Preparation and anticoagulant activity of N-succinyl chitosan sulfates

Wang, Tan; Zhou, Yue; Xie, Weiguo; Chen, Lingyun; Zheng, Hua; Fan, Lihong

doi:10.1016/j.ijbiomac.2012.07.029

Cited by 35 publications

(22 citation statements)

References 21 publications

(18 reference statements)

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“…As a source of polysaccharide for sulfonation, chitosan (deacetyl chitin) has been considered due to the presence of β‐(1 → 4) linkages, linearity, and the presence of amino and acetamido groups (features in common with heparin) . Chitosan does not have any anticoagulant effects but partial enzymatic depolymerization and sulfonation of the amino and hydroxy functional groups and/or addition of carboxyl groups endows it with anticoagulant activity . Different methods of preparation of sulfated chitosan have been reviewed by Tamura et al.…”

Section: Heparin Mimeticsmentioning

confidence: 99%

“…126 Chitosan does not have any anticoagulant effects but partial enzymatic depolymerization and sulfonation of the amino and hydroxy functional groups and/or addition of carboxyl groups endows it with anticoagulant activity. [126][127][128][129][130][131][132][133][134][135][136][137][138][139][140][141][142] Different methods of preparation of sulfated chitosan have been reviewed by Tamura et al For sulfated chitosan, Nsulfation at the C-2 position is required to inhibit blood coagulation. [143][144][145] It has also been found that the 6-O-sulfate group is critical for anticoagulant activity and the absence of sulfation at this position totally ablates the anticoagulant activity.…”

Section: Chemical Modification Of Naturally Occurring Polysaccharidesmentioning

confidence: 99%

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Heparin mimetics with anticoagulant activity

Al-Nahain

Ignjatović

Monagle

et al. 2018

Medicinal Research Reviews

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Heparin, a sulfated polysaccharide belonging to the glycosaminoglycan family, has been widely used as an anticoagulant drug for decades and remains the most commonly used parenteral anticoagulant in adults and children. However, heparin has important clinical limitations and is derived from animal sources which pose significant safety and supply problems. The ever growing shortage of the raw material for heparin manufacturing may become a very significant issue in the future. These global limitations have prompted much research, especially following the recent well-publicized contamination scandal, into the development of alternative anticoagulants derived from non-animal and/or totally synthetic sources that mimic the structural features and properties of heparin. Such compounds, termed heparin mimetics, are also needed as anticoagulant materials for use in biomedical applications (e.g., stents, grafts, implants etc.). This review encompasses the development of heparin mimetics of various structural classes, including synthetic polymers and non-carbohydrate small molecules as well as sulfated oligo- and polysaccharides, and fondaparinux derivatives and conjugates, with a focus on developments in the past 10 years.

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Section: Heparin Mimeticsmentioning

confidence: 99%

Section: Chemical Modification Of Naturally Occurring Polysaccharidesmentioning

confidence: 99%

Heparin mimetics with anticoagulant activity

Al-Nahain

Ignjatović

Monagle

et al. 2018

Medicinal Research Reviews

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“…An example of such derivatives is N-succinyl chitosan (SCS), which can be obtained from a simple reaction between CS and succinic anhydride. [7][8][9][10] SCS exhibits low toxicity, biocompatibility and it is less biodegradable than CS, showing long systemic circulation in mice, for which is considered as an excellent drug carrier candidate. [11] The Succinyl functionalization has been used for further modification of chitosan with folic acid or antibodies in order to prepare vectorized nanoparticles for cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of Succinyl‐Chitosan Nanoparticles for Drug Delivery

Monsalve

Sierra

López

2015

Macromolecular Symposia

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Summary: Succinyl-Chitosan (SCS), a water soluble CS derivative, exhibits biocompatibility, low toxicity and long-term retention in the body. SCS offers unique characteristics as polymer for obtaining drug delivery nanosystems, due to its many reactive amino, hydroxyl, and carboxylic acid pendant groups. Chemical modifications of SCS with antibodies and other active species are easily achieved through bonding with these groups, allowing targeting and detection. In this work, SCS was obtained by amidation of primary amine groups of CS with succinic anhydride. The succinylation degree, determined by 1 H-NMR, was 28%. Evaluation by zeta potential measurements of SCS showed a pH-dependent charge profile, which can be conveniently exploited to prepare pH-sensitive nanoparticles. Colloidal stable SCS/CS and SCS nanoparticles, useful in drug delivery, were prepared by ionic crosslinking from mixtures of CS and SCS in different weight percentages. Nanoparticles with sizes between 140-250 nm (after purification process) are obtained, which through further surface functionalization are suitable for application in drug delivery. The colloidal stability of the particles in water was studied by particle size measurements during 30 days and aggregation or formation of larger particles was not observed.

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“…It is the most abundant natural amino polysaccharide and is characterized by poly‐(1,4)‐2‐amino‐2‐deoxy‐D‐glucose by partial deacetylation of chitin. Because chitosan and its derivatives have remarkable bioactivities, including anti‐tumor, anticoagulation, blood fat reduction and immunity enhancement, chitosan is widely used in pharmaceutical preparations, health products, cosmetics and other additives . Thus, it is of great importance to accurately determine the quantity of chitosan.…”

Section: Introductionmentioning

confidence: 99%

Resonance Rayleigh scattering methods for the determination of chitosan with Congo red as probe

Zhang

Guo

et al. 2017

Luminescence

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Two methods were presented for the sensitive and selective determination of chitosan (CTS) with Congo red (CR) as probe based on resonance Rayleigh scattering (RRS) intensities in health products. In weakly acidic buffer solution, the binding of CTS to CR, could result in the enhancement of the RRS intensities. Moreover, after adding OP emulsifier (octyl-phenyl polyoxyethylene ether) to the system, the RRS intensities showed more significantly enhancement. The maximum RRS signals for the CTS-CR system and the CTS-CR-OP system were located at 380 nm and 376 nm, respectively. Under optimum experimental conditions, the increased RRS intensities (ΔI) of these two systems were linear to CTS concentration in the range of 0.40-8.00 μg/ml and 0.05-1.00 μg/ml. Their limits of detection (LOD) were 44.81 ng/ml and 6.99 ng/ml, which indicated that the latter system was more sensitive than the former. In this work, the optimum conditions and the effects of some foreign substances on the determination were studied. In addition, the effect of the molecular weight of CTS and the reasons for the enhancement of resonance light scattering were discussed. Finally, these two methods were applied to the determination of chitosan in health products with satisfactory results.

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Preparation and anticoagulant activity of N-succinyl chitosan sulfates

Cited by 35 publications

References 21 publications

Heparin mimetics with anticoagulant activity

Heparin mimetics with anticoagulant activity

Preparation and Characterization of Succinyl‐Chitosan Nanoparticles for Drug Delivery

Resonance Rayleigh scattering methods for the determination of chitosan with Congo red as probe

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