MedKoo Cat#: 574850 | Name: Psammaplin A
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Description:

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

Psammaplin A is a symmetrical bromotyrosine-derived disulfide marine metabolite which is seen to possibly inhibit HDAC1/2/3 through its thiol monomer. Psammaplin A possesses histone deacetylase (HDAC) inhibition and acts through reduced monomer PsA-SH.

Chemical Structure

Psammaplin A
Psammaplin A
CAS#110659-91-1

Theoretical Analysis

MedKoo Cat#: 574850

Name: Psammaplin A

CAS#: 110659-91-1

Chemical Formula: C22H24Br2N4O6S2

Exact Mass: 661.9504

Molecular Weight: 664.38

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 Quantity
5mg USD 340.00 2 Weeks
10mg USD 525.00 2 Weeks
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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
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.

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:
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.
1: Jiang Y, Tang Y, Li Y, Liu L, Yue K, Li X, Qiu P, Yin R, Jiang T. Psammaplin A analogues with modified disulfide bond targeting histone deacetylases: Synthesis and biological evaluation. Eur J Med Chem. 2024 Sep 5;275:116541. doi: 10.1016/j.ejmech.2024.116541. Epub 2024 May 31. PMID: 38851056. 2: Alvariño R, Alfonso A, Tabudravu JN, González-Jartín J, Al Maqbali KS, Elhariry M, Vieytes MR, Botana LM. Psammaplin A and Its Analogs Attenuate Oxidative Stress in Neuronal Cells through Peroxisome Proliferator-Activated Receptor γ Activation. J Nat Prod. 2024 Apr 26;87(4):1187-1196. doi: 10.1021/acs.jnatprod.4c00153. Epub 2024 Apr 17. PMID: 38632902; PMCID: PMC11061836. 3: 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. 4: Maietta I, Martínez-Pérez A, Álvarez R, De Lera ÁR, González-Fernández Á, Simón-Vázquez R. Synergistic Antitumoral Effect of Epigenetic Inhibitors and Gemcitabine in Pancreatic Cancer Cells. Pharmaceuticals (Basel). 2022 Jul 2;15(7):824. doi: 10.3390/ph15070824. PMID: 35890123; PMCID: PMC9323654. 5: 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. 6: Ju Han H, Sub Byun W, Ho Lee G, Kyung Kim W, Jang K, Yang S, Yang J, Woo Ha M, Hong S, Lee J, Shin J, Bong Oh K, Kook Lee S, Park HG. Synthesis and biological activity of selenopsammaplin A and its analogues as antitumor agents with DOT1L inhibitory activity. Bioorg Med Chem. 2021 Apr 1;35:116072. doi: 10.1016/j.bmc.2021.116072. Epub 2021 Feb 11. PMID: 33636429. 7: Bao Y, Xu Q, Wang L, Wei Y, Hu B, Wang J, Liu D, Zhao L, Jing Y. Studying Histone Deacetylase Inhibition and Apoptosis Induction of Psammaplin A Monomers with Modified Thiol Group. ACS Med Chem Lett. 2021 Jan 5;12(1):39-47. doi: 10.1021/acsmedchemlett.0c00369. PMID: 33488962; PMCID: PMC7812609. 8: Oluwabusola ET, Tabudravu JN, Al Maqbali KS, Annang F, Pérez-Moreno G, Reyes F, Jaspars M. Antiparasitic Activity of Bromotyrosine Alkaloids and New Analogues Isolated from the Fijian Marine Sponge Aplysinella rhax. Chem Biodivers. 2020 Oct;17(10):e2000335. doi: 10.1002/cbdv.202000335. Epub 2020 Sep 29. PMID: 32697400. 9: Hayashi-Takanaka Y, Kina Y, Nakamura F, Becking LE, Nakao Y, Nagase T, Nozaki N, Kimura H. Histone modification dynamics as revealed by multicolor immunofluorescence-based single-cell analysis. J Cell Sci. 2020 Jul 21;133(14):jcs243444. doi: 10.1242/jcs.243444. PMID: 32576661; PMCID: PMC7390643. 10: 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. 11: Jing Q, Hu X, Ma Y, Mu J, Liu W, Xu F, Li Z, Bai J, Hua H, Li D. Marine- Derived Natural Lead Compound Disulfide-Linked Dimer Psammaplin A: Biological Activity and Structural Modification. Mar Drugs. 2019 Jun 27;17(7):384. doi: 10.3390/md17070384. PMID: 31252563; PMCID: PMC6669562. 12: Zhang B, Shan G, Zheng Y, Yu X, Ruan ZW, Li Y, Lei X. Synthesis and Preliminary Biological Evaluation of Two Fluoroolefin Analogs of Largazole Inspired by the Structural Similarity of the Side Chain Unit in Psammaplin A. Mar Drugs. 2019 Jun 3;17(6):333. doi: 10.3390/md17060333. PMID: 31163697; PMCID: PMC6628159. 13: Andjouh S, Blache Y. Parallel synthesis of a bis-triazoles library as psammaplin A analogues: A new wave of antibiofilm compounds? Bioorg Med Chem Lett. 2019 Feb 15;29(4):614-618. doi: 10.1016/j.bmcl.2018.12.047. Epub 2018 Dec 21. PMID: 30600205. 14: Zhou YD, Li J, Du L, Mahdi F, Le TP, Chen WL, Swanson SM, Watabe K, Nagle DG. Biochemical and Anti-Triple Negative Metastatic Breast Tumor Cell Properties of Psammaplins. Mar Drugs. 2018 Nov 10;16(11):442. doi: 10.3390/md16110442. PMID: 30423844; PMCID: PMC6265740. 15: Franci G, Folliero V, Cammarota M, Zannella C, Sarno F, Schiraldi C, de Lera AR, Altucci L, Galdiero M. Epigenetic modulator UVI5008 inhibits MRSA by interfering with bacterial gyrase. Sci Rep. 2018 Sep 3;8(1):13117. doi: 10.1038/s41598-018-31135-9. PMID: 30177735; PMCID: PMC6120918. 16: Richard K, Williams DE, de Silva ED, Brockman MA, Brumme ZL, Andersen RJ, Tietjen I. Identification of Novel HIV-1 Latency-Reversing Agents from a Library of Marine Natural Products. Viruses. 2018 Jun 27;10(7):348. doi: 10.3390/v10070348. PMID: 29954099; PMCID: PMC6071113. 17: Samiec M, Skrzyszowska M. Intrinsic and extrinsic molecular determinants or modulators for epigenetic remodeling and reprogramming of somatic cell-derived genome in mammalian nuclear-transferred oocytes and resultant embryos. Pol J Vet Sci. 2018 Mar;21(1):217-227. doi: 10.24425/119040. PMID: 29624006. 18: Cincinelli R, Musso L, Artali R, Guglielmi M, Bianchino E, Cardile F, Colelli F, Pisano C, Dallavalle S. Camptothecin-psammaplin A hybrids as topoisomerase I and HDAC dual-action inhibitors. Eur J Med Chem. 2018 Jan 1;143:2005-2014. doi: 10.1016/j.ejmech.2017.11.021. Epub 2017 Nov 8. PMID: 29150335. 19: Traoré MDM, Zwick V, Simões-Pires CA, Nurisso A, Issa M, Cuendet M, Maynadier M, Wein S, Vial H, Jamet H, Wong YS. Hydroxyl Ketone-Based Histone Deacetylase Inhibitors To Gain Insight into Class I HDAC Selectivity versus That of HDAC6. ACS Omega. 2017 Apr 30;2(4):1550-1562. doi: 10.1021/acsomega.6b00481. Epub 2017 Apr 20. PMID: 30023639; PMCID: PMC6044785. 20: Bagnall NH, Hines BM, Lucke AJ, Gupta PK, Reid RC, Fairlie DP, Kotze AC. Insecticidal activities of histone deacetylase inhibitors against a dipteran parasite of sheep, Lucilia cuprina. Int J Parasitol Drugs Drug Resist. 2017 Apr;7(1):51-60. doi: 10.1016/j.ijpddr.2017.01.001. Epub 2017 Jan 10. PMID: 28110187; PMCID: PMC5247571.