Calicheamicin

Calicheamicin, an antitumor antibiotic, is a cytotoxic agent that causes double-strand DNA breaks. Calicheamicin is a DNA synthesis inhibitor[1]. Calicheamicin is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

Product Specifications

CAS Number

[108212-75-5]

Product Name Alternative

Calicheamicin γ1

UNSPSC

12352203

Hazard Statement

H300+H330, H340, H360, H370, H372, H412

Target

ADC Payload; Antibiotic; Apoptosis; Bacterial; DNA Alkylator/Crosslinker

Type

ADC Related

Related Pathways

Antibody-drug Conjugate/ADC Related; Anti-infection; Apoptosis; Cell Cycle/DNA Damage

Applications

Cancer-programmed cell death

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/Calicheamicin.html

Purity

98.92

Solubility

DMSO : 25 mg/mL (ultrasonic)

Smiles

O[C@](CC1=O)(C#C/C=C\C#C2)/C(C([C@H]2O[C@@](O[C@H](C)[C@@H](NO[C@H](O[C@H](C)[C@H]3SC(C(C(C)=C(I)C(O[C@H](O[C@@H](C)[C@H](O)[C@H]4OC)[C@@H]4O)=C5OC)=C5OC)=O)C[C@@H]3O)[C@@H]6O)([H])[C@@H]6O[C@@](OC[C@@H]7NCC)([H])C[C@@H]7OC)=C1NC(OC)=O)=C/CSSSC

Molecular Formula

C55H74IN3O21S4

Molecular Weight

1368.35

Precautions

H300+H330, H340, H360, H370, H372, H412

References & Citations

[1]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|[2]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|[3]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.