NLCQ-1 HCl | CAS#221292-08-6 | 444576-78-7 | Bioreductive drug

MedKoo Cat#: 406187 | Name: NLCQ-1 HCl

Description:

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

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

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: 368.22

Elemental Analysis: C, 48.93; H, 4.11; Cl, 19.25; N, 19.02; O, 8.69

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.

Bulk Inquiry

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 368.22 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: 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.