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Chemical Structure| 3544-24-9 Chemical Structure| 3544-24-9

Structure of 3-Aminobenzamide
CAS No.: 3544-24-9

Chemical Structure| 3544-24-9

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INO-1001 is a potent inhibitor of PARP with IC50 of < 50 nM in CHO cells and a mediator of oxidant-induced myocyte dysfunction during reperfusion.

Synonyms: PARP-IN-1; 3-(Aminocarbonyl) Aniline; 3-Carboxamidoaniline

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Product Citations

Product Citations

Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong ; Han, Min Su ;

Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

Alternative Products

Product Details of 3-Aminobenzamide

CAS No. :3544-24-9
Formula : C7H8N2O
M.W : 136.15
SMILES Code : O=C(N)C1=CC=CC(N)=C1
Synonyms :
PARP-IN-1; 3-(Aminocarbonyl) Aniline; 3-Carboxamidoaniline
MDL No. :MFCD00007989
InChI Key :GSCPDZHWVNUUFI-UHFFFAOYSA-N
Pubchem ID :1645

Safety of 3-Aminobenzamide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Related Pathways of 3-Aminobenzamide

epigenetics
DNA

Isoform Comparison

Biological Activity

Target
  • PARP

    PARP, IC50:<50 nM

In Vitro:

Cell Line
Concentration Treated Time Description References
HSG cells 10 µM 30 minutes Inhibit PARP1 activity, reduce H2O2-induced Ca2+ increase Nat Commun. 2013;4:1515.
CHO-K1 cells 7 mM 72 hours Induced centrosome amplification and chromosomal aneuploidy Int J Mol Sci. 2023 Dec 27;25(1):383.
H9C2 cells 20 µM 12 hours Inhibited DOX-induced PARylation, reduced cardiomyocyte apoptosis and mitochondrial damage Acta Pharm Sin B. 2019 Jul;9(4):782-793.
Human intestinal organoids 20 mM 12 hours Inhibited PARP1-dependent parthanatos and reduced cell death Cell Death Discov. 2024 Jul 31;10(1):345.
HeLa cells 10 mM 20 hours To investigate the effect of 3-aminobenzamide on cell surface peptidase activity in UVB-induced apoptotic HeLa cells. Results showed that 3AB treatment significantly reduced cell surface peptidase activity in apoptotic cells. Int J Mol Sci. 2012;13(3):2650-2675.
Neonatal rat cardiomyocytes 500 µM 24 hours Inhibition of PARP-1 activity, attenuating isoprenaline-induced cardiomyocyte hypertrophy Br J Pharmacol. 2015 Jun;172(11):2852-63.
Rice seedlings 1 mM 24 hours 3-Aminobenzamide, as a PARP inhibitor, enhanced cold tolerance in rice seedlings by reducing NAD+ consumption and maintaining energy homeostasis. Antioxidants (Basel). 2022 Dec 29;12(1):79.
Caco-2 cells 20 mM 6 hours Inhibited PARP1-dependent parthanatos and reduced cell death Cell Death Discov. 2024 Jul 31;10(1):345.
Immortalized MEF 7 mM 72 hours Induced centrosome amplification but did not cause chromosomal aneuploidy Int J Mol Sci. 2023 Dec 27;25(1):383.
U-937 cells 5 µM 8 hours Evaluate the antileukemic potential of MAC681 in U-937 cells, showing induction of DNA damage and necroptotic-like cell death. Biomark Res. 2024 May 4;12(1):47.
K-562 cells 5 µM 8 hours Evaluate the antileukemic potential of MAC681 in K-562 cells, showing induction of DNA damage, mitochondrial dysfunction, and necroptotic-like cell death. Biomark Res. 2024 May 4;12(1):47.
Rd2 organotypic retinal cultures 10 nM one week Significantly reduced PARylation levels and photoreceptor cell death Acta Neuropathol Commun. 2025 Apr 1;13(1):68.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Rice Rice seedlings Foliar spray 1 mM Single treatment, 24 hours of cold stress The combination of 3-aminobenzamide and OPCs significantly enhanced cold tolerance in rice seedlings by inhibiting PARP activity and enhancing ATPase activity to maintain energy homeostasis. Antioxidants (Basel). 2022 Dec 29;12(1):79.
Rats Haemorrhagic shock model Intravenous injection 10 mg/kg Single dose 5 min prior to resuscitation To evaluate the effects of 3-aminobenzamide on organ injury and dysfunction caused by haemorrhagic shock. Results showed that 3-aminobenzamide attenuated renal dysfunction, hepatocellular injury, and pancreatic injury. Br J Pharmacol. 1999 Nov;128(6):1339-45
Mice TRPM2+/+ mice Intraperitoneal injection 20 mg/kg Once, 1 hour before radiation Inhibit PARP1 activity, reduce radiation-induced TRPM2 activation, significantly restore salivary gland fluid secretion Nat Commun. 2013;4:1515.
BALB/C57 mice Light-induced retinal damage model Intraperitoneal injection 20 mg/kg Consecutive 7 days To evaluate the protective effect of 3-Aminobenzamide on light-induced retinal damage. Results showed that 3-Aminobenzamide significantly alleviated light-induced structural and functional damage to the retina. Cell Commun Signal. 2020 Feb 17;18(1):27
SD rats Abdominal aortic constriction (AAC) surgery-induced cardiac hypertrophy model Intraperitoneal injection 20 mg/kg Once daily for 6 weeks Pre-treatment with 3AB alleviated AAC-induced translocation of nuclear HMGB1 protein, cardiac hypertrophy, and heart dysfunction Acta Pharmacol Sin. 2019 May;40(5):589-598
Mice Necrotizing enterocolitis model Intraperitoneal injection 20 μg/g 4 consecutive days Inhibited parthanatos and alleviated intestinal epithelial damage and inflammatory response Cell Death Discov. 2024 Jul 31;10(1):345.
Sprague-Dawley rats DOX-induced cardiomyopathy model Intraperitoneal injection 40 mg/kg/day Once daily for 7 days Alleviated DOX-induced cardiac apoptosis, mitochondrial dysfunction and heart dysfunction Acta Pharm Sin B. 2019 Jul;9(4):782-793.
C57BL/6 mice C1498 cell xenograft model Subcutaneous injection 5 µM Single injection, observed for one week Evaluate the immunogenic potential of MAC681 in vivo, showing that MAC681-treated cells could generate an immunogenic vaccine and significantly reduce tumor growth. Biomark Res. 2024 May 4;12(1):47.
Female rats Takotsubo syndrome model Intraperitoneal injection 50 mg/kg Single dose, lasting 24 hours Pretreatment with 3-aminobenzamide (a PARP-1 inhibitor) attenuates negative inotropic changes JACC Basic Transl Sci. 2018 Apr 18;3(2):213-226

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

7.34mL

1.47mL

0.73mL

36.72mL

7.34mL

3.67mL

73.45mL

14.69mL

7.34mL

Dissolving Methods
The prepared working fluid is recommended to be prepared now and used up as soon as possible in a short period of time. The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

References

 

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