Psammaplin A | CAS# 110659-91-1 | DNA methyltransferase inhibitor

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

MedKoo CAT#: 574850

CAS#: 110659-91-1

Description: Psammaplin A is a DNA methyltransferase inhibitor.

Chemical Structure

Psammaplin A

CAS# 110659-91-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 574850
Name: Psammaplin A
CAS#: 110659-91-1
Chemical Formula: C22H24Br2N4O6S2
Exact Mass: 661.95
Molecular Weight: 664.380
Elemental Analysis: C, 39.77; H, 3.64; Br, 24.05; N, 8.43; O, 14.45; S, 9.65

Price and Availability

Size	Price	Availability
5mg	USD 340	2 Weeks
10mg	USD 525	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: (E,E)-Psammaplin A; Bisprasin; Psammaplin A; UVI 5000; UVI-5000; UVI5000; Bisprasin;

IUPAC/Chemical Name: (E,E)-N,N'-(Dithiodi-2,1-ethanediyl)bis[3-bromo-4-hydroxy-α-(hydroxyimino)-benzenepropanamide]

InChi Key: LMAFSGDNHVBIHU-XUIWWLCJSA-N

InChi Code: InChI=1S/C22H24Br2N4O6S2/c23-15-9-13(1-3-19(15)29)11-17(27-33)21(31)25-5-7-35-36-8-6-26-22(32)18(28-34)12-14-2-4-20(30)16(24)10-14/h1-4,9-10,29-30,33-34H,5-8,11-12H2,(H,25,31)(H,26,32)/b27-17+,28-18+

SMILES Code: O=C(NCCSSCCNC(/C(CC1=CC=C(O)C(Br)=C1)=N/O)=O)/C(CC2=CC=C(O)C(Br)=C2)=N/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: To be determined

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:

Product Data:

Product Data

Instruction:

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Biological target:	Psammaplin A ia a highly potent and selective DAC1 inhibitor with an IC50 of 0.9 nM. Psammaplin A possess antimicrobial effects on Gram-positive bacteria and inhibits DNA synthesis and DNA gyrase activity. Psammaplin A also has antitumor activity.
In vitro activity:	On bovine parthenogenetic (PA) embryos, psammaplin A demonstrated potent HDAC inhibition. In the embryos, psammaplin A reduced the blastocyst formation rate. Psammaplin A had inhibitory effects on HDAC1 and DNMT1. Psammaplin A treatment enhanced the acetylation level of H3K9 but left DNA methylation relatively unchanged. Psammaplin A induced oxidative stress by increasing ROS generation. Reference: Am J Vet Res. 2023 Feb 21;84(4):ajvr.22.09.0159. https://pubmed.ncbi.nlm.nih.gov/36795551/
In vivo activity:	Following intravenous administration in mice, psammaplin A exhibited rapid elimination, with a short average half-life and significant systemic clearance. Psammaplin A was found to be highly distributed to lung tissues, with the lung-to-serum partition coefficients (K(p)) ranging from 49.9 to 60.2. Psammaplin A concentrations in other tissues were either comparable with or less than serum concentrations. Reference: Arch Pharm Res. 2012 Oct;35(10):1849-54. https://pubmed.ncbi.nlm.nih.gov/23139138/

Preparing Stock Solutions

The following data is based on the product molecular weight 664.38 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

Formulation protocol:	1. Ma X, Zhan C, Ma P, Jing G, Liyan S, Zhang Y, Jing Z, Liu H, Wang J, Lu W. PsA inhibits the development of bovine embryos through epigenetic and oxidative stress. Am J Vet Res. 2023 Feb 21;84(4):ajvr.22.09.0159. doi: 10.2460/ajvr.22.09.0159. PMID: 36795551. 2. Oluwabusola ET, Katermeran NP, Poh WH, Goh TMB, Tan LT, Diyaolu O, Tabudravu J, Ebel R, Rice SA, Jaspars M. Inhibition of the Quorum Sensing System, Elastase Production and Biofilm Formation in Pseudomonas aeruginosa by Psammaplin A and Bisaprasin. Molecules. 2022 Mar 6;27(5):1721. doi: 10.3390/molecules27051721. PMID: 35268822; PMCID: PMC8911947. 3. Byun WS, Kim WK, Han HJ, Chung HJ, Jang K, Kim HS, Kim S, Kim D, Bae ES, Park S, Lee J, Park HG, Lee SK. Targeting Histone Methyltransferase DOT1L by a Novel Psammaplin A Analog Inhibits Growth and Metastasis of Triple-Negative Breast Cancer. Mol Ther Oncolytics. 2019 Oct 1;15:140-152. doi: 10.1016/j.omto.2019.09.005. PMID: 31720371; PMCID: PMC6838941. 4. Kim HJ, Kim TH, Seo WS, Yoo SD, Kim IH, Joo SH, Shin S, Park ES, Ma ES, Shin BS. Pharmacokinetics and tissue distribution of psammaplin A, a novel anticancer agent, in mice. Arch Pharm Res. 2012 Oct;35(10):1849-54. doi: 10.1007/s12272-012-1019-5. Epub 2012 Nov 9. PMID: 23139138.
In vitro protocol:	1. Ma X, Zhan C, Ma P, Jing G, Liyan S, Zhang Y, Jing Z, Liu H, Wang J, Lu W. PsA inhibits the development of bovine embryos through epigenetic and oxidative stress. Am J Vet Res. 2023 Feb 21;84(4):ajvr.22.09.0159. doi: 10.2460/ajvr.22.09.0159. PMID: 36795551. 2. Oluwabusola ET, Katermeran NP, Poh WH, Goh TMB, Tan LT, Diyaolu O, Tabudravu J, Ebel R, Rice SA, Jaspars M. Inhibition of the Quorum Sensing System, Elastase Production and Biofilm Formation in Pseudomonas aeruginosa by Psammaplin A and Bisaprasin. Molecules. 2022 Mar 6;27(5):1721. doi: 10.3390/molecules27051721. PMID: 35268822; PMCID: PMC8911947.
In vivo protocol:	1. Byun WS, Kim WK, Han HJ, Chung HJ, Jang K, Kim HS, Kim S, Kim D, Bae ES, Park S, Lee J, Park HG, Lee SK. Targeting Histone Methyltransferase DOT1L by a Novel Psammaplin A Analog Inhibits Growth and Metastasis of Triple-Negative Breast Cancer. Mol Ther Oncolytics. 2019 Oct 1;15:140-152. doi: 10.1016/j.omto.2019.09.005. PMID: 31720371; PMCID: PMC6838941. 2. Kim HJ, Kim TH, Seo WS, Yoo SD, Kim IH, Joo SH, Shin S, Park ES, Ma ES, Shin BS. Pharmacokinetics and tissue distribution of psammaplin A, a novel anticancer agent, in mice. Arch Pharm Res. 2012 Oct;35(10):1849-54. doi: 10.1007/s12272-012-1019-5. Epub 2012 Nov 9. PMID: 23139138.

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