ML355 free base
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MedKoo CAT#: 533249

CAS#: 1532593-30-8

Description: ML355 is a potent and selective inhibitor of human 12-lipoxygenase.

Chemical Structure

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ML355 free base
CAS# 1532593-30-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 533249
Name: ML355 free base
CAS#: 1532593-30-8
Chemical Formula: C21H19N3O4S2
Exact Mass: 441.08
Molecular Weight: 441.520
Elemental Analysis: C, 57.13; H, 4.34; N, 9.52; O, 14.49; S, 14.52

Price and Availability

Size Price Availability Quantity
5g USD -1 2 Weeks
50mg USD 350 2 Weeks
100mg USD 550 2 Weeks
200mg USD 950 2 Weeks
500mg USD 1850 2 Weeks
1g USD 2950 2 Weeks
2g USD 5250 2 Weeks
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Synonym: ML355; ML 355; ML-355.

IUPAC/Chemical Name: N-2-benzothiazolyl-4-[[(2-hydroxy-3-methoxyphenyl)methyl]amino]-benzenesulfonamide

InChi Key: OWHBVKBNNRYMIN-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H19N3O4S2/c1-28-18-7-4-5-14(20(18)25)13-22-15-9-11-16(12-10-15)30(26,27)24-21-23-17-6-2-3-8-19(17)29-21/h2-12,22,25H,13H2,1H3,(H,23,24)

SMILES Code: O=S(C1=CC=C(NCC2=CC=CC(OC)=C2O)C=C1)(NC3=NC4=CC=CC=C4S3)=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

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: ML355 is a potent and selective inhibitor of 12-Lipoxygenase (12-LOX) with an IC50 of 0.34 μM.
In vitro activity: Here, this study showed that ML355 inhibited platelet activation induced by thrombin or thromboxane A2, but not by collagen-related peptide. ML355 blocked protein kinase B, phosphoinositide 3-kinase, and extracellular signal-regulated kinase, but not p38 kinase, spleen tyrosine kinase (Syk), or phospholipase Cγ2 phosphorylation in activated platelets. The main inhibitory effect of low doses of ML355 (1-20 μM) on thrombin activated platelets was mediated by the decrease in reactive oxygen species level, whereas high doses of ML355 (50 μM) caused cyclic adenosine monophosphate activation. Reference: J Pharmacol Exp Ther. 2022 May;381(2):164-175. https://pubmed.ncbi.nlm.nih.gov/35197320/
In vivo activity: To assess if the ALOX-12 inhibitor ML355 has any therapeutic potential, in vivo studies in mice were initiated. ML355 was administered to mice 30 minutes before GEN injection. Mice receiving GEN had cytolysis and vacuolization of epithelia, with loss of tubular brush border, as compared with control mice (Figure 9, A, B, and L). With concomitant administration of ML355, the normal morphology of tubular epithelia was largely restored and had features similar to the control (Figure 9, A, C, and L). Interestingly, some of the other renal functional parameters, such as urinary protein excretion, were also restored to normal with attenuation of albuminuria following ML355 treatment (Figure 9K). Reference: JCI Insight. 2022 Mar 22;7(6):e155487. https://pubmed.ncbi.nlm.nih.gov/35315361/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 1.0 2.26
DMSO 43.7 98.90
DMSO:PBS (pH 7.2) (1:3) 0.3 0.57

Preparing Stock Solutions

The following data is based on the product molecular weight 441.52 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.

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. Shpakova V, Rukoyatkina N, Al Arawe N, Prilepskaya A, Kharazova A, Sharina I, Gambaryan S, Martin E. ML355 Modulates Platelet Activation and Prevents ABT-737 Induced Apoptosis in Platelets. J Pharmacol Exp Ther. 2022 May;381(2):164-175. doi: 10.1124/jpet.121.000973. Epub 2022 Feb 23. PMID: 35197320; PMCID: PMC9073945. 2. Ma K, Xiao A, Park SH, Glenn L, Jackson L, Barot T, Weaver JR, Taylor-Fishwick DA, Luci DK, Maloney DJ, Mirmira RG, Imai Y, Nadler JL. 12-Lipoxygenase Inhibitor Improves Functions of Cytokine-Treated Human Islets and Type 2 Diabetic Islets. J Clin Endocrinol Metab. 2017 Aug 1;102(8):2789-2797. doi: 10.1210/jc.2017-00267. PMID: 28609824; PMCID: PMC5546865. 3. Sharma I, Liao Y, Zheng X, Kanwar YS. Modulation of gentamicin-induced acute kidney injury by myo-inositol oxygenase via the ROS/ALOX-12/12-HETE/GPR31 signaling pathway. JCI Insight. 2022 Mar 22;7(6):e155487. doi: 10.1172/jci.insight.155487. PMID: 35315361; PMCID: PMC8986073. 4. He H, Adili R, Liu L, Hong K, Holinstat M, Schwendeman A. Synthetic high-density lipoproteins loaded with an antiplatelet drug for efficient inhibition of thrombosis in mice. Sci Adv. 2020 Dec 4;6(49):eabd0130. doi: 10.1126/sciadv.abd0130. PMID: 33277254; PMCID: PMC7821904.
In vitro protocol: 1. Shpakova V, Rukoyatkina N, Al Arawe N, Prilepskaya A, Kharazova A, Sharina I, Gambaryan S, Martin E. ML355 Modulates Platelet Activation and Prevents ABT-737 Induced Apoptosis in Platelets. J Pharmacol Exp Ther. 2022 May;381(2):164-175. doi: 10.1124/jpet.121.000973. Epub 2022 Feb 23. PMID: 35197320; PMCID: PMC9073945. 2. Ma K, Xiao A, Park SH, Glenn L, Jackson L, Barot T, Weaver JR, Taylor-Fishwick DA, Luci DK, Maloney DJ, Mirmira RG, Imai Y, Nadler JL. 12-Lipoxygenase Inhibitor Improves Functions of Cytokine-Treated Human Islets and Type 2 Diabetic Islets. J Clin Endocrinol Metab. 2017 Aug 1;102(8):2789-2797. doi: 10.1210/jc.2017-00267. PMID: 28609824; PMCID: PMC5546865.
In vivo protocol: 1. Sharma I, Liao Y, Zheng X, Kanwar YS. Modulation of gentamicin-induced acute kidney injury by myo-inositol oxygenase via the ROS/ALOX-12/12-HETE/GPR31 signaling pathway. JCI Insight. 2022 Mar 22;7(6):e155487. doi: 10.1172/jci.insight.155487. PMID: 35315361; PMCID: PMC8986073. 2. He H, Adili R, Liu L, Hong K, Holinstat M, Schwendeman A. Synthetic high-density lipoproteins loaded with an antiplatelet drug for efficient inhibition of thrombosis in mice. Sci Adv. 2020 Dec 4;6(49):eabd0130. doi: 10.1126/sciadv.abd0130. PMID: 33277254; PMCID: PMC7821904.

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1: Luci D, Jameson JB II, Yasgar A, Diaz G, Joshi N, Kantz A, Markham K, Perry S, Kuhn N, Yeung J, Schultz L, Holinstat M, Nadler J, Taylor-Fishwick DA, Jadhav A, Simeonov A, Holman TR, Maloney DJ. Discovery of ML355, a Potent and Selective Inhibitor of Human 12-Lipoxygenase. 2013 Apr 12 [updated 2014 Sep 18]. Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010-. Available from http://www.ncbi.nlm.nih.gov/books/NBK259188/ PubMed PMID: 25506969.