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MedKoo Cat#: 527083 | Name: NPPB
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Description:

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

NPPB is a voltage-dependent cystic fibrosis transmembrane conductance regulator (CFTR) channel blocker.

Chemical Structure

NPPB
NPPB
CAS#107254-86-4

Theoretical Analysis

MedKoo Cat#: 527083

Name: NPPB

CAS#: 107254-86-4

Chemical Formula: C16H16N2O4

Exact Mass: 300.1110

Molecular Weight: 300.31

Elemental Analysis: C, 63.99; H, 5.37; N, 9.33; O, 21.31

Price and Availability

Size Price Availability Quantity
10mg USD 225.00 2 Weeks
25mg USD 390.00 2 Weeks
50mg USD 615.00 2 Weeks
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Related CAS #
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Synonym
NPPB
IUPAC/Chemical Name
5-Nitro-2-(3-phenylpropylamino) benzoic acid
InChi Key
WBSMIPAMAXNXFS-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H16N2O4/c19-16(20)14-11-13(18(21)22)8-9-15(14)17-10-4-7-12-5-2-1-3-6-12/h1-3,5-6,8-9,11,17H,4,7,10H2,(H,19,20)
SMILES Code
O=C(O)C1=CC([N+]([O-])=O)=CC=C1NCCCC2=CC=CC=C2
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:
NPPB is a blocker of the outwardly rectifying chloride channel (ORCC).
In vitro activity:
This study developed a novel compound, TMZ conjugated with NPPB (TMZ-NPPB), as a potential anticancer drug. TMZ-NPPB blocked chloride currents in U373MG, a severely invasive human glioma cell line, and suppressed migration and invasion of U373MG cells. Moreover, TMZ-NPPB exhibited DNA modification activity similar to that of TMZ, and surprisingly showed remarkably enhanced cytotoxicity relative to TMZ by inducing apoptotic cell death via DNA damage. Reference: ACS Chem Neurosci. 2016 Mar 16;7(3):275-85. https://pubmed.ncbi.nlm.nih.gov/26711895/
In vivo activity:
NPPB inhibited PGE1-stimulated Isc in rabbit distal colon and ileum at concentrations in the range 20 to 100 microM. However, NPPB at the same concentrations also inhibited glucose-stimulated Isc in rabbit ileum, suggesting that its effects were not restricted to those on Cl- transport. Consistent with this, exposure of rabbit distal colon to 100 microM NPPB was found to reduce endogenous ATP levels by 69%, implying that, at these concentrations, NPPB could impair active transport processes by an effect on cellular energy metabolism. Reference: Biochim Biophys Acta. 1991 Nov 14;1115(1):42-8. https://pubmed.ncbi.nlm.nih.gov/1720331/
Solvent mg/mL mM
Solubility
DMF 50.0 166.49
DMSO 76.7 255.32
DMSO:PBS (pH 7.2) (1:1) 0.5 255.32
Ethanol 1.0 3.33
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 300.31 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. Park M, Song C, Yoon H, Choi KH. Double Blockade of Glioma Cell Proliferation and Migration by Temozolomide Conjugated with NPPB, a Chloride Channel Blocker. ACS Chem Neurosci. 2016 Mar 16;7(3):275-85. doi: 10.1021/acschemneuro.5b00178. Epub 2016 Jan 8. PMID: 26711895. 2. Taniguchi Y, Tonai-Kachi H, Shinjo K. 5-Nitro-2-(3-phenylpropylamino)benzoic acid is a GPR35 agonist. Pharmacology. 2008;82(4):245-9. doi: 10.1159/000157625. Epub 2008 Sep 26. PMID: 18818509. 3. Lu C, Lu H, Huang X, Liu S, Zang J, Li Y, Chen J, Xu W. Colonic Transit Disorder Mediated by Downregulation of Interstitial Cells of Cajal/Anoctamin-1 in Dextran Sodium Sulfate-induced Colitis Mice. J Neurogastroenterol Motil. 2019 Apr 30;25(2):316-331. doi: 10.5056/jnm18173. PMID: 30982243; PMCID: PMC6474700. 4. Keeling DJ, Taylor AG, Smith PL. Effects of NPPB (5-nitro-2-(3-phenylpropylamino)benzoic acid) on chloride transport in intestinal tissues and the T84 cell line. Biochim Biophys Acta. 1991 Nov 14;1115(1):42-8. doi: 10.1016/0304-4165(91)90009-6. PMID: 1720331.
In vitro protocol:
1. Park M, Song C, Yoon H, Choi KH. Double Blockade of Glioma Cell Proliferation and Migration by Temozolomide Conjugated with NPPB, a Chloride Channel Blocker. ACS Chem Neurosci. 2016 Mar 16;7(3):275-85. doi: 10.1021/acschemneuro.5b00178. Epub 2016 Jan 8. PMID: 26711895. 2. Taniguchi Y, Tonai-Kachi H, Shinjo K. 5-Nitro-2-(3-phenylpropylamino)benzoic acid is a GPR35 agonist. Pharmacology. 2008;82(4):245-9. doi: 10.1159/000157625. Epub 2008 Sep 26. PMID: 18818509.
In vivo protocol:
1. Lu C, Lu H, Huang X, Liu S, Zang J, Li Y, Chen J, Xu W. Colonic Transit Disorder Mediated by Downregulation of Interstitial Cells of Cajal/Anoctamin-1 in Dextran Sodium Sulfate-induced Colitis Mice. J Neurogastroenterol Motil. 2019 Apr 30;25(2):316-331. doi: 10.5056/jnm18173. PMID: 30982243; PMCID: PMC6474700. 2. Keeling DJ, Taylor AG, Smith PL. Effects of NPPB (5-nitro-2-(3-phenylpropylamino)benzoic acid) on chloride transport in intestinal tissues and the T84 cell line. Biochim Biophys Acta. 1991 Nov 14;1115(1):42-8. doi: 10.1016/0304-4165(91)90009-6. PMID: 1720331.
1: Sun L, Dong Y, Zhao J, Yin Y, Tong B, Zheng Y, Xin H. NPPB modulates apoptosis, proliferation, migration and extracellular matrix synthesis of conjunctival fibroblasts by inhibiting PI3K/AKT signaling. Int J Mol Med. 2017 Dec 15. doi: 10.3892/ijmm.2017.3323. [Epub ahead of print] PubMed PMID: 29286070. 2: Salo PP, Havulinna AS, Tukiainen T, Raitakari O, Lehtimäki T, Kähönen M, Kettunen J, Männikkö M, Eriksson JG, Jula A, Blankenberg S, Zeller T, Salomaa V, Kristiansson K, Perola M. Genome-Wide Association Study Implicates Atrial Natriuretic Peptide Rather Than B-Type Natriuretic Peptide in the Regulation of Blood Pressure in the General Population. Circ Cardiovasc Genet. 2017 Dec;10(6). pii: e001713. doi: 10.1161/CIRCGENETICS.117.001713. PubMed PMID: 29237677. 3: van Eldik W, den Adel B, Monshouwer-Kloots J, Salvatori D, Maas S, van der Made I, Creemers EE, Frank D, Frey N, Boontje N, van der Velden J, Steendijk P, Mummery C, Passier R, Beqqali A. Z-disc protein CHAPb induces cardiomyopathy and contractile dysfunction in the postnatal heart. PLoS One. 2017 Dec 5;12(12):e0189139. doi: 10.1371/journal.pone.0189139. eCollection 2017. PubMed PMID: 29206857; PubMed Central PMCID: PMC5716575. 4: Wang W, Jiang W, Hou L, Duan H, Wu Y, Xu C, Tan Q, Li S, Zhang D. Weighted gene co-expression network analysis of expression data of monozygotic twins identifies specific modules and hub genes related to BMI. BMC Genomics. 2017 Nov 13;18(1):872. doi: 10.1186/s12864-017-4257-6. PubMed PMID: 29132311; PubMed Central PMCID: PMC5683603. 5: Kashyap A, Turek JW, Wagner SJ, Felderman L, Jaggers EA, Gruber PJ, Edens RE. Development of a Pediatric Cardiac Mechanical Support Program. Artif Organs. 2017 Nov 3. doi: 10.1111/aor.12963. [Epub ahead of print] PubMed PMID: 29105103. 6: Gu G, Na Y, Chung H, Seok SH, Lee HY. Zebrafish Larvae Model of Dilated Cardiomyopathy Induced by Terfenadine. Korean Circ J. 2017 Nov;47(6):960-969. doi: 10.4070/kcj.2017.0080. Epub 2017 Sep 20. PubMed PMID: 29035434; PubMed Central PMCID: PMC5711688. 7: Chandra M, Escalante-Alcalde D, Bhuiyan MS, Orr AW, Kevil C, Morris AJ, Nam H, Dominic P, McCarthy KJ, Miriyala S, Panchatcharam M. Cardiac-specific inactivation of LPP3 in mice leads to myocardial dysfunction and heart failure. Redox Biol. 2018 Apr;14:261-271. doi: 10.1016/j.redox.2017.09.015. Epub 2017 Sep 28. PubMed PMID: 28982073; PubMed Central PMCID: PMC5635346. 8: Ccai SA, Chen JF, Chen MJ, Lin JC, Feng JQ, Lin K, Zhi XM, Zhang WJ, Wu W. [Angiotensin-(1-7) protects cardiac myocytes against high glucose-induced injury by inhibiting ClC-3 chloride channels]. Nan Fang Yi Ke Da Xue Xue Bao. 2017 Jul 20;37(7):895-901. Chinese. PubMed PMID: 28736364. 9: Chiang IN, Pu YS, Huang CY, Young TH. Far infrared radiation promotes rabbit renal proximal tubule cell proliferation and functional characteristics, and protects against cisplatin-induced nephrotoxicity. PLoS One. 2017 Jul 17;12(7):e0180872. doi: 10.1371/journal.pone.0180872. eCollection 2017. PubMed PMID: 28715443; PubMed Central PMCID: PMC5513434. 10: Takahashi N, Omi A, Uchino H, Kudo Y. Different characteristics of cell volume and intracellular calcium ion concentration dynamics between the hippocampal CA1 and lateral cerebral cortex of male mouse brain slices during exposure to hypotonic stress. J Neurosci Res. 2018 Jan;96(1):117-127. doi: 10.1002/jnr.24086. Epub 2017 Jul 12. PubMed PMID: 28699288. 11: Fahanik-Babaei J, Shayanfar F, Khodaee N, Saghiri R, Eliassi A. Electro-pharmacological profiles of two brain mitoplast anion channels: Inferences from single channel recording. EXCLI J. 2017 Apr 18;16:531-545. doi: 10.17179/excli2016-808. eCollection 2017. PubMed PMID: 28694756; PubMed Central PMCID: PMC5491910. 12: Huhtinen A, Hongisto V, Laiho A, Löyttyniemi E, Pijnenburg D, Scheinin M. Gene expression profiles and signaling mechanisms in α(2B)-adrenoceptor-evoked proliferation of vascular smooth muscle cells. BMC Syst Biol. 2017 Jun 28;11(1):65. doi: 10.1186/s12918-017-0439-8. PubMed PMID: 28659168; PubMed Central PMCID: PMC5490158. 13: Newman MS, Nguyen T, Watson MJ, Hull RW, Yu HG. Transcriptome profiling reveals novel BMI- and sex-specific gene expression signatures for human cardiac hypertrophy. Physiol Genomics. 2017 Jul 1;49(7):355-367. doi: 10.1152/physiolgenomics.00122.2016. Epub 2017 May 12. PubMed PMID: 28500252; PubMed Central PMCID: PMC5538878. 14: Valinsky WC, Touyz RM, Shrier A. Characterization of constitutive and acid-induced outwardly rectifying chloride currents in immortalized mouse distal tubular cells. Biochim Biophys Acta. 2017 Aug;1861(8):2007-2019. doi: 10.1016/j.bbagen.2017.05.004. Epub 2017 May 5. PubMed PMID: 28483640; PubMed Central PMCID: PMC5482324. 15: Qi L, Huang C, Wu X, Tao Y, Yan J, Shi T, Cao C, Han L, Qiu M, Ma Q, Liu Z, Liu Y. Hierarchical Specification of Pruriceptors by Runt-Domain Transcription Factor Runx1. J Neurosci. 2017 May 31;37(22):5549-5561. doi: 10.1523/JNEUROSCI.0094-17.2017. Epub 2017 May 5. PubMed PMID: 28476948. 16: Li J, Yousefi K, Ding W, Singh J, Shehadeh LA. Osteopontin RNA aptamer can prevent and reverse pressure overload-induced heart failure. Cardiovasc Res. 2017 May 1;113(6):633-643. doi: 10.1093/cvr/cvx016. PubMed PMID: 28453726. 17: Ji LD, Li JY, Yao BB, Cai XB, Shen QJ, Xu J. Are genetic polymorphisms in the renin-angiotensin-aldosterone system associated with essential hypertension? Evidence from genome-wide association studies. J Hum Hypertens. 2017 Nov;31(11):695-698. doi: 10.1038/jhh.2017.29. Epub 2017 Apr 20. Review. PubMed PMID: 28425437. 18: Yang H, Ma L, Wang Y, Zuo W, Li B, Yang Y, Chen Y, Chen L, Wang L, Zhu L. Activation of ClC-3 chloride channel by 17β-estradiol relies on the estrogen receptor α expression in breast cancer. J Cell Physiol. 2018 Feb;233(2):1071-1081. doi: 10.1002/jcp.25963. Epub 2017 Jun 9. PubMed PMID: 28419445. 19: Ma L, Yang Y, Yin Z, Liu M, Wang L, Chen L, Zhu L, Yang H. Emodin suppresses the nasopharyngeal carcinoma cells by targeting the chloride channels. Biomed Pharmacother. 2017 Jun;90:615-625. doi: 10.1016/j.biopha.2017.03.088. Epub 2017 Apr 12. PubMed PMID: 28411554. 20: Fedan JS, Thompson JA, Meighan TG, Zeidler-Erdely PC, Antonini JM. Altered ion transport in normal human bronchial epithelial cells following exposure to chemically distinct metal welding fume particles. Toxicol Appl Pharmacol. 2017 Jul 1;326:1-6. doi: 10.1016/j.taap.2017.04.008. Epub 2017 Apr 12. PubMed PMID: 28411035.