Varacine | CAS#134029-48-4 | antibiotic

MedKoo Cat#: 145462 | Name: Varacine

Description:

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

Varacine is a low-molecular weight compound. Varacin is capable of causing DNA-cleavage with high efficiency in the presence of thiols. Varacin is an anti-cancer compound. Varacin employs an intricate combination of reduction and oxidation processes to develop their therapeutic potential inside cells.

Chemical Structure

Varacine

CAS#134029-48-4

Theoretical Analysis

MedKoo Cat#: 145462

Name: Varacine

CAS#: 134029-48-4

Chemical Formula: C10H13NO2S5

Exact Mass: 338.9600

Molecular Weight: 339.52

Elemental Analysis: C, 35.38; H, 3.86; N, 4.13; O, 9.42; S, 47.21

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Varacine; Varacin;

IUPAC/Chemical Name

2-(8,9-dimethoxybenzo[f][1,2,3,4,5]pentathiepin-6-yl)ethan-1-amine

InChi Key

HIKCOAGMCNIBMP-UHFFFAOYSA-N

InChi Code

1S/C10H13NO2S5/c1-12-7-5-6(3-4-11)9-10(8(7)13-2)15-17-18-16-14-9/h5H,3-4,11H2,1-2H3

SMILES Code

COC1=CC(CCN)=C2SSSSSC2=C1OC

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 339.52 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.

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: Zhou J, Li WL, Wang ZX, Chen NY, Tang Y, Hu XX, Deng JH, Lu Y, Lu GD. Varacin-1, a novel analog of varacin C, induces p53-independent apoptosis in cancer cells through ROS-mediated reduction of XIAP. Acta Pharmacol Sin. 2019 Feb;40(2):222-230. doi: 10.1038/s41401-018-0005-y. Epub 2018 May 17. PMID: 29773887; PMCID: PMC6329757. 2: Makarieva TN, Stonik VA, Dmitrenok AS, Grebnev BB, Isakov VV, Rebachyk NM, Rashkes YW. Varacin and three new marine antimicrobial polysulfides from the far-eastern ascidian Polycitor sp. J Nat Prod. 1995 Feb;58(2):254-8. doi: 10.1021/np50116a015. PMID: 7769392. 3: Lee AH, Chen J, Liu D, Leung TY, Chan AS, Li T. Acid-promoted DNA-cleaving activities and total synthesis of varacin C. J Am Chem Soc. 2002 Nov 27;124(47):13972-3. doi: 10.1021/ja020531i. PMID: 12440877. 4: Kulikov AV, Tikhonova MA, Kulikova EA, Volcho KP, Khomenko TM, Salakhutdinov NF, Popova NK. A new synthetic varacin analogue, 8-(trifluoromethyl)-1,2,3,4,5-benzopentathiepin-6-amine hydrochloride (TC-2153), decreased hereditary catalepsy and increased the BDNF gene expression in the hippocampus in mice. Psychopharmacology (Berl). 2012 Jun;221(3):469-78. doi: 10.1007/s00213-011-2594-8. Epub 2011 Nov 30. PMID: 22127556. 5: Mahendran A, Ghogare AA, Bittman R, Arthur G, Greer A. Synthesis and antiproliferative properties of a new ceramide analog of varacin. Chem Phys Lipids. 2016 Jan;194:165-70. doi: 10.1016/j.chemphyslip.2015.07.023. Epub 2015 Aug 5. PMID: 26254858; PMCID: PMC4718750. 6: Mahendran A, Vuong A, Aebisher D, Gong Y, Bittman R, Arthur G, Kawamura A, Greer A. Synthesis, characterization, mechanism of decomposition, and antiproliferative activity of a class of PEGylated benzopolysulfanes structurally similar to the natural product varacin. J Org Chem. 2010 Aug 20;75(16):5549-57. doi: 10.1021/jo100870q. PMID: 20704430; PMCID: PMC3329777. 7: Kudryavtsev D, Shelukhina I, Vulfius C, Makarieva T, Stonik V, Zhmak M, Ivanov I, Kasheverov I, Utkin Y, Tsetlin V. Natural compounds interacting with nicotinic acetylcholine receptors: from low-molecular weight ones to peptides and proteins. Toxins (Basel). 2015 May 14;7(5):1683-701. doi: 10.3390/toxins7051683. PMID: 26008231; PMCID: PMC4448168. 8: Jacob C. A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms. Nat Prod Rep. 2006 Dec;23(6):851-63. doi: 10.1039/b609523m. Epub 2006 Sep 28. PMID: 17119635. 9: Greer A. On the origin of cytotoxicity of the natural product varacin. A novel example of a pentathiepin reaction that provides evidence for a triatomic sulfur intermediate. J Am Chem Soc. 2001 Oct 24;123(42):10379-86. doi: 10.1021/ja016495p. PMID: 11603989. 10: Lee AH, Chan AS, Li T. Acid-accelerated DNA-cleaving activities of antitumor antibiotic varacin. Chem Commun (Camb). 2002 Sep 21;(18):2112-3. doi: 10.1039/b204920c. PMID: 12357803. 11: Chatterji T, Gates KS. DNA cleavage by 7-methylbenzopentathiepin: a simple analog of the antitumor antibiotic varacin. Bioorg Med Chem Lett. 1998 Mar 3;8(5):535-8. doi: 10.1016/s0960-894x(98)00066-3. PMID: 9871613. 12: Fry FH, Jacob C. Sensor/effector drug design with potential relevance to cancer. Curr Pharm Des. 2006;12(34):4479-99. doi: 10.2174/138161206779010512. PMID: 17168755. 13: Asquith CRM, Machado ACS, de Miranda LHM, Konstantinova LS, Almeida-Paes R, Rakitin OA, Pereira SA. Synthesis and Identification of Pentathiepin-Based Inhibitors of Sporothrix brasiliensis. Antibiotics (Basel). 2019 Dec 3;8(4):249. doi: 10.3390/antibiotics8040249. PMID: 31816950; PMCID: PMC6963766. 14: Kudryavtsev D, Makarieva T, Utkina N, Santalova E, Kryukova E, Methfessel C, Tsetlin V, Stonik V, Kasheverov I. Marine natural products acting on the acetylcholine-binding protein and nicotinic receptors: from computer modeling to binding studies and electrophysiology. Mar Drugs. 2014 Mar 28;12(4):1859-75. doi: 10.3390/md12041859. PMID: 24686559; PMCID: PMC4012456. 15: Chatterji T, Keerthi K, Gates KS. Generation of reactive oxygen species by a persulfide (BnSSH). Bioorg Med Chem Lett. 2005 Sep 1;15(17):3921-4. doi: 10.1016/j.bmcl.2005.05.110. PMID: 16005218. 16: Nakazawa T, Xu J, Nishikawa T, Oda T, Fujita A, Ukai K, Mangindaan RE, Rotinsulu H, Kobayashi H, Namikoshi M. Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium. J Nat Prod. 2007 Mar;70(3):439-42. doi: 10.1021/np060593c. Epub 2007 Feb 2. PMID: 17269824. 17: Asquith CRM, Laitinen T, Konstantinova LS, Tizzard G, Poso A, Rakitin OA, Hofmann-Lehmann R, Hilton ST. Investigation of the Pentathiepin Functionality as an Inhibitor of Feline Immunodeficiency Virus (FIV) via a Potential Zinc Ejection Mechanism, as a Model for HIV Infection. ChemMedChem. 2019 Feb 19;14(4):454-461. doi: 10.1002/cmdc.201800718. Epub 2019 Jan 25. PMID: 30609219. 18: Brzostowska EM, Greer A. The role of amine in the mechanism of pentathiepin (polysulfur) antitumor agents. J Am Chem Soc. 2003 Jan 15;125(2):396-404. doi: 10.1021/ja027416s. PMID: 12517151.