Verticillin A

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

MedKoo CAT#: 525663

CAS#: 889640-30-6

Description: Verticillin A is an apoptosis inducer, inhibiting Leiomyosarcoma and Malignant peripheral nerve sheath tumor growth.


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Verticillin A is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 525663
Name: Verticillin A
CAS#: 889640-30-6
Chemical Formula: C30H28N6O6S4
Exact Mass: 696.0953
Molecular Weight: 696.83
Elemental Analysis: C, 51.71; H, 4.05; N, 12.06; O, 13.78; S, 18.40


Synonym: Verticillin A

IUPAC/Chemical Name: (3S,3'S,5aR,5'aR,10bS,10'bs,11S,11'S,11aS,11'aS)-2,2',3,3',5a,5'a,6,6'-octahydro-11,11'-dihydroxy-2,2',3,3'-tetramethyl-(10b,10'b(11H,11'H)-bi-3,11a-epidithio-11aH-pyrazino(1',2':1,5)pyrrolo(2,3-b)indole)-1,1',4,4'-tetrone

InChi Key: KYTVBRRGHYFEOC-VQXQXQDSSA-N

InChi Code: InChI=1S/C30H28N6O6S4/c1-27-23(39)35-21-18(20(38)29(35,45-43-27)25(41)32(27)3)17-13(31-21)9-7-11-15(17)34-14-10-6-5-8-12(14)16-19(37)30-26(42)33(4)28(2,44-46-30)24(40)36(30)22(16)34/h5-11,16,18-22,31,37-38H,1-4H3/t16?,18-,19+,20?,21-,22-,27+,28+,29+,30+/m1/s1

SMILES Code: O=C1N(C)[C@]2(C)C(N3[C@]1(SS2)C(O)[C@]4([H])[C@]3([H])NC5=C4C(N6[C@@](N7[C@](C(N(C)[C@]8(C)C7=O)=O)(SS8)[C@H]9O)([H])C9C%10=C6C=CC=C%10)=CC=C5)=O


Technical Data

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).

Harmonized System Code:
2934990300


References

1: Wang J, Zhu X, Kolli S, Wang H, Pearce CJ, Oberlies NH, Phelps MA. Plasma pharmacokinetics and bioavailability of verticillin A following different routes of administration in mice using liquid chromatography tandem mass spectrometry. J Pharm Biomed Anal. 2017 May 30;139:187-192. doi: 10.1016/j.jpba.2017.02.051. Epub 2017 Mar 1. PubMed PMID: 28284083; PubMed Central PMCID: PMC5399420.

2: Zewdu A, Lopez G, Braggio D, Kenny C, Constantino D, Bid HK, Batte K, Iwenofu OH, Oberlies NH, Pearce CJ, Strohecker AM, Lev D, Pollock RE. Verticillin A Inhibits Leiomyosarcoma and Malignant Peripheral Nerve Sheath Tumor Growth via Induction of Apoptosis. Clin Exp Pharmacol. 2016 Nov;6(6). pii: 221. doi: 10.4172/2161-1459.1000221. Epub 2016 Oct 24. PubMed PMID: 28184331; PubMed Central PMCID: PMC5295762.

3: Paschall AV, Liu K. Epigenetic Regulation of Apoptosis and Cell Cycle Regulatory Genes in Human Colon Carcinoma Cells. Genom Data. 2015 Sep 1;5:189-191. PubMed PMID: 26309812; PubMed Central PMCID: PMC4542010.

4: Paschall AV, Yang D, Lu C, Choi JH, Li X, Liu F, Figueroa M, Oberlies NH, Pearce C, Bollag WB, Nayak-Kapoor A, Liu K. H3K9 Trimethylation Silences Fas Expression To Confer Colon Carcinoma Immune Escape and 5-Fluorouracil Chemoresistance. J Immunol. 2015 Aug 15;195(4):1868-82. doi: 10.4049/jimmunol.1402243. Epub 2015 Jul 1. PubMed PMID: 26136424; PubMed Central PMCID: PMC4530033.

5: Kim J, Movassaghi M. Biogenetically-inspired total synthesis of epidithiodiketopiperazines and related alkaloids. Acc Chem Res. 2015 Apr 21;48(4):1159-71. doi: 10.1021/ar500454v. Epub 2015 Apr 6. PubMed PMID: 25843276; PubMed Central PMCID: PMC4408872.

6: Figueroa M, Graf TN, Ayers S, Adcock AF, Kroll DJ, Yang J, Swanson SM, Munoz-Acuna U, Carcache de Blanco EJ, Agrawal R, Wani MC, Darveaux BA, Pearce CJ, Oberlies NH. Cytotoxic epipolythiodioxopiperazine alkaloids from filamentous fungi of the Bionectriaceae. J Antibiot (Tokyo). 2012 Nov;65(11):559-64. doi: 10.1038/ja.2012.69. Epub 2012 Sep 12. PubMed PMID: 22968289; PubMed Central PMCID: PMC3573876.

7: Liu F, Liu Q, Yang D, Bollag WB, Robertson K, Wu P, Liu K. Verticillin A overcomes apoptosis resistance in human colon carcinoma through DNA methylation-dependent upregulation of BNIP3. Cancer Res. 2011 Nov 1;71(21):6807-16. doi: 10.1158/0008-5472.CAN-11-1575. Epub 2011 Sep 12. PubMed PMID: 21911457; PubMed Central PMCID: PMC3206150.

8: Schenke D, Böttcher C, Lee J, Scheel D. Verticillin A is likely not produced by Verticillium sp. J Antibiot (Tokyo). 2011 Jul;64(7):523-4. doi: 10.1038/ja.2011.36. Epub 2011 Apr 27. PubMed PMID: 21522159.

9: Kim J, Movassaghi M. Biogenetically inspired syntheses of alkaloid natural products. Chem Soc Rev. 2009 Nov;38(11):3035-50. doi: 10.1039/b819925f. Epub 2009 Sep 23. Review. PubMed PMID: 19847339.

10: Dong JY, He HP, Shen YM, Zhang KQ. Nematicidal epipolysulfanyldioxopiperazines from Gliocladium roseum. J Nat Prod. 2005 Oct;68(10):1510-3. PubMed PMID: 16252916.

11: Zhang YX, Chen Y, Guo XN, Zhang XW, Zhao WM, Zhong L, Zhou J, Xi Y, Lin LP, Ding J. 11,11'-dideoxy-verticillin: a natural compound possessing growth factor receptor tyrosine kinase-inhibitory effect with anti-tumor activity. Anticancer Drugs. 2005 Jun;16(5):515-24. PubMed PMID: 15846117.

12: Joshi BK, Gloer JB, Wicklow DT. New verticillin and glisoprenin analogues from gliocladium catenulatum, a mycoparasite of aspergillus flavus sclerotia . J Nat Prod. 1999 May;62(5):730-3. PubMed PMID: 10346956.

13: Chu M, Truumees I, Rothofsky ML, Patel MG, Gentile F, Das PR, Puar MS, Lin SL. Inhibition of c-fos proto-oncogene induction by Sch 52900 and Sch 52901, novel diketopiperazine produced by Gliocladium sp. J Antibiot (Tokyo). 1995 Dec;48(12):1440-5. PubMed PMID: 8557601.

14: Argoudelis AD, Mizsak SA. Melinacidins II, III and IV. Structural studies. J Antibiot (Tokyo). 1977 Jun;30(6):468-73. PubMed PMID: 885807.

15: Minato H, Matsumoto M, Katayama T. Studies on the metabolites of Verticillium sp. structures of Verticillins A, B, and C. J Chem Soc Perkin 1. 1973;17:1819-25. PubMed PMID: 4796650.

16: Katagiri K, Sato K, Hayakawa S, Matsushima T, Minato H. Verticillin A, a new antibiotic from Verticillium sp. J Antibiot (Tokyo). 1970 Aug;23(8):420-2. PubMed PMID: 5465723.