Plitidepsin
Grundinformationen
- CAS
137219-37-5- Standard-SMILES
CC[C@H](C)[C@H]1NC(=O)[C@@H](NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]2CCCN2C(=O)C(C)=O)[C@@H](C)OC(=O)[C@H](Cc2ccc(OC)cc2)N(C)C(=O)[C@@H]2CCCN2C(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)C(=O)[C@H](C(C)C)OC(=O)C[C@@H]1O- InChIKey
UUSZLLQJYRSZIS-LXNNNBEUSA-N- Summenformel
- C57H87N7O15
- Durchschnittliche Molmasse
- 1.110,3 g/mol
- Monoisotopische Masse
- 1.109,62601509
Überblick
Plitidepsin is a didemnin that is didemin B in which the hydroxy group of the 1-(2-hydroxypropanoyl)-L-prolinamide moiety has been oxidised to the corresponding ketone. It was originally isolated from the Mediterranean tunicate Aplidium albicans. It has a role as an anticoronaviral agent, an antineoplastic agent and a marine metabolite.
Namen und Bezeichner
- Bevorzugter Name
- Plitidepsin
- IUPAC
- (2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide
- Englischer Name
- Plitidepsin
- Summenformel
- C57H87N7O15
- Molmasse
- 1110.34
Namen und Synonyme
plitidepsinAplidine137219-37-5aplidinDehydrodidemnin BplitidepsinaplitidepsineY76ID234HW(2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamideCHEBI:90205NSC638719plitidepsinum
Weitere Namen anzeigen
Plitidepsin top3cyclic peptide deriv.Plitidepsin (Aplidine)Aplidine, 10 mM in DMSODidemnin A, N-(1-(1,2-dioxopropyl)-L-prolyl)-2-9-Didemnin B, 2-(1-(1,2-dioxopropyl)-L-proline)-Inhibitor,DNA/RNA Synthesis,MOLT-4,SARS coronavirus,infection,SARS-CoV,Plitidepsin,Leukemia,VEGF,COVID-19,Antiviral,inhibit,Aplidine,advanced cancer,anticancer,Advanced Malignancies
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,7
- Polarare Oberfläche (TPSA)
- 285 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 15
- Frei drehbare Bindungen
- 15
- Schwere Atome
- 79
- Formalladung
- 0
- Komplexität
- 2.200
Physikochemische Eigenschaften
- Schmelzpunkt
- 152 · 152-160°
- Dichte
- 1.24 · 1.24±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- DMSO: soluble
- pka
- 11.28 · 11.28±0.70(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to off-white
- InChIKey
- UUSZLLQJYRSZIS-NIORUGPLNA-N
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- Alarmwort
- Achtung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H225
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Mechanism of Action
Plitidepsin has antineoplastic activity which stems from plitidepsin's ability to inhibit cell growth and induce apoptosis. Plitidepsin's primary intracellular target is the eukaryotic elongation factor 1A2 (eEF1A2). It also inhibits the growth and induces apoptosis in MOLT-4 cells by inhibiting VEGF secretion, which blocks the VEGF/VEGFR-1 autocrine loop that is required for the growth of the MOLT-4 cells. Through inhibition of eEF1A, plitidepsin also demonstrated antiviral activity against SARS-CoV-2. The exact mechanism of action is not fully understood and plitidepsin may have multiple modes of action.
Metabolism/MetabolitesHepatic
Anwendungen
BeschreibungPlitidepsin is a cyclic depsipeptide that was first isolated from a Mediterranean marine tunicate (Aplidium albicans) and, at present, is manufactured by total synthesis and commercialized as Aplidin. Its antitumor activity, observed in preclinical in vitro and in vivo studies has prompted numerous clinical trials to be conducted over the last 17 years, alone or in combination with other anticancer agents.
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武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
湖北海克斯生化有限公司17362916295; 17362916295 · [email protected]
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