N-Acetyl calicheamicin
new
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 408158

CAS#: 108212-76-6

Description: N-Acetyl calicheamicin is a derivative of calicheamicin, and is a potent enediyne antitumor antibiotic. Calicheamicins target DNA and cause strand scission. Calicheamicins bind with DNA in the minor groove, wherein they then undergo a reaction analogous to the Bergman cyclization to generate a diradical species. This diradical, 1,4-didehydrobenzene, then abstracts hydrogen atoms from the deoxyribose (sugar) backbone of DNA, which ultimately leads to strand scission. The specificity of binding of calicheamicin to the minor groove of DNA was demonstrated by Crothers et al. (1999) to be due to the aryltetrasaccharide group of the molecule.

Chemical Structure

img
N-Acetyl calicheamicin
CAS# 108212-76-6
Instruction

Theoretical Analysis

MedKoo Cat#: 408158
Name: N-Acetyl calicheamicin
CAS#: 108212-76-6
Chemical Formula: C57H76IN3O22S4
Exact Mass: 1,409.28
Molecular Weight: 1,410.379
Elemental Analysis: C, 48.54; H, 5.43; I, 9.00; N, 2.98; O, 24.96; S, 9.09

Price and Availability

Size Price Availability Quantity
1mg USD 650 2 Weeks
5mg USD 1050 2 Weeks
10mg USD 1650 2 Weeks
25mg USD 3250 2 Weeks
50mg USD 5150 2 Weeks
100mg USD 9250 2 Weeks
Bulk inquiry

Synonym: N-Acetyl calicheamicin; N-Acetyl-γ-calicheamicin; N-Acetylcalicheamicin γ;

IUPAC/Chemical Name: S-((2R,3S,4S,6S)-6-((((2R,3S,4S,5R,6R)-5-(((2S,4S,5S)-5-(N-ethylacetamido)-4-methoxytetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(((2S,5Z,9R,13Z)-9-hydroxy-12-((methoxycarbonyl)amino)-13-(2-(methyltrisulfanyl)ethylidene)-11-oxobicyclo[7.3.1]trideca-1(12),5-dien-3,7-diyn-2-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl)amino)oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl) 4-(((2S,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3-iodo-5,6-dimethoxy-2-methylbenzothioate

InChi Key: WPDOZYZAJKUVRZ-DPACUSKXSA-N

InChi Code: 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

SMILES Code: O=C1C[C@]2(O)/C(C([C@]([H])(C#C/C=C\C#C2)O[C@@H]3O[C@H](C)[C@@H](NO[C@@H]4O[C@H](C)[C@@H](SC(C5=C(C)C(I)=C(O[C@H]6[C@H](O)[C@H](OC)[C@@H](O)[C@H](C)O6)C(OC)=C5OC)=O)[C@@H](O)C4)[C@H](O)[C@H]3O[C@H]7C[C@H](OC)[C@@H](N(CC)C(C)=O)CO7)=C1NC(OC)=O)=C\CSSSC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: It was isolated originally in the mid-1980s from the chalky soil, or "caliche pits", located in Kerrville, Texas. The sample was collected by a scientist working for Lederle Labs. It is extremely toxic to all cells and, in 2000, a CD33 antigen-targeted immunoconjugate N-acetyl dimethyl hydrazide calicheamicin was developed and marketed as targeted therapy against the non-solid tumor cancer acute myeloid leukemia (AML). A second calicheamicin-linked monoclonal antibody, inotuzumab ozogamicin (marketed as Besponsa) an anti-CD22-directed antibody-drug conjugate, was approved by the U.S. Food and Drug Administration on August 17, 2017, for use in the treatment of adults with relapsed or refractory B-cell precursor acute lymphoblastic leukemia.Calicheamicin γ1 and the related enediyne esperamicin are the two of the most potent antitumor agents known.

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,410.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x