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Calcimycin (A-23187) is an antibiotic isolated from Streptomyces chartreusensis. It inhibits the growth of Gram-positive bacteria and some fungi. Calcimycin is a unique divalent cation ionophore (like calcium and magnesium) and can induce Ca2+-dependent cell death by increasing intracellular calcium concentration. The pyrrole polyether antibiotic calcimycin (A23187) is a rare ionophore that is specific for divalent cations. It is widely used as a biochemical and pharmacological tool because of its multiple, unique biological effects.
| ln Vitro |
The killing of branching E is mediated by calcimycin (A-23187). coli by using P2RX7 activation to trigger intracellular calcium-regulated autophagy [4].
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| ln Vivo |
Protein leakage is induced by intrapleural injection of calcimycin (A-23187) at 2.5 or 7.5 nM [5].
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| Animal Protocol |
Animal/Disease Models: Mouse (ICR, 25-30 g) [5]
Doses: 2.5 or 7.5 nM Route of Administration: Intrapleural injection Experimental Results: 2.5 nM two hrs (hrs (hours)) after challenge or 7.5 nM three hrs (hrs (hours)) after challenge, protein in the pleural cavity Levels correspond to approximately half of their corresponding peak values. |
| References |
[1]. Wu Q, et al. Characterization of the biosynthesis gene cluster for the pyrrole polyether antibiotic calcimycin(A23187) in Streptomyces chartreusis NRRL 3882. Antimicrob Agents Chemother. 2011 Mar;55(3):974-82.
[2]. Elliott JI, et al. IKCa1 activity is required for cell shrinkage, phosphatidylserine translocation and death in Tlymphocyte apoptosis. EMBO Rep. 2003 Feb;4(2):189-94. [3]. Engedal N, et al. Modulation of intracellular calcium homeostasis blocks autophagosome formation. Autophagy. 2013 Oct;9(10):1475-90. [4]. Mawatwal S, et al. Calcimycin mediates mycobacterial killing by inducing intracellular calcium-regulated autophagy in a P2RX7 dependent manner. Biochim Biophys Acta Gen Subj. 2017 Dec;1861(12):3190-3200. [5]. Wang JP, et al. Effect of norathyriol, isolated from Tripterospermum lanceolatum, on A23187-induced pleurisy and analgesia in mice. Naunyn Schmiedebergs Arch Pharmacol. 1994 Jul;350(1):90-5. |
| Molecular Formula |
C29H37N3O6
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|---|---|
| Molecular Weight |
523.63
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| Exact Mass |
523.2682
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| Elemental Analysis |
C, 66.52; H, 7.12; N, 8.02; O, 18.33
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| CAS # |
52665-69-7
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| Related CAS # |
Calcimycin hemicalcium salt;59450-89-4;Calcimycin hemimagnesium;72124-77-7
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| Appearance |
Solid powder
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| SMILES |
O=C(C1=C2N=C(C[C@H]3O[C@]4(O[C@@H]([C@@H](C)C(C5=CC=CN5)=O)[C@@H](C)C[C@@H]4C)CC[C@H]3C)OC2=CC=C1NC)O
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| InChi Key |
HIYAVKIYRIFSCZ-BNJSRTAHSA-N
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| InChi Code |
InChI=1S/C29H37N3O6/c1-15-10-11-29(17(3)13-16(2)27(38-29)18(4)26(33)20-7-6-12-31-20)37-22(15)14-23-32-25-21(36-23)9-8-19(30-5)24(25)28(34)35/h6-9,12,15-18,22,27,30-31H,10-11,13-14H2,1-5H3,(H,34,35)/t15-,16+,17+,18+,22-,27-,29+/m1/s1
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| Chemical Name |
4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-((3,9,11-trimethyl-8-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undec-2-yl)methyl)-, (6S-(6alpha(2S*,3S*),8beta(R*),9beta,11alpha))-
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| Synonyms |
Calcimycin; A23187; A 23187; A-23187; Ionophore A23187; Antibiotic 23187
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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 : ~33.33 mg/mL (~63.65 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.77 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.77 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (4.77 mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9097 mL | 9.5487 mL | 19.0975 mL | |
| 5 mM | 0.3819 mL | 1.9097 mL | 3.8195 mL | |
| 10 mM | 0.1910 mL | 0.9549 mL | 1.9097 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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