Calcimycin

Names

[ Name ]:
Calcimycin

[Synonym ]:
Ethacrynic acid-d5
4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-[[(2S,3S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-
MFCD00151202
CALCIUM PHOSPHINATE
Lime hypophosphite
CALCIUMHYPOPHOSPHITE,PURIFIED
CALCIUM HYPOPHOSPHITE TECHNICAL
CALCIUM HYPOPHOSPHITE EXTRA PURE,DAC
5-(Methylamino)-2-({(2S,3S,8S,9R,11R)-3,9,11-trimethyl-8-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)-2-propanyl]-1,7-dioxaspiro[5.5]undec-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid
ANTIBIOTIC A 23187
Phosphinicacid,calciumsalt
Calcium bisphosphinate
5-(Methylamino)-2-({(2S,3S,8S,9R,11R)-3,9,11-trimethyl-8-[(2R)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undec-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid
Calcium hydrophosphite
EINECS 258-084-1
6S-[6a(2S*,3S*),8b(R*),9b,11a]-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]-4-benzoxazolecarboxylic Acid
Calcimycin
A23187,free acid

Biological Activity

[Description]:

Calcimycin (A23187) is an antibiotic and a unique divalent cation ionophore (like calcium and magnesium). It induces Ca2+-dependent cell death by increasing intracellular calcium concentration. Calcimycin inhibits the growth of Gram-positive bacteria and some fungi. Calcimycin also inhibits the activity of ATPase and uncouples oxidative phosphorylation of mammalian cells. It induces apoptosis[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Autophagy >> Autophagy

[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.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
710.3±55.0 °C at 760 mmHg

[ Melting Point ]:
187-190 °C

[ Molecular Formula ]:
C₂₉H₃₇N₃O₆

[ Molecular Weight ]:
523.621

[ Flash Point ]:
383.4±31.5 °C

[ Exact Mass ]:
523.268250

[ PSA ]:
126.68000

[ LogP ]:
5.66

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.611

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38-20/21/22

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DM4676000

[ HS Code ]:
29349990

Precursor & DownStream

Precursor

DownStream

Articles

[Characterisation of enucleated cells apoptosis: human platelets and erythrocytes].

Ross. Fiziol. Zh. Im. I. M. Sechenova 99(1) , 92-110, (2013)

Apoptosis is a common mechanism of programmed cell death in virtually all nucleated cells. In spite of the fact that platelets and erythrocytes are the only enucleated cells in mammals they contain mo...

Chemical genetics reveals a complex functional ground state of neural stem cells.

Nat. Chem. Biol. 3(5) , 268-273, (2007)

The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain canc...

Potent trypanocidal curcumin analogs bearing a monoenone linker motif act on trypanosoma brucei by forming an adduct with trypanothione.

Mol. Pharmacol. 87(3) , 451-64, (2015)

We have previously reported that curcumin analogs with a C7 linker bearing a C4-C5 olefinic linker with a single keto group at C3 (enone linker) display midnanomolar activity against the bloodstream f...