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A4262

Sigma-Aldrich

Actinomycin D

from Streptomyces sp., ≥95% (HPLC)

Synonyme(s) :

Actinomycin C1, Actinomycin IV, Dactinomycin

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About This Item

Formule empirique (notation de Hill):
C62H86N12O16
Numéro CAS:
50-76-0
Poids moléculaire :
1255.42
Numéro Beilstein :
605235
Numéro CE :
200-063-6
Numéro MDL:
MFCD00005033
Code UNSPSC :
51282001
ID de substance PubChem :
24890842
Nomenclature NACRES :
NA.76

Source biologique

Streptomyces sp.

Niveau de qualité

200

Pureté

≥95% (HPLC)

Forme

powder

Couleur

red, powder

Pf

251-253

Solubilité

ethanol, DMSO: soluble

Spectre d'activité de l'antibiotique

neoplastics

Mode d’action

DNA synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

CC(C)[C@H]1NC(=O)[C@@H](NC(=O)c2ccc(C)c3OC4=C(C)C(=O)C(N)=C(C(=O)N[C@H]5[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]6CCCN6C(=O)[C@H](NC5=O)C(C)C)C4=Nc23)[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]7CCCN7C1=O

InChI

1S/C62H86N12O16/c1-27(2)42-59(84)73-23-17-19-36(73)57(82)69(13)25-38(75)71(15)48(29(5)6)61(86)88-33(11)44(55(80)65-42)67-53(78)35-22-21-31(9)51-46(35)64-47-40(41(63)50(77)32(10)52(47)90-51)54(79)68-45-34(12)89-62(87)49(30(7)8)72(16)39(76)26-70(14)58(83)37-20-18-24-74(37)60(85)43(28(3)4)66-56(45)81/h21-22,27-30,33-34,36-37,42-45,48-49H,17-20,23-26,63H2,1-16H3,(H,65,80)(H,66,81)(H,67,78)(H,68,79)/t33-,34-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1

Clé InChI

RJURFGZVJUQBHK-IIXSONLDSA-N

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Description générale

Chemical structure: peptide

Application

Actinomycin D is an antineoplastic antibiotic that inhibits cell proliferation with wide-ranging applications ranging from a selection agent in cell culture, use in studies of suppressing HIV-replication and programmed cell death of PC12 cells. Recommended for us in cell culture applications at 1μg/mL.

Actions biochimiques/physiologiques

Actinomycin D inhibits the proliferation of cells by forming a stable complex with double-stranded DNA, inhibiting DNA-primed RNA synthesis and causing single-stranded breaks in DNA. It has been shown to be an inhibitor of the minus-strand transfer step in reverse transcriptase.

Attention

This product is hygroscopic and light-sensitive. If stored protected from light and moisture at 2-8°C, it remains unchanged, by HPLC testing, for at least 15 months. Unused dilute solutions of Actinomycin D are extremely sensitive to light and tend to adsorb to plastic and glass and should be discarded. However, frozen aliquots of concentrated stock solution are stable for at least a month.

Notes préparatoires

Actinomycin D is sold as red, shiny crystals and is soluble in acetonitrilie or acetone at 10 mg/mL and in DMSO at a minimum of 1 mg/mL. Some references also show slight solubility in water of 0.5 mg/mL.

Autres remarques

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H300,H350,H360FD

Classification des risques

Acute Tox. 2 Oral - Carc. 1B - Repr. 1B

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Antonio Rescifina et al.
Journal of medicinal chemistry, 49(2), 709-715 (2006-01-20)
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Leilei Zhou et al.
Genome biology, 20(1), 156-156 (2019-08-08)
Methylation of nucleotides, notably in the forms of 5-methylcytosine (5mC) in DNA and N6-methyladenosine (m6A) in mRNA, carries important information for gene regulation. 5mC has been elucidated to participate in the regulation of fruit ripening, whereas the function of m6A
Arkady Khoutorsky et al.
Neuron, 78(2), 298-311 (2013-04-30)
Control of protein synthesis is critical for synaptic plasticity and memory formation. However, the molecular mechanisms linking neuronal activity to activation of mRNA translation are not fully understood. Here, we report that the translational repressor poly(A)-binding protein (PABP)-interacting protein 2A
Rolf Schreckenberg et al.
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H Sun et al.
British journal of cancer, 111(2), 281-291 (2014-06-20)
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