Name: N-Acetyl-Calicheamicin
Brand: BOC Sciences
Price: 1999 USD
Availability: MadeToOrder

Synonyms

N-Acetyl-Calicheamicin γ1; N-Acetyl-Calicheamicin γ; N-Acetyl-Calicheamicin; N-Acetyl-γ-calicheamicin

IUPAC Name

S-[(2R,3S,4S,6S)-6-[[(2R,3S,4S,5R,6R)-5-[(2S,4S,5S)-5-[acetyl(ethyl)amino]-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[(2S,5Z,9R,13E)-9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate

Canonical SMILES

CCN(C1COC(CC1OC)OC2C(C(C(OC2OC3C#CC=CC#CC4(CC(=O)C(=C3C4=CCSSSC)NC(=O)OC)O)C)NOC5CC(C(C(O5)C)SC(=O)C6=C(C(=C(C(=C6OC)OC)OC7C(C(C(C(O7)C)O)OC)O)I)C)O)O)C(=O)C

InChI

InChI=1S/C57H76IN3O22S4/c1-13-61(30(6)62)32-25-76-37(23-36(32)71-7)81-50-45(66)42(27(3)78-55(50)80-35-18-16-14-15-17-20-57(70)24-34(64)43(59-56(69)75-11)40(35)31(57)19-21-85-87-84-12)60-83-38-22-33(63)52(29(5)77-38)86-53(68)39-26(2)41(58)48(51(74-10)47(39)72-8)82-54-46(67)49(73-9)44(65)28(4)79-54/h14-15,19,27-29,32-33,35-38,42,44-46,49-50,52,54-55,60,63,65-67,70H,13,21-25H2,1-12H3,(H,59,69)/b15-14-,31-19+/t27-,28+,29-,32+,33+,35+,36+,37+,38+,42-,44+,45+,46-,49-,50-,52-,54+,55+,57+/m1/s1

InChIKey

WPDOZYZAJKUVRZ-IOCYQWGVSA-N

Density

1.6±0.1 g/cm3

Solubility

Soluble in DMSO (10 mm)

Appearance

Solid Powder

Quantity

Milligrams-Grams

Shelf Life

As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly

Shipping

Room temperature

Storage

Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)

Pictograms

Irritant; Acute Toxic; Health Hazard

Signal Word

Danger

N-Acetyl-Calicheamicin is a highly potent enediyne antibiotic and a notable ADC cytotoxin widely utilized as an ADC payload in antibody-drug conjugates. It induces DNA double-strand breaks by binding to the minor groove of DNA and generating free radical-mediated cleavage, leading to rapid apoptosis in dividing tumor cells. Its extraordinary cytotoxicity makes it ideal for precision-targeted oncology therapeutics.

Within antibody-drug conjugates, N-Acetyl-Calicheamicin is typically conjugated to monoclonal antibodies via stable or cleavable linker systems. This design ensures the payload remains inactive during systemic circulation and is released only after ADC internalization and intracellular processing within tumor cells. The tumor-specific release mechanism allows for potent cytotoxic effects at low drug-to-antibody ratios (DARs) while minimizing off-target toxicity, enhancing the therapeutic index of ADCs.

Applications of N-Acetyl-Calicheamicin include its use in clinical and preclinical ADC candidates targeting hematologic malignancies and solid tumors, such as acute myeloid leukemia (AML), non-Hodgkin lymphoma, and other MMP-2 or antigen-overexpressing cancers. Its chemical structure supports conjugation with a variety of linker chemistries, optimizing payload stability, tumor-selective release, and overall ADC performance. Researchers leverage N-Acetyl-Calicheamicin to design next-generation ADCs with high potency, improved selectivity, and enhanced antitumor efficacy.

1.Gemtuzumab ozogamicin in the treatment of acute myeloid leukemia.

Stasi R;Evangelista ML;Buccisano F;Venditti A;Amadori S Cancer Treat Rev. 2008 Feb;34(1):49-60. Epub 2007 Oct 17.

Gemtuzumab ozogamicin (GO) is a chemotherapeutic agent that consists of a humanized anti-CD33 antibody (hP67.6) linked to N-acetyl-calicheamicin 1,2-dimethyl hydrazine dichloride, a potent enediyne antitumor antibiotic. GO was approved conditionally by the Federal Drug Administration in May 2000 as single-agent therapy for first recurrence of acute myeloid leukemia (AML) in patients over the age of 60 years who are unfit for conventional cytotoxic therapy. In this setting, it produces a complete response (CR) rate of 13%, with another 13% achieving CR with inadequate platelet recovery (CRp). The most common adverse effects associated with GO are infusion-related reactions and myelosuppression. GO monotherapy at the dose of 9 mg/m(2) is complicated with hepatic veno-occlusive disease in approximately 5% of cases, particularly prior to or following stem cell transplantation. Attenuated doses of GO or fractionated doses appear to be equally effective and better tolerated. GO has shown remarkable activity in acute promyelocytic leukemia, particularly for the elimination of minimal residual disease. Combinations of GO with chemotherapy as induction or post-remission therapy are promising, and phase III trials are ongoing.

Catalog	Product Name	CAS	Inquiry
BADC-00089	Calicheamicin	108212-75-5

What is N-Acetyl-Calicheamicin?

N-Acetyl-Calicheamicin is a potent enediyne cytotoxin that induces DNA double-strand breaks, causing apoptosis. It is commonly used as a payload in ADCs due to its high potency and the ability to be selectively delivered via antibody conjugation.

5/1/2017

Could you explain how N-Acetyl-Calicheamicin is applied in ADCs?

In ADCs, N-Acetyl-Calicheamicin is linked to targeting antibodies, allowing selective cytotoxicity to antigen-expressing cells. This minimizes off-target effects and enhances the therapeutic precision of ADC constructs.

9/8/2021

Could you advise which linker types are compatible with N-Acetyl-Calicheamicin?

Both cleavable linkers, which release the payload in intracellular environments, and non-cleavable linkers, which enhance circulation stability, are suitable. Linker choice is critical for controlling release kinetics and therapeutic efficiency.

24/10/2017

Could you kindly advise what handling safety measures are recommended for N-Acetyl-Calicheamicin?

Due to extreme cytotoxicity, N-Acetyl-Calicheamicin requires handling in containment facilities with PPE, biosafety hoods, and strict adherence to regulatory protocols to prevent exposure during synthesis and conjugation.

28/4/2020

Dear team, what research benefits are provided by N-Acetyl-Calicheamicin ADCs?

These ADCs provide highly potent targeted cytotoxicity, enabling precise preclinical evaluation of antibody specificity, payload efficacy, and pharmacokinetics, supporting the development of safer and more effective cancer therapies.

1/9/2018

— Dr. David Miller, Senior Scientist (USA)

N-Acetyl-Calicheamicin was delivered with outstanding purity, supporting our ADC development seamlessly.

24/10/2017

— Ms. Laura Fischer, Biopharmaceutical Scientist (Germany)

Our experience with N-Acetyl-Calicheamicin has been outstanding. The compound’s potency and well-maintained stability gave us confidence in our ADC feasibility studies.

1/9/2018

— Dr. Felix Schneider, Biochemist (Germany)

Technical support was highly responsive for N-Acetyl-Calicheamicin. Documentation was complete.

28/4/2020

— Prof. Luca Bianchi, Pharmaceutical Sciences Professor (Italy)

N-Acetyl-Calicheamicin from BOC Sciences has been integral to our ADC proof-of-concept. The compound retained potency through extended storage and was delivered with precise documentation.

5/1/2017

— Dr. Robert Hughes, Research Fellow (USA)

N-Acetyl-Calicheamicin batches were consistent and met all analytical requirements.

— Dr. Sofia Romero, Oncology Project Lead (Spain)

N-Acetyl-Calicheamicin is a delicate payload, yet BOC Sciences provided material that remained active and well-characterized. Their technical support ensured smooth integration into our workflows.

9/8/2021