Cyclochlorotine

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

Hodoodo CAT#: H341135

CAS#: 12663-46-6

Description: Cyclochlorotine is a mycotoxin produced by the fungus Penicillium islandicum that causes liver damage and has carcinogenic properties.


Chemical Structure

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Cyclochlorotine
CAS# 12663-46-6

Theoretical Analysis

Hodoodo Cat#: H341135
Name: Cyclochlorotine
CAS#: 12663-46-6
Chemical Formula: C24H31Cl2N5O7
Exact Mass: 571.16
Molecular Weight: 572.440
Elemental Analysis: C, 50.36; H, 5.46; Cl, 12.39; N, 12.23; O, 19.56

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Cyclochlorotine; CCRIS 1316

IUPAC/Chemical Name: Cyclic(L-3-phenyl-beta-alanyl-L-seryl-(3S-cis)-3,4-dichloro-L-prolyl-L-alpha-aminobutyryl-L-seryl)

InChi Key: PMBVHCCVEPYDSN-KXPAZRKESA-N

InChi Code: InChI=1S/C24H31Cl2N5O7/c1-2-14-21(35)30-16(10-32)22(36)29-15(12-6-4-3-5-7-12)8-18(34)27-17(11-33)24(38)31-9-13(25)19(26)20(31)23(37)28-14/h3-7,13-17,19-20,32-33H,2,8-11H2,1H3,(H,27,34)(H,28,37)(H,29,36)(H,30,35)/t13-,14-,15-,16+,17-,19-,20+/m1/s1

SMILES Code: CC[C@@H]1C(=O)N[C@H](C(=O)N[C@H](CC(=O)N[C@@H](C(=O)N2C[C@H]([C@H]([C@H]2C(=O)N1)Cl)Cl)CO)c3ccccc3)CO

Appearance: Solid powder

Purity: >98% (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: >2 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 572.44 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Schafhauser T, Kirchner N, Kulik A, Huijbers MM, Flor L, Caradec T, Fewer DP, Gross H, Jacques P, Jahn L, Jokela J, Leclère V, Ludwig-Müller J, Sivonen K, van Berkel WJ, Weber T, Wohlleben W, van Pée KH. The cyclochlorotine mycotoxin is produced by the nonribosomal peptide synthetase CctN in Talaromyces islandicus ('Penicillium islandicum'). Environ Microbiol. 2016 Nov;18(11):3728-3741. doi: 10.1111/1462-2920.13294. Epub 2016 Jun 27. PubMed PMID: 26954535.

2: Schafhauser T, Wibberg D, Rückert C, Winkler A, Flor L, van Pée KH, Fewer DP, Sivonen K, Jahn L, Ludwig-Müller J, Caradec T, Jacques P, Huijbers MM, van Berkel WJ, Weber T, Wohlleben W, Kalinowski J. Draft genome sequence of Talaromyces islandicus ("Penicillium islandicum") WF-38-12, a neglected mold with significant biotechnological potential. J Biotechnol. 2015 Oct 10;211:101-2. doi: 10.1016/j.jbiotec.2015.07.004. Epub 2015 Jul 18. PubMed PMID: 26197417.

3: Wang L, Li MD, Cao PP, Zhang CF, Huang F, Xu XH, Liu BL, Zhang M. Astin B, a cyclic pentapeptide from Aster tataricus, induces apoptosis and autophagy in human hepatic L-02 cells. Chem Biol Interact. 2014 Nov 5;223:1-9. doi: 10.1016/j.cbi.2014.09.003. Epub 2014 Sep 16. PubMed PMID: 25219577.

4: Mizutani K, Hirasawa Y, Sugita-Konishi Y, Mochizuki N, Morita H. Structural and conformational analysis of hydroxycyclochlorotine and cyclochlorotine, chlorinated cyclic peptides from Penicillium islandicum. J Nat Prod. 2008 Jul;71(7):1297-300. doi: 10.1021/np800150m. Epub 2008 Jun 18. PubMed PMID: 18558744.

5: Udagawa S, Tatsuno T. [Safety of rice grains and mycotoxins - a historical review of yellow rice mycotoxicoses]. Yakushigaku Zasshi. 2004;39(2):321-42. Japanese. PubMed PMID: 16025655.

6: Ohmi K, Enosawa S, Nonomura Y, Tatsuno T, Ueno Y. Acceleration of actin polymerization and rapid microfilament reorganization in cultured hepatocytes by cyclochlorotin, a hepatotoxic cyclic peptide. Toxicon. 2001 Feb-Mar;39(2-3):303-8. PubMed PMID: 10978748.

7: Matsuoka A, Sakamoto H, Tadokoro S, Tada A, Terao Y, Nukaya H, Wakabayashi K. The 2-phenylbenzotriazole-type water pollutant PBTA-2 has cytochalasin B-mimetic activity. Mutat Res. 2000 Jan 24;464(2):161-7. PubMed PMID: 10648903.

8: Ueno Y, Umemori K, Niimi E, Tanuma S, Nagata S, Sugamata M, Ihara T, Sekijima M, Kawai K, Ueno I, et al. Induction of apoptosis by T-2 toxin and other natural toxins in HL-60 human promyelotic leukemia cells. Nat Toxins. 1995;3(3):129-37. PubMed PMID: 7648021.

9: Zhou ZH, Komiyama M, Terao K, Shimada Y. Effects of cyclochlorotine on myofibrils in cardiomyocytes and on actin filament bundles in fibroblasts in vitro. Nat Toxins. 1994;2(6):378-85. PubMed PMID: 7704452.

10: Ueno Y. [Hepatotoxicity of cyclochlorotine--a cyclic peptide produced by Penicillium islandicum]. Prikl Biokhim Mikrobiol. 1992 Nov-Dec;28(6):899-906. Russian. PubMed PMID: 1494575.

11: Ueno Y. The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. Review. PubMed PMID: 3158480.

12: Ueno Y, Tanaka Y, Sato K, Sakakibara K, Tachibana T, Tanaka A. Similarity of chloropeptide to phalloidin in toxicity to isolated hepatocytes. J Toxicol Sci. 1984 May;9(2):117-30. PubMed PMID: 6481822.

13: Terao K, Ito E, Tatsuno T. Liver injuries induced by cyclochlorotine isolated from Penicillium islandicum. Arch Toxicol. 1984 Mar;55(1):39-46. PubMed PMID: 6732503.

14: Ito H, Watanabe K, Koyama J. The immunosuppressive effects of trichothecenes and cyclochlorotine on the antibody responses in guinea pigs. J Pharmacobiodyn. 1982 Jun;5(6):403-9. PubMed PMID: 7120038.

15: Ueno Y, Ito T, Yoshizawa-Nakaki H, Omata Y, Ichiman K. Cytotoxicity of chloropeptide in isolated hepatocytes and its inactivation by microsomes. J Toxicol Sci. 1982 May;7(2):111-22. PubMed PMID: 7131597.

16: Ito T, Kosugi E, Niwa M, Ishikawa I, Ueno Y. Effects of chloropeptide on liver components and serum enzyme activities in mice. J Toxicol Sci. 1981 May;6(2):105-13. PubMed PMID: 6168765.

17: Anderegg RJ, Biemann K, Manmade A, Ghosh AC. Mass spectrometric peptide sequencing: cyclochlorotine. Biomed Mass Spectrom. 1979 Mar;6(3):129-34. PubMed PMID: 420918.

18: Stark AA, Townsend JM, Wogan GN, Demain AL, Manmade A, Ghosh AC. Mutagenicity and antibacterial activity of mycotoxins produced by Penicillium islandicum Sopp and Penicillium rugulosum. J Environ Pathol Toxicol. 1978 Nov-Dec;2(2):313-24. PubMed PMID: 368283.

19: Ghosh AC, Manmade A, Bousquet A, Townsend JM, Demain AL. A convenient thin layer chromatographic method for the detection of cyclochlorotine and simatoxin, toxins from Penicillium islandicum Sopp. Experientia. 1978 Jun 15;34(6):819-20. PubMed PMID: 658315.

20: Ghosh AC, Manmade A, Townsend JM, Bousquet A, Howes JF, Demain AL. Production of cyclochlorotine and a new metabolite, simatoxin, by Penicillium islandicum Sopp. Appl Environ Microbiol. 1978 Jun;35(6):1074-8. PubMed PMID: 677874; PubMed Central PMCID: PMC242987.