NLCQ-1 HCl

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MedKoo CAT#: 406187

CAS#: 221292-08-6 (HCl)

Description: NLCQ-1 is a novel weak DNA-intercalative bioreductive compound. NLCQ-1 exhibited a C50 of 44 microM. NLCQ-1 demonstrated significant hypoxic selectivity in several rodent (V79, EMT6, SCCVII) or human (A549, OVCAR-3) tumor cell lines. Its potency as a hypoxic cytotoxin ranged between 10 and 136 microM x h, for the cell lines tested, at 30 microM input concentration. NLCQ-1 was a very potent and efficient radiosensitizer of hypoxic V79 cells, providing SER values of 2.27-2.56 at 20-80 microM concentration (measured at 10% survival level). Preclinical results suggest a possible use of NLCQ-1 as adjuvants to radiotherapy.


Chemical Structure

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NLCQ-1 HCl
CAS# 221292-08-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 406187
Name: NLCQ-1 HCl
CAS#: 221292-08-6 (HCl)
Chemical Formula: C15H15Cl2N5O2
Exact Mass: 331.0836
Molecular Weight: 368.218
Elemental Analysis: C, 48.93; H, 4.11; Cl, 19.25; N, 19.02; O, 8.69

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 444576-78-7 (free base)   221292-08-6 (HCl).  

Synonym: NLCQ1; NSC 709257; NLCQ-1, NLCQ 1

IUPAC/Chemical Name: 7-chloro-N-(3-(2-nitro-1H-imidazol-1-yl)propyl)quinolin-4-amine hydrochloride

InChi Key: LWTUZIMLIKOKDI-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H14ClN5O2.ClH/c16-11-2-3-12-13(4-6-18-14(12)10-11)17-5-1-8-20-9-7-19-15(20)21(22)23;/h2-4,6-7,9-10H,1,5,8H2,(H,17,18);1H

SMILES Code: O=[N+](C1=NC=CN1CCCNC2=CC=NC3=CC(Cl)=CC=C23)[O-].[H]Cl

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: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 368.218 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

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1: Papadopoulou MV, Ji M, Bloomer WD. Hypoxia-dependent retinal toxicity of NLCQ-1 (NSC 709257) in BALB/c mice. Comparison with tirapazamine. Basic Clin Pharmacol Toxicol. 2011 Jun;108(6):396-9. doi: 10.1111/j.1742-7843.2010.00667.x. Epub 2011 Jan 26. PubMed PMID: 21205223.

2: Lunt SJ, Cawthorne C, Ali M, Telfer BA, Babur M, Smigova A, Julyan PJ, Price PM, Stratford IJ, Bloomer WD, Papadopoulou MV, Williams KJ. The hypoxia-selective cytotoxin NLCQ-1 (NSC 709257) controls metastatic disease when used as an adjuvant to radiotherapy. Br J Cancer. 2010 Jul 13;103(2):201-8. doi: 10.1038/sj.bjc.6605753. Epub 2010 Jun 29. PubMed PMID: 20588272; PubMed Central PMCID: PMC2906743.

3: Papadopoulou MV, Bloomer WD, Torti VR, Page JG. Investigational new drug-directed, 5-day repeat dose toxicity study of 4-[3-(2-nitro-1-imidazolyl)-propylamino]-7-chloroquinoline hydrochloride (NLCQ-1, NSC 709257) administered with or without Taxol in Sprague-Dawley rats. Basic Clin Pharmacol Toxicol. 2010 Jun;106(6):497-504. doi: 10.1111/j.1742-7843.2009.00530.x. Epub 2010 Jan 14. PubMed PMID: 20074267.

4: Papadopoulou MV, Bloomer WD, Torti VR, Page JG. Investigational new drug-directed toxicology and pharmacokinetic study of 4-[3-(2-nitro-1-imidazolyl)-propylamino]-7-chloroquinoline hydrochloride (NLCQ-1, NSC 709257) in Beagle dogs. Basic Clin Pharmacol Toxicol. 2010 Jun;106(6):511-22. doi: 10.1111/j.1742-7843.2009.00532.x. Epub 2010 Jan 14. PubMed PMID: 20074266.

5: Papadopoulou MV, Bloomer WD, Taylor AP, Hernandez M, Blumenthal RD, Hollingshead MG. Advantage of combining NLCQ-1 (NSC 709257) with radiation in treatment of human head and neck xenografts. Radiat Res. 2007 Jul;168(1):65-71. PubMed PMID: 17722994.

6: Papadopoulou MV, Bloomer WD. DNA repair mechanisms are involved in the hypoxia-dependent toxicity of NLCQ-1 (NSC 709257) and its synergistic interaction with alkylating agents. In Vivo. 2007 Mar-Apr;21(2):175-80. PubMed PMID: 17436565.

7: Papadopoulou MV, Bloomer WD, McNeil MR. NLCQ-1 and NLCQ-2, two new agents with activity against dormant Mycobacterium tuberculosis. Int J Antimicrob Agents. 2007 Jun;29(6):724-7. Epub 2007 Mar 26. PubMed PMID: 17379483.

8: Papadopoulou MV, Ji X, Bloomer WD. Potentiation of alkylating agents by NLCQ-1 or TPZ in vitro and in vivo. J Exp Ther Oncol. 2006;5(4):261-72. PubMed PMID: 17024967.

9: Papadopoulou MV, Ji X, Bloomer WD. Mechanisms involved in the potentiation of paclitaxel or 5-fU by the hypoxic cytotoxin NLCQ-1 (NSC 709257) in vitro. Anticancer Res. 2005 May-Jun;25(3B):2161-70. PubMed PMID: 16158959.

10: Papadopoulou MV, Bloomer WD, Hollingshead MG. NLCQ-1 (NSC 709257) in combination with radiation against human glioma U251 xenografts. Anticancer Res. 2005 May-Jun;25(3B):1865-9. PubMed PMID: 16158918.



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