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| 2mg |
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Purity: ≥98%
Calicheamicin, formerly known as Calicheamicin gamma(1,I) or Calichemicin gamma1, is an potent enediyne antitumor antibiotics derived from the bacterium Micromonospora echinospora. Calicheamicin targets DNA and cause strand scission. Calicheamicin binds with DNA in the minor groove, wherein it then undergos a reaction analogueous 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 is due to the aryltetrasaccharide group of the molecule.
| Targets |
Calicheamicins
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|---|---|
| ln Vitro |
With an average drug-to-antibody ratio (DAR) of 4.6, PF-06647263 (anti-EFNA4-ADC) is produced by conjugating hE22 lysine residues to the AcButDMH-N-Ac-calicheamicin-γ1 linker-payload. Antigen- and concentration-dependent cytotoxicity is elicited by PF-06647263, as exposure to the compound for 96 hours causes cell death (EC50 = approximately 1 ng/mL)[1]. In vitro treatment of pediatric primary B-cell precursor acute lymphoblastic leukemia (BCP-ALL) cells is facilitated by CMC-544, which consists of a humanized CD22 Ab conjugated to calicheamicin. With IC50 values ranging from 0.15 to 4.9 ng/mL, CMC-544 causes dose- and time-dependent cell death in a variety of ALL cell lines. In primary BCP-ALL cells, CMC-544 (10 ng/mL) exhibits efficacy and specificity [2]. Compared to G5/44-treated cells, the level of CD22 in CMC-544-treated cells has dropped and has remained low[3].
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| ln Vivo |
In both TNBC and ovarian cancer PDX, an ADC containing a humanized anti-EFNA4 monoclonal antibody coupled to the DNA-damaging agent calicheamicin results in long-lasting tumor regressions in vivo. In TNBC xenografts, PF-06647263 (0.27, 0.36 mg/kg) causes notable tumor regressions[1].
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| References |
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| Molecular Formula |
C55H74IN3O21S4
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|---|---|
| Molecular Weight |
1368.3415
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| Exact Mass |
1367.2742
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| Elemental Analysis |
C, 48.28; H, 5.45; I, 9.27; N, 3.07; O, 24.55; S, 9.37
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| CAS # |
108212-75-5
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| Related CAS # |
N-Acetyl-Calicheamicin;108212-76-6
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| Appearance |
Solid powder
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| SMILES |
O=C(S[C@@H]1[C@@H](C)O[C@@H](ON[C@@H]2[C@@H](C)OC(O[C@@H](C#C/C=C\C#C[C@@]3(O)C4)C(/C3=C\CSSSC)=C(NC(OC)=O)C4=O)[C@H](O[C@H]5C[C@H](OC)[C@@H](NCC)CO5)[C@H]2O)C[C@@H]1O)C6=C(OC)C(OC)=C(O[C@H]7[C@H](O)[C@H](OC)[C@@H](O)[C@H](C)O7)C(I)=C6C
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| InChi Key |
HXCHCVDVKSCDHU-IXTZGUNISA-N
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| InChi Code |
InChI=1S/C55H74IN3O21S4/c1-12-57-30-24-73-35(22-34(30)68-6)78-48-43(63)40(26(3)75-53(48)77-33-17-15-13-14-16-19-55(67)23-32(61)41(58-54(66)72-10)38(33)29(55)18-20-82-84-81-11)59-80-36-21-31(60)50(28(5)74-36)83-51(65)37-25(2)39(56)46(49(71-9)45(37)69-7)79-52-44(64)47(70-8)42(62)27(4)76-52/h13-14,18,26-28,30-31,33-36,40,42-44,47-48,50,52-53,57,59-60,62-64,67H,12,20-24H2,1-11H3,(H,58,66)/b14-13-,29-18+/t26-,27+,28-,30+,31+,33+,34+,35+,36+,40-,42+,43+,44-,47-,48-,50-,52+,53?,55-/m1/s1
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| Chemical Name |
S-((2R,3S,4S,6S)-6-((((2R,3S,4S,5R)-5-(((2S,4S,5S)-5-(ethylamino)-4-methoxytetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(((2S,5Z,9S,13E)-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
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| Synonyms |
Calicheamicin; Calicheamicin gamma(1,I); Calichemicin gamma1; Calicheamicin gamma(1)I.
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~25 mg/mL (~18.27 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (2.19 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: ≥ 2.5 mg/mL (1.83 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. View More
Solubility in Formulation 3: 2.5 mg/mL (1.83 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Solubility in Formulation 4: 10% DMSO+90% Corn Oil: ≥ 3 mg/mL (2.19 mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.7308 mL | 3.6541 mL | 7.3081 mL | |
| 5 mM | 0.1462 mL | 0.7308 mL | 1.4616 mL | |
| 10 mM | 0.0731 mL | 0.3654 mL | 0.7308 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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