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{{chembox |
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{{chembox |
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|ImageFile=Maytansine structure.svg |
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| verifiedrevid = 387461214 |
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|ImageSize=200px |
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| ImageFile=Maitansine2DCSD.svg |
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|IUPACName= |
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|OtherNames=Maytansin |
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| IUPACName= |
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| OtherNames=Maytansin |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=35846-53-8 |
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| CASNo=35846-53-8 |
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| PubChem=5281828 |
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| PubChem=5281828 |
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| SMILES=C/C(CC1=CC(OC)=C(Cl)C(N3C)=C1)=C\C=C\(OC)2(O)C((C)4(O4)(C)(OC((C)N(C)C(C)=O)=O)CC3=O)()OC(N2)=O |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 6701 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 488931 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 14083FR882 |
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| SMILES=C/C(CC1=CC(OC)=C(Cl)C(N3C)=C1)=C\C=C\(OC)2(O)C((C)4(O4)(C)(OC((C)N(C)C(C)=O)=O)CC3=O)()OC(N2)=O |
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| ChemSpiderID = 10274768 |
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| StdInChI = 1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10+,18-11+/t19-,20+,25+,26-,27+,30+,33+,34+/m1/s1 |
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| StdInChIKey = WKPWGQKGSOKKOO-RSFHAFMBSA-N |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>34</sub>H<sub>46</sub>ClN<sub>3</sub>O<sub>10</sub> |
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| Formula=C<sub>34</sub>H<sub>46</sub>ClN<sub>3</sub>O<sub>10</sub> |
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| MolarMass=692.20 g/mol |
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| MolarMass=692.20 g/mol |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Maytansine''' is a ]. It inhibits the assembly of ]s by binding to ] at the ] binding site.<ref name="NCI"></ref> |
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'''Maitansine''' (]), or '''maytansine''' (]), is a ]. It inhibits the assembly of ]s by binding to ] at the ] binding site.<ref name="NCI"></ref> The maytansine binding site and binding mode has been characterized.<ref name="s228">{{cite journal | last=Menchon | first=Grégory | last2=Prota | first2=Andrea E. | last3=Lucena-Agell | first3=Daniel | last4=Bucher | first4=Pascal | last5=Jansen | first5=Rolf | last6=Irschik | first6=Herbert | last7=Müller | first7=Rolf | last8=Paterson | first8=Ian | last9=Díaz | first9=J. Fernando | last10=Altmann | first10=Karl-Heinz | last11=Steinmetz | first11=Michel O. | title=A fluorescence anisotropy assay to discover and characterize ligands targeting the maytansine site of tubulin | journal=Nature Communications | publisher=Springer Science and Business Media LLC | volume=9 | issue=1 | date=2018-05-29 | issn=2041-1723 | doi=10.1038/s41467-018-04535-8 | doi-access=free | page=| pmc=5974090 }}</ref> |
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It is a ] of the ] type and can be isolated from plants of the genus '']''.<ref name="NCI" /> |
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It is a ] of the ] type and can be isolated from plants of the genus '']''.<ref name="NCI" /> |
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==Maytansinoids== |
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Derivatives are known as ]s.<ref>{{cite journal | last1 = Yu | first1 = T.-W. | last2 = Bai | first2 = L | last3 = Clade | first3 = D | last4 = Hoffmann | first4 = D | last5 = Toelzer | first5 = S | last6 = Trinh | first6 = KQ | last7 = Xu | first7 = J | last8 = Moss | first8 = SJ | last9 = Leistner | first9 = E | title = The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnemapretiosum | journal = Proceedings of the National Academy of Sciences | volume = 99 | issue = 12 | pages = 7968 | year = 2002 | pmid = 12060743 | pmc = 123004 | doi = 10.1073/pnas.092697199 }}</ref> |
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Derivatives of maitansine are known as maytansinoids.<ref name="Yu">{{cite journal | last1 = Yu | first1 = T.-W. | last2 = Bai | first2 = L | last3 = Clade | first3 = D | last4 = Hoffmann | first4 = D | last5 = Toelzer | first5 = S | last6 = Trinh | first6 = KQ | last7 = Xu | first7 = J | last8 = Moss | first8 = SJ | last9 = Leistner | first9 = E | title = The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnemapretiosum | journal = Proceedings of the National Academy of Sciences | volume = 99 | issue = 12 | pages = 7968–7973 | year = 2002 | pmid = 12060743 | pmc = 123004 | doi = 10.1073/pnas.092697199 | bibcode = 2002PNAS...99.7968Y | doi-access = free }}</ref><ref>{{cite journal|last1=Lopus|first1=M|last2=Oroudjev|first2=E|last3=Wilson|first3=L|last4=Wilhelm|first4=S|last5=Widdison|first5=W|last6=Chari|first6=R|last7=Jordan|first7=MA|title=Maytansine and cellular metabolites of antibody-maytansinoid conjugates strongly suppress microtubule dynamics by binding to microtubules|journal=Mol Cancer Ther|date=2010|volume=9|issue=10|pages=2689–99|doi=10.1158/1535-7163.MCT-10-0644|pmid=20937594|pmc=2954514}}</ref> |
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Some are being investigated as the cytotoxic component of ]s for cancer treatment,<ref name=Chari-1992>{{cite journal | url = http://cancerres.aacrjournals.org/content/52/1/127.full.pdf | pmid= 1727373 |title=Immunoconjugates containing novel maytansinoids: promising anticancer drugs. | volume=52 | date=January 1992 | journal=Cancer Res. | pages=127–31 | last1 = Chari | first1 = RV | last2 = Martell | first2 = BA | last3 = Gross | first3 = JL | issue= 1 |display-authors=etal }}</ref> and the antibody-drug conjugate ] is an approved drug for the treatment of certain kinds of ] in the EU and in the US.<ref>{{cite web | title=Kadcyla EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/kadcyla }}</ref><ref name="FDA Approval">{{cite web | title=Drug Approval Package: ado-trastuzumab emtansine | website=U.S. ] (FDA) | date=22 February 2013 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/125427Orig1s000TOC.cfm | archive-url=https://web.archive.org/web/20191204061612/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/125427Orig1s000TOC.cfm | archive-date=4 December 2019 | url-status=live | access-date=3 December 2019}}</ref> |
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Examples of maytansinoids are: |
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*]<ref name="Yu" /> |
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*] / emtansine (DM1) |
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*] / soravtansine (DM4) |
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==See also== |
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==See also== |
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* ], developer of maytansinoid based drugs |
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* ], a derivative |
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==References== |
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==References== |
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