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MedKoo Cat#: 574095 | Name: Chlamydocin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Chlamydocin is a histone deacetylase (HDAC) inhibitor with anticancer properties. Chlamydocin increases acetylation of histone H3 and histone H4 and inhibits growth of A2780, Malme-3M, MCF-7, HT-29, and HeLa cancer cells. Chlamydocin also increases lifespan by 10% in a P185 mouse allograft model.

Chemical Structure

Chlamydocin
Chlamydocin
CAS#53342-16-8

Theoretical Analysis

MedKoo Cat#: 574095

Name: Chlamydocin

CAS#: 53342-16-8

Chemical Formula: C28H38N4O6

Exact Mass: 526.2791

Molecular Weight: 526.63

Elemental Analysis: C, 63.86; H, 7.27; N, 10.64; O, 18.23

Price and Availability

Size Price Availability Quantity
1mg USD 685.00 2 Weeks
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Related CAS #
No Data
Synonym
Chlamydocin
IUPAC/Chemical Name
(3S,9S,14aR)-9-benzyl-6,6-dimethyl-3-(6-((S)-oxiran-2-yl)-6-oxohexyl)decahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone
InChi Key
SGYJGGKDGBXCNY-QXUYBEEESA-N
InChi Code
InChI=1S/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
SMILES Code
O=C([C@H](CCCCCC([C@H]1OC1)=O)NC([C@]2([H])N3CCC2)=O)NC(C)(C)C(N[C@@H](CC4=CC=CC=C4)C3=O)=O
Appearance
Solid powder
Purity
>70% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 526.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Nishino N, Jose B, Shinta R, Kato T, Komatsu Y, Yoshida M. Chlamydocin- hydroxamic acid analogues as histone deacetylase inhibitors. Bioorg Med Chem. 2004 Nov 15;12(22):5777-84. doi: 10.1016/j.bmc.2004.08.041. PMID: 15498654. 2: Bernardi E, Fauchere JL, Atassi G, Viallefont P, Lazaro R. Antitumoral cyclic peptide analogues of chlamydocin. Peptides. 1993 Nov-Dec;14(6):1091-3. doi: 10.1016/0196-9781(93)90160-i. PMID: 8134289. 3: Bhuiyan MP, Kato T, Okauchi T, Nishino N, Maeda S, Nishino TG, Yoshida M. Chlamydocin analogs bearing carbonyl group as possible ligand toward zinc atom in histone deacetylases. Bioorg Med Chem. 2006 May 15;14(10):3438-46. doi: 10.1016/j.bmc.2005.12.063. Epub 2006 Jan 24. PMID: 16439135. 4: De Schepper S, Bruwiere H, Verhulst T, Steller U, Andries L, Wouters W, Janicot M, Arts J, Van Heusden J. Inhibition of histone deacetylases by chlamydocin induces apoptosis and proteasome-mediated degradation of survivin. J Pharmacol Exp Ther. 2003 Feb;304(2):881-8. doi: 10.1124/jpet.102.042903. PMID: 12538846. 5: Kamimura S, Inoue K, Mizutani E, Kim JM, Inoue H, Ogonuki N, Miyamoto K, Ihashi S, Itami N, Wakayama T, Ito A, Nishino N, Yoshida M, Ogura A. Improved development of mouse somatic cell nuclear transfer embryos by chlamydocin analogues, class I and IIa histone deacetylase inhibitors†. Biol Reprod. 2021 Aug 3;105(2):543-553. doi: 10.1093/biolre/ioab096. PMID: 33982061; PMCID: PMC8335354. 6: Tani H, Fujii Y, Nakajima H. Chlamydocin analogues from the soil fungus Peniophora sp.: structures and plant growth-retardant activity. Phytochemistry. 2001 Sep;58(2):305-10. doi: 10.1016/s0031-9422(01)00209-6. PMID: 11551555. 7: Closse A, Huguenin R. Isolierung und Strukturaufklärung von Chlamydocin [Isolation and structural clarification of chlamydocin]. Helv Chim Acta. 1974 Apr 27;57(3):533-45. German. doi: 10.1002/hlca.19740570306. PMID: 4857466. 8: Rich DH, Jasensky RD, Mueller GC, Anderson KE. Analogues of the cytostatic cyclic tetrapeptide chlamydocin. Synthesis of N beta-(N-maleoylglycyl) and N beta-(tert-butyloxycarbonyl) derivatives of cyclo(Gly-L-Phe-D-Pro-L-Dap). J Med Chem. 1981 May;24(5):567-72. doi: 10.1021/jm00137a017. PMID: 7241514. 9: Stähelin H, Trippmacher A. Cytostatic activity of chlamydocin, a rapidly inactivated cyclic tetrapeptide. Eur J Cancer (1965). 1974 Dec;10(12):801-8. doi: 10.1016/0014-2964(74)90137-6. PMID: 4218812. 10: Shute RE, Dunlap B, Rich DH. Analogues of the cytostatic and antimitogenic agents chlamydocin and HC-toxin: synthesis and biological activity of chloromethyl ketone and diazomethyl ketone functionalized cyclic tetrapeptides. J Med Chem. 1987 Jan;30(1):71-8. doi: 10.1021/jm00384a013. PMID: 3806605. 11: Tani H, Honma T, Fujii Y, Yoneyama K, Nakajima H. A plant growth retardant related to chlamydocin and its proposed mechanism of action. Phytochemistry. 2003 Apr;62(7):1133-40. doi: 10.1016/s0031-9422(02)00685-4. PMID: 12591268. 12: Elek GZ, Koppel K, Zubrytski DM, Konrad N, Järving I, Lopp M, Kananovich DG. Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via a Late- Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin. Org Lett. 2019 Oct 18;21(20):8473-8478. doi: 10.1021/acs.orglett.9b03305. Epub 2019 Oct 9. PMID: 31596600. 13: Rich DH, Kawai M, Jasensky RD. Conformational studies of cyclic tetrapeptides. Evidence for a bis gamma-turn conformation for chlamydocin and Ala4-chlamydocin in nonpolar solvents. Int J Pept Protein Res. 1983 Jan;21(1):35-42. PMID: 6826281. 14: Shivashimpi GM, Amagai S, Kato T, Nishino N, Maeda S, Nishino TG, Yoshida M. Molecular design of histone deacetylase inhibitors by aromatic ring shifting in chlamydocin framework. Bioorg Med Chem. 2007 Dec 15;15(24):7830-9. doi: 10.1016/j.bmc.2007.08.041. Epub 2007 Aug 26. PMID: 17881232. 15: Wang S, Li X, Wei Y, Xiu Z, Nishino N. Discovery of potent HDAC inhibitors based on chlamydocin with inhibitory effects on cell migration. ChemMedChem. 2014 Mar;9(3):627-37. doi: 10.1002/cmdc.201300372. Epub 2013 Nov 27. PMID: 24285590. 16: Walton JD, Earle ED, Stähelin H, Grieder A, Hirota A, Suzuki A. Reciprocal biological activities of the cyclic tetrapeptides chlamydocin and HC-toxin. Experientia. 1985 Mar 15;41(3):348-50. doi: 10.1007/BF02004498. PMID: 3918884. 17: Islam MS, Bhuiyan MP, Islam MN, Nsiama TK, Oishi N, Kato T, Nishino N, Ito A, Yoshida M. Evaluation of functional groups on amino acids in cyclic tetrapeptides in histone deacetylase inhibition. Amino Acids. 2012 Jun;42(6):2103-10. doi: 10.1007/s00726-011-0947-6. Epub 2011 Jun 3. PMID: 21638021. 18: Nishino N, Shivashimpi GM, Soni PB, Bhuiyan MP, Kato T, Maeda S, Nishino TG, Yoshida M. Interaction of aliphatic cap group in inhibition of histone deacetylases by cyclic tetrapeptides. Bioorg Med Chem. 2008 Jan 1;16(1):437-45. doi: 10.1016/j.bmc.2007.09.021. Epub 2007 Sep 15. PMID: 17900911. 19: Chung BKW, White CJ, Yudin AK. Solid-phase synthesis, cyclization, and site- specific functionalization of aziridine-containing tetrapeptides. Nat Protoc. 2017 Jun;12(6):1277-1287. doi: 10.1038/nprot.2017.035. Epub 2017 May 24. PMID: 28538738. 20: Young JC, Wu S, Hansteen G, Du C, Sambucetti L, Remiszewski S, O'Farrell AM, Hill B, Lavau C, Murray LJ. Inhibitors of histone deacetylases promote hematopoietic stem cell self-renewal. Cytotherapy. 2004;6(4):328-36. doi: 10.1080/14653240410004899. PMID: 16146885.