Shishijimicin A information

Shishijimicin A
Names
	IUPAC name Methyl {(1R,4Z,8S,13Z)-8-({6-deoxy-2-O-[2,4-dideoxy-4-(isopropylamino)-3-O-methyl-α-L-threo-pentopyranosyl]-4-C-[(6-hydroxy-9H-β-carbolin-1-yl)carbonyl]-4-S-methyl-4-thio-β-D-galactopyranosyl}oxy)-1-hydroxy-13-[2-(methyltrisulfanyl)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl}carbamate
Identifiers
CAS Number	503860-50-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	8388877;
PubChem CID	10213385;
	InChI InChI=1S/C46H52N4O12S4/c1-24(2)48-31-23-59-35(21-34(31)57-4)62-40-42(54)46(63-6,41(53)39-37-27(15-18-47-39)28-20-26(51)13-14-30(28)49-37)25(3)60-43(40)61-33-12-10-8-9-11-17-45(56)22-32(52)38(50-44(55)58-5)36(33)29(45)16-19-65-66-64-7/h8-9,13-16,18,20,24-25,31,33-35,40,42-43,48-49,51,54,56H,19,21-23H2,1-7H3,(H,50,55)/b9-8-,29-16-/t25-,31+,33+,34+,35+,40-,42-,43+,45+,46-/m1/s1 Key: FVNYJZKDBPDHIP-UXLTXATLSA-N;
	SMILES CC1C(C(C(C(O1)OC2C#CC=CC#CC3(CC(=O)C(=C2C3=CCSSSC)NC(=O)OC)O)OC4CC(C(CO4)NC(C)C)OC)O)(C(=O)C5=NC=CC6=C5NC7=C6C=C(C=C7)O)SC;
Properties
Chemical formula	C46H52N4O12S4
Molar mass	981.18 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Shishijimicin A is an enediyne antitumor antibiotic isolated from Didemnum proliferum.^[1] Isolated in 2003^[2] it is part of the family of 10 member ringed enediyne antitumor antibiotic agents, which includes: namenamicin, esperamicin and, calicheamicin. Due to its high potency from cytotoxicity, Shishjimicin A is currently undergoing testing as a possible Antibody-antibiotic Conjugate (ADCs) cancer treatment. Laboratory tests indicate it to be “more than 1,000 times as toxic to cancer cells as the anticancer drug taxol”,^[3] also known as Paclitaxel, a prevalent chemotherapy medication. As such, theoretically, only an administration of a minuscule dose of the molecule would be necessary per each treatment. As shishjimicin A supply is scarce and the full extent of its side effects is not yet established, there is still a need for further biological and clinical studies.

^ Nicolaou KC, Kiappes JL, Tian W, Gondi VB, Becker J (August 2011). "Synthesis of the carboline disaccharide domain of shishijimicin A". Organic Letters. 13 (15): 3924–3927. doi:10.1021/ol201444t. PMC 3146563. PMID 21711032.
^ Cite error: The named reference :0 was invoked but never defined (see the help page).
^ "Rice lab synthesizes cancer-killing compound". TMC News. 2015-07-13. Retrieved 2021-11-29.

[1] Nicolaou KC, Kiappes JL, Tian W, Gondi VB, Becker J (August 2011). "Synthesis of the carboline disaccharide domain of shishijimicin A". Organic Letters. 13 (15): 3924–3927. doi:10.1021/ol201444t. PMC 3146563. PMID 21711032.

[:0-2] Cite error: The named reference :0 was invoked but never defined (see the help page).

[3] "Rice lab synthesizes cancer-killing compound". TMC News. 2015-07-13. Retrieved 2021-11-29.

Shishijimicin A information

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Shishijimicin A

Didemnum fragile