| Revision as of 11:38, 24 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit |
Latest revision as of 21:44, 23 February 2023 edit undoOzzie10aaaa (talk | contribs)Autopatrolled, Extended confirmed users, New page reviewers212,351 editsm Cleaned up using AutoEd |
| (50 intermediate revisions by 28 users not shown) |
| Line 1: |
Line 1: |
|
|
{{refimprove|date=February 2015}} |
|
|
|
|
|
{{distinguish|anthracimycin}} |
|
|
|
|
{{Chembox |
|
{{Chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 443392561 |
|
|
|
| Watchedfields = changed |
| ⚫ |
| ImageFile = Anthramycin.png |
|
|
⚫ |
| verifiedrevid = 457132162 |
|
| ImageSize = |
|
|
⚫ |
| ImageFile = Anthramycin.svg |
| ⚫ |
| ImageAlt = |
|
|
| IUPACName = |
|
| ImageSize = 222 |
|
⚫ |
| ImageAlt = |
|
|
| PIN = (2''E'')-3- benzodiazepin-2-yl]prop-2-enamide |
|
| OtherNames = |
|
| OtherNames = |
|
|
|
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
| ⚫ |
| CASNo = |
|
|
|
| CASNo_Ref = {{cascite|changed|??}} |
| ⚫ |
| PubChem = |
|
|
⚫ |
| CASNo = 4803-27-4 |
| ⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
⚫ |
| PubChem = 5311005 |
|
⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 25056543 |
|
| ChemSpiderID = 25056543 |
|
|
| ChEBI = 40699 |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = VGQOVCHZGQWAOI-HYUHUPJXSA-N |
|
| StdInChIKey = VGQOVCHZGQWAOI-HYUHUPJXSA-N |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI=1S/C16H17N3O4/c1-8-2-4-10-13(14(8)21)18-15(22)11-6-9(3-5-12(17)20)7-19(11)16(10)23/h2-5,7,11,15,18,21-22H,6H2,1H3,(H2,17,20)/b5-3+/t11-,15-/m0/s1 |
|
| StdInChI=1S/C16H17N3O4/c1-8-2-4-10-13(14(8)21)18-15(22)11-6-9(3-5-12(17)20)7-19(11)16(10)23/h2-5,7,11,15,18,21-22H,6H2,1H3,(H2,17,20)/b5-3+/t11-,15-/m0/s1 |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL = <!-- blanked - oldvalue: 1230992 --> |
|
| ChEMBL = 2311109 |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII = 0WZD9Y66WN |
|
| UNII = 0WZD9Y66WN |
|
| SMILES = Cc1ccc2C(=O)N3C=C(C3(O)Nc2c1O)\C=C\C(=O)N }} |
|
| SMILES = Cc1ccc2C(=O)N3C=C(C3(O)Nc2c1O)\C=C\C(=O)N }} |
|
|
|
|
| Section2 = {{Chembox Properties |
|
| Section2 = {{Chembox Properties |
|
| Formula = C16 H17 N3 O4 |
|
| C=16 | H=17 | N=3 | O=4 |
|
|
| Appearance = |
|
| MolarMass = 315.3 g/mol |
|
|
| Appearance = |
|
| MeltingPt = |
|
| Density = |
|
| BoilingPt = |
|
| MeltingPt = |
|
| Solubility = }} |
|
|
|
|
| BoilingPt = |
|
|
⚫ |
|Section3={{Chembox Hazards |
|
| Solubility = }} |
|
|
|
| MainHazards = |
| ⚫ |
| Section3 = {{Chembox Hazards |
|
|
| MainHazards = |
|
| FlashPt = |
|
|
| AutoignitionPt = }} |
|
| FlashPt = |
|
|
| Autoignition = }} |
|
|
}} |
|
}} |
|
|
|
|
|
'''Anthramycin''' is a pyrrolobenzodiazepine ] with ] activity.<ref>{{Cite journal |
|
'''Anthramycin''' is a ] ] with ] activity.<ref>{{Cite journal |
|
| doi = 10.1016/j.tet.2004.07.040 |
|
| doi = 10.1016/j.tet.2004.07.040 |
|
| volume = 60 |
|
| volume = 60 |
|
| issue = 43 |
|
| issue = 43 |
|
| pages = 9649–9657 |
|
| pages = 9649–57 |
|
| last = Kitamura |
|
| last = Kitamura |
|
| first = Tsuyoshi |
|
| first = Tsuyoshi |
|
| coauthors = Yoshihiro Sato, Miwako Mori |
|
| author2=Yoshihiro Sato |author3=Miwako Mori |
|
| title = Synthetic study of (+)-anthramycin using ring-closing enyne metathesis and cross-metathesis |
|
| title = Synthetic study of (+)-anthramycin using ring-closing enyne metathesis and cross-metathesis |
|
| journal = Tetrahedron |
|
| journal = Tetrahedron |
|
| year=2004 |
|
| year=2004 |
|
|
}}</ref> First derived from the ] ] ''Streptomyces refuineus'' by M. D. Tendler and S Korman in the 1950s, it was first successfully synthesized in a laboratory setting by Leimgruber ''et al.'' in 1965. Due to the unstable nature of the chemical structure, characterization of the species was done on its ], anthrmycin-11-methyl-ether. This derivative can be formed by ] of anthramycin from hot ]. |
|
}}</ref> |
|
|
|
|
|
|
==Chemical structure== |
|
|
The chemical structure of anthramycin was first elucidated by Leimgruber using ] and ]. Using another similarly structured fermentation product simply referred to as 'yellow pigment' as a basis of comparison, he was able to identify all major functional groups of the structure. The structure of the species was narrowed down to one of two possible candidates: one with a pyrrolobenzodiazepine nucleus, and another with a pyridoquinazoline skeleton. The first structure was confirmed through the use of ]. |
|
|
|
|
|
==Medical uses== |
|
|
Anthramycin is an active anti-tumor agent and antibiotic.<ref>{{cite book|last1=Sartorelli|first1=Alan C.|last2=Johns|first2=David G.|title=Antineoplastic and Immunosuppressive Agents|date=27 November 2013|publisher=Springer Science & Business Media|isbn=9783642658068|page=647|url=https://books.google.com/books?id=aU_oCAAAQBAJ&dq=Anthramycin&pg=PA647|access-date=1 November 2016|language=en}}</ref> It works by inhibiting the synthesis of ] and ] of carcinoma cells. It is a competitive inhibitor of cell-free RNA and DNA synthesis, and blocks the action of ]. Anthramycin-methyl-ether (AME) forms a complex with DNA which blocks off synthesis by prohibiting DNA binding with proper enzymes. The species is heavily ]. Anthramycin has been shown particularly effective against ], ], and gastrointestinal ].{{cn|date=August 2018}} |
|
|
|
|
|
==Side effects== |
|
|
Use of anthramycin has been largely limited due to a ] so high that it limits dosing. Acute tissue ] has also been noted at the injection site of the antibiotic, and side effect of its high cytotoxicity. Repeated injections in mice have been shown to adversely affect mitochondrial metabolism. The mice also showed abnormal ]. As such, the side effects of such medication may outweigh the benefits. Alternatives such as ] are today more widely available and prescribed, due to more mild side effects along with increased anti-tumor action. |
|
|
|
|
|
==See also== |
|
|
* ] |
|
|
* ] |
|
|
|
|
|
==References== |
|
==References== |
|
{{reflist}} |
|
{{reflist}} |
|
|
|
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
|
] |
|
|
|
|
|
{{Benzodiazepines}} |