A novel 1,3,4‑thiadiazole modified chitosan: synthesis, characterization, antimicrobial activity, and release study from film dressings

다국어 초록 (Multilingual Abstract)

Herein, two new polymers designated as Cs-EATT and Cs-BATT have been synthesized via linking the chitosan with the synthesized 1,3,4-thiadiazole compounds. They were characterized using
1
H,
13
C-NMR, FT-IR, TGA, Elemental analysis, Mass spectrum, and UV–vis spectrophotometer. The synthesized polymers exhibit high activity to control the growth of pathogenic bacteria (
S. aureus
,
B. subtilis
,
E. coli,
and
P. aeruginosa
), and unicellular fungi (
C. albicans
). The MIC values were in the range of 25–100 µg mL
–1
for Cs-EATT and 25–200 µg mL
–1
for Cs-BATT with varied clear zones. The new polymers were mixed with three film-forming agents: polyvinyl alcohol, hydroxyethyl cellulose, and carboxymethyl cellulose to form six film dressings designated as E1, E2, and E3 for Cs-EATT, and B1, B2, and B3 for Cs-BATT, respectively. The evaluation of film dressings showed that the formed films had transparency, uniformity, homogeneity, elasticity, and non-irritation pH values for skin within the normal range. The maximum percentages of Cs-E/B-ATT content were recorded for film dressings E2 and B2, with values of 92.5% and 94.9%, respectively. Also, the release percentages varied according to film dressing formulation, with values in the ranges of 83.88–93.2% for Cs-EATT and (87.7–97.35%) for Cs-EATT after 9 h.

참고문헌 (Reference)

1 Liang N, "α-Tocopherol succinate-modified chitosan as a micellar delivery system for paclitaxel : preparation, characterization and in vitro/in vivo evaluations" 423 : 480-488, 2012

2 Zhang H, "Uptake of Pb(II)and Cd(II)on chitosan microsphere surface successively grafted by methyl acrylate and diethylenetriamine" 9 : 11144-11155, 2017

3 AsrofiM, "Tensile, thermal and moisture absorption properties of polyvinyl alcohol(PVA)/bengkuang(Pachyrhizus erosus)starch blend films" 16 : 70-75, 2019

4 Al-Zubiady SF, "Synthesis, characterization of new1, 3, 4-thiadiazole derivatives with studying their biological activity" 11 : 284-293, 2018

5 Jakovljević K, "Synthesis, antioxidant and antiproliferative activities of 1, 3, 4-thiadiazoles derived from phenolic acids" 27 : 3709-3715, 2017

6 Yan L, "Synthesis of N-pyrimidin [1, 3, 4] oxadiazoles and N-pyrimidin [1, 3, 4]-thiadiazoles from 1, 3, 4-oxadiazol-2-amines and 1, 3, 4-thiadiazol-2-amines via Pd-catalyzed heteroarylamination" 60 : 1359-1362, 2019

7 Abd-Elaziz AM, "Synthesis and characterization of the novel pyrimidine’s derivatives, as a promising tool for antimicrobial agent and in-vitro cytotoxicity" 19 (19): 2279-2296, 2021

8 Mohamed AE, "Synthesis and characterization of new functionalized chitosan and its antimicrobial and in-vitro release behavior from topical gel" 207 : 242-253, 2022

9 Gamal A, "Synthesis and characterization of a novel benzothiazole functionalized chitosan and its use for effective adsorption of Cu(II)" 183 : 1283-1292, 2021

10 Muğlu H, "Synthesis and characterization of 1, 3, 4-thiadiazole compounds derived from 4-phenoxybutyric acid for antimicrobial activities" 1174 : 151-159, 2018

11 Fascio ML, "Synthesis and antiviral activity of some imidazo [1, 2-b][1, 3, 4] thiadiazole carbohydrate derivatives" 480 : 61-66, 2019

12 Kaur H, "Synthesis and antipsychotic and anticonvulsant activity of some new substituted oxa/thiadiazolylazetidinonyl/thiazolidinonylcarbazoles" 45 : 2777-2783, 2010

13 Li Q, "Synthesis and antifungal activity of thiadiazole-functionalized chitosan derivatives" 373 : 103-107, 2013

14 Chawla G, "Syntheses and evaluation of anti-inflammatory, analgesic and ulcerogenic activities of 1, 3, 4-oxadiazole and 1, 2, 4-triazolo [3, 4-b]-1, 3, 4-thiadiazole derivatives" 27 : 658-665, 2012

15 Yusuf M, "Syntheses and anti-depressant activity of 5-amino-1, 3, 4-thiadiazole-2-thiol imines and thiobenzyl derivatives" 16 : 8029-8034, 2008

16 Zheng L-Y, "Study on antimicrobial activity of chitosan with different molecular weights" 54 : 527-530, 2003

17 Veeraswamy B, "Studies on synthesis of novel pyrido[2, 3-d]pyrimidine derivatives, evaluation of their antimicrobial activity and molecular docking" 28 : 1670-1675, 2018

18 Wang Y, "Selective adsorption toward Hg(II)and inhibitory effect on bacterial growth occurring on thiosemicarbazide-functionalized chitosan microsphere surface" 10 : 40302-40316, 2018

19 Valgas C, "Screening methods to determine antibacterial activity of natural products" 38 : 369-380, 2007

20 Nithiyananthan TS, "Preparation and evaluation of ciprofloxacin ocuserts" 2 : 1496-1499, 2009

21 Ahmad M, "Preparation and characterization of antibacterial thiosemicarbazide chitosan as efficient Cu(II)adsorbent" 132 : 164-172, 2015

22 Alharbi WS, "Phytosomes as an emerging nanotechnology platform for the topical delivery of bioactive phytochemicals" 13 : 1475-, 2021

23 Chen Y-C, "Physical characterizations and sustained release profiling of gastroretentive drug delivery systems with improved floating and swelling capabilities" 441 : 162-169, 2013

24 Fouda A, "Photocatalytic degradation of real textile and tannery effluent using biosynthesized magnesium oxide nanoparticles(MgO-NPs), heavy metal adsorption, phytotoxicity, and antimicrobial activity" 9 : 105346-, 2021

25 Hamza MF, "Phosphorylation of guar gum/magnetite/chitosan nanocomposites for uranium(VI)sorption and antibacterial applications" 26 (26): 1920-, 2021

26 Irfan M, "Orally disintegrating films : a modern expansion in drug delivery system" 24 : 537-546, 2016

27 Patale RL, "O, N-carboxymethyl chitosan–zinc complex : a novel chitosan complex with enhanced antimicrobial activity" 85 (85): 105-110, 2011

28 Er M, "Novel substituted benzothiazole and Imidazo [2, 1-b][1, 3, 4] thiadiazole derivatives : synthesis, characterization, molecular docking study, and investigation of their in vitro antileishmanial and antibacterial activities" 1194 : 284-296, 2019

29 Zhang J, "Novel diosgenin derivatives containing 1, 3, 4-oxadiazole/thiadiazole moieties as potential antitumor agents : design, synthesis and cytotoxic evaluation" 186 : 111897-, 2020

30 Li Q, "Novel amino-pyridine functionalized chitosan quaternary ammonium derivatives : design, synthesis, and antioxidant activity" 22 (22): 156-, 2017

31 Chen J, "Novel amide derivatives containing 1, 3, 4-thiadiazole moiety : design, synthesis, nematocidal and antibacterial activities" 29 : 1203-1210, 2019

32 Sadat-Ebrahimi SE, "Novel 5-(nitrothiophene-2-yl)-1, 3, 4-thiadiazole derivatives : synthesis and antileishmanial activity against promastigote stage of leishmania major" 18 : 1816-, 2019

33 Jakovljević K, "Novel 1, 3, 4-thiadiazole conjugates derived from protocatechuic acid : synthesis, antioxidant activity, and computational and electrochemical studies" 22 : 585-598, 2019

34 El-Naggar MM, "New synthetic chitosan hybrids bearing some heterocyclic moieties with potential activity as anticancer and apoptosis inducers" 150 : 1323-1330, 2020

35 Muğlu H, "New 1, 3, 4-thiadiazoles based on thiophene-2-carboxylic acid : synthesis, characterization, and antimicrobial activities" 1203 : 127470-, 2020

36 Kenawy E-R, "Modification of chitosan and polymethyl methacrylate with 5-phenyl-1, 3, 4-oxadiazole derivatives and their antifungal activity" 40 : 59-70, 2019

37 Ashara KC, "Microemulsion based emulgel : a novel topical drug delivery system" 4 : S27-S32, 2014

38 Mircioiu C, "Mathematical modeling of release kinetics from supramolecular drug delivery systems" 11 : 140-, 2019

39 Siepmann J, "Mathematical modeling of drug release from lipid dosage forms" 418 : 42-53, 2011

40 Sandulovici R, "Mathematical and phenomenological criteria in selection of pharmacokinetic model for M1 metabolite of pentoxyphylline" 57 : 235-247, 2009

41 Singhvi G, "In-vitro drug release characterization models" 2 : 77-84, 2011

42 El-Belely EF, "Green synthesis of zinc oxide nanoparticles(ZnO-NPs)using arthrospira platensis(Class : Cyanophyceae)and evaluation of their biomedical activities" 11 (11): 95-, 2021

43 Hamza MF, "Functionalized biobased composite for metal decontamination—insight on uranium and application to water samples collected from wells in mining areas(Sinai, Egypt)" 431 : 133967-, 2021

44 Hamza MF, "Functionalization of magnetic chitosan microparticles for high-performance removal of chromate from aqueous solutions and tannery effluent" 428 : 131775-, 2022

45 Zade PS, "Formulation, evaluation and optimization of fast dissolving tablet containing tizanidine hydrochloride" 1 : 34-42, 2009

46 Ahmed MG, "Formulation of chitosan-based ciprofloxacin and diclofenac film for periodontitis therapy" 8 : 33-41, 2009

47 Koteswari P, "Formulation development and evaluation of zolmitriptan oral soluble films using 22 factorial designs" 6 : 201-, 2016

48 Patel J, "Formulation and evaluation of topical aceclofenac gel using different gelling agent" 3 : 156-164, 2011

49 Sudatta BP, "Extraction, characterization and antimicrobial activity of chitosan from pen shell, Pinna bicolor" 163 : 423-430, 2020

50 Sanjay D, "Enhanced percutaneous permeability of acyclovir by dmso from topical gel formulation" 1 (1): 13-18, 2009

51 Suyatma NE, "Effects of hydrophilic plasticizers on mechanical, thermal, and surface properties of chitosan films" 53 : 3950-3957, 2005

52 Kumar B, "Effect of penetration enhancer DMSO on in-vitro skin permeation of acyclovir transdermal microemulsion formulation" 3 (3): 83-94, 2011

53 AsrofiM, "Effect of duration of sonication during gelatinization on properties of tapioca starch water hyacinth fiber biocomposite" 108 : 167-176, 2018

54 Aya M. Dawaba ; Hamdy M. Dawaba, "Development and evaluation of extended release ciprofloxacin HCl ocular inserts employing natural and synthetic film forming agents" 한국약제학회 49 (49): 245-257, 2019

55 Montazer MN, "Design, synthesis, docking study and urease inhibitory activity evaluation of novel 2-((5-amino-1, 3, 4-thiadiazol-2-yl)thio)-N-arylacetamide derivatives" 30 : 729-742, 2021

56 Aghcheli A, "Design, synthesis, and biological evaluation of 1-(5-(benzylthio)-1, 3, 4-thiadiazol-2-yl)-3-phenylurea derivatives as anticancer agents" 29 : 2000-2010, 2020

57 Ruan X, "Design, synthesis, and biological activity of novel myricetin derivatives containing amide, thioether, and 1, 3, 4-thiadiazole moieties" 23 : 3132-, 2018

58 Haider S, "Design, synthesis and biological evaluation of benzoxazolinone-containing 1, 3, 4-thiadiazoles as TNF-α inhibitors" 5 : e01503-, 2019

59 Quintana C, "Cyrhetrenyl and ferrocenyl 1, 3, 4-thiadiazole derivatives : synthesis, characterization, crystal structures and in vitro antitubercular activity" 55 : 48-50, 2015

60 Baran T, "Cu(II)and Pd(II)complexes of water soluble O-carboxymethyl chitosan Schiffbases : synthesis, characterization" 79 : 542-554, 2015

61 Ibrahim AG, "Chitosang-maleic acid for effective removal of copper and nickel ions from their solutions" 121 : 1287-1294, 2019

62 Salahuddin N, "Chitosan modified with 1, 3, 4-oxa(thia)diazole derivatives with high efficacy to heal burn infection by Staphylococcus aureus" 33 : 254-268, 2018

63 Cheung RC, "Chitosan : an update on potential biomedical and pharmaceutical applications" 13 : 5156-5186, 2015

64 Luszczki JJ, "Characterization and preliminary anticonvulsant assessment of some 1, 3, 4-thiadiazole derivatives" 67 : 588-592, 2015

65 Mujeeb Rahman P, "Applications of chitosan powder with in situ synthesized nano ZnO particles as an antimicrobial agent" 77 : 266-272, 2015

66 Gonelimali FD, "Antimicrobial properties and mechanism of action of some plant extracts against food pathogens and spoilage microorganisms" 9 : 1639-, 2018

67 Möller H, "Antimicrobial and physicochemical properties of chitosan-HPMC-based films" 52 : 6585-6591, 2004

68 Turner S, "Antihypertensive thiadiazoles. 1. Synthesis of some 2-aryl-5-hydrazino-1, 3, 4-thiadiazoles with vasodilator activity" 31 : 902-906, 1988

69 Xing K, "Antifungal and eliciting properties of chitosan against Ceratocystis fimbriata in sweet potato" 268 : 188-195, 2018

70 Avelelas F, "Antifungal and antioxidant properties of chitosan polymers obtained from nontraditional Polybius henslowii sources" 17 : 239-, 2019

71 Sudarshan NR, "Antibacterial action of chitosan" 6 : 257-272, 1992

72 Bayat M, "An efficient one-pot synthesis of bis butenolides" 53 : 1661-1664, 2016

73 Kumar D, "A review on the synthesis of graft copolymers of chitosan and their potential applications" 163 : 2097-2112, 2020

74 Mojallal-Tabatabaei Z, "2-(Bipiperidin-1-yl)-5-(nitroaryl)-1, 3, 4-thiadiazoles : synthesis, evaluation of in vitro leishmanicidal activity, and mechanism of action" 27 : 3682-3691, 2019

75 Oruç EE, "1, 3, 4-thiadiazole derivatives. Synthesis, structure elucidation, and structure-antituberculosis activity relationship investigation" 47 : 6760-6767, 2004