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Revision as of 12:58, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CASNo').← Previous edit Latest revision as of 22:06, 25 January 2024 edit undoCitation bot (talk | contribs)Bots5,424,103 edits Add: s2cid, pmid, pages, issue, volume, journal, date, title, authors 1-6. | Use this bot. Report bugs. | Suggested by Marbletan | #UCB_webform 
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{{this|the protease inhbitor|the article about pain relief|analgesic}} {{about|the protease inhbitor|the article about pain relief|analgesic}}
{{Chembox {{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457811721
| ImageFile = antipain.svg | ImageFile = antipain.svg
| ImageSize = 250px | ImageSize = 250px
| IUPACName = ''N''<sup>2</sup>-{carbamoyl}-''N''<sup>5</sup>-(diaminomethylidene)-<small>L</small>-ornithyl-''N''-{(2''S'')-5--1-oxopentan-2-yl}-<small>L</small>-valinamide | IUPACName = ''N''<sup>2</sup>-{carbamoyl}-''N''<sup>5</sup>-(diaminomethylidene)-<small>L</small>-ornithyl-''N''-{(2''S'')-5--1-oxopentan-2-yl}-<small>L</small>-valinamide
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = <!-- blanked - oldvalue: 37691-11-5 --> | CASNo = 37691-11-5
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|changed|??}}
| PubChem = 37817 | PubChem = 37817
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 34678 | ChemSpiderID = 34678
⚫ | SMILES = O=C(NC(=O)(NC(=O)(NC(=O)N(C(=O)O)Cc1ccccc1)CCC/N=C(\N)N)C(C)C)CCC/N=C(\N)N
| UNII_Ref = {{fdacite|changed|FDA}}
⚫ | InChI = 1/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1
| UNII = 47V479BE6L
⚫ | InChIKey = SDNYTAYICBFYFH-TUFLPTIABE
⚫ | SMILES = O=C(NC(=O)(NC(=O)(NC(=O)N(C(=O)O)Cc1ccccc1)CCC/N=C(\N)N)C(C)C)CCC/N=C(\N)N
⚫ | StdInChI = 1S/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1
⚫ | InChI = 1/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1
⚫ | StdInChIKey = SDNYTAYICBFYFH-TUFLPTIASA-N
⚫ | InChIKey = SDNYTAYICBFYFH-TUFLPTIABE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChI = 1S/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = SDNYTAYICBFYFH-TUFLPTIASA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=27|H=44|N=10|O=6 | C=27 | H=44 | N=10 | O=6
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}


'''Antipain''' is an ] used in biochemical research as a ].<ref>{{cite journal| pmid = 5052959| year = 1972| last1 = Umezawa| first1 = S| last2 = Tatsuta| first2 = K| last3 = Fujimoto| first3 = K| last4 = Tsuchiya| first4 = T| last5 = Umezawa| first5 = H| title = Structure of antipain, a new Sakaguchi-positive product of streptomyces| volume = 25| issue = 4| pages = 267–70| journal = The Journal of antibiotics}}</ref> Specifically, it is an inhibitor of ] and ].<ref>{{cite journal | pmid = 4559651 | year = 1972 | last1 = Suda | first1 = H | last2 = Aoyagi | first2 = T | last3 = Hamada | first3 = M | last4 = Takeuchi | first4 = T | last5 = Umezawa | first5 = H | title = Antipain, a new protease inhibitor isolated from actinomycetes | volume = 25 | issue = 4 | pages = 263–6 | journal = The Journal of antibiotics}}</ref> '''Antipain''' is an ] that is isolated from ] and used in biochemical research as a ] of ] and ].<ref>{{cite journal | vauthors = Suda H, Aoyagi T, Hamada M, Takeuchi T, Umezawa H | title = Antipain, a new protease inhibitor isolated from actinomycetes | journal = The Journal of Antibiotics | volume = 25 | issue = 4 | pages = 263–266 | date = April 1972 | pmid = 4559651 | doi = 10.7164/antibiotics.25.263 | doi-access = free }}</ref> It was discovered in 1972 and was the first natural peptide found that contained an ] group.<ref>{{cite journal | vauthors = Umezawa S, Tatsuta K, Fujimoto K, Tsuchiya T, Umezawa H | title = Structure of antipain, a new Sakaguchi-positive product of streptomyces | journal = The Journal of Antibiotics | volume = 25 | issue = 4 | pages = 267–270 | date = April 1972 | pmid = 5052959 | doi = 10.7164/antibiotics.25.267 | doi-access = free }}</ref> Antipain can aid in prevention of ] in blood. It is an inhibitor of serine and cysteine proteases.<ref>{{Cite book| vauthors = Lackie J |title=A Dictionary of Biomedicine|publisher=Oxford University Press|year=2012|isbn=9780199549351}}</ref>


It has been crystallized in complexes with ], which is obtained from ],<ref>PDB ENTRY {{PDBe|1bcr}} {{cite journal | vauthors = Bullock TL, Breddam K, Remington SJ | title = Peptide aldehyde complexes with wheat serine carboxypeptidase II: implications for the catalytic mechanism and substrate specificity | journal = Journal of Molecular Biology | volume = 255 | issue = 5 | pages = 714–725 | date = February 1996 | pmid = 8636973 | doi = 10.1006/jmbi.1996.0058 }}</ref> and '']'' ] B.<ref>PDB ENTRY {{PDBe|2xe4}} {{cite journal | vauthors = McLuskey K, Paterson NG, Bland ND, Isaacs NW, Mottram JC | title = Crystal structure of Leishmania major oligopeptidase B gives insight into the enzymatic properties of a trypanosomatid virulence factor | journal = The Journal of Biological Chemistry | volume = 285 | issue = 50 | pages = 39249–39259 | date = December 2010 | pmid = 20926390 | pmc = 2998157 | doi = 10.1074/jbc.M110.156679 | doi-access = free }}</ref> In both cases, the backbone carbonyl of the terminal ] of antipain forms a covalent bond to the active site ] in the protease.
⚫ ==References==
⚫ {{reflist}}


A study was performed for information on the effect of antipain on the quality of post-thawed ram ].<ref name=Akhtarshenas>{{Cite journal | doi = 10.1111/rda.13253 | title = The protease inhibitor antipain has a beneficial synergistic effect with trehalose for ram semen cryopreservation | date = 2018 | last1 = Akhtarshenas | first1 = Bahareh | last2 = Karami Shabankareh | first2 = Hamed | last3 = Hajarian | first3 = Hadi | last4 = Bucak | first4 = Mustafa Numan | last5 = Abdolmohammadi | first5 = Ali Reza | last6 = Dashtizad | first6 = Mojtaba | journal = Reproduction in Domestic Animals | volume = 53 | issue = 6 | pages = 1359–1366 | pmid = 30011087 | s2cid = 51629940 }}</ref> The results from this experiment concluded that antipain aided in the quality of ram semen by maintaining the sperm mobility.<ref name=Akhtarshenas/> Antipain includes the function to inhibit a degrading enzyme, called ], permitting this substance to be able to improve the resistance of membrane disruption by freezing temperatures.<ref name=Akhtarshenas/>


Antipain Y, a similar chemical compound that is an ] of antipain, which was isolated from a species of '']'', inhibits the release of neurotransmitters in rat dorsal root ganglion neurons.<ref>{{cite journal | vauthors = Nakae K, Kojima F, Sawa R, Kubota Y, Igarashi M, Kinoshita N, Adachi H, Nishimura Y, Akamatsu Y | display-authors = 6 | title = Antipain Y, a new antipain analog that inhibits neurotransmitter release from rat dorsal root ganglion neurons | journal = The Journal of Antibiotics | volume = 63 | issue = 1 | pages = 41–44 | date = January 2010 | pmid = 19911027 | doi = 10.1038/ja.2009.109 | doi-access = free }}</ref>
⚫ ]

⚫ == References ==
⚫ {{reflist}}


⚫ ]
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