The preparation and antioxidant activity of the sulfanilamide derivatives of chitosan and chitosan sulfates

Zhong, Zhimei; Ji, Xia; Xing, Ronge; Liu, Song; Tan, Wenqiang; Chen, Xiaolin; Li, Pengcheng

doi:10.1016/j.bmc.2007.03.036

Cited by 71 publications

(31 citation statements)

References 16 publications

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“…Yen et al [11] reported reducing power of approximately 0.2 at 1 mg/mL for crab chitosans while. Zhong et al [10] found that reducing power of low molecular weight (MW = 4 kDa) chitosan was approximately 0.06 at 1 mg/mL. Thus, CSacetate, CS-HOBt and CS-EDTA had reducing power similar to the previous study.…”

Section: Discussionsupporting

confidence: 59%

“…The derivative studied include water-soluble disaccharide chitosan [5], carboxymethyl chitosan [6], sulfated chitosan [7,8], quaternized chitosan [9], sulfanilamide derivatives of chitosan [10], chitosan crab shells [11], chitosan-N-2-hydroxypropyl trimethyl ammonium chloride [12], 2-[phenylhydrazine -thiosemicarbazone] -chitosan [13] and dietary chitosan [14].…”

Section: Introductionmentioning

confidence: 99%

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<i>In Vitro</i> Antioxidant Activity of Chitosan Aqueous Solution: Effect of Salt Form

Charernsriwilaiwat¹,

Opanasopit²,

Rojanarata³

et al. 2012

Trop. J. Pharm Res

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Section: Discussionsupporting

confidence: 59%

Section: Introductionmentioning

confidence: 99%

<i>In Vitro</i> Antioxidant Activity of Chitosan Aqueous Solution: Effect of Salt Form

Charernsriwilaiwat¹,

Opanasopit²,

Rojanarata³

et al. 2012

Trop. J. Pharm Res

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“…However, excessive generation of ROS in host cells that are infected with bacteria is known to induce cell death. Recently, COS was found to have several beneficial biological effects including free radical scavenging activity (26)(27)(28), a stimulatory effect on macrophages, and chemoattractive effects on neutrophils in vitro and in vivo (13)(14)(15)(16). Therefore, COS A may have a greater effect than COS B via the inhibition of cytotoxic factors such as cytolysin, metalloproteinase, elastase, and RTX toxin in V. vulnificus or through the suppression of excessive ROS by V. vulnificus-infected cells.…”

Section: Discussionmentioning

confidence: 99%

“…COS are watersoluble due to their shorter chain lengths and free amino groups in D-glucosamine units. Specifically, many of these compounds were found to have beneficial biological effects including anti-tumor (17)(18)(19), antimicrobial (20)(21)(22), cholesterol-reducing (23)(24)(25), and free radical scavenging (26)(27)(28) activity. In addition to its lack of toxicity and allergenicity, the biodegradability and biocompatibility of chitosan and COS make it potentially useful for biomaterial, medical, and pharmaceutical applications (29).…”

Section: Introductionmentioning

confidence: 99%

In vitro and in vivo antimicrobial activity of water-soluble chitosan oligosaccharides against Vibrio vulnificus

Kim

2009

Int J Mol Med

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Abstract.Vibrio vulnificus is a Gram-negative bacterium that induces severely rapid pathological progress. In this study, we evaluated the antibacterial activity of two water-soluble chitosan oligosaccharides, COS A (MW, 10,000 Da) and COS B (MW, 1,000 Da), from 90-95% deacetylated chitosan, against V. vulnificus in vitro and in vivo. Treatment with COS A resulted in significantly higher suppressive effects on the growth of V. vulnificus than treatment with COS B. The growth of V. vulnificus was inhibited within 1 h of treatment with water-soluble COS A in concentrations ranging from 0.5 to 10 mg/ml. Additionally, treatment with COS A completely inhibited V. vulnificus-induced cytotoxicity in human intestinal epithelial INT-407 cells, while COS B did not. Furthermore, the administration of COS A (0.1-0.5 mg per mouse) significantly increased the survival period of V. vulnificus-infected mice. The number of viable V. vulnificus in the spleen, liver, small intestine, and blood was significantly lower in COS A-treated mice than in untreated mice. Here, we clearly demonstrate that COS A is a potential agent for the prevention and treatment of infection with V. vulnificus.

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“…The clinically useful sulfonamides are derived from sulfanilamide, which is similar to para-aminobenzoic acid, afactor required by bacteria for folic acid synthesis [1]. Sulfanilamide was introduced in therapy about half acentury ago for prevention and cure of bacterial infections in humans, and so many derivatives of sulfanilamide have been developed [2][3][4][5]. In the title molecule ( figure, top), the C2-O1 bond lengths (1.205(3).Å)i sl onger than that of standard C=O double bond length 1.170 Å,while the C2-N1 bond distance (1.364(4) Å)is shorter than atypical C-Nbond length (ca.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N-(4-(3-cyclohexyl-5-methyl-2,4-dioxoimidazolidin- 1-ylsulfonyl)phenyl)acetamide, C18H23N3O5S

Cai¹,

Xie²,

Yan³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material N-(4-(3-cyclohexyl-5-methyl-2,4-dioxoimidazolidin-1-ylsulfonyl)phenyl) acetamide was prepared by reacting of 2-(4-acetamidophenylsulfonamido)propanoic acid (0.01 mol) and dicyclohexylcarbodiimide (0.01 mol) in dry N,N-dimethylformamide (dmf) over 36 hours at 298 K. After filtration, reduced pressure distillation of dmf, and column chromatography separation, the title compound was obtained. The purified product was dissolved in 95 %ethanol and single crystals were separated after 10 days. Experimental detailsAll Hatoms were positioned geometrically and allowed to ride on their parent atoms at distances of d(Csp 2 -H) =0.93 Å with U iso = 1.2 U eq (parent atom), d(Csp 3 -H) =0 .97 Å with U iso =1 .5 U eq (parent atom) and d(N-H) =0.86 Å with U iso =1.2 U eq (parent atom). DiscussionSulfonamides are among the most widely used antibacterial angents in the world, chiefly because of their low cost, low toxicity, and excellent activity against bacterial diseases. The clinically useful sulfonamides are derived from sulfanilamide, which is similar to para-aminobenzoic acid, afactor required by bacteria for folic acid synthesis [1]. Sulfanilamide was introduced in therapy about half acentury ago for prevention and cure of bacterial infections in humans, and so many derivatives of sulfanilamide have been developed [2][3][4][5]. In the title molecule ( figure, top), the C2-O1 bond lengths (1.205(3).Å)i sl onger than that of standard C=O double bond length 1.170 Å,while the C2-N1 bond distance (1.364(4) Å)is shorter than atypical C-Nbond length (ca. 1.443(4) Å), but longer than atypical double C=N bond (ca. 1.269(2) Å), indicating the electron delocalization at the O1, C2 and N1 atoms [6]. The acetyl-amidocyanogen and the phenyl ring are in the same plane with an r.m.s. deviation of 0.0455 Å (plane p1). The imidazolidine ring and the two oxygen atoms (O4 and O5) are coplanar (r.m.s. deviation =0.0255 Å,plane p2). The dihedral angles formed by p1 and p2 are 81.99(5)°.The unique cyclohexyl group is in achair conformation. Pairs of molecules are linked by intermolecular N1−H1···O5 A (symmetry code A: −x +2,−y,−z+2) hydrogen bond to form ac entrosymmetric hydrogen bonded dimer (figure, bottom) which can be described in graph-set motif of R 2 2 20 () [7].

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The preparation and antioxidant activity of the sulfanilamide derivatives of chitosan and chitosan sulfates

Cited by 71 publications

References 16 publications

<i>In Vitro</i> Antioxidant Activity of Chitosan Aqueous Solution: Effect of Salt Form

<i>In Vitro</i> Antioxidant Activity of Chitosan Aqueous Solution: Effect of Salt Form

In vitro and in vivo antimicrobial activity of water-soluble chitosan oligosaccharides against Vibrio vulnificus

Crystal structure of N-(4-(3-cyclohexyl-5-methyl-2,4-dioxoimidazolidin- 1-ylsulfonyl)phenyl)acetamide, C18H23N3O5S

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