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108212-75-5,MFCD30478834
Catalog No.:AA008TIQ

108212-75-5 | calicheamicin gamma(1)I

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Purity
Availability
Price(USD)
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1mg
98%
in stock  
$397.00   $278.00
- +
5mg
98%
in stock  
$1,057.00   $740.00
- +
10mg
98%
in stock  
$1,456.00   $1,019.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA008TIQ
Chemical Name:
calicheamicin gamma(1)I
CAS Number:
108212-75-5
Molecular Formula:
C55H74IN3O21S4
Molecular Weight:
1368.3480
MDL Number:
MFCD30478834
SMILES:
CSSSC/C=C\1/C2=C(NC(=O)OC)C(=O)C[C@@]1(O)C#C/C=C\C#C[C@@H]2O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O[C@@H]1OC[C@@H]([C@H](C1)OC)NCC)O)NO[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)SC(=O)c1c(C)c(I)c(c(c1OC)OC)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)OC)O
Properties
Computed Properties
 
Complexity:
2500  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
19  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
84  
Hydrogen Bond Acceptor Count:
27  
Hydrogen Bond Donor Count:
8  
Rotatable Bond Count:
24  
XLogP3:
2  

Downstream Synthesis Route
103321-49-9    108212-75-5   
C72H87IN4O24S4 

[1]CurrentPatentAssignee:SORRENTOTHERAPEUTICSINC-US2017/281758,2017,A1Locationinpatent:Paragraph0070;0071

Literature

Title: A total synthesis trilogy: calicheamicin γ1(I), Taxol®, and brevetoxin A.

Journal: Chemical record (New York, N.Y.) 20120801

Title: A DNA-dependent stress response involving DNA-PK occurs in hypoxic cells and contributes to cellular adaptation to hypoxia.

Journal: Journal of cell science 20110601

Title: Calicheamicin γ1(I) and phenyl tert-butyl nitrone (PBN): observation of a kinetic isotope effect by an ESR study.

Journal: Chemical communications (Cambridge, England) 20100207

Title: Inspirations, discoveries, and future perspectives in total synthesis.

Journal: The Journal of organic chemistry 20090206

Title: The reactivity of calicheamicin gamma(1)(I) in the minor groove of DNA: the decisive role of the environment.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

Title: Spin-trapping of the p-benzyne intermediates from ten-membered enediyne calicheamicin gamma1I.

Journal: Organic letters 20061123

Title: Involvement of poly(ADP-ribose) polymerase-1 and XRCC1/DNA ligase III in an alternative route for DNA double-strand breaks rejoining.

Journal: The Journal of biological chemistry 20041231

Title: Antibody-targeted chemotherapy with the calicheamicin conjugate hu3S193-N-acetyl gamma calicheamicin dimethyl hydrazide targets Lewisy and eliminates Lewisy-positive human carcinoma cells and xenografts.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040701

Title: Resistance to enediyne antitumor antibiotics by CalC self-sacrifice.

Journal: Science (New York, N.Y.) 20030912

Title: Activation of the DNA-dependent protein kinase by drug-induced and radiation-induced DNA strand breaks.

Journal: Radiation research 20030901

Title: Synthesis of a novel N[bond]O-interglycosidic disaccharide.

Journal: Carbohydrate research 20030812

Title: On the origin of deoxypentoses: evidence to support a glucose progenitor in the biosynthesis of calicheamicin.

Journal: Chembiochem : a European journal of chemical biology 20021104

Title: Thiols alter the partitioning of calicheamicin-induced deoxyribose 4'-oxidation reactions in the absence of DNA radical repair.

Journal: Chemical research in toxicology 20010501

Title: Damelin M, et al. Anti-EFNA4 Calicheamicin Conjugates Effectively Target Triple-Negative Breast and Ovarian Tumor-Initiating Cells to Result in Sustained Tumor Regressions. Clin Cancer Res. 2015 Sep 15;21(18):4165-73

Title: de Vries JF, et al. The novel calicheamicin-conjugated CD22 antibody inotuzumab ozogamicin (CMC-544) effectively kills primary pediatric acute lymphoblastic leukemia cells. Leukemia. 2012 Feb;26(2):255-64

Title: Takeshita A, et al. CMC-544 (inotuzumab ozogamicin), an anti-CD22 immuno-conjugate of calicheamicin, alters the levels of target molecules of malignant B-cells. Leukemia. 2009 Jul;23(7):1329-36.

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