53342-16-8

Basic information

• Product Name: CHLAMYDOCIN
• Synonyms: CHLAMYDOCIN;2-Methylcyclo[Ala-L-Phe-D-Pro-6-[(S)-2-oxo-2-oxiranylethyl]-L-Nle-];Antibiotic SL-3440;SL-3440;Cyclo[2-methylalanyl-L-phenylalanyl-D-prolyl-(aS,2S)-a-amino-h-oxo-2-oxiraneoctanoyl]
• CAS NO: 53342-16-8
• Molecular Formula: C₂₈H₃₈N₄O₆
• Molecular Weight: 526.62
• Product Categories: Antibiotic
• Mol File: 53342-16-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 861.8°Cat760mmHg
• Flash Point: 475°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 4.49E-30mmHg at 25°C
• Refractive Index: 1.589
• PKA: 13.36±0.70(Predicted)
• CAS DataBase Reference: CHLAMYDOCIN(CAS DataBase Reference)
• NIST Chemistry Reference: CHLAMYDOCIN(53342-16-8)
• EPA Substance Registry System: CHLAMYDOCIN(53342-16-8)

Safety Data

• Hazardous Substances Data: 53342-16-8(Hazardous Substances Data)

Usage

Description

Chlamydocin is a histone deacetylase (HDAC) inhibitor that was originally isolated from D. chlamydosporia and has anticancer properties. It is selective for HDAC1 over HDAC6 and increases acetylation of histone H3 and histone H4 in A2780 cells. Chlamydocin also inhibits the growth of various cancer cell lines and has the potential to increase lifespan in a P185 mouse allograft model.

Uses

Used in Anticancer Applications:
Chlamydocin is used as an anticancer agent for its ability to inhibit the growth of various cancer cell lines, including A2780, Malme-3M, MCF-7, HT-29, and HeLa. It functions as an irreversible HDAC inhibitor, selectively targeting HDAC1 over HDAC6, and increasing the acetylation of histone H3 and histone H4, which contributes to its anticancer properties.
Used in Drug Delivery Systems:
While the provided materials do not specifically mention drug delivery systems for Chlamydocin, it can be inferred that Chlamydocin could potentially be used in drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes in cancer treatment. This may involve the development of novel drug delivery systems, such as organic or metallic nanoparticles, to improve the efficacy of Chlamydocin in targeting cancer cells.

InChI:InChI=1/C28H38N4O6/c1-28(2)27(37)30-20(16-18-10-5-3-6-11-18)26(36)32-15-9-13-21(32)25(35)29-19(24(34)31-28)12-7-4-8-14-22(33)23-17-38-23/h3,5-6,10-11,19-21,23H,4,7-9,12-17H2,1-2H3,(H,29,35)(H,30,37)(H,31,34)/t19-,20-,21+,23-/m0/s1

Upstream product

• 52574-63-7 (5S,11S,13aR)-5-Benzyl-8,8-dimethyl-11-(6-oxo-oct-7-enyl)-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone 
• 52574-64-8 (5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-6-oxiranyl-hexyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone 
• 52574-64-8 Dihydrochlamydocin 
• 89278-34-2 8-Benzyloxy-6(S),7(S)-O-isopropylidene-1-octanal 
• 89278-30-8 (E/Z)-8-Benzyloxy-6(S),7(S)-O-isopropylidene-4-octenal 
• 108071-96-1 Methyl 2(S)-benzyloxycarbonylamino-10-hydroxy-8(S),9(S)-O-isopropylidenedecanoate 
• 89278-33-1 cyclo-<(2(S)-Amino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl)-dimethylglycyl-(S)-phenylalanyl-(R)-prolyl> 
• 108071-98-3 Methyl of N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate 
• 89321-01-7 Pentafluorophenyl N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate 
• 88568-96-1 Methyl N-(dimethylglycyl)-(S)-phenylalanyl-(R)-prolinate 
• 89278-31-9 Methyl 10-Benzyloxy-2-(S)-benzyloxycarbonylamino-8(S),9(S)-O-isopropylidene-2(E/Z),6(E/Z)-decadienoate 
• 108071-97-2 (S)-2-Benzyloxycarbonylamino-7-((4S,5S)-5-chloromethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptanoic acid methyl ester 
• 89278-32-0 (S)-2-Benzyloxycarbonylamino-7-((4S,5R)-5-chloromethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptanoic acid 
• 50628-92-7 ethyl 6-oxo-7-octenoate 

Relevant articles and documents

Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via a Late-Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin

A unified step-economical strategy for accessing histone deacetylase inhibitory peptides is proposed, based on the late-stage installation of multiple zinc-binding functionalities via the cleavage of the strained cyclopropane ring in the common pluripoten

Stereospecific synthesis of chlamydocin

A stereospecific synthesis of the cyclic tetrapeptide chlamydocin via free radical homologation from a (S)-2-amino-5-iodopentanoic acid containing cyclic tetrapeptide is described.

Amino Acids and Peptides; 55. Synthesis of Biologically Active Cyclopeptides; 7. Total Synthesis of Chlamydocin

Methods for the synthesis of cyclopeptides containing non-essential amino acids are described.The total synthesis of the highly cancerostatic Chlamydocin is published.