Poliglusam | CAS# 9012-76-4 | xxx

MedKoo Cat#: 581182 | Name: Poliglusam

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Poliglusam is also known as Chitosan. Chitosan is a linear polysaccharide composed of randomly distributed β-(1→4)-linked D-glucosamine (deacetylated unit) and N-acetyl-D-glucosamine (acetylated unit). It is made by treating the chitin shells of shrimp and other crustaceans with an alkaline substance, like sodium hydroxide. Deacetylated CHITIN, a linear polysaccharide of deacetylated beta-1,4-D-glucosamine. It is used in HYDROGEL and to treat WOUNDS.

Chemical Structure

Poliglusam

CAS#9012-76-4

Theoretical Analysis

MedKoo Cat#: 581182

Name: Poliglusam

CAS#: 9012-76-4

Chemical Formula: C56H103N9O39

Exact Mass: 1525.6353

Molecular Weight: 1526.46

Elemental Analysis: C, 44.06; H, 6.80; N, 8.26; O, 40.88

Price and Availability

Size	Price	Availability	Quantity
50g	USD 190.00
250g	USD 300.00
500g	USD 640.00

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Related CAS #

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Synonym

Poliglusam; Chitosan; Dac 70; Deacetylchitin; Chitosan;

IUPAC/Chemical Name

methyl ((2S,3R,4R,5S,6R)-5-(((2S,3R,4R,5S,6R)-3-amino-5-(((2S,3R,4R,5S,6R)-3-amino-5-(((2S,3R,4R,5S,6R)-3-amino-5-(((2S,3R,4R,5S,6R)-3-amino-5-(((2S,3R,4R,5S,6R)-3-amino-5-(((2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-(((2R,3S,4R,5R,6S)-5-amino-6-(((2R,3S,4S,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

InChi Key

FLASNYPZGWUPSU-FBKXNGQRSA-N

InChi Code

InChI=1S/C56H103N9O39/c1-87-56(86)65-28-38(84)46(19(10-74)96-55(28)104-45-18(9-73)95-49(27(64)37(45)83)97-39-12(3-67)88-47(85)20(57)31(39)77)103-54-26(63)36(82)44(17(8-72)94-54)102-53-25(62)35(81)43(16(7-71)93-53)101-52-24(61)34(80)42(15(6-70)92-52)100-51-23(60)33(79)41(14(5-69)91-51)99-50-22(59)32(78)40(13(4-68)90-50)98-48-21(58)30(76)29(75)11(2-66)89-48/h11-55,66-85H,2-10,57-64H2,1H3,(H,65,86)/t11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31+,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48+,49+,50+,51+,52+,53+,54+,55+/m1/s1

SMILES Code

O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O[C@@H]8O[C@H](CO)[C@@H](O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9N)[C@H](O)[C@H]8N)[C@H](O)[C@H]7N)[C@H](O)[C@H]6N)[C@H](O)[C@H]5N)[C@H](O)[C@H]4N)[C@H](O)[C@H]3NC(OC)=O)[C@H](O)[C@H]2N)[C@H]([C@H]1N)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Chitosan (MW 30000) (Deacetylated chitin (MW 30000)) is a polycationic linear polysaccharide derived from chitin with the molecular weight of 30000.

In vitro activity:

The results revealed that whereas chitosan decreased adhesion of primary melanoma A375 cell line and decreased proliferation of primary melanoma SKMEL28 cell line, it had potent pro-apoptotic effects against RPMI7951, a metastatic melanoma cell line. In these latter cells, inhibition of specific caspases confirmed that apoptosis was effected through the mitochondrial pathway and Western blot analyses showed that chitosan induced an up regulation of pro-apoptotic molecules such as Bax and a down regulation of anti-apoptotic proteins like Bcl-2 and Bcl-XL. More interestingly, chitosan exposure induced an exposition of a greater number of CD95 receptor at RPMI7951 surface, making them more susceptible to FasL-induced apoptosis. Reference: Int J Biol Macromol. 2015 Jan;72:370-9. https://pubmed.ncbi.nlm.nih.gov/25193096/

In vivo activity:

This study aimed at assessing the impact of chitosan nanoparticles either uncoated (CS NPs) or Tween 80-coated (T-CS NPs) on the effects of SF on oxidative stress markers and antioxidant enzyme activities in rats. Interestingly, SF-CS NPs and T-SF-CS-NPs treatments significantly attenuated the inhibitory effects of SF on the activity of these enzymes whereas, GST activity was inhibited. Moreover, the protein expression of GST was downregulated upon treatment of rats with free SF, SF-CS-NPs, and T-SF CS-NPs. In contrast, the activity and protein expression of GPx was induced by SF-CS NPs and T-SF-CS-NPs treatments. The histopathological study showed that SF induced multiple adverse effects on the rat liver architecture which were markedly suppressed particularly by T-SF-CS NPs. Reference: Oxid Med Cell Longev. 2023 Jan 31;2023:9944985. https://pubmed.ncbi.nlm.nih.gov/36891377/

	Solvent	mg/mL	mM	comments
Solubility
	Water	1.1	0.72

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,526.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Mehmood T, Pichyangkura R, Muanprasat C. Chitosan Oligosaccharide Promotes Junction Barrier through Modulation of PI3K/AKT and ERK Signaling Intricate Interplay in T84 Cells. Polymers (Basel). 2023 Mar 28;15(7):1681. doi: 10.3390/polym15071681. PMID: 37050295; PMCID: PMC10096774. 2. Gibot L, Chabaud S, Bouhout S, Bolduc S, Auger FA, Moulin VJ. Anticancer properties of chitosan on human melanoma are cell line dependent. Int J Biol Macromol. 2015 Jan;72:370-9. doi: 10.1016/j.ijbiomac.2014.08.033. Epub 2014 Sep 2. PMID: 25193096. 3. Sheweita SA, Alian DME, Haroun M, Nounou MI, Patel A, El-Khordagui L. Chitosan Nanoparticles Alleviated the Adverse Effects of Sildenafil on the Oxidative Stress Markers and Antioxidant Enzyme Activities in Rats. Oxid Med Cell Longev. 2023 Jan 31;2023:9944985. doi: 10.1155/2023/9944985. PMID: 36891377; PMCID: PMC9988388. 4. Wen J, Chen S, Bao M, Hu C, Wu L, Yong Y, Liu X, Li Y, Yu Z, Ma X, Eun JB, Shim JH, Warda M, Abd El-Aty AM, Ju X. Slc9a1 plays a vital role in chitosan oligosaccharide transport across the intestinal mucosa of mice. Carbohydr Polym. 2023 Jan 1;299:120179. doi: 10.1016/j.carbpol.2022.120179. Epub 2022 Sep 30. PMID: 36876794.

In vitro protocol:

In vivo protocol:

1. Sheweita SA, Alian DME, Haroun M, Nounou MI, Patel A, El-Khordagui L. Chitosan Nanoparticles Alleviated the Adverse Effects of Sildenafil on the Oxidative Stress Markers and Antioxidant Enzyme Activities in Rats. Oxid Med Cell Longev. 2023 Jan 31;2023:9944985. doi: 10.1155/2023/9944985. PMID: 36891377; PMCID: PMC9988388. 2. Wen J, Chen S, Bao M, Hu C, Wu L, Yong Y, Liu X, Li Y, Yu Z, Ma X, Eun JB, Shim JH, Warda M, Abd El-Aty AM, Ju X. Slc9a1 plays a vital role in chitosan oligosaccharide transport across the intestinal mucosa of mice. Carbohydr Polym. 2023 Jan 1;299:120179. doi: 10.1016/j.carbpol.2022.120179. Epub 2022 Sep 30. PMID: 36876794.

1: Patrulea V, Ostafe V, Borchard G, Jordan O. Chitosan as a starting material for wound healing applications. Eur J Pharm Biopharm. 2015 Nov;97(Pt B):417-26. doi: 10.1016/j.ejpb.2015.08.004. Review. PubMed PMID: 26614560. 2: Younes I, Rinaudo M. Chitin and chitosan preparation from marine sources. Structure, properties and applications. Mar Drugs. 2015 Mar 2;13(3):1133-74. doi: 10.3390/md13031133. Review. PubMed PMID: 25738328; PubMed Central PMCID: PMC4377977. 3: Zhu L, Peng L, Zhang YQ. The processing of chitosan and its derivatives and their application for postoperative anti-adhesion. Mini Rev Med Chem. 2015;15(4):330-7. Review. PubMed PMID: 25723456. 4: Liao ZX, Chuang EY, Hsiao CW, Sung HW. 21. pH-sensitive chitosan-based nanoparticles for protein drug delivery: oral approaches: Original research article: a novel pH-sensitive hydrogel composed of carboxymethyl chitosan and alginate cross-linked by genipin for protein drug delivery, 2004. J Control Release. 2014 Sep 28;190:68-70. PubMed PMID: 25356494. 5: Kerch G. The potential of chitosan and its derivatives in prevention and treatment of age-related diseases. Mar Drugs. 2015 Apr 13;13(4):2158-82. doi: 10.3390/md13042158. Review. PubMed PMID: 25871293; PubMed Central PMCID: PMC4413205. 6: Patrulea V, Applegate LA, Ostafe V, Jordan O, Borchard G. Optimized synthesis of O-carboxymethyl-N,N,N-trimethyl chitosan. Carbohydr Polym. 2015 May 20;122:46-52. doi: 10.1016/j.carbpol.2014.12.014. Epub 2014 Dec 25. PubMed PMID: 25817641. 7: Devarayan K, Sathishkumar Y, Lee YS, Kim BS. Effect of Microgravity on Fungistatic Activity of an α-Aminophosphonate Chitosan Derivative against Aspergillus niger. PLoS One. 2015 Oct 15;10(10):e0139303. doi: 10.1371/journal.pone.0139303. eCollection 2015. PubMed PMID: 26468641; PubMed Central PMCID: PMC4607506. 8: Jimtaisong A, Saewan N. Utilization of carboxymethyl chitosan in cosmetics. Int J Cosmet Sci. 2014 Feb;36(1):12-21. doi: 10.1111/ics.12102. Epub 2013 Dec 6. Review. PubMed PMID: 24152381. 9: Jiang Z, Han B, Li H, Li X, Yang Y, Liu W. Preparation and anti-tumor metastasis of carboxymethyl chitosan. Carbohydr Polym. 2015 Jul 10;125:53-60. doi: 10.1016/j.carbpol.2015.02.039. Epub 2015 Feb 26. PubMed PMID: 25857959. 10: Chen H, Cui S, Zhao Y, Zhang C, Zhang S, Peng X. Grafting chitosan with polyethylenimine in an ionic liquid for efficient gene delivery. PLoS One. 2015 Apr 13;10(4):e0121817. doi: 10.1371/journal.pone.0121817. eCollection 2015. PubMed PMID: 25875475; PubMed Central PMCID: PMC4395340. 11: Petit C, Reynaud S, Desbrieres J. Amphiphilic derivatives of chitosan using microwave irradiation. Toward an eco-friendly process to chitosan derivatives. Carbohydr Polym. 2015 Feb 13;116:26-33. doi: 10.1016/j.carbpol.2014.04.083. Epub 2014 Apr 28. PubMed PMID: 25458269. 12: Sahariah P, Óskarsson BM, Hjálmarsdóttir MÁ, Másson M. Synthesis of guanidinylated chitosan with the aid of multiple protecting groups and investigation of antibacterial activity. Carbohydr Polym. 2015;127:407-17. doi: 10.1016/j.carbpol.2015.03.061. Epub 2015 Mar 30. PubMed PMID: 25965500. 13: Hecq J, Siepmann F, Siepmann J, Amighi K, Goole J. Development and evaluation of chitosan and chitosan derivative nanoparticles containing insulin for oral administration. Drug Dev Ind Pharm. 2015;41(12):2037-44. doi: 10.3109/03639045.2015.1044904. Epub 2015 May 26. PubMed PMID: 26006329. 14: Veraldi S, Raia DD, Schianchi R, De Micheli P, Barbareschi M. Treatment of symptoms of erythemato-telangiectatic rosacea with topical potassium azeloyl diglycinate and hydroxypropyl chitosan: Results of a sponsor-free, multicenter, open study. J Dermatolog Treat. 2015 Apr;26(2):191-2. doi: 10.3109/09546634.2014.921275. Epub 2014 May 27. PubMed PMID: 24831156. 15: Nwe N, Furuike T, Tamura H. Isolation and characterization of chitin and chitosan from marine origin. Adv Food Nutr Res. 2014;72:1-15. doi: 10.1016/B978-0-12-800269-8.00001-4. Review. PubMed PMID: 25081074. 16: Szymańska E, Winnicka K. Stability of chitosan-a challenge for pharmaceutical and biomedical applications. Mar Drugs. 2015 Apr 1;13(4):1819-46. doi: 10.3390/md13041819. Review. PubMed PMID: 25837983; PubMed Central PMCID: PMC4413189. 17: Lalatsa A, Schätzlein AG, Garrett NL, Moger J, Briggs M, Godfrey L, Iannitelli A, Freeman J, Uchegbu IF. Chitosan amphiphile coating of peptide nanofibres reduces liver uptake and delivers the peptide to the brain on intravenous administration. J Control Release. 2015 Jan 10;197:87-96. doi: 10.1016/j.jconrel.2014.10.028. Epub 2014 Nov 5. PubMed PMID: 25449808. 18: Abd El-Rehim HA, Zahran DA, El-Sawy NM, Hegazy el-SA, Elbarbary AM. Gamma irradiated chitosan and its derivatives as antioxidants for minced chicken. Biosci Biotechnol Biochem. 2015;79(6):997-1004. doi: 10.1080/09168451.2014.997187. Epub 2015 Jan 6. PubMed PMID: 25562396. 19: Şalva E, Turan SÖ, Eren F, Akbuğa J. The enhancement of gene silencing efficiency with chitosan-coated liposome formulations of siRNAs targeting HIF-1α and VEGF. Int J Pharm. 2015 Jan 15;478(1):147-154. doi: 10.1016/j.ijpharm.2014.10.065. Epub 2014 Nov 13. PubMed PMID: 25445537. 20: Sahariah P, Benediktssdóttir BE, Hjálmarsdóttir MÁ, Sigurjonsson OE, Sørensen KK, Thygesen MB, Jensen KJ, Másson M. Impact of chain length on antibacterial activity and hemocompatibility of quaternary N-alkyl and n,n-dialkyl chitosan derivatives. Biomacromolecules. 2015 May 11;16(5):1449-60. doi: 10.1021/acs.biomac.5b00163. Epub 2015 Apr 16. PubMed PMID: 25830631.