SAMT-247 | CAS#850715-59-2 | HIV inhibitor

MedKoo Cat#: 562955 | Name: SAMT-247

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Description:

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

SAMT-247 is an inhibitor of HIV. It acts by modifying the nucleocapsid NCp7 region of Gag in infected cells and blocking Gag processing and reducing infectivity.

Chemical Structure

SAMT-247

CAS#850715-59-2

Theoretical Analysis

MedKoo Cat#: 562955

Name: SAMT-247

CAS#: 850715-59-2

Chemical Formula: C12H14N2O3S

Exact Mass: 266.0725

Molecular Weight: 266.32

Elemental Analysis: C, 54.12; H, 5.30; N, 10.52; O, 18.02; S, 12.04

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks

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Related CAS #

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Synonym

SAMT-247; SAMT 247; SAMT247;

IUPAC/Chemical Name

N-[2-Acetylthiobenzoyl]-beta-alaninamide

InChi Key

UNACIIIRYSLSOD-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H14N2O3S/c1-8(15)18-10-5-3-2-4-9(10)12(17)14-7-6-11(13)16/h2-5H,6-7H2,1H3,(H2,13,16)(H,14,17)

SMILES Code

CC(=O)SC1=CC=CC=C1C(=O)NCCC(=O)N

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

Certificate of Analysis

View CoA: current batch, Lot# M23P05S11

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

View Updated Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

SAMT-247 is a microbicide that selectively inactivates NCp7, causing zinc ejection and preventing RNA encapsidation.

In vitro activity:

This paper characterized the unique mechanism by which SAMT-247 interfered with HIV maturation via a series of selective acetylations at highly conserved cysteine and lysine residues in Gag and Gag-Pol polyproteins. Reference: J Am Chem Soc. 2019 May 22;141(20):8327-8338. https://pubmed.ncbi.nlm.nih.gov/31042030/

In vivo activity:

SAMT-247 boosts natural killer cytotoxicity, monocyte efferocytosis, and reduces T-cell activation, strengthening vaccine protection. The combination of a modified SIV envelope immunogen vaccine and SAMT-247 reduces the risk of SIVmac251 acquisition by over 90%. 80% of macaques treated with SAMT-247 and the vaccine remained uninfected, compared to 40% with the vaccine alone, showing the combination's superior effectiveness. Reference: Nat Microbiol. 2023 May;8(5):905-918. https://pubmed.ncbi.nlm.nih.gov/37024617/

Preparing Stock Solutions

The following data is based on the product molecular weight 266.32 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. Miller Jenkins LM, Paine EL, Deshmukh L, Nikolayevskiy H, Lyons GC, Scerba MT, George Rosenker K, Luecke HF, Louis JM, Chertova E, Gorelick RJ, Ott DE, Clore GM, Appella DH. Inhibition of HIV Maturation via Selective Unfolding and Cross-Linking of Gag Polyprotein by a Mercaptobenzamide Acetylator. J Am Chem Soc. 2019 May 22;141(20):8327-8338. doi: 10.1021/jacs.9b02743. Epub 2019 May 13. PMID: 31042030; PMCID: PMC8496520. 2. Nikolayevskiy H, Scerba MT, Deschamps JR, Appella DH. Reaction Kinetics Direct a Rational Synthesis of an HIV-1 Inactivator of Nucleocapsid Protein 7 and Provide Mechanistic Insight into Cellular Metabolism and Antiviral Activity. Chemistry. 2018 Jul 5;24(38):9485-9489. doi: 10.1002/chem.201801253. Epub 2018 May 25. PMID: 29653024. 3. Rahman MA, Bissa M, Silva de Castro I, Helmold Hait S, Stamos JD, Bhuyan F, Hunegnaw R, Sarkis S, Gutowska A, Doster MN, Moles R, Hoang T, Miller Jenkins LM, Appella E, Venzon DJ, Choo-Wosoba H, Cardozo T, Baum MM, Appella DH, Robert-Guroff M, Franchini G. Vaccine plus microbicide effective in preventing vaginal SIV transmission in macaques. Nat Microbiol. 2023 May;8(5):905-918. doi: 10.1038/s41564-023-01353-7. Epub 2023 Apr 6. Erratum in: Nat Microbiol. 2023 Aug;8(8):1600. PMID: 37024617; PMCID: PMC10159859. 4. Helmold Hait S, Hogge CJ, Rahman MA, Ko EJ, Hunegnaw R, Mushtaq Z, Enyindah-Asonye G, Hoang T, Miller Jenkins LM, Appella E, Appella DH, Robert-Guroff M. An SAMT-247 Microbicide Provides Potent Protection against Intravaginal Simian Immunodeficiency Virus Infection of Rhesus Macaques, whereas an Added Vaccine Component Elicits Mixed Outcomes. J Immunol. 2020 Jun 15;204(12):3315-3328. doi: 10.4049/jimmunol.2000165. Epub 2020 May 11. PMID: 32393514; PMCID: PMC7392472.

In vitro protocol:

In vivo protocol:

1. Rahman MA, Bissa M, Silva de Castro I, Helmold Hait S, Stamos JD, Bhuyan F, Hunegnaw R, Sarkis S, Gutowska A, Doster MN, Moles R, Hoang T, Miller Jenkins LM, Appella E, Venzon DJ, Choo-Wosoba H, Cardozo T, Baum MM, Appella DH, Robert-Guroff M, Franchini G. Vaccine plus microbicide effective in preventing vaginal SIV transmission in macaques. Nat Microbiol. 2023 May;8(5):905-918. doi: 10.1038/s41564-023-01353-7. Epub 2023 Apr 6. Erratum in: Nat Microbiol. 2023 Aug;8(8):1600. PMID: 37024617; PMCID: PMC10159859. 2. Helmold Hait S, Hogge CJ, Rahman MA, Ko EJ, Hunegnaw R, Mushtaq Z, Enyindah-Asonye G, Hoang T, Miller Jenkins LM, Appella E, Appella DH, Robert-Guroff M. An SAMT-247 Microbicide Provides Potent Protection against Intravaginal Simian Immunodeficiency Virus Infection of Rhesus Macaques, whereas an Added Vaccine Component Elicits Mixed Outcomes. J Immunol. 2020 Jun 15;204(12):3315-3328. doi: 10.4049/jimmunol.2000165. Epub 2020 May 11. PMID: 32393514; PMCID: PMC7392472.

1: Nikolayevskiy H, Scerba MT, Deschamps JR, Appella DH. Reaction Kinetics Direct a Rational Synthesis of an HIV-1 Inactivator of Nucleocapsid Protein 7 and Provide Mechanistic Insight into Cellular Metabolism and Antiviral Activity. Chemistry. 2018 Apr 13. doi: 10.1002/chem.201801253. [Epub ahead of print] PubMed PMID: 29653024.