Dyngo-4a | CAS#1256493-34-1 | dynamin inhibitor

MedKoo Cat#: 562445 | Name: Dyngo-4a

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Description:

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

Dyngo-4a is a dynamin inhibitor.

Chemical Structure

Dyngo-4a

CAS#1256493-34-1

Theoretical Analysis

MedKoo Cat#: 562445

Name: Dyngo-4a

CAS#: 1256493-34-1

Chemical Formula: C18H14N2O5

Exact Mass: 338.0903

Molecular Weight: 338.32

Elemental Analysis: C, 63.90; H, 4.17; N, 8.28; O, 23.64

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,450.00	2 Weeks
1g	USD 3,250.00	2 Weeks
2g	USD 5,450.00	2 Weeks

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Synonym

Dyngo-4a; Dyngo 4a; Dyngo4a; Hydroxy Dynasore; Hydroxy-Dynasore

IUPAC/Chemical Name

3-Hydroxynaphthalene-2-carboxylic acid 2-[(2,4,5-trihydroxyphenyl)methylene]hydrazide

InChi Key

UAXHPUSKEWEOAP-DJKKODMXSA-N

InChi Code

InChI=1S/C18H14N2O5/c21-14-8-17(24)16(23)7-12(14)9-19-20-18(25)13-5-10-3-1-2-4-11(10)6-15(13)22/h1-9,21-24H,(H,20,25)/b19-9+

SMILES Code

O=C(C1=C(O)C=C2C=CC=CC2=C1)N/N=C/C3=CC(O)=C(O)C=C3O

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:

Hydroxy Dynasore (Dyngo-4a), a structural analog of Dynasore (HY-15304), is an potency improved, low cytotoxicity and non‐specific binding Dynamin inhibitor with IC50 values of 0.38 μM and 2.3 μM for brain dynamin I and recombinant rat dynamin II, respectively.

In vitro activity:

Dyngo-4a induced Neuro-2a cell differentiation and increased Tuj-1 positive staining by the 6th day post- treatment. Dyngo-4a also inhibited Neuro-2a cell proliferation in a dose-dependent manner. Regarding the mechanism, dyngo-4a treatment showed a significant increase in p-AKT and p-ERK1/2 but not in p-EGFR. Conclusion At a level comparable to RA, dynamin inhibition with dyngo-4a lowers proliferation and causes differentiation of Neuro-2a mouse NB cells in vitro. Reference: CNS Neurol Disord Drug Targets. 2022 Dec 2. https://pubmed.ncbi.nlm.nih.gov/36476431/

In vivo activity:

Two pharmacological inhibitors of dynamin, dynasore and Dyngo-4a, blocked the in vitro induction of acrosomal exocytosis by progesterone, but not by the calcium ionophore A23187, and elicited a concomitant reduction of in vitro fertilization. In vivo treatment with these inhibitors also resulted in spermatozoa displaying reduced acrosome reaction potential. Dynamin 1 and 2 phosphorylation increased on progesterone treatment, and this was also selectively blocked by dynasore. Reference: J Biol Chem. 2012 Nov 2;287(45):37659-72. https://pubmed.ncbi.nlm.nih.gov/22977254/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	88.67
	DMSO	48.2	142.42
	DMSO:PBS (pH 7.2) (1:3)	0.3	0.74

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 338.32 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. Huang J, Zhou Y, Zheng S, Xu J, Liu L, Grothusen J, Liu R. Dyngo-4a induces neuroblastoma cell differentiation through the AKT and ERK1/2 pathway. CNS Neurol Disord Drug Targets. 2022 Dec 2. doi: 10.2174/1871527322666221202145437. Epub ahead of print. PMID: 36476431. 2. Strauch BM, Hubele W, Hartwig A. Impact of Endocytosis and Lysosomal Acidification on the Toxicity of Copper Oxide Nano- and Microsized Particles: Uptake and Gene Expression Related to Oxidative Stress and the DNA Damage Response. Nanomaterials (Basel). 2020 Apr 3;10(4):679. doi: 10.3390/nano10040679. PMID: 32260290; PMCID: PMC7221514. 3. Reid AT, Lord T, Stanger SJ, Roman SD, McCluskey A, Robinson PJ, Aitken RJ, Nixon B. Dynamin regulates specific membrane fusion events necessary for acrosomal exocytosis in mouse spermatozoa. J Biol Chem. 2012 Nov 2;287(45):37659-72. doi: 10.1074/jbc.M112.392803. Epub 2012 Sep 12. PMID: 22977254; PMCID: PMC3488043. 4. Harper CB, Martin S, Nguyen TH, Daniels SJ, Lavidis NA, Popoff MR, Hadzic G, Mariana A, Chau N, McCluskey A, Robinson PJ, Meunier FA. Dynamin inhibition blocks botulinum neurotoxin type A endocytosis in neurons and delays botulism. J Biol Chem. 2011 Oct 14;286(41):35966-35976. doi: 10.1074/jbc.M111.283879. Epub 2011 Aug 5. PMID: 21832053; PMCID: PMC3195592.

In vitro protocol:

In vivo protocol:

1. Reid AT, Lord T, Stanger SJ, Roman SD, McCluskey A, Robinson PJ, Aitken RJ, Nixon B. Dynamin regulates specific membrane fusion events necessary for acrosomal exocytosis in mouse spermatozoa. J Biol Chem. 2012 Nov 2;287(45):37659-72. doi: 10.1074/jbc.M112.392803. Epub 2012 Sep 12. PMID: 22977254; PMCID: PMC3488043. 2. Harper CB, Martin S, Nguyen TH, Daniels SJ, Lavidis NA, Popoff MR, Hadzic G, Mariana A, Chau N, McCluskey A, Robinson PJ, Meunier FA. Dynamin inhibition blocks botulinum neurotoxin type A endocytosis in neurons and delays botulism. J Biol Chem. 2011 Oct 14;286(41):35966-35976. doi: 10.1074/jbc.M111.283879. Epub 2011 Aug 5. PMID: 21832053; PMCID: PMC3195592.

1: Huang J, Zhou Y, Zeng S, Xu J, Liu L, Grothusen J, Liu R. Dyngo-4a Induces Neuroblastoma Cell Differentiation Through The AKT and ERK1/2 Pathway. CNS Neurol Disord Drug Targets. 2023;22(10):1526-1534. doi: 10.2174/1871527322666221202145437. PMID: 36476431. 2: Zhang Q, Zhang Q, Xu Z, Tang Q, Liu X, Niu D, Gao X, Lan K, Wu S. Dyngo-4a protects mice from rotavirus infection by affecting the formation of dynamin 2 oligomers. Sci Bull (Beijing). 2020 Nov 15;65(21):1796-1799. doi: 10.1016/j.scib.2020.07.029. Epub 2020 Jul 25. PMID: 36659118. 3: Robertson MJ, Deane FM, Robinson PJ, McCluskey A. Synthesis of Dynole 34-2, Dynole 2-24 and Dyngo 4a for investigating dynamin GTPase. Nat Protoc. 2014 Apr;9(4):851-70. doi: 10.1038/nprot.2014.046. Epub 2014 Mar 20. PMID: 24651498. 4: Ahmed A, Trezza A, Gentile M, Paccagnini E, Panti A, Lupetti P, Spiga O, Bova S, Fusi F. Dynamin-independent CaV1.2 and KCa1.1 channels regulation and vascular tone modulation by the mitochondrial fission inhibitors dynasore and dyngo-4a. Eur J Pharmacol. 2023 Jul 15;951:175786. doi: 10.1016/j.ejphar.2023.175786. Epub 2023 May 11. PMID: 37179045. 5: McCluskey A, Daniel JA, Hadzic G, Chau N, Clayton EL, Mariana A, Whiting A, Gorgani NN, Lloyd J, Quan A, Moshkanbaryans L, Krishnan S, Perera S, Chircop M, von Kleist L, McGeachie AB, Howes MT, Parton RG, Campbell M, Sakoff JA, Wang X, Sun JY, Robertson MJ, Deane FM, Nguyen TH, Meunier FA, Cousin MA, Robinson PJ. Building a better dynasore: the dyngo compounds potently inhibit dynamin and endocytosis. Traffic. 2013 Dec;14(12):1272-89. doi: 10.1111/tra.12119. Epub 2013 Oct 9. PMID: 24025110; PMCID: PMC4138991. 6: Zhang X, Chen X, Lu L, Fang Q, Liu C, Lin Z. Identification of small-molecule inhibitors of human MUS81-EME1/2 by FRET-based high-throughput screening. Bioorg Med Chem. 2023 Jul 15;90:117383. doi: 10.1016/j.bmc.2023.117383. Epub 2023 Jun 19. PMID: 37352577. 7: Zhang Y, Zhu J, Xu H, Yi Q, Yan L, Ye L, Zhang X, Tan B. [The off-target effects of dynamin inhibitor Dyngo-4a during the internalization of dextran by bone marrow mesenchymal stem cells in rat]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2023 Jan;39(1):57-62. Chinese. PMID: 36631016. 8: Pergel E, Veres I, Csigi GI, Czirják G. Translocation of TMEM175 Lysosomal Potassium Channel to the Plasma Membrane by Dynasore Compounds. Int J Mol Sci. 2021 Sep 29;22(19):10515. doi: 10.3390/ijms221910515. PMID: 34638858; PMCID: PMC8508992. 9: Harper CB, Martin S, Nguyen TH, Daniels SJ, Lavidis NA, Popoff MR, Hadzic G, Mariana A, Chau N, McCluskey A, Robinson PJ, Meunier FA. Dynamin inhibition blocks botulinum neurotoxin type A endocytosis in neurons and delays botulism. J Biol Chem. 2011 Oct 14;286(41):35966-35976. doi: 10.1074/jbc.M111.283879. Epub 2011 Aug 5. PMID: 21832053; PMCID: PMC3195592. 10: Xi C, Liang X, Chen C, Babazada H, Li T, Liu R. Hypoxia Induces Internalization of κ-Opioid Receptor. Anesthesiology. 2017 May;126(5):842-854. doi: 10.1097/ALN.0000000000001571. PMID: 28230651; PMCID: PMC5395330. 11: Mohanakrishnan A, Tran TVM, Kumar M, Chen H, Posner BA, Schmid SL. A highly- sensitive high throughput assay for dynamin's basal GTPase activity. PLoS One. 2017 Sep 28;12(9):e0185639. doi: 10.1371/journal.pone.0185639. PMID: 28957392; PMCID: PMC5619819. 12: Basagiannis D, Zografou S, Goula E, Gkeka D, Kolettas E, Christoforidis S. Chemical Inhibitors of Dynamin Exert Differential Effects in VEGF Signaling. Cells. 2021 Apr 23;10(5):997. doi: 10.3390/cells10050997. PMID: 33922806; PMCID: PMC8145957. 13: Li E, Loen V, van Ham WB, Kool W, van der Heyden MAG, Takanari H. Quantitative Analysis of the Cytoskeleton's Role in Inward Rectifier K IR 2.1 Forward and Backward Trafficking. Front Physiol. 2022 Jan 25;12:812572. doi: 10.3389/fphys.2021.812572. PMID: 35145427; PMCID: PMC8821923. 14: Jang D, Eliseeva E, Klubo-Gwiezdzinska J, Neumann S, Gershengorn MC. TSH stimulation of human thyroglobulin and thyroid peroxidase gene transcription is partially dependent on internalization. Cell Signal. 2022 Feb;90:110212. doi: 10.1016/j.cellsig.2021.110212. Epub 2021 Dec 9. PMID: 34896620; PMCID: PMC8725617. 15: Xu J, Chen F, Wang S, Akins NS, Hossain MI, Zhou Y, Huang J, Ji J, Xi J, Lin W, Grothusen J, Le HV, Liu R. Kappa opioid receptors internalization is protective against oxygen-glucose deprivation through β-arrestin activation and Akt-mediated signaling pathway. Neurochem Int. 2020 Jul;137:104748. doi: 10.1016/j.neuint.2020.104748. Epub 2020 Apr 24. PMID: 32339667; PMCID: PMC7321825. 16: Heldin J, Sander MR, Leino M, Thomsson S, Lennartsson J, Söderberg O. Dynamin inhibitors impair platelet-derived growth factor β-receptor dimerization and signaling. Exp Cell Res. 2019 Jul 1;380(1):69-79. doi: 10.1016/j.yexcr.2019.04.004. Epub 2019 Apr 7. PMID: 30970237. 17: Kogel A, Fecher-Trost C, Wissenbach U, Flockerzi V, Schaefer M. Ca2+ transport via TRPV6 is regulated by rapid internalization of the channel. Cell Calcium. 2022 Sep;106:102634. doi: 10.1016/j.ceca.2022.102634. Epub 2022 Jul 16. PMID: 35917684. 18: Seki H, Xue S, Hixon MS, Pellett S, Remes M, Johnson EA, Janda KD. Toward the discovery of dual inhibitors for botulinum neurotoxin A: concomitant targeting of endocytosis and light chain protease activity. Chem Commun (Camb). 2015 Apr 11;51(28):6226-9. doi: 10.1039/c5cc00677e. PMID: 25759983. 19: Dunn VK, Gleason E. Inhibition of endocytosis suppresses the nitric oxide- dependent release of Cl- in retinal amacrine cells. PLoS One. 2018 Jul 25;13(7):e0201184. doi: 10.1371/journal.pone.0201184. PMID: 30044876; PMCID: PMC6059450. 20: von Beek C, Alriksson L, Palle J, Gustafson AM, Grujic M, Melo FR, Sellin ME, Pejler G. Dynamin inhibition causes context-dependent cell death of leukemia and lymphoma cells. PLoS One. 2021 Sep 7;16(9):e0256708. doi: 10.1371/journal.pone.0256708. PMID: 34492077; PMCID: PMC8423305.