NBD-556 | NBD556 | CAS#333353-44-9 | HIV-1 entry inhibitor

MedKoo Cat#: 526801 | Name: NBD-556

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Description:

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

NBD-556 is a HIV-1 entry inhibitor. NBD-556 inhibited cell–cell fusion between H9/HIV-1IIIB and MT-2 (IC50 ~3 μM). NBD-556 prevent gp120 binding to CD4. The HIV-1 entry into host cells is a complex, multi-factors involved, and multi-step process. Especially, the attachment of HIV-1 envelope glycoprotein gp120 to the host cell receptor CD4 is the first key step during entry process, representing a promising antiviral therapeutic target.

Chemical Structure

NBD-556

CAS#333353-44-9 (free base)

Theoretical Analysis

MedKoo Cat#: 526801

Name: NBD-556

CAS#: 333353-44-9 (free base)

Chemical Formula: C17H24ClN3O2

Exact Mass: 337.1557

Molecular Weight: 337.85

Elemental Analysis: C, 60.44; H, 7.16; Cl, 10.49; N, 12.44; O, 9.47

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 410.00
100mg	USD 1,000.00

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Related CAS #

333353-44-9 (free base) NBD-556 HCl

Synonym

NBD-556; NBD 556; NBD556.

IUPAC/Chemical Name

N1-(4-chlorophenyl)-N2-(2,2,6,6-tetramethylpiperidin-4-yl)oxalamide

InChi Key

ZKXLQCIOURANAD-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H24ClN3O2/c1-16(2)9-13(10-17(3,4)21-16)20-15(23)14(22)19-12-7-5-11(18)6-8-12/h5-8,13,21H,9-10H2,1-4H3,(H,19,22)(H,20,23)

SMILES Code

O=C(NC1CC(C)(C)NC(C)(C)C1)C(NC2=CC=C(Cl)C=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

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:

NBD-556, a CD4 mimetic, is a potent HIV-1 entry inhibitor that blocks the gp120-CD4 interaction.

In vitro activity:

NBD-556, like CD4, activates the binding of gp120 to the HIV-1 coreceptor, CCR5, and to the 17b monoclonal antibody, which recognizes the coreceptor binding site of gp120. NBD-556 stimulates HIV-1 infection of CD4-negative, CCR5-expressing cells. NBD-556 is a competitive inhibitor of sCD4 and elicits a similar structuring of the coreceptor binding site, whereas BMS-378806 does not compete with sCD4 and does not induce coreceptor binding. Reference: Biochemistry. 2006 Sep 12;45(36):10973-80. https://pubmed.ncbi.nlm.nih.gov/16953583/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	8.80
	DMSO	43.8	129.58
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.48
	Ethanol	6.5	19.24

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 337.85 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

Formulation protocol:

1. Yoshimura K, Harada S, Shibata J, Hatada M, Yamada Y, Ochiai C, Tamamura H, Matsushita S. Enhanced exposure of human immunodeficiency virus type 1 primary isolate neutralization epitopes through binding of CD4 mimetic compounds. J Virol. 2010 Aug;84(15):7558-68. doi: 10.1128/JVI.00227-10. Epub 2010 May 26. PMID: 20504942; PMCID: PMC2897603. 2. Schön A, Madani N, Klein JC, Hubicki A, Ng D, Yang X, Smith AB 3rd, Sodroski J, Freire E. Thermodynamics of binding of a low-molecular-weight CD4 mimetic to HIV-1 gp120. Biochemistry. 2006 Sep 12;45(36):10973-80. doi: 10.1021/bi061193r. PMID: 16953583; PMCID: PMC2504686.

In vitro protocol:

In vivo protocol:

TBD

1: Curreli F, Kwon YD, Zhang H, Scacalossi D, Belov DS, Tikhonov AA, Andreev IA, Altieri A, Kurkin AV, Kwong PD, Debnath AK. Structure-Based Design of a Small Molecule CD4-Antagonist with Broad Spectrum Anti-HIV-1 Activity. J Med Chem. 2015 Sep 10;58(17):6909-27. doi: 10.1021/acs.jmedchem.5b00709. Epub 2015 Aug 28. PubMed PMID: 26301736; PubMed Central PMCID: PMC4676410. 2: Liu T, Huang B, Zhan P, De Clercq E, Liu X. Discovery of small molecular inhibitors targeting HIV-1 gp120-CD4 interaction drived from BMS-378806. Eur J Med Chem. 2014 Oct 30;86:481-90. doi: 10.1016/j.ejmech.2014.09.012. Epub 2014 Sep 6. Review. PubMed PMID: 25203778. 3: Curreli F, Kwon YD, Zhang H, Yang Y, Scacalossi D, Kwong PD, Debnath AK. Binding mode characterization of NBD series CD4-mimetic HIV-1 entry inhibitors by X-ray structure and resistance study. Antimicrob Agents Chemother. 2014 Sep;58(9):5478-91. doi: 10.1128/AAC.03339-14. Epub 2014 Jul 7. PubMed PMID: 25001301; PubMed Central PMCID: PMC4135886. 4: Guttman M, Garcia NK, Cupo A, Matsui T, Julien JP, Sanders RW, Wilson IA, Moore JP, Lee KK. CD4-induced activation in a soluble HIV-1 Env trimer. Structure. 2014 Jul 8;22(7):974-84. doi: 10.1016/j.str.2014.05.001. Epub 2014 Jun 12. PubMed PMID: 24931470; PubMed Central PMCID: PMC4231881. 5: Kwon YD, LaLonde JM, Yang Y, Elban MA, Sugawara A, Courter JR, Jones DM, Smith AB 3rd, Debnath AK, Kwong PD. Crystal structures of HIV-1 gp120 envelope glycoprotein in complex with NBD analogues that target the CD4-binding site. PLoS One. 2014 Jan 28;9(1):e85940. doi: 10.1371/journal.pone.0085940. eCollection 2014. PubMed PMID: 24489681; PubMed Central PMCID: PMC3904841. 6: Schön A, Brown RK, Hutchins BM, Freire E. Ligand binding analysis and screening by chemical denaturation shift. Anal Biochem. 2013 Dec 1;443(1):52-7. doi: 10.1016/j.ab.2013.08.015. Epub 2013 Aug 29. PubMed PMID: 23994566; PubMed Central PMCID: PMC3809086. 7: LaLonde JM, Kwon YD, Jones DM, Sun AW, Courter JR, Soeta T, Kobayashi T, Princiotto AM, Wu X, Schön A, Freire E, Kwong PD, Mascola JR, Sodroski J, Madani N, Smith AB 3rd. Structure-based design, synthesis, and characterization of dual hotspot small-molecule HIV-1 entry inhibitors. J Med Chem. 2012 May 10;55(9):4382-96. doi: 10.1021/jm300265j. Epub 2012 Apr 23. PubMed PMID: 22497421; PubMed Central PMCID: PMC3376652. 8: Kwon YD, Finzi A, Wu X, Dogo-Isonagie C, Lee LK, Moore LR, Schmidt SD, Stuckey J, Yang Y, Zhou T, Zhu J, Vicic DA, Debnath AK, Shapiro L, Bewley CA, Mascola JR, Sodroski JG, Kwong PD. Unliganded HIV-1 gp120 core structures assume the CD4-bound conformation with regulation by quaternary interactions and variable loops. Proc Natl Acad Sci U S A. 2012 Apr 10;109(15):5663-8. doi: 10.1073/pnas.1112391109. Epub 2012 Mar 26. PubMed PMID: 22451932; PubMed Central PMCID: PMC3326499. 9: Dogo-Isonagie C, Lam S, Gustchina E, Acharya P, Yang Y, Shahzad-ul-Hussan S, Clore GM, Kwong PD, Bewley CA. Peptides from second extracellular loop of C-C chemokine receptor type 5 (CCR5) inhibit diverse strains of HIV-1. J Biol Chem. 2012 Apr 27;287(18):15076-86. doi: 10.1074/jbc.M111.332361. Epub 2012 Mar 8. PubMed PMID: 22403408; PubMed Central PMCID: PMC3340262. 10: Shrivastava I, LaLonde JM. Enhanced dynamics of HIV gp120 glycoprotein by small molecule binding. Biochemistry. 2011 May 17;50(19):4173-83. doi: 10.1021/bi2002218. Epub 2011 Apr 21. PubMed PMID: 21488663; PubMed Central PMCID: PMC3121314. 11: Singh IP, Chauthe SK. Small molecule HIV entry inhibitors: Part II. Attachment and fusion inhibitors: 2004-2010. Expert Opin Ther Pat. 2011 Mar;21(3):399-416. doi: 10.1517/13543776.2011.550876. Review. PubMed PMID: 21342055. 12: Schön A, Madani N, Smith AB, Lalonde JM, Freire E. Some binding-related drug properties are dependent on thermodynamic signature. Chem Biol Drug Des. 2011 Mar;77(3):161-5. doi: 10.1111/j.1747-0285.2010.01075.x. Epub 2011 Feb 2. PubMed PMID: 21288305; PubMed Central PMCID: PMC3079564. 13: Yoshimura K, Harada S, Shibata J, Hatada M, Yamada Y, Ochiai C, Tamamura H, Matsushita S. Enhanced exposure of human immunodeficiency virus type 1 primary isolate neutralization epitopes through binding of CD4 mimetic compounds. J Virol. 2010 Aug;84(15):7558-68. doi: 10.1128/JVI.00227-10. Epub 2010 May 26. PubMed PMID: 20504942; PubMed Central PMCID: PMC2897603. 14: Brower ET, Schön A, Freire E. Naturally occurring variability in the envelope glycoprotein of HIV-1 and development of cell entry inhibitors. Biochemistry. 2010 Mar 23;49(11):2359-67. doi: 10.1021/bi1000933. PubMed PMID: 20166763; PubMed Central PMCID: PMC2840190. 15: Madani N, Schön A, Princiotto AM, Lalonde JM, Courter JR, Soeta T, Ng D, Wang L, Brower ET, Xiang SH, Kwon YD, Huang CC, Wyatt R, Kwong PD, Freire E, Smith AB 3rd, Sodroski J. Small-molecule CD4 mimics interact with a highly conserved pocket on HIV-1 gp120. Structure. 2008 Nov 12;16(11):1689-701. doi: 10.1016/j.str.2008.09.005. PubMed PMID: 19000821; PubMed Central PMCID: PMC2597202. 16: Repik A, Clapham PR. Plugging gp120s cavity. Structure. 2008 Nov 12;16(11):1603-4. doi: 10.1016/j.str.2008.10.003. PubMed PMID: 19000812. 17: Schön A, Madani N, Klein JC, Hubicki A, Ng D, Yang X, Smith AB 3rd, Sodroski J, Freire E. Thermodynamics of binding of a low-molecular-weight CD4 mimetic to HIV-1 gp120. Biochemistry. 2006 Sep 12;45(36):10973-80. PubMed PMID: 16953583; PubMed Central PMCID: PMC2504686. 18: Zhao Q, Ma L, Jiang S, Lu H, Liu S, He Y, Strick N, Neamati N, Debnath AK. Identification of N-phenyl-N'-(2,2,6,6-tetramethyl-piperidin-4-yl)-oxalamides as a new class of HIV-1 entry inhibitors that prevent gp120 binding to CD4. Virology. 2005 Sep 1;339(2):213-25. PubMed PMID: 15996703.