MedKoo Cat#: 562128 | Name: NSAH
Featured

Description:

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

NSAH is a nonnucleoside inhibitor of human ribonucleotide reductase (hRR).

Chemical Structure

NSAH
NSAH
CAS#1099592-35-4

Theoretical Analysis

MedKoo Cat#: 562128

Name: NSAH

CAS#: 1099592-35-4

Chemical Formula: C18H14N2O3

Exact Mass: 306.1004

Molecular Weight: 306.32

Elemental Analysis: C, 70.58; H, 4.61; N, 9.15; O, 15.67

Price and Availability

Size Price Availability Quantity
5mg USD 260.00 2 Weeks
25mg USD 770.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
NSAH; Naphthyl salicylic acyl hydrazone;
IUPAC/Chemical Name
(E)-2-Hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)benzohydrazide
InChi Key
ZZSJOLDICPVVAV-YBFXNURJSA-N
InChi Code
InChI=1S/C18H14N2O3/c21-16-8-4-3-7-14(16)18(23)20-19-11-15-13-6-2-1-5-12(13)9-10-17(15)22/h1-11,21-22H,(H,20,23)/b19-11+
SMILES Code
O=C(N/N=C/C1=C2C=CC=CC2=CC=C1O)C3=CC=CC=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
Biological target:
NSAH is a reversible and competitive nonnucleoside ribonucleotide reductase (RR) inhibitor.
In vitro activity:
NSAH binds to hRRM1 with an apparent dissociation constant of 37 µM, and steady-state kinetics reveal a competitive mode of inhibition. A 2.66-Å resolution crystal structure of NSAH in complex with hRRM1 demonstrates that NSAH functions by binding at the catalytic site (C-site) where it makes both common and unique contacts with the enzyme compared with NDP substrates. Importantly, the IC50 for NSAH is within twofold of gemcitabine for growth inhibition of multiple cancer cell lines, while demonstrating little cytotoxicity against normal mobilized peripheral blood progenitor cells. NSAH depresses dGTP and dATP levels in the dNTP pool causing S-phase arrest, providing evidence for RR inhibition in cells. Reference: Proc Natl Acad Sci U S A. 2017 Aug 1;114(31):8241-8246. https://pubmed.ncbi.nlm.nih.gov/28716944/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 61.3 200.00
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 306.32 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.

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:
Ahmad MF, Alam I, Huff SE, Pink J, Flanagan SA, Shewach D, Misko TA, Oleinick NL, Harte WE, Viswanathan R, Harris ME, Dealwis CG. Potent competitive inhibition of human ribonucleotide reductase by a nonnucleoside small molecule. Proc Natl Acad Sci U S A. 2017 Aug 1;114(31):8241-8246. doi: 10.1073/pnas.1620220114. Epub 2017 Jul 17. Erratum in: Proc Natl Acad Sci U S A. 2020 Dec 1;117(48):30858. PMID: 28716944; PMCID: PMC5547592.
In vitro protocol:
Ahmad MF, Alam I, Huff SE, Pink J, Flanagan SA, Shewach D, Misko TA, Oleinick NL, Harte WE, Viswanathan R, Harris ME, Dealwis CG. Potent competitive inhibition of human ribonucleotide reductase by a nonnucleoside small molecule. Proc Natl Acad Sci U S A. 2017 Aug 1;114(31):8241-8246. doi: 10.1073/pnas.1620220114. Epub 2017 Jul 17. Erratum in: Proc Natl Acad Sci U S A. 2020 Dec 1;117(48):30858. PMID: 28716944; PMCID: PMC5547592.
In vivo protocol:
TBD
1: Huff SE, Mohammed FA, Yang M, Agrawal P, Pink J, Harris ME, Dealwis CG, Viswanathan R. Structure-Guided Synthesis and Mechanistic Studies Reveal Sweetspots on Naphthyl Salicyl Hydrazone Scaffold as Non-Nucleosidic Competitive, Reversible Inhibitors of Human Ribonucleotide Reductase. J Med Chem. 2018 Feb 8;61(3):666-680. doi: 10.1021/acs.jmedchem.7b00530. Epub 2018 Jan 5. PubMed PMID: 29253340; PubMed Central PMCID: PMC5808567. 2: Lecky FE, Russell W, McClelland G, Pennington E, Fuller G, Goodacre S, Han K, Curran A, Holliman D, Chapman N, Freeman J, Byers S, Mason S, Potter H, Coats T, Mackway-Jones K, Peters M, Shewan J. Bypassing nearest hospital for more distant neuroscience care in head-injured adults with suspected traumatic brain injury: findings of the head injury transportation straight to neurosurgery (HITS-NS) pilot cluster randomised trial. BMJ Open. 2017 Oct 5;7(10):e016355. doi: 10.1136/bmjopen-2017-016355. PubMed PMID: 28982816; PubMed Central PMCID: PMC5640033. 3: Kolkhir P, Pogorelov D, Olisova O. CRP, D-dimer, fibrinogen and ESR as predictive markers of response to standard doses of levocetirizine in patients with chronic spontaneous urticaria. Eur Ann Allergy Clin Immunol. 2017 Jul;49(4):189-192. PubMed PMID: 28752724. 4: Ahmad MF, Alam I, Huff SE, Pink J, Flanagan SA, Shewach D, Misko TA, Oleinick NL, Harte WE, Viswanathan R, Harris ME, Dealwis CG. Potent competitive inhibition of human ribonucleotide reductase by a nonnucleoside small molecule. Proc Natl Acad Sci U S A. 2017 Aug 1;114(31):8241-8246. doi: 10.1073/pnas.1620220114. Epub 2017 Jul 17. PubMed PMID: 28716944; PubMed Central PMCID: PMC5547592. 5: Dos Santos Schmidt TC, Slotte A, Kennedy J, Sundby S, Johannessen A, Óskarsson GJ, Kurita Y, Stenseth NC, Kjesbu OS. Oogenesis and reproductive investment of Atlantic herring are functions of not only present but long-ago environmental influences as well. Proc Natl Acad Sci U S A. 2017 Mar 7;114(10):2634-2639. doi: 10.1073/pnas.1700349114. Epub 2017 Feb 21. PubMed PMID: 28223491; PubMed Central PMCID: PMC5347595. 6: Huisman MV, Rothman KJ, Paquette M, Teutsch C, Diener HC, Dubner SJ, Halperin JL, Ma CS, Zint K, Elsaesser A, Bartels DB, Lip GY; GLORIA-AF Investigators. The Changing Landscape for Stroke Prevention in AF: Findings From the GLORIA-AF Registry Phase 2. J Am Coll Cardiol. 2017 Feb 21;69(7):777-785. doi: 10.1016/j.jacc.2016.11.061. PubMed PMID: 28209218. 7: Lecky F, Russell W, Fuller G, McClelland G, Pennington E, Goodacre S, Han K, Curran A, Holliman D, Freeman J, Chapman N, Stevenson M, Byers S, Mason S, Potter H, Coats T, Mackway-Jones K, Peters M, Shewan J, Strong M. The Head Injury Transportation Straight to Neurosurgery (HITS-NS) randomised trial: a feasibility study. Health Technol Assess. 2016 Jan;20(1):1-198. doi: 10.3310/hta20010. PubMed PMID: 26753808; PubMed Central PMCID: PMC4780924. 8: Wenz H, Ehrlich G, Wenz R, Al Mahdi MM, Scharf J, Groden C, Schmiedek P, Seiz-Rosenhagen M. MR angiography follow-up 10 years after cryptogenic nonperimesencephalic subarachnoid hemorrhage. PLoS One. 2015 Feb 17;10(2):e0117925. doi: 10.1371/journal.pone.0117925. eCollection 2015. PubMed PMID: 25688554; PubMed Central PMCID: PMC4331285. 9: Schiffer PH, Nsah NA, Grotehusmann H, Kroiher M, Loer C, Schierenberg E. Developmental variations among Panagrolaimid nematodes indicate developmental system drift within a small taxonomic unit. Dev Genes Evol. 2014 Jun;224(3):183-8. doi: 10.1007/s00427-014-0471-2. Epub 2014 May 22. PubMed PMID: 24849338. 10: Silva PM, Costa AC, Mendes A, Barbosa MP. Long-term efficacy of omalizumab in seven patients with treatment-resistant chronic spontaneous urticaria. Allergol Immunopathol (Madr). 2015 Mar-Apr;43(2):168-73. doi: 10.1016/j.aller.2013.11.007. Epub 2014 Apr 14. PubMed PMID: 24731771. 11: Schiffer PH, Kroiher M, Kraus C, Koutsovoulos GD, Kumar S, Camps JI, Nsah NA, Stappert D, Morris K, Heger P, Altmüller J, Frommolt P, Nürnberg P, Thomas WK, Blaxter ML, Schierenberg E. The genome of Romanomermis culicivorax: revealing fundamental changes in the core developmental genetic toolkit in Nematoda. BMC Genomics. 2013 Dec 27;14:923. doi: 10.1186/1471-2164-14-923. PubMed PMID: 24373391; PubMed Central PMCID: PMC3890508. 12: Moss AJ, Schuger C, Beck CA, Brown MW, Cannom DS, Daubert JP, Estes NA 3rd, Greenberg H, Hall WJ, Huang DT, Kautzner J, Klein H, McNitt S, Olshansky B, Shoda M, Wilber D, Zareba W; MADIT-RIT Trial Investigators. Reduction in inappropriate therapy and mortality through ICD programming. N Engl J Med. 2012 Dec 13;367(24):2275-83. doi: 10.1056/NEJMoa1211107. Epub 2012 Nov 6. PubMed PMID: 23131066. 13: Healey JS, Connolly SJ, Gold MR, Israel CW, Van Gelder IC, Capucci A, Lau CP, Fain E, Yang S, Bailleul C, Morillo CA, Carlson M, Themeles E, Kaufman ES, Hohnloser SH; ASSERT Investigators. Subclinical atrial fibrillation and the risk of stroke. N Engl J Med. 2012 Jan 12;366(2):120-9. doi: 10.1056/NEJMoa1105575. Erratum in: N Engl J Med. 2016 Mar 10;374(10):998. PubMed PMID: 22236222. 14: Connolly SJ, Eikelboom J, Joyner C, Diener HC, Hart R, Golitsyn S, Flaker G, Avezum A, Hohnloser SH, Diaz R, Talajic M, Zhu J, Pais P, Budaj A, Parkhomenko A, Jansky P, Commerford P, Tan RS, Sim KH, Lewis BS, Van Mieghem W, Lip GY, Kim JH, Lanas-Zanetti F, Gonzalez-Hermosillo A, Dans AL, Munawar M, O'Donnell M, Lawrence J, Lewis G, Afzal R, Yusuf S; AVERROES Steering Committee and Investigators. Apixaban in patients with atrial fibrillation. N Engl J Med. 2011 Mar 3;364(9):806-17. doi: 10.1056/NEJMoa1007432. Epub 2011 Feb 10. PubMed PMID: 21309657. 15: Connolly SJ, Ezekowitz MD, Yusuf S, Eikelboom J, Oldgren J, Parekh A, Pogue J, Reilly PA, Themeles E, Varrone J, Wang S, Alings M, Xavier D, Zhu J, Diaz R, Lewis BS, Darius H, Diener HC, Joyner CD, Wallentin L; RE-LY Steering Committee and Investigators. Dabigatran versus warfarin in patients with atrial fibrillation. N Engl J Med. 2009 Sep 17;361(12):1139-51. doi: 10.1056/NEJMoa0905561. Epub 2009 Aug 30. Erratum in: N Engl J Med. 2010 Nov 4;363(19):1877. PubMed PMID: 19717844. 16: Fleischmann KE, Orav EJ, Lamas GA, Mangione CM, Schron EB, Lee KL, Goldman L; MOST investigators. Atrial fibrillation and quality of life after pacemaker implantation for sick sinus syndrome: data from the Mode Selection Trial (MOST). Am Heart J. 2009 Jul;158(1):78-83.e2. doi: 10.1016/j.ahj.2009.02.023. PubMed PMID: 19540395. 17: Koplan BA, Gilligan DM, Nguyen LS, Lau TK, Thackeray LM, Berg KC; ULTRA Study Investigators. A randomized trial of the effect of automated ventricular capture on device longevity and threshold measurement in pacemaker patients. Pacing Clin Electrophysiol. 2008 Nov;31(11):1467-74. doi: 10.1111/j.1540-8159.2008.01211.x. PubMed PMID: 18950305. 18: Coman J, Freedman R, Koplan BA, Reeves R, Santucci P, Stolen KQ, Kraus SM, Meyer TE; LIFE Study Results. A blended sensor restores chronotropic response more favorably than an accelerometer alone in pacemaker patients: the LIFE study results. Pacing Clin Electrophysiol. 2008 Nov;31(11):1433-42. doi: 10.1111/j.1540-8159.2008.01207.x. PubMed PMID: 18950301. 19: Bardy GH, Lee KL, Mark DB, Poole JE, Toff WD, Tonkin AM, Smith W, Dorian P, Packer DL, White RD, Longstreth WT Jr, Anderson J, Johnson G, Bischoff E, Yallop JJ, McNulty S, Ray LD, Clapp-Channing NE, Rosenberg Y, Schron EB; HAT Investigators. Home use of automated external defibrillators for sudden cardiac arrest. N Engl J Med. 2008 Apr 24;358(17):1793-804. doi: 10.1056/NEJMoa0801651. Epub 2008 Apr 1. PubMed PMID: 18381485. 20: Koplan BA, Weiner S, Gilligan D, Thackeray L, Merkel S, Berg KC; REFLEx Study Investigators. Clinical and electrical performance of expanded polytetrafluoroethylene-covered defibrillator leads in comparison to traditional leads. Pacing Clin Electrophysiol. 2008 Jan;31(1):47-55. doi: 10.1111/j.1540-8159.2007.00924.x. PubMed PMID: 18181909.