53342-16-8

Usage

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

• 52574-64-8 (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 
• 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 
• 52574-64-8 (5S,11S,13aR)-5-Benzyl-11-((R)-6-hydroxy-6-(S)-oxiranyl-hexyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone 
• 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 
• 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 

Relevant academic research and scientific papers

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

Synthesis of chlamydocin by chelate-Claisen rearrangement

Chelate-Claisen rearrangement of a chiral allylic ester allows the synthesis of the unusual epoxyketo amino acid Aoe found in chlamydocin, one representative of a group of peptide-based HDAc inhibitors. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

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.

AMINOSAEUREN UND PEPTIDE - XXXXII. SYNTHESE VON CHLAMYDOCIN + EPI-CHLAMYDOCIN

The total synthesis of the cytostatic Chlamydocin together with his diastereomer epi-Chlamydocin is described.

Synthesis of the cytostatic cyclic tetrapeptide, chlamydocin

Chlamydocin has been synthesized by a route utilizing allylic hydroxylation and epoxidation of the DL-2-amino-9-decenoic acid residue to form the 2-amino-8-oxo-9,10-epoxydecanoic acid residue.