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MedKoo Cat#: 558221 | Name: KNK437
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Description:

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

KNK437 is a novel inhibitor of acquisition of thermotolerance and heat shock protein. KNK437 inhibit stress-induced synthesis of heat shock proteins (HSPs). KNK437 is an effective radiosensitizer that targets multiple pro-survival stress response pathways. KNK437 is a useful agent for enhancing the efficiency of hyperthermic therapy which has less toxic side-effects in prostate cancer.

Chemical Structure

KNK437
KNK437
CAS#218924-25-5

Theoretical Analysis

MedKoo Cat#: 558221

Name: KNK437

CAS#: 218924-25-5

Chemical Formula: C13H11NO4

Exact Mass: 245.0688

Molecular Weight: 245.23

Elemental Analysis: C, 63.67; H, 4.52; N, 5.71; O, 26.10

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,350.00 2 Weeks
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Related CAS #
No Data
Synonym
KNK437; KNK-437; KNK 437.
IUPAC/Chemical Name
(Z)-3-(benzo[d][1,3]dioxol-5-ylmethylene)-2-oxopyrrolidine-1-carbaldehyde
InChi Key
NJBBLOIWMSYVCQ-VZTVMPNDSA-N
InChi Code
InChI=1S/C33H41N5O6S2/c1-33(2,3)37-31(42)26-19-46-20-38(26)32(43)29(40)24(15-21-9-6-5-7-10-21)36-30(41)25(18-45-4)35-28(39)17-44-27-12-8-11-22-16-34-14-13-23(22)27/h5-14,16,24-26,29,40H,15,17-20H2,1-4H3,(H,35,39)(H,36,41)(H,37,42)/t24-,25-,26-,29-/m0/s1
SMILES Code
O=CN1C(/C(CC1)=C\C2=CC=C(OCO3)C3=C2)=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, not in water
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:
KNK437 is a HSP inhibitor, and inhibits the induction of HSP105, HSP70, and HSP40.
In vitro activity:
KNK437 and quercetin inhibited thermotolerance in a dose-dependent manner in PC-3 cells. KNK437 and quercetin decreased heat-induced accumulation of Hsp70 mRNA and protein in PC-3 and LNCaP cells. KNK437 and quercetin pretreatment enhanced the apoptotic effect of hyperthermia in both cells. Reference: Int J Hyperthermia. 2011;27(1):63-73. https://pubmed.ncbi.nlm.nih.gov/21204621/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMF 10.0 40.78
DMF:PBS (pH 7.2) (1:5) 0.1 0.41
DMSO 19.4 79.18
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 245.23 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. Sahin E, Sahin M, Sanlioğlu AD, Gümüslü S. KNK437, a benzylidene lactam compound, sensitises prostate cancer cells to the apoptotic effect of hyperthermia. Int J Hyperthermia. 2011;27(1):63-73. doi: 10.3109/02656736.2010.528139. Epub 2011 Jan 4. PMID: 21204621. 2. Matsuda K, Nakagawa SY, Nakano T, Asaumi J, Jagetia GC, Kawasaki S. Effects of KNK437 on heat-induced methylation of histone H3 in human oral squamous cell carcinoma cells. Int J Hyperthermia. 2006 Dec;22(8):729-35. doi: 10.1080/02656730601074375. PMID: 17391001.
In vitro protocol:
1. Sahin E, Sahin M, Sanlioğlu AD, Gümüslü S. KNK437, a benzylidene lactam compound, sensitises prostate cancer cells to the apoptotic effect of hyperthermia. Int J Hyperthermia. 2011;27(1):63-73. doi: 10.3109/02656736.2010.528139. Epub 2011 Jan 4. PMID: 21204621. 2. Matsuda K, Nakagawa SY, Nakano T, Asaumi J, Jagetia GC, Kawasaki S. Effects of KNK437 on heat-induced methylation of histone H3 in human oral squamous cell carcinoma cells. Int J Hyperthermia. 2006 Dec;22(8):729-35. doi: 10.1080/02656730601074375. PMID: 17391001.
In vivo protocol:
TBD
1: Oommen D, Prise KM. KNK437, abrogates hypoxia-induced radioresistance by dual targeting of the AKT and HIF-1α survival pathways. Biochem Biophys Res Commun. 2012 May 11;421(3):538-43. doi: 10.1016/j.bbrc.2012.04.040. Epub 2012 Apr 13. PubMed PMID: 22521642. 2: Sahin E, Sahin M, Sanlioğlu AD, Gümüslü S. KNK437, a benzylidene lactam compound, sensitises prostate cancer cells to the apoptotic effect of hyperthermia. Int J Hyperthermia. 2011;27(1):63-73. doi: 10.3109/02656736.2010.528139. Epub 2011 Jan 4. PubMed PMID: 21204621. 3: Taba K, Kuramitsu Y, Ryozawa S, Yoshida K, Tanaka T, Mori-Iwamoto S, Maehara S, Maehara Y, Sakaida I, Nakamura K. KNK437 downregulates heat shock protein 27 of pancreatic cancer cells and enhances the cytotoxic effect of gemcitabine. Chemotherapy. 2011;57(1):12-6. doi: 10.1159/000321019. Epub 2010 Dec 3. PubMed PMID: 21124027. 4: Inoue H, Uyama T, Hayashi J, Watanabe A, Kobayashi K, Tadokoro T, Yamamoto Y. N-Formyl-3,4-methylenedioxy-benzylidene-gamma-butyrolaetam, KNK437 induces caspase-3 activation through inhibition of mTORC1 activity in Cos-1 cells. Biochem Biophys Res Commun. 2010 Apr 23;395(1):56-60. doi: 10.1016/j.bbrc.2010.03.134. Epub 2010 Mar 27. PubMed PMID: 20350529. 5: Wu YC, Yen WY, Lee TC, Yih LH. Heat shock protein inhibitors, 17-DMAG and KNK437, enhance arsenic trioxide-induced mitotic apoptosis. Toxicol Appl Pharmacol. 2009 Apr 15;236(2):231-8. doi: 10.1016/j.taap.2009.02.003. Epub 2009 Feb 12. PubMed PMID: 19371599. 6: Voyer J, Heikkila JJ. Comparison of the effect of heat shock factor inhibitor, KNK437, on heat shock- and chemical stress-induced hsp30 gene expression in Xenopus laevis A6 cells. Comp Biochem Physiol A Mol Integr Physiol. 2008 Oct;151(2):253-61. doi: 10.1016/j.cbpa.2008.07.004. Epub 2008 Jul 10. PubMed PMID: 18675372. 7: Manwell LA, Heikkila JJ. Examination of KNK437- and quercetin-mediated inhibition of heat shock-induced heat shock protein gene expression in Xenopus laevis cultured cells. Comp Biochem Physiol A Mol Integr Physiol. 2007 Nov;148(3):521-30. Epub 2007 Jul 5. PubMed PMID: 17681842. 8: Matsuda K, Nakagawa SY, Nakano T, Asaumi J, Jagetia GC, Kawasaki S. Effects of KNK437 on heat-induced methylation of histone H3 in human oral squamous cell carcinoma cells. Int J Hyperthermia. 2006 Dec;22(8):729-35. PubMed PMID: 17391001. 9: Koike T, Uno S, Ishizawa M, Takahashi H, Ikeda K, Yokota S, Makishima M. The heat shock protein inhibitor KNK437 induces neurite outgrowth in PC12 cells. Neurosci Lett. 2006 Dec 27;410(3):212-7. Epub 2006 Oct 18. PubMed PMID: 17055158. 10: Ohnishi K, Yokota S, Takahashi A, Ohnishi T. Induction of radiation resistance by a heat shock protein inhibitor, KNK437, in human glioblastoma cells. Int J Radiat Biol. 2006 Aug;82(8):569-75. PubMed PMID: 16966184. 11: Sakurai H, Kitamoto Y, Saitoh J, Nonaka T, Ishikawa H, Kiyohara H, Shioya M, Fukushima M, Akimoto T, Hasegawa M, Nakano T. Attenuation of chronic thermotolerance by KNK437, a benzylidene lactam compound, enhances thermal radiosensitization in mild temperature hyperthermia combined with low dose-rate irradiation. Int J Radiat Biol. 2005 Sep;81(9):711-8. PubMed PMID: 16368649. 12: Ohnishi K, Takahashi A, Yokota S, Ohnishi T. Effects of a heat shock protein inhibitor KNK437 on heat sensitivity and heat tolerance in human squamous cell carcinoma cell lines differing in p53 status. Int J Radiat Biol. 2004 Aug;80(8):607-14. PubMed PMID: 15370972. 13: Koishi M, Yokota S, Mae T, Nishimura Y, Kanamori S, Horii N, Shibuya K, Sasai K, Hiraoka M. The effects of KNK437, a novel inhibitor of heat shock protein synthesis, on the acquisition of thermotolerance in a murine transplantable tumor in vivo. Clin Cancer Res. 2001 Jan;7(1):215-9. PubMed PMID: 11205912. 14: Yokota S, Kitahara M, Nagata K. Benzylidene lactam compound, KNK437, a novel inhibitor of acquisition of thermotolerance and heat shock protein induction in human colon carcinoma cells. Cancer Res. 2000 Jun 1;60(11):2942-8. PubMed PMID: 10850441.