S J Yao, D Q Lin, P L Cen, Z Q Zhu. Biocompatibility of NaCS and PDADMAC microcapsules with Bacillus thuringiensis. CIESC Journal, 1999, 50(5): 592–597
45
L HMei, D Q Lin, S J Yao, Z X Han. Study on immobilization of bacillus thuringiensis by microencapsules of NaCS and PDADMAC. Journal of Zhejiang University (Engineering Science), 2000, 34(6): 694–695 (in Chinese)
46
JZhang, S J Yao, Y X Guan. Preparation of macroporous sodium cellulose sulphate/poly(dimethyldiallylammonium chloride) capsules and their characteristics. Journal of Membrane Science, 2005, 255(1-2): 89–98 https://doi.org/10.1016/j.memsci.2005.01.025
47
HDautzenberg, U Schuldt, GGrasnick, PKarle, PMuller, MLohr, M Pelegrin, MPiechaczyk, K VRombs, W HGunzburg, et al.Development of cellulose sulfate-based polyelectrolyte complex microcapsules for medical applications. Annals of the New York Academy of Sciences, 1999, 875(1): 46–63 https://doi.org/10.1111/j.1749-6632.1999.tb08493.x
48
BSalmons, W H Gunzburg. Therapeutic application of cell microencapsulation in cancer. Berlin: Springer-Verlag Press, 2010, 92–103
49
LYildirimer, A M Seifalian. Three-dimensional biomaterial degradation—material choice, design and extrinsic factor considerations. Biotechnology Advances, 2014, 32(5): 984–999 https://doi.org/10.1016/j.biotechadv.2014.04.014
50
J MMacy, J R Farrand, L Montgomery. Cellulolytic and non-cellulolytic bacteria in rat gastrointestinal tracts. Applied and Environmental Microbiology, 1982, 44(6): 1428–1434
51
CRobert, A Bernalier-Donadille. The cellulolytic microflora of the human colon: Evidence of microcrystalline cellulose-degrading bacteria in methane-excreting subjects. FEMS Microbiology Ecology, 2003, 46(1): 81–89 https://doi.org/10.1016/S0168-6496(03)00207-1
52
Q XWu, M Z Li, S J Yao. Performances of NaCS-WSC protein drug microcapsules with different degree of substitution of NaCS using sodium polyphosphate as cross-linking agent. Cellulose (London, England), 2014, 21(3): 1897–1908 https://doi.org/10.1007/s10570-014-0209-3
53
L YZhu. Study on colon-specific drug delivery carrier based on chitosan and sodium cellulose sulfate. Dissertation for the Doctoral Degree.Hangzhou: Zhejiang University, 2011, 20–24 (in Chinese)
54
KZhang, E Brendler, S F TFischer. Raman investigation of sodium cellulose sulfate. Cellulose (London, England), 2010, 17(2): 427–435 https://doi.org/10.1007/s10570-009-9375-0
55
M JWang, S J Yao. Determination of molecular weight of sodium cellulose sulfate by low angle laser light scattering. Chinese Journal of Process Engineering, 2009, 9(6): 1159–1163 (in Chinese)
56
Q LZhang, D Q Lin, S J Yao. Review on biomedical and bioengineering applications of cellulose sulfate. Carbohydrate Polymers, 2015, 132: 311–322 https://doi.org/10.1016/j.carbpol.2015.06.041
57
L HMei, J T Yao, S J Yao. Immobilized culture of Bacillus subtilis in NACS-PDMDAAC microcapsules for production of new anti-thrombus enzyme. CIESC Journal, 2000, 51(6): 814–817
58
Z RZhang, Q D Zheng, S J Yao. Cultivation of encapsulated Monascus purpureus in NaCS-PDMDAAC capsules. Food and Fermentation Industries, 2003, 29(11): 1–4
59
L HMei, X Z Zhang, B Y Ai, Q Sheng, D QLin, S JYao, Z QZhu. Immobilized culture of Bacillus subtilis in SA/CS-CaCl2/PMCG microcapsule for production of nattokinase. CIESC Journal, 2004, 55(8): 1319–1323
60
L HMei, J L Yang, C H Zhong, D Q Lin, S J Yao. Cultivation of Brevibacterium flavum in new microcapsule system and production of glutamic acid. Journal of Zhejiang University (Engineering Science), 2005, 39(9): 1400–1403 (in Chinese)
61
Y YJi, S J Yao, J Zhang, Y XGuan, D QLin. Cultivation of encapsulated C.valida for producing lipase in macro-porous NaCS-PDMDAAC microcapsules. CIESC Journal, 2005, 56(11): 2162–2165
62
Y NZhao, G Chen, S JYao. Microbial production of 1,3-propanediol from glycerol by encapsulated Klebsiella pneumoniae. Biochemical Engineering Journal, 2006, 32(2): 93–99 https://doi.org/10.1016/j.bej.2006.09.007
63
GChen, Y N Zhao, H Huang, S JYao. 1,3-Propanediol production from glycerol by Klebsiella pneumoniae encapsulated in NACS/PDMDAAC capsules. CIESC Journal, 2006, 57(12): 2933–2937
64
GChen, Y N Zhao, S J Yao, B S Fang. Production of 1,3-propanediol by co-culture of two immobilized microbes in series. Journal of Beijing University of Chemical Technology, 2007, 34(6): 640–644 (in Chinese)
65
Q LMa, D Q Lin, S J Yao. Immobilization of mixed bacteria by microcapsulation for hydrogen production—a trial of pseudo “Cell Factory”. Chinese Journal of Biotechnology, 2010, 26(10): 1444–1450
66
MLohr, P Muller, PKarle, JStange, SMitzner, RJesnowski, HNizze, BNebe, S Liebe, BSalmons, W HGunzburg. Targeted chemotherapy by intratumour injection of encapsulated cells engineered to produce CYP2B1, an ifosfamide activating cytochrome P450. Gene Therapy, 1998, 5(8): 1070–1078 https://doi.org/10.1038/sj.gt.3300671
67
WWeber, M Rinderknecht, MBaba, F Nde Glutz, DAubel, MFussenegger. CellMAC: A novel technology for encapsulation of mammalian cells in cellulose sulfate/pDADMAC capsules assembled on a transient alginate/Ca2+ scaffold. Journal of Biotechnology, 2004, 114(3): 315–326 https://doi.org/10.1016/j.jbiotec.2004.07.014
68
P BStiegler, V Stadlbauer, SSchaffellner, GHalwachs, CLackner, OHauser, FIberer, KTscheliessnigg. Cryopreservation of insulin-producing cells microencapsulated in sodium cellulose sulfate. Transplantation Proceedings, 2006, 38(9): 3026–3030 https://doi.org/10.1016/j.transproceed.2006.08.188
69
PStiegler, V Matzi, EPierer, OHauser, SSchaffellner, HRenner, JGreilberger, RAigner, AMaier, CLackner, FIberer, F MSmolle-Jüttner, KTscheliessnigg, VStadlbauer. Creation of a prevascularized site for cell transplantation in rats. Xenotransplantation, 2010, 17(5): 379–390 https://doi.org/10.1111/j.1399-3089.2010.00606.x
70
X HZeng, M K Danquah, C Zheng, RPotumarthi, X DChen, Y HLu. NaCS-PDMDAAC immobilized autotrophic cultivation of Chlorella sp. for wastewater nitrogen and phosphate removal. Chemical Engineering Journal, 2012, 187: 185–192 https://doi.org/10.1016/j.cej.2012.01.119
71
Q XWu, D Q Lin, S J Yao. Design of chitosan and its water soluble derivatives-based drug carriers with polyelectrolyte complexes. Marine Drugs, 2014, 12(12): 6236–6253 https://doi.org/10.3390/md12126236
72
Q XWu, S J Yao. Novel NaCS-CS-PPS microcapsules as a potential enzyme-triggered release carrier for highly-loading 5-ASA. Colloids and Surfaces. B, Biointerfaces, 2013, 109: 147–153 https://doi.org/10.1016/j.colsurfb.2013.03.035
73
Q XWu, Q L Zhang, D Q Lin, S J Yao. Characterization of novel lactoferrin loaded capsules prepared with polyelectrolyte complexes. International Journal of Pharmaceutics, 2013, 455(1-2): 124–131 https://doi.org/10.1016/j.ijpharm.2013.07.048
74
Y LXie, M J Wang, S J Yao. Layer-by-layer self-assembly complex membrane composed of sodium cellulose sulfate-chitosan. CIESC Journal, 2008, 59(11): 2910–2915
75
Y LXie, M J Wang, S J Yao. Preparation and characterization of biocompatible microcapsules of sodium cellulose sulfate/chitosan by means of layer-by-layer self-assembly. Langmuir, 2009, 25(16): 8999–9005 https://doi.org/10.1021/la9014338
76
SSugiura, M Nakajima, JTong, HNabetani, MSeki. Preparation of monodispersed solid lipid microspheres using a microchannel emulsification technique. Journal of Colloid and Interface Science, 2000, 227(1): 95–103 https://doi.org/10.1006/jcis.2000.6843
77
Q XWu, D Q Lin, S J Yao. Fabrication and formation studies on single-walled CA/NaCS-WSC microcapsules. Materials Science & Engineering C-Materials for Biological Applications, 2016, 59: 909–915 https://doi.org/10.1016/j.msec.2015.10.090