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Revision as of 12:56, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472856489 of page Halichondrin_B for the Chem/Drugbox validation project (updated: '').  Latest revision as of 17:42, 27 October 2024 edit Photocyte (talk | contribs)Extended confirmed users1,788 editsm See also linkout to analogous Altohyrtin A 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 461766224
| Watchedfields = changed
⚫ | verifiedrevid = 476997373
| ImageFile = Halichondrin B.svg | ImageFile = Halichondrin B.svg
| ImageSize = 250px | ImageSize = 280
| ImageAlt = Skeletal formula of halichondrin B
⚫ | IUPACName = (1''S'',2''S'',2′''S'',3''S'',3a''S'',3a′''S'',5''R'',6''S'',7''S'',7′''S'',7a''S'',7a′''S'',9''S'',12''S'',14''R'',16''R'',18''S'',20''S'',22''R'',26''R'',28''S'',29''S'',30''R'',34''R'',37''S'',39''R'',40''S'',41''R'',43''R'',44''S'')-7,7′,14′′,29′′-tetramethyl-8′′,15′′-dimethylidene-2-(1,3,4-trihydroxybutyl)decahydro-3′''H'',32′′''H''-dispiropyran-5,5′-furopyran-2′,24′′-undecaoxaundecacyclo[32.9.2.1~3,40~.1~3,41~.1~6,9~.1~12,16
| ImageFile1 = Halichondrin B 3D ball A.png
⚫ ~.0~18,30~.0~20,28~.0~22,26~.0~37,44~.0~39,43~]nonatetracontan]-32′′-one
| ImageSize1 = 280
| IUPACName_hidden=yes
| ImageAlt1 = Space-filling model of the halichondrin B molecule
⚫ | IUPACName = (1''S'',2''S'',2{{prime}}''S'',3''S'',3a''S'',3a{{prime}}''S'',5''R'',6''S'',7''S'',7{{prime}}''S'',7a''S'',7a{{prime}}''S'',9''S'',12''S'',14''R'',16''R'',18''S'',20''S'',22''R'',26''R'',28''S'',29''S'',30''R'',34''R'',37''S'',39''R'',40''S'',41''R'',43''R'',44''S'')-7,7{{prime}},14{{prime}}{{prime}},29{{prime}}{{prime}}-tetramethyl-8{{prime}}{{prime}},15{{prime}}{{prime}}-dimethylidene-2-(1,3,4-trihydroxybutyl)decahydro-3{{prime}}''H'',32{{prime}}{{prime}}''H''-dispiropyran-5,5{{prime}}-furopyran-2{{prime}},24{{prime}}{{prime}}-undecaoxaundecacyclo[32.9.2.1~3,40~.1~3,41~.1~6,9~.1~12,16
⚫ ~.0~18,30~.0~20,28~.0~22,26~.0~37,44~.0~39,43~]nonatetracontan]-32{{prime}}{{prime}}-one
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| InChI = 1S/C60H86O19/c1-26-13-33-7-9-37-27(2)14-35(65-37)11-12-58-23-46-54(78-58)55-56(72-46)57(79-58)53-38(69-55)10-8-34(67-53)16-48(64)73-52-31(6)51-43(68-42(52)17-39(66-33)30(26)5)19-41-45(71-51)22-60(74-41)24-47-50(77-60)29(4)21-59(76-47)20-28(3)49-44(75-59)18-40(70-49)36(63)15-32(62)25-61/h26,28-29,31-47,49-57,61-63H,2,5,7-25H2,1,3-4,6H3/t26-,28+,29+,31+,32?,33+,34-,35+,36?,37+,38+,39-,40+,41-,42+,43+,44+,45-,46-,47+,49+,50+,51+,52-,53+,54+,55+,56-,57+,58+,59-,60+/m1/s1 | InChI = 1S/C60H86O19/c1-26-13-33-7-9-37-27(2)14-35(65-37)11-12-58-23-46-54(78-58)55-56(72-46)57(79-58)53-38(69-55)10-8-34(67-53)16-48(64)73-52-31(6)51-43(68-42(52)17-39(66-33)30(26)5)19-41-45(71-51)22-60(74-41)24-47-50(77-60)29(4)21-59(76-47)20-28(3)49-44(75-59)18-40(70-49)36(63)15-32(62)25-61/h26,28-29,31-47,49-57,61-63H,2,5,7-25H2,1,3-4,6H3/t26-,28+,29+,31+,32?,33+,34-,35+,36?,37+,38+,39-,40+,41-,42+,43+,44+,45-,46-,47+,49+,50+,51+,52-,53+,54+,55+,56-,57+,58+,59-,60+/m1/s1
| InChIKey1 = FXNFULJVOQMBCW-CGIYHSFGSA-N | InChIKey1 = FXNFULJVOQMBCW-CGIYHSFGSA-N
| InChI1 = 1S/C60H86O19/c1-26-13-33-7-9-37-27(2)14-35(65-37)11-12-58-23-46-54(78-58)55-56(72-46)57(79-58)53-38(69-55)10-8-34(67-53)16-48(64)73-52-31(6)51-43(68-42(52)17-39(66-33)30(26)5)19-41-45(71-51)22-60(74-41)24-47-50(77-60)29(4)21-59(76-47)20-28(3)49-44(75-59)18-40(70-49)36(63)15-32(62)25-61/h26,28-29,31-47,49-57,61-63H,2,5,7-25H2,1,3-4,6H3/t26-,28+,29+,31+,32?,33+,34-,35+,36?,37+,38+,39-,40+,41-,42+,43+,44+,45-,46-,47+,49+,50+,51+,52-,53+,54+,55+,56-,57+,58+,59-,60+/m1/s1 | InChI1 = 1S/C60H86O19/c1-26-13-33-7-9-37-27(2)14-35(65-37)11-12-58-23-46-54(78-58)55-56(72-46)57(79-58)53-38(69-55)10-8-34(67-53)16-48(64)73-52-31(6)51-43(68-42(52)17-39(66-33)30(26)5)19-41-45(71-51)22-60(74-41)24-47-50(77-60)29(4)21-59(76-47)20-28(3)49-44(75-59)18-40(70-49)36(63)15-32(62)25-61/h26,28-29,31-47,49-57,61-63H,2,5,7-25H2,1,3-4,6H3/t26-,28+,29+,31+,32?,33+,34-,35+,36?,37+,38+,39-,40+,41-,42+,43+,44+,45-,46-,47+,49+,50+,51+,52-,53+,54+,55+,56-,57+,58+,59-,60+/m1/s1
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|changed|??}}
| CASNo = | CASNo = 103614-76-2
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem =
| UNII = 269R6PFM59
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | PubChem = 5488895
| ChEMBL = 387466
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10256208 | ChemSpiderID = 10256208
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FXNFULJVOQMBCW-CGIYHSFGSA-N | StdInChIKey = FXNFULJVOQMBCW-CGIYHSFGSA-N
| SMILES = OCC(O)CC(O)1C2O3(C(C)2O1)C(C)4O%10(C4O3)C%11O%12(C)%13OC(=O)C8CC9O76O5(O(7O6C5)9O8)CC%15C/C(=C)(CC%14C(C)\C(=C)(C%13O%12C%11O%10)O%14)O%15 | SMILES = OCC(O)CC(O)1C2O3(C(C)2O1)C(C)4O%10(C4O3)C%11O%12(C)%13OC(=O)C8CC9O76O5(O(7O6C5)9O8)CC%15C/C(=C)(CC%14C(C)\C(=C)(C%13O%12C%11O%10)O%14)O%15
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChI = 1S/C60H86O19/c1-26-13-33-7-9-37-27(2)14-35(65-37)11-12-58-23-46-54(78-58)55-56(72-46)57(79-58)53-38(69-55)10-8-34(67-53)16-48(64)73-52-31(6)51-43(68-42(52)17-39(66-33)30(26)5)19-41-45(71-51)22-60(74-41)24-47-50(77-60)29(4)21-59(76-47)20-28(3)49-44(75-59)18-40(70-49)36(63)15-32(62)25-61/h26,28-29,31-47,49-57,61-63H,2,5,7-25H2,1,3-4,6H3/t26-,28+,29+,31+,32?,33+,34-,35+,36?,37+,38+,39-,40+,41-,42+,43+,44+,45-,46-,47+,49+,50+,51+,52-,53+,54+,55+,56-,57+,58+,59-,60+/m1/s1
| StdInChI = StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ }}
⚫ | StdInChI=1S/C60H86O19/c1-26-13-33-7-9-37-27(2)14-35(65-37)11-12-58-23-46-54(78-58)55-56(72-46)57(79-58)53-38(69-55)10-8-34(67-53)16-48(64)73-52-31(6)51-43(68-42(52)17-39(66-33)30(26)5)19-41-45(71-51)22-60(74-41)24-47-50(77-60)29(4)21-59(76-47)20-28(3)49-44(75-59)18-40(70-49)36(63)15-32(62)25-61/h26,28-29,31-47,49-57,61-63H,2,5,7-25H2,1,3-4,6H3/t26-,28+,29+,31+,32?,33+,34-,35+,36?,37+,38+,39-,40+,41-,42+,43+,44+,45-,46-,47+,49+,50+,51+,52-,53+,54+,55+,56-,57+,58+,59-,60+/m1/s1
⚫ |Section2={{Chembox Properties
⚫ }}
⚫ | C=60 | H=86 | O=19
⚫ | Section2 = {{Chembox Properties
| MolarMass =
⚫ | C=60|H=86|O=19
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}

'''Halichondrin B''' is a ] ] originally isolated from the marine sponge ''] okadai'' by Hirata and Uemura in 1986.<ref name="Hirata_1986">{{ cite journal |vauthors=Hirata Y, Uemura D | title=Halichondrins - antitumor polyether macrolides from a marine sponge | journal=Pure Appl. Chem. | year = 1986 | volume = 58 | issue = 5 | pages = 701–710 | doi = 10.1351/pac198658050701| s2cid=38138047 | doi-access = free }}</ref> In the same report, these authors also reported the exquisite ] activity of halichondrin B against murine cancer cells both in culture and in ''in vivo'' studies. Halichondrin B was highly prioritized for development as a novel ] therapeutic by the United States ]<ref>{{cite web | url = http://www.dtp.nci.nih.gov/timeline/noflash/success_stories/S4_halichondrinB.htm | title = Success Story: Halichondrin B (NSC 609395) E7389 (NSC 707389) | publisher = Developmental Therapeutics Program, ] | url-status = dead | archive-url = https://web.archive.org/web/20090710205200/http://dtp.nci.nih.gov/timeline/noflash/success_stories/S4_halichondrinB.htm | archive-date = 2009-07-10 }}</ref> and, in 1991, was the original test case for identification of mechanism of action (in this case, ]-targeted ]) by NCI's then-brand-new "]"<ref>{{cite web | url = http://www.dtp.nci.nih.gov/branches/btb/ivclsp.html | title = NCI-60 DTP Human Tumor Cell Line Screen | publisher = Developmental Therapeutics Program, National Cancer Institute | url-status = dead | archive-url = https://web.archive.org/web/20090710183850/http://dtp.nci.nih.gov/branches/btb/ivclsp.html | archive-date = 2009-07-10 }}</ref><ref name="pmid1874739">{{cite journal |vauthors=Bai RL, Paull KD, Herald CL, Malspeis L, Pettit GR, Hamel E | title = Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. Discovery of tubulin-based mechanism of action by analysis of differential cytotoxicity data | journal = J. Biol. Chem. | volume = 266 | issue = 24 | pages = 15882–9 |date=August 1991 | doi = 10.1016/S0021-9258(18)98491-7 | pmid = 1874739 | doi-access = free }}</ref>

The complete chemical synthesis of halichondrin B was achieved by ] and colleagues at ] in 1992,<ref name="Aicher_1992">{{cite journal | vauthors = Aicher TD, Buszek KR, Fang FG, Forsyth CJ, Jung SH, Kishi Y, Matelich MC, Scola PM, Spero DM, Yoon SK | author6-link = Kishi Y | title = Total synthesis of halichondrin B and norhalichondrin B | journal = J. Am. Chem. Soc. | year = 1992 | volume = 114 | issue = 8 | pages = 3162–3164 | doi = 10.1021/ja00034a086}}</ref> an achievement that ultimately enabled the discovery and development of the structurally simplified and pharmaceutically optimized analog ] (E7389, ER-086526, NSC-707389).<ref name="pmid11221827">{{cite journal | vauthors = Towle MJ, Salvato KA, Budrow J, Wels BF, Kuznetsov G, Aalfs KK, Welsh S, Zheng W, Seletsk BM, Palme MH, Habgood GJ, Singer LA, Dipietro LV, Wang Y, Chen JJ, Quincy DA, Davis A, Yoshimatsu K, Kishi Y, Yu MJ, Littlefield BA | author19-link = Kishi Y | title = In vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogues of halichondrin B | journal = Cancer Res. | volume = 61 | issue = 3 | pages = 1013–21 |date=February 2001 | pmid = 11221827 }}</ref><ref name="isbn0-8493-1863-7">{{cite book | veditors = Newman DJ, ((Kingston DGI)), Cragg GM | title = Anticancer agents from natural products | publisher = Taylor & Francis | location = Washington, DC | year = 2005 | chapter = Discovery of E7389, a fully synthetic macrocyclic ketone analogue of halichondrin B | vauthors = Yu MJ, Kishi Y, Littlefield BA | author2-link = Kishi Y | isbn = 978-0-8493-1863-4 }}</ref> ] was approved by the U.S. Food and Drug Administration on November 15, 2010, to treat patients with metastatic breast cancer who have received at least two prior chemotherapy regimens for late-stage disease, including both anthracycline- and taxane-based chemotherapies.<ref>{{cite press release | title = FDA approves new treatment option for late-stage breast cancer | publisher = USFDA | date = 2010-11-15 | url = https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm233863.htm | access-date = November 15, 2010}}</ref> ] is marketed by ] under the tradename Halaven.

==Biosynthesis==
While a producer organism for Halichondrin B has never been isolated in pure culture, the structural features of Halichondrin B, such as the 'odd-even' rule of methylation, and the abundance of oxygen heterocycles, suggest it is a product of dinoflagellate polyether metabolism.<ref name="Van_Wagoner2014">{{cite journal | last1=Van Wagoner | first1=Ryan M. | last2=Satake | first2=Masayuki | last3=Wright | first3=Jeffrey L. C. | title=Polyketide biosynthesis in dinoflagellates: what makes it different? | journal=Natural Product Reports | publisher=Royal Society of Chemistry (RSC) | volume=31 | issue=9 | date=2014-06-16 | pages=1101–37 | issn=0265-0568 | doi=10.1039/c4np00016a | pmid=24930430 }}</ref> In support of this conjecture, the known dinoflagellate toxin ] was isolated from the same species of sponge.<ref name="Tachibana_1981">{{cite journal | last1=Tachibana | first1=Kazuo | last2=Scheuer | first2=Paul J. | last3=Tsukitani | first3=Yasumasa | last4=Kikuchi | first4=Hiroyuki | last5=Van Engen | first5=Donna | last6=Clardy | first6=Jon | last7=Gopichand | first7=Yalamanchili | last8=Schmitz | first8=Francis J. | title=Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria | journal=Journal of the American Chemical Society | publisher=American Chemical Society (ACS) | volume=103 | issue=9 | year=1981 | issn=0002-7863 | doi=10.1021/ja00399a082 | pages=2469–2471}}</ref> But, Halichondrin B is not found in '']'' or '']'' which are found in similar tide pools in Japan as '']''.<ref name="o521">{{cite journal | last=Abe | first=Takahiro | last2=Sahin | first2=Fatma Pinar | last3=Akiyama | first3=Kiyotaka | last4=Naito | first4=Takayuki | last5=Kishigami | first5=Mizoe | last6=Miyamoto | first6=Kenji | last7=Sakakibara | first7=Yasufumi | last8=Uemura | first8=Daisuke | title=Construction of a Metagenomic Library for the Marine Sponge Halichondria okadai | journal=Bioscience, Biotechnology, and Biochemistry | volume=76 | issue=4 | date=2012-04-23 | issn=0916-8451 | doi=10.1271/bbb.110533 | pages=633–639}}</ref>

==See also==
* ]

==References==
{{reflist|2}}

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