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MedKoo Cat#: 562764 | Name: HNHA
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Description:

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

HNHA is a histone deacetylase (HDAC) inhibitor.

Chemical Structure

HNHA
HNHA
CAS#926908-04-5

Theoretical Analysis

MedKoo Cat#: 562764

Name: HNHA

CAS#: 926908-04-5

Chemical Formula: C17H21NO2S

Exact Mass: 303.1293

Molecular Weight: 303.42

Elemental Analysis: C, 67.30; H, 6.98; N, 4.62; O, 10.55; S, 10.57

Price and Availability

Size Price Availability Quantity
5mg USD 285.00 2 Weeks
10mg USD 450.00 2 Weeks
25mg USD 850.00 2 Weeks
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Related CAS #
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Synonym
HNHA;
IUPAC/Chemical Name
7-(Naphthalen-2-ylsulfanyl)-heptanoic acid hydroxyamide
InChi Key
KPNNXHVGOKRBEF-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H21NO2S/c19-17(18-20)9-3-1-2-6-12-21-16-11-10-14-7-4-5-8-15(14)13-16/h4-5,7-8,10-11,13,20H,1-3,6,9,12H2,(H,18,19)
SMILES Code
O=C(NO)CCCCCCSC1=CC=C2C=CC=CC2=C1
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:
HNHA is a potent histone deacetylase (HDAC) inhibitor.
In vitro activity:
To investigate the anti-cancer activity of HNHA alongside two well-known HDAC inhibitors (TSA and SAHA), this study assayed ATC (SNU-80) and PTC (SNU-790) cell proliferation in the presence and absence of these compounds using an MTT assay (Table 1). HNHA had a lower half-maximal inhibitory concentration (IC50) than TSA and SAHA in ATC and PTC cells. Further characterization of the effects of HDAC inhibitors on ATC and PTC cell viability showed that they all reduced the viability of ATC and PTC cells, as compared to vehicle control-treated cells. However, HNHA provided the most significant suppression of cell proliferation (Fig. 1a and c) and this effect was concentration-dependent (Fig. 1b and d). Reference: BMC Cancer. 2015 Dec 23;15:1003. https://pubmed.ncbi.nlm.nih.gov/26698299/
In vivo activity:
HNHA, FUMA and SAHA were injected intraperitoneally to evaluate their effect in vivo. The HNHA-treated group had smaller tumor volumes and survived longer than the other groups (Fig. 5a). In addition, the survival rate of the HNHA-treated group was higher than the other groups (Fig. 5b). Reference: Cancer Sci. 2011 Feb;102(2):343-50. https://pubmed.ncbi.nlm.nih.gov/21159061/
Solvent mg/mL mM
Solubility
DMSO 30.0 98.87
DMSO:PBS (pH 7.2) (1:1) 0.5 1.65
Ethanol 20.0 65.92
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 303.42 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. Kim SM, Park KC, Jeon JY, Kim BW, Kim HK, Chang HJ, Choi SH, Park CS, Chang HS. Potential anti-cancer effect of N-hydroxy-7-(2-naphthylthio) heptanomide (HNHA), a novel histone deacetylase inhibitor, for the treatment of thyroid cancer. BMC Cancer. 2015 Dec 23;15:1003. doi: 10.1186/s12885-015-1982-6. PMID: 26698299; PMCID: PMC4690331. 2. Park KC, Kim SW, Park JH, Song EH, Yang JW, Chung HJ, Jung HJ, Suh JS, Kwon HJ, Choi SH. Potential anti-cancer activity of N-hydroxy-7-(2-naphthylthio) heptanomide (HNHA), a histone deacetylase inhibitor, against breast cancer both in vitro and in vivo. Cancer Sci. 2011 Feb;102(2):343-50. doi: 10.1111/j.1349-7006.2010.01798.x. Epub 2010 Dec 15. PMID: 21159061.
In vitro protocol:
1. Kim SM, Park KC, Jeon JY, Kim BW, Kim HK, Chang HJ, Choi SH, Park CS, Chang HS. Potential anti-cancer effect of N-hydroxy-7-(2-naphthylthio) heptanomide (HNHA), a novel histone deacetylase inhibitor, for the treatment of thyroid cancer. BMC Cancer. 2015 Dec 23;15:1003. doi: 10.1186/s12885-015-1982-6. PMID: 26698299; PMCID: PMC4690331. 2. Park KC, Kim SW, Park JH, Song EH, Yang JW, Chung HJ, Jung HJ, Suh JS, Kwon HJ, Choi SH. Potential anti-cancer activity of N-hydroxy-7-(2-naphthylthio) heptanomide (HNHA), a histone deacetylase inhibitor, against breast cancer both in vitro and in vivo. Cancer Sci. 2011 Feb;102(2):343-50. doi: 10.1111/j.1349-7006.2010.01798.x. Epub 2010 Dec 15. PMID: 21159061.
In vivo protocol:
1. Kim SM, Park KC, Jeon JY, Kim BW, Kim HK, Chang HJ, Choi SH, Park CS, Chang HS. Potential anti-cancer effect of N-hydroxy-7-(2-naphthylthio) heptanomide (HNHA), a novel histone deacetylase inhibitor, for the treatment of thyroid cancer. BMC Cancer. 2015 Dec 23;15:1003. doi: 10.1186/s12885-015-1982-6. PMID: 26698299; PMCID: PMC4690331. 2. Park KC, Kim SW, Park JH, Song EH, Yang JW, Chung HJ, Jung HJ, Suh JS, Kwon HJ, Choi SH. Potential anti-cancer activity of N-hydroxy-7-(2-naphthylthio) heptanomide (HNHA), a histone deacetylase inhibitor, against breast cancer both in vitro and in vivo. Cancer Sci. 2011 Feb;102(2):343-50. doi: 10.1111/j.1349-7006.2010.01798.x. Epub 2010 Dec 15. PMID: 21159061.
1: Lee YS, Kim SM, Kim BW, Chang HJ, Kim SY, Park CS, Park KC, Chang HS. Anti-cancer Effects of HNHA and Lenvatinib by the Suppression of EMT-Mediated Drug Resistance in Cancer Stem Cells. Neoplasia. 2018 Feb;20(2):197-206. doi: 10.1016/j.neo.2017.12.003. Epub 2018 Jan 12. PubMed PMID: 29331886; PubMed Central PMCID: PMC5767911. 2: Park KC, Kim SM, Jeon JY, Kim BW, Kim HK, Chang HJ, Lee YS, Kim SY, Choi SH, Park CS, Chang HS. Synergistic Activity of N-hydroxy-7-(2-naphthylthio) Heptanomide and Sorafenib Against Cancer Stem Cells, Anaplastic Thyroid Cancer. Neoplasia. 2017 Mar;19(3):145-153. doi: 10.1016/j.neo.2016.12.005. Epub 2017 Jan 28. PubMed PMID: 28142087; PubMed Central PMCID: PMC5279904. 3: Kim SM, Park KC, Jeon JY, Kim BW, Kim HK, Chang HJ, Choi SH, Park CS, Chang HS. Potential anti-cancer effect of N-hydroxy-7-(2-naphthylthio) heptanomide (HNHA), a novel histone deacetylase inhibitor, for the treatment of thyroid cancer. BMC Cancer. 2015 Dec 23;15:1003. doi: 10.1186/s12885-015-1982-6. PubMed PMID: 26698299; PubMed Central PMCID: PMC4690331. 4: Park KC, Heo JH, Jeon JY, Choi HJ, Jo AR, Kim SW, Kwon HJ, Hong SJ, Han KS. The novel histone deacetylase inhibitor, N-hydroxy-7-(2-naphthylthio) hepatonomide, exhibits potent antitumor activity due to cytochrome-c-release-mediated apoptosis in renal cell carcinoma cells. BMC Cancer. 2015 Jan 23;15:19. doi: 10.1186/s12885-014-1003-1. PubMed PMID: 25613585; PubMed Central PMCID: PMC4318161. 5: Park KC, Park JH, Jeon JY, Kim SY, Kim JM, Lim CY, Lee TH, Kim HK, Lee HG, Kim SM, Kwon HJ, Suh JS, Kim SW, Choi SH. A new histone deacetylase inhibitor improves liver fibrosis in BDL rats through suppression of hepatic stellate cells. Br J Pharmacol. 2014 Nov;171(21):4820-30. doi: 10.1111/bph.12590. Epub 2014 Sep 5. PubMed PMID: 24467283; PubMed Central PMCID: PMC4232907. 6: Rosenman DJ, Connors CR, Chen W, Wang C, García AE. Aβ monomers transiently sample oligomer and fibril-like configurations: ensemble characterization using a combined MD/NMR approach. J Mol Biol. 2013 Sep 23;425(18):3338-59. doi: 10.1016/j.jmb.2013.06.021. Epub 2013 Jun 25. PubMed PMID: 23811057; PubMed Central PMCID: PMC3780797. 7: Park KC, Kim SW, Park JH, Song EH, Yang JW, Chung HJ, Jung HJ, Suh JS, Kwon HJ, Choi SH. Potential anti-cancer activity of N-hydroxy-7-(2-naphthylthio) heptanomide (HNHA), a histone deacetylase inhibitor, against breast cancer both in vitro and in vivo. Cancer Sci. 2011 Feb;102(2):343-50. doi: 10.1111/j.1349-7006.2010.01798.x. Epub 2010 Dec 15. PubMed PMID: 21159061. 8: Otten R, Wood K, Mulder FA. Comprehensive determination of (3)J (HNHalpha) for unfolded proteins using (13)C'-resolved spin-echo difference spectroscopy. J Biomol NMR. 2009 Dec;45(4):343-9. doi: 10.1007/s10858-009-9382-3. Epub 2009 Nov 7. PubMed PMID: 19898942; PubMed Central PMCID: PMC2777233. 9: Pantoja-Uceda D, Santoro J. Aliasing in reduced dimensionality NMR spectra: (3,2)D HNHA and (4,2)D HN(COCA)NH experiments as examples. J Biomol NMR. 2009 Dec;45(4):351-6. doi: 10.1007/s10858-009-9383-2. Epub 2009 Oct 23. PubMed PMID: 19851713. 10: Kim JH, Kim JH, Oh M, Yu YS, Kim KW, Kwon HJ. N-hydroxy-7-(2-naphthylthio) heptanomide inhibits retinal and choroidal angiogenesis. Mol Pharm. 2009 Mar-Apr;6(2):513-9. doi: 10.1021/mp800178b. PubMed PMID: 19718802. 11: Walker CA, Hinderhofer M, Witte DJ, Boos W, Möller HM. Solution structure of the soluble domain of the NfeD protein YuaF from Bacillus subtilis. J Biomol NMR. 2008 Sep;42(1):69-76. doi: 10.1007/s10858-008-9261-3. Epub 2008 Aug 12. PubMed PMID: 18696230. 12: He Y, Yang X, Wang H, Estephan R, Francis F, Kodukula S, Storch J, Stark RE. Solution-state molecular structure of apo and oleate-liganded liver fatty acid-binding protein. Biochemistry. 2007 Nov 6;46(44):12543-56. Epub 2007 Oct 10. PubMed PMID: 17927211. 13: Barnwal RP, Rout AK, Chary KV, Atreya HS. Rapid measurement of 3J(H N-H alpha) and 3J(N-H beta) coupling constants in polypeptides. J Biomol NMR. 2007 Dec;39(4):259-63. Epub 2007 Oct 4. PubMed PMID: 17914658. 14: Kim DH, Lee J, Kim KN, Kim HJ, Jeung HC, Chung HC, Kwon HJ. Anti-tumor activity of N-hydroxy-7-(2-naphthylthio) heptanomide, a novel histone deacetylase inhibitor. Biochem Biophys Res Commun. 2007 Apr 27;356(1):233-8. Epub 2007 Mar 2. PubMed PMID: 17353008. 15: Peng K, Lin Y, Liang SP. Nuclear magnetic resonance studies on huwentoxin-XI from the Chinese bird spider Ornithoctonus huwena: 15N labeling and sequence-specific 1H, 15N nuclear magnetic resonance assignments. Acta Biochim Biophys Sin (Shanghai). 2006 Jul;38(7):457-66. PubMed PMID: 16820861. 16: Zhang X, Xu Y, Zhang J, Wu J, Shi Y. Structural and dynamic characterization of the acid-unfolded state of hUBF HMG box 1 provides clues for the early events in protein folding. Biochemistry. 2005 Jun 7;44(22):8117-25. PubMed PMID: 15924431. 17: Pantoja-Uceda D, Bruix M, Giménez-Gallego G, Rico M, Santoro J. Solution structure of RicC3, a 2S albumin storage protein from Ricinus communis. Biochemistry. 2003 Dec 2;42(47):13839-47. PubMed PMID: 14636051. 18: Malmodin D, Papavoine CH, Billeter M. Fully automated sequence-specific resonance assignments of hetero- nuclear protein spectra. J Biomol NMR. 2003 Sep;27(1):69-79. PubMed PMID: 12878842. 19: Cicero DO, Barbato G, Koch U, Ingallinella P, Bianchi E, Sambucini S, Neddermann P, De Francesco R, Pessi A, Bazzo R. Measurement of homonuclear three-bond J(H(N)Halpha) coupling constants in unlabeled peptides complexed with labeled proteins: application to a decapeptide inhibitor bound to the proteinase domain of the NS3 protein of hepatitis C virus (HCV). J Biomol NMR. 2001 May;20(1):23-9. PubMed PMID: 11430752. 20: Wang YX, Jacob J, Wingfield PT, Palmer I, Stahl SJ, Kaufman JD, Huang PL, Huang PL, Lee-Huang S, Torchia DA. Anti-HIV and anti-tumor protein MAP30, a 30 kDa single-strand type-I RIP, shares similar secondary structure and beta-sheet topology with the A chain of ricin, a type-II RIP. Protein Sci. 2000 Jan;9(1):138-44. PubMed PMID: 10739256; PubMed Central PMCID: PMC2144446.