Saliphenylhalamide| CAS#398478-65-4 | V-ATPase inhibitor

MedKoo Cat#: 208346 | Name: Saliphenylhalamide

Description:

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

SaliPhe, also known as saliphenylhalamide, is a potent inhibitor of vacuolar-type H⁺-ATPases (V-ATPases), exhibiting strong cytotoxic activity across a range of cancer cell lines. It disrupts lysosomal acidification and autophagic flux by targeting the V₀ subunit of V-ATPase, leading to impaired cellular homeostasis. In vitro, SaliPhe demonstrates low nanomolar IC₅₀ values in various tumor models, such as 20–40 nM in prostate and breast cancer cells. Mechanistically, its activity is similar to bafilomycin A1 but with improved metabolic stability. Due to its ability to induce apoptosis through lysosomal stress, Saliphenylhalamide is under investigation as a candidate for anticancer drug development.

Chemical Structure

Saliphenylhalamide

CAS#398478-65-4

Theoretical Analysis

MedKoo Cat#: 208346

Name: Saliphenylhalamide

CAS#: 398478-65-4

Chemical Formula: C28H29NO5

Exact Mass: 459.2046

Molecular Weight: 459.54

Elemental Analysis: C, 73.18; H, 6.36; N, 3.05; O, 17.41

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.

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Related CAS #

No Data

Synonym

Saliphe, Saliphenylhalamide;

IUPAC/Chemical Name

N-[(E)-3-[(4S,6R,7S,9E)-6,16-Dihydroxy-7-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-4-yl]prop-1-enyl]-3-phenylprop-2-ynamide

InChi Key

FTBLSENPBXIDKK-ZZHCZQHNSA-N

InChi Code

InChI=1S/C28H29NO5/c1-20-9-5-6-12-22-13-7-15-24(30)27(22)28(33)34-23(19-25(20)31)14-8-18-29-26(32)17-16-21-10-3-2-4-11-21/h2-8,10-11,13,15,18,20,23,25,30-31H,9,12,14,19H2,1H3,(H,29,32)/b6-5+,18-8+/t20-,23-,25+/m0/s1

SMILES Code

O=C(N/C=C/C[C@@H]1OC(C2=C(C=CC=C2O)C/C=C/C[C@H](C)[C@H](O)C1)=O)C#CC3=CC=CC=C3

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 459.54 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: Garcia-Rodriguez J, Mendiratta S, White MA, Xie XS, De Brabander JK. Synthesis and structure-activity studies of the V-ATPase inhibitor saliphenylhalamide (SaliPhe) and simplified analogs. Bioorg Med Chem Lett. 2015 Oct 15;25(20):4393-8. doi: 10.1016/j.bmcl.2015.09.021. Epub 2015 Sep 8. PMID: 26372654. 2: Bimbo LM, Denisova OV, Mäkilä E, Kaasalainen M, De Brabander JK, Hirvonen J, Salonen J, Kakkola L, Kainov D, Santos HA. Inhibition of influenza A virus infection in vitro by saliphenylhalamide-loaded porous silicon nanoparticles. ACS Nano. 2013 Aug 27;7(8):6884-93. doi: 10.1021/nn402062f. Epub 2013 Aug 1. PMID: 23889734. 3: Denisova OV, Kakkola L, Feng L, Stenman J, Nagaraj A, Lampe J, Yadav B, Aittokallio T, Kaukinen P, Ahola T, Kuivanen S, Vapalahti O, Kantele A, Tynell J, Julkunen I, Kallio-Kokko H, Paavilainen H, Hukkanen V, Elliott RM, De Brabander JK, Saelens X, Kainov DE. Obatoclax, saliphenylhalamide, and gemcitabine inhibit influenza a virus infection. J Biol Chem. 2012 Oct 12;287(42):35324-35332. doi: 10.1074/jbc.M112.392142. Epub 2012 Aug 21. PMID: 22910914; PMCID: PMC3471742. 4: Söderholm S, Anastasina M, Islam MM, Tynell J, Poranen MM, Bamford DH, Stenman J, Julkunen I, Šaulienė I, De Brabander JK, Matikainen S, Nyman TA, Saelens X, Kainov D. Immuno-modulating properties of saliphenylhalamide, SNS-032, obatoclax, and gemcitabine. Antiviral Res. 2016 Feb;126:69-80. doi: 10.1016/j.antiviral.2015.12.011. Epub 2015 Dec 29. PMID: 26738783. 5: Kuivanen S, Bespalov MM, Nandania J, Ianevski A, Velagapudi V, De Brabander JK, Kainov DE, Vapalahti O. Obatoclax, saliphenylhalamide and gemcitabine inhibit Zika virus infection in vitro and differentially affect cellular signaling, transcription and metabolism. Antiviral Res. 2017 Mar;139:117-128. doi: 10.1016/j.antiviral.2016.12.022. Epub 2016 Dec 31. PMID: 28049006. 6: Müller KH, Kainov DE, El Bakkouri K, Saelens X, De Brabander JK, Kittel C, Samm E, Muller CP. The proton translocation domain of cellular vacuolar ATPase provides a target for the treatment of influenza A virus infections. Br J Pharmacol. 2011 Sep;164(2):344-57. doi: 10.1111/j.1476-5381.2011.01346.x. PMID: 21418188; PMCID: PMC3174415. 7: Adcock RS, Chu YK, Golden JE, Chung DH. Evaluation of anti-Zika virus activities of broad-spectrum antivirals and NIH clinical collection compounds using a cell-based, high-throughput screen assay. Antiviral Res. 2017 Feb;138:47-56. doi: 10.1016/j.antiviral.2016.11.018. Epub 2016 Dec 3. PMID: 27919709. 8: Kissing S, Hermsen C, Repnik U, Nesset CK, von Bargen K, Griffiths G, Ichihara A, Lee BS, Schwake M, De Brabander J, Haas A, Saftig P. Vacuolar ATPase in phagosome-lysosome fusion. J Biol Chem. 2015 May 29;290(22):14166-80. doi: 10.1074/jbc.M114.628891. Epub 2015 Apr 22. PMID: 25903133; PMCID: PMC4447986. 9: Bodzęta A, Kahms M, Klingauf J. The Presynaptic v-ATPase Reversibly Disassembles and Thereby Modulates Exocytosis but Is Not Part of the Fusion Machinery. Cell Rep. 2017 Aug 8;20(6):1348-1359. doi: 10.1016/j.celrep.2017.07.040. PMID: 28793259. 10: Müller KH, Spoden GA, Scheffer KD, Brunnhöfer R, De Brabander JK, Maier ME, Florin L, Muller CP. Inhibition by cellular vacuolar ATPase impairs human papillomavirus uncoating and infection. Antimicrob Agents Chemother. 2014 May;58(5):2905-11. doi: 10.1128/AAC.02284-13. Epub 2014 Mar 10. PMID: 24614368; PMCID: PMC3993236.