Misplaced Pages

Galactosamine: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 14:44, 19 November 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot|...← Previous edit Latest revision as of 04:42, 22 February 2023 edit undoGünniX (talk | contribs)Extended confirmed users312,603 editsm brackets fixed 
(28 intermediate revisions by 19 users not shown)
Line 1: Line 1:
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461116190 | verifiedrevid = 461116190
| reference = <ref>''Merck Index'', 11th Edition, '''4240'''.</ref> | Reference = <ref>''Merck Index'', 11th Edition, '''4240'''.</ref>
| ImageFile = galactosamine.png | ImageFile = galactosamine.png
| ImageFile1 = alpha-D-galactosamine.png | ImageFile1 = D-(+)-Galactosamine Structural Formulae V.1.svg
| ImageSize = 150px | ImageSize =
| ImageSize1 = 150px | ImageSize1 =
| IUPACName = 2-Amino-2-deoxy-D-galactose | IUPACName = 2-Amino-2-deoxy-D-galactose
| OtherNames = α-D-galactosamine | OtherNames = α-D-galactosamine
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 22576 | ChemSpiderID = 22576
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
Line 20: Line 21:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MSWZFWKMSRAUBD-GASJEMHNSA-N | StdInChIKey = MSWZFWKMSRAUBD-GASJEMHNSA-N
| CASNo_Ref = {{cascite|changed|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 7535-00-4 | CASNo = 7535-00-4
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 24154
| UNII = 4Y6R29688W
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | PubChem = 24154
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 60312 | ChEBI = 60312
| SMILES = O1(O)(OC(O)1N)CO | SMILES = O1(O)(OC(O)1N)CO
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=6 | H=13 | N=1 | O=5
| Formula = C<sub>6</sub>H<sub>13</sub>NO<sub>5</sub>
| Appearance =
| MolarMass = 179.171 g/mol
| Appearance = | Density =
| Density = | MeltingPtC = 180
| MeltingPt = 180 °C (HCl salt) | MeltingPt_notes = (HCl salt)
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
⚫ }}
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| AutoignitionPt =
⚫ }}
}} }}


'''Galactosamine''' is a ] derived from ] with the molecular formula C<sub>6</sub>H<sub>13</sub>NO<sub>5</sub>. This ] is a constituent of some ] ]s such as ] (FSH) and ] (LH). Other sugar constituents of FSH and LH include ], ] and ]. '''Galactosamine''' is a ] derived from ] with the molecular formula C<sub>6</sub>H<sub>13</sub>NO<sub>5</sub>. This ] is a constituent of some ] ]s such as ] (FSH) and ] (LH).

Precursors such as ] (UDP), UDP-''N''-acetyl-<small>D</small>-glucosamine, or ] are used to synthesize galactosamine in the human body. A derivative of this compound is ].<ref name=":0"/>


Galactosamine is a ], or liver-damaging, agent that is sometimes used in ]s of ]. Galactosamine is a ], or liver-damaging, agent that is sometimes used in ]s of ].

== Hepatotoxicity ==
Galactosamine is used to induce hepatitis in rodent liver for research purposes. The result of using galactosamine to induce hepatitis is a disease model in which there is ] and inflammation of the liver. This type of tissue damage triggered by galactosamine resembles drug-induced liver disease in humans.<ref name=":1">{{Cite journal |last1=Das |first1=Joydeep |last2=Ghosh |first2=Jyotirmoy |last3=Roy |first3=Anandita |last4=Sil |first4=Parames C. |date=April 2012 |title=Mangiferin exerts hepatoprotective activity against D-galactosamine induced acute toxicity and oxidative/nitrosative stress via Nrf2–NFκB pathways |url=https://linkinghub.elsevier.com/retrieve/pii/S0041008X12000269 |journal=Toxicology and Applied Pharmacology |language=en |volume=260 |issue=1 |pages=35–47 |doi=10.1016/j.taap.2012.01.015|pmid=22310181 }}</ref>

=== Mechanism of hepatotoxicity ===
The proposed mechanism behind galactosamine-induced hepatitis is depletion of the energy source of ]s. In the ] galactosamine is metabolized into galactosamine-1-phosphate (by ]) and UDP-galactosamine (by UDP-galactose ]). It is hypothesized that this leads to UDP-galactosamine accumulation within cells, and ] (UTP), UDP, and ] (UMP) decrease.<ref name=":0">{{Citation |last=Apte |first=U. |title=Galactosamine |date=2014 |url=https://linkinghub.elsevier.com/retrieve/pii/B9780123864543003158 |encyclopedia=Encyclopedia of Toxicology |pages=689–690 |publisher=Elsevier |language=en |doi=10.1016/b978-0-12-386454-3.00315-8 |isbn=978-0-12-386455-0 |access-date=2022-12-08}}</ref> The depletion of high-energy molecules such as UTP leads to a disruption in hepatocyte metabolism. Additionally, other derivatives of uridine such as UDP-glucose are depleted and this interferes with ] in the cell.

Another recent hypothesis states that overexpression of pro-inflammatory cytokines (such as ] (TNFα) and ]-dependent ] (iNOS) over expression play a role in galactosamine-induced damage to liver cells.<ref name=":1" />


==See also== ==See also==
*] * ]
* ]


==References== ==References==
{{More citations needed|date=March 2012}}
{{Reflist}} {{Reflist}}


Line 56: Line 71:
* {{MeshName|Galactosamine}} * {{MeshName|Galactosamine}}


] ]


{{biochem-stub}}

]
]
]
]

Latest revision as of 04:42, 22 February 2023

Galactosamine
Names
IUPAC name 2-Amino-2-deoxy-D-galactose
Other names α-D-galactosamine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1Key: MSWZFWKMSRAUBD-GASJEMHNSA-N
  • InChI=1/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1Key: MSWZFWKMSRAUBD-GASJEMHNBA
SMILES
  • O1(O)(OC(O)1N)CO
Properties
Chemical formula C6H13NO5
Molar mass 179.172 g·mol
Melting point 180 °C (356 °F; 453 K) (HCl salt)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Galactosamine is a hexosamine derived from galactose with the molecular formula C6H13NO5. This amino sugar is a constituent of some glycoprotein hormones such as follicle-stimulating hormone (FSH) and luteinizing hormone (LH).

Precursors such as uridine diphosphate (UDP), UDP-N-acetyl-D-glucosamine, or glucosamine are used to synthesize galactosamine in the human body. A derivative of this compound is N-acetyl-D-galactosamine.

Galactosamine is a hepatotoxic, or liver-damaging, agent that is sometimes used in animal models of liver failure.

Hepatotoxicity

Galactosamine is used to induce hepatitis in rodent liver for research purposes. The result of using galactosamine to induce hepatitis is a disease model in which there is necrosis and inflammation of the liver. This type of tissue damage triggered by galactosamine resembles drug-induced liver disease in humans.

Mechanism of hepatotoxicity

The proposed mechanism behind galactosamine-induced hepatitis is depletion of the energy source of hepatocytes. In the Leloir pathway galactosamine is metabolized into galactosamine-1-phosphate (by galactokinase) and UDP-galactosamine (by UDP-galactose uridyltransferase). It is hypothesized that this leads to UDP-galactosamine accumulation within cells, and uridine triphosphate (UTP), UDP, and uridine monophosphate (UMP) decrease. The depletion of high-energy molecules such as UTP leads to a disruption in hepatocyte metabolism. Additionally, other derivatives of uridine such as UDP-glucose are depleted and this interferes with glycogen synthesis in the cell.

Another recent hypothesis states that overexpression of pro-inflammatory cytokines (such as tumor necrosis factor (TNFα) and NFκB-dependent inducible nitric oxide synthase (iNOS) over expression play a role in galactosamine-induced damage to liver cells.

See also

References

This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed.
Find sources: "Galactosamine" – news · newspapers · books · scholar · JSTOR (March 2012) (Learn how and when to remove this message)
  1. Merck Index, 11th Edition, 4240.
  2. ^ Apte, U. (2014), "Galactosamine", Encyclopedia of Toxicology, Elsevier, pp. 689–690, doi:10.1016/b978-0-12-386454-3.00315-8, ISBN 978-0-12-386455-0, retrieved 2022-12-08
  3. ^ Das, Joydeep; Ghosh, Jyotirmoy; Roy, Anandita; Sil, Parames C. (April 2012). "Mangiferin exerts hepatoprotective activity against D-galactosamine induced acute toxicity and oxidative/nitrosative stress via Nrf2–NFκB pathways". Toxicology and Applied Pharmacology. 260 (1): 35–47. doi:10.1016/j.taap.2012.01.015. PMID 22310181.

External links

Category:
Galactosamine: Difference between revisions Add topic