BAPTA-AM - 10mM in DMSO , CAS No.126150-97-8

CAS: 126150-97-8 Cat. No.: B421097 Molecular Weight: 764.68 Beilstein Registry Number: 7458530 EC Number: 634-129-4

GRADE & PURITY 10mM in DMSO

Synonyms

1,2-Bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid,tetraacetoxymethyl ester | FT-0606289 | Tetrakis(acetoxymethyl) 1,2-Bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetate | A14023 | BAPTA AM | Glycine, N,N'-[1,2-ethanediylbis(oxy-2,1-phenylene)]bis[N-[

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

BAPTA/AM [1,2-Bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid tetrakis(acetoxymethyl ester)] is a non-fluorescent, membrane-permeable form of BAPTA. Whereas the BAPTA, Free acid is not cell permeable and is only useful for manipulating extracellular Ca2+ levels, BAPTA/AM can be used with a wide variety of cells, where it is hydrolyzed by cytosolic esterases and trapped intracellularly. Experiments have shown that BAPTA/AM abolishes vitamin D3-induced increase in intracellular Ca2+, and may induce inactivation of protein kinase C. Has also been shown to inhibit thapsigargin-induced apoptosis in rat thymocytes. This product is a high quality and sensitive compound for calcium signaling studies, investigation of signal transduction and apoptotic cascades, and neuroscience research.
A membrane-permeable form of BAPTA;Selective chelator of intracellular Ca2+ stores.

Specifications

Synonyms

1, 2-Bis(2-aminophenoxy)ethane-N, N, N', N'-tetraacetic acid, tetraacetoxymethyl ester | FT-0606289 | Tetrakis(acetoxymethyl) 1, 2-Bis(2-aminophenoxy)ethane-N, N, N', N'-tetraacetate | A14023 | BAPTA AM | Glycine, N, N'-[1, 2-ethanediylbis(oxy-2, 1-phenylene)]bis[N-[

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Selective chelator of intracellular Ca2+ stores.Selective Ca 2+ chelator. Cell-permeable analog of BAPTA . Useful for manipulation of intracellular free Ca 2+ levels. Shows varied biological activity. Blocks hK v 1.5, K v 11.1 (hERG) and hK v 1.3 channels

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CC(=O)OCOC(=O)CN(CC(=O)OCOC(=O)C)C1=CC=CC=C1OCCOC2=CC=CC=C2N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C
• IUPAC Name: acetyloxymethyl 2-[N-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]phenoxy]ethoxy]anilino]acetate
• InChIKey: YJIYWYAMZFVECX-UHFFFAOYSA-N
• INCHI: 1S/C34H40N2O18/c1-23(37)47-19-51-31(41)15-35(16-32(42)52-20-48-24(2)38)27-9-5-7-11-29(27)45-13-14-46-30-12-8-6-10-28(30)36(17-33(43)53-21-49-25(3)39)18-34(44)54-22-50-26(4)40/h5-12H,13-22H2,1-4H3
• Isomeric SMILES: CC(=O)OCOC(=O)CN(CC(=O)OCOC(=O)C)C1=CC=CC=C1OCCOC2=CC=CC=C2N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C
• WGK Germany: 3
• Molecular Weight: 764.68
• Beilstein: 7458530
• Reaxy-Rn: 7458534
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7458534&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acid esters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Alpha amino acid esters
• Alternative Parents: Aminophenyl ethers Phenoxy compounds Dialkylarylamines Aniline and substituted anilines Alkyl aryl ethers Acylals Acetals Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alpha-amino acid ester - Aminophenyl ether - Phenoxy compound - Aniline or substituted anilines - Dialkylarylamine - Tertiary aliphatic/aromatic amine - Phenol ether - Alkyl aryl ether - Acylal - Monocyclic benzene moiety - Benzenoid - Carboxylic acid ester - Tertiary amine - Acetal - Ether - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Amine - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

POLK Tbio DNA polymerase kappa (8653 Activities)

Discover Target: POLK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

Discover Target: ffp

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat sensitive
• Melt Point(°C): 98 °C
• Molecular Weight: 764.700 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 31
• Exact Mass: 764.228 Da
• Monoisotopic Mass: 764.228 Da
• Topological Polar Surface Area: 235.000 Ų
• Heavy Atom Count: 54
• Formal Charge: 0
• Complexity: 1100.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yanan Wang, Huichao Wei, Keyang Li, Liru Liu, Yingfei Zhu, Xinyuan Wang, Jiahui Yan, Liangmin Yu, Xuefeng Yan, Zhiyu He.  (2023)  Ros-responsive dextran-phenylboronic acid-silibinin nanoparticles for targeting delivery of BAPTA-AM to effectively eliminate calcium overload-mediated inflammatory cascades and mitochondrial apoptosis: Alleviating acute liver injury.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2023.148283]

2. Chehao Lee, Guang Xin, Fan Li, Chengyu Wan, Xiuxian Yu, Lijuan Feng, Ao Wen, Yu Cao, Wen Huang.  (2023)  Calcium/P53/Ninjurin 1 Signaling Mediates Plasma Membrane Rupture of Acinar Cells in Severe Acute Pancreatitis.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  24  (14): (11554).  [PMID:37511311] [10.3390/ijms241411554]

3. Jiqiang Song, Yanping Yu, Zhichao Yan, Shan Xiao, Xianxin Zhao, Fang Wang, Qi Fang, Gongyin Ye.  (2023)  Chloride intracellular channel gene knockdown induces insect cell lines death and level increases of intracellular calcium ions.  Frontiers in Physiology,      [PMID:37485065] [10.3389/fphys.2023.1217954]

4. Jiahui Yan, Jingwen Zhang, Yanan Wang, Hong Liu, Xueping Sun, Aixin Li, Pengfei Cui, Liangmin Yu, Xuefeng Yan, Zhiyu He.  (2023)  Rapidly Inhibiting the Inflammatory Cytokine Storms and Restoring Cellular Homeostasis to Alleviate Sepsis by Blocking Pyroptosis and Mitochondrial Apoptosis Pathways.  Advanced Science,  10  (14): (2207448).  [PMID:36932048] [10.1002/advs.202207448]

5. Jiahui Yan, Yanan Wang, Jingwen Zhang, Xiaohu Liu, Liangmin Yu, Zhiyu He.  (2023)  Rapidly Blocking the Calcium Overload/ROS Production Feedback Loop to Alleviate Acute Kidney Injury via Microenvironment-Responsive BAPTA-AM/BAC Co-Delivery Nanosystem.  Small,  19  (17): (2206936).  [PMID:36719986] [10.1002/smll.202206936]

6. Ling Guo, Yanling Jin, You Yang, Jing Liu, Chunyan Liu, Yan Zeng, Qulian Guo, Wenjun Liu.  (2022)  Calcicoptosis Induced by Purple Sweet Potato Anthocyanins through the Nonosmotic Regulation of the NFAT5/S100A4-S100A9 Pathway in Acute Lymphoblastic Leukemia.  CHEMISTRY & BIODIVERSITY,  19  (9): (e202200447).  [PMID:35924786] [10.1002/cbdv.202200447]

7. Bin Liu, Yulong Bian, Shuang Liang, Meng Yuan, Shuming Dong, Fei He, Shili Gai, Piaoping Yang, Ziyong Cheng, Jun Lin.  (2021)  One-Step Integration of Tumor Microenvironment-Responsive Calcium and Copper Peroxides Nanocomposite for Enhanced Chemodynamic/Ion-Interference Therapy.  ACS Nano,      [PMID:34957819] [10.1021/acsnano.1c07893]

8. Bin Liu, Wanxin Cao, Jiping Li, Jun Liu.  (2018)  Lysosomal exocytosis of ATP is coupled to P2Y2 receptor in marginal cells in the stria vascular in neonatal rats.  CELL CALCIUM,      [PMID:30273839] [10.1016/j.ceca.2018.09.006]

9. Zailin Fu, Dingsheng Wang, Caiyun Zheng, Minghua Xie, Yifang Chen, Yi Zhou, Yan Huang, Ying Song, Weiyong Hong.  (2024)  Elimination of intracellular Ca2+ overload by BAPTA‑AM liposome nanoparticles: A promising treatment for acute pancreatitis.  INTERNATIONAL JOURNAL OF MOLECULAR MEDICINE,  53  (4): (1-16).  [PMID:38390952] [10.3892/ijmm.2024.5358]

10. Yanan Wang, Xinyuan Wang, Xue Zhang, Baomei Zhang, Xinlei Meng, Deyao Qian, Yatao Xu, Liangmin Yu, Xuefeng Yan, Zhiyu He.  (2024)  Inflammation and Acinar Cell Dual-Targeting Nanomedicines for Synergistic Treatment of Acute Pancreatitis via Ca2+ Homeostasis Regulation and Pancreas Autodigestion Inhibition.  ACS Nano,      [PMID:38652869] [10.1021/acsnano.4c00218]

11. Yanan Wang, Xutao Ma, Xinyuan Wang, Liru Liu, Xue Zhang, Qiuyue Wang, Yingfei Zhu, Huanhua Xu, Liangmin Yu, Zhiyu He.  (2025)  Traditional Chinese Medicine Borneol-Based Polymeric Micelles Intracerebral Drug Delivery System for Precisely Pathogenesis-Adaptive Treatment of Ischemic Stroke.  Advanced Science,      [PMID:39804950] [10.1002/advs.202410889]

12. Lin Liu, Shimiao Wu, Jingya Xiu, Yang Liu, Bingrong Hong, Yihong Peng, Lingao Yin, Yilin Song, Ziqi Li, Ziyun Lin, Degong Yang, Chunrong Yang.  (2025)  Biomimetic Targeted Nanoplatform Exerts a Combined Effect of Alleviating Calcium Overload and Scavenging ROS to Attenuate the Inflammatory Response in Myocardial Ischemia-Reperfusion Injury.  ACS Applied Materials & Interfaces,      [PMID:40747849] [10.1021/acsami.5c08306]

13. Qian Jing, Mengnan Zhao, Yan Tang, Tao Chen, Mingyan Sun, Dandan Mi, Lan Zou, Rujing Wang, Jun Lu, Sanjun Shi.  (2025)  A systemic immunogenic reactor leveraging modified γ-cyclodextrins for photo-controlled cancer Ca2+ interference via modulating MICU1.  Acta Pharmaceutica Sinica B,      [PMID:41685149] [10.1016/j.apsb.2025.10.046]

14. Hao Dong, Yuan Gao, Dongyue Jiang, Chenjie Feng, Xinyue Gu, Xiyunyi Cai, Yulin Liu, Guangyu Zhang, Jiacheng Wen, Weiwei Diao, Ying Zhou, Ruixin Li, Dayang Xu, Weijia Xie, Liang Wu.  (2025)  Synthesis and Biological Evaluation of a Caffeic Acid Phenethyl Ester Derivatives as Anti-Hepatocellular Carcinoma Agents via Inhibition of Mitochondrial Respiration and Disruption of Cellular Metabolism.  Cancers,  18  (1): (92).  [PMID:41514605] [10.3390/cancers18010092]

15. Mao Tang, Laixian Zhou, Haitao Ran.  (2026)  Cerium-based nanoplatforms inhibiting goblet cell–associated antigen passages to stabilize barrier function in ulcerative colitis.  Biomaterials Advances,      [PMID:41512469] [10.1016/j.bioadv.2026.214706]

16. Xueqi Liang, Zhen Liu, Nan Wang, Xiao-kun Ouyang, Junhong Ling.  (2026)  Synergistic Calcium Overload and Hydrogen Release Potentiate Robust Antitumor Immunity.  Advanced Healthcare Materials,      [PMID:41580925] [10.1002/adhm.202505332]

17. Shengnan Huang, Weiwei Zhi, Mengjie Zhao, Gaojian Wei, Manyu Zhang, Yu Chen, Yijing Li, Lihua Cao, Jingyi Qiao, Yurong Hu, Hui Zhao, Mingsan Miao, Xiali Zhu.  (2026)  Synergistic Induction of Calcium Overload and ROS Burst by a Core-Shell Nanoparticle for Potentiated Tumor Suppression in Breast Cancer.  COLLOIDS AND SURFACES B-BIOINTERFACES,      [PMID:41702151] [10.1016/j.colsurfb.2026.115534]

18. Yang Chen, Ranjie Lei, Qi Guo, Kehao Liu, Huaiyi Cheng, Sanyang Yu, Yuzhou Li, Ping He, Sheng Yang.  (2026)  Charge-Adaptive Nanoparticle Attenuates Inflammation via Targeting Neutrophil Extracellular Traps (NETs) and Breaking NETs–Macrophage Crosstalk.  ACS Nano,      [PMID:] [10.1021/acsnano.6c02254]