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.

Chemical Structure

Verticillin A
CAS# 889640-30-6

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

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 or click below button.
Note: Price will be listed if it is available in the future.

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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 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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 696.83 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

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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.