K3394

Sigma-Aldrich

KH7

≥98% (HPLC)

Synonym(s):
(E)-2-(1H-Benzo[d]imidazol-2-ylthio)-N′-(5-bromo-2-hydroxybenzylidene)propanehydrazide
Empirical Formula (Hill Notation):
C17H15BrN4O2S
CAS Number:
Molecular Weight:
419.30
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

assay

≥98% (HPLC)

form

powder

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

CC(Sc1nc2ccccc2[nH]1)C(=O)N\N=C\c3cc(Br)ccc3O

InChI

1S/C17H15BrN4O2S/c1-10(25-17-20-13-4-2-3-5-14(13)21-17)16(24)22-19-9-11-8-12(18)6-7-15(11)23/h2-10,23H,1H3,(H,20,21)(H,22,24)/b19-9+

InChI key

WILMXUAKQKGGCC-DJKKODMXSA-N

Application

KH7 has been used:
  • as a soluble adenyl cyclase (sAC) antagonist to study its effect on the signaling pathway mediated by the action of transient  receptor type 1 (TRPV1) in sperm cells.
  • as a selective sAC antagonist to study its effect on the signaling pathway of proton gated channels (HV1) induced action in sperm cells.
  • as a sAC inhibitor to study its effects on cAMP increase in monophosphorylated myosin light chain (pMLC).

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

KH7 is a selective inhibitor of soluble adenylyl cyclase. Soluble adenylyl cyclase (sAC) is an ubiquitously expressed, essential component of cAMP-signaling.

Features and Benefits

This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Suitability

KH7 is not active against sAC in the presence of detergents. When used in cellular experiments, KH7 exhibits non-specific membrane disruption effects at concentrations above 50 μM.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

RIDADR

UN 2811 6.1 / PGIII

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Frances Evans et al.
Journal of cellular physiology, 235(3), 2947-2962 (2019-09-20)
In previous work, we reported that plasma membrane potential depolarization (PMPD) provokes cortical F-actin remodeling in bovine corneal endothelial (BCE) cells in culture, which eventually leads to the appearance of intercellular gaps. In kidney epithelial cells it has been shown...
Carresse L Gerald et al.
Alcoholism, clinical and experimental research, 40(2), 273-283 (2016-02-05)
Farm workers in rural areas consume more alcohol than those who reside in urban areas. Occupational exposures such as agricultural work can pose hazards on the respiratory system. It is established that hog barn dust induces inflammation in the airway...
Xiudan Wang et al.
Fish & shellfish immunology, 66, 140-147 (2017-05-10)
Ocean acidification (OA) has deleterious impacts on immune response and energy homeostasis status of Mollusca. In the present study, the apoptosis ratio of hemocytes and the adenosine triphosphate (ATP) allocation in gill tissues were determined after Pacific oysters Crassostrea gigas...
Nanshan Song et al.
Biochemical pharmacology, 150, 245-255 (2018-02-16)
β2-Aderenergic receptor (β2AR) agonist, Salmeterol exhibits anti-inflammatory activities. However, the inhibitory effects of Salmeterol on inflammasome activation are elusive and the underlying mechanisms need to be explored. In this study, we established inflammatory model in primary bone marrow-derived macrophages (BMDM)...
Chathura Priyadarshana et al.
Biology of reproduction, 99(5), 1000-1009 (2018-05-23)
Both transcriptionally and translationally inactive sperm need preassembled pathways into specific cellular compartments to function. Although initiation of the acrosome reaction (AR) involves several signaling pathways including protein kinase A (PKA) activation, how these are regulated remains poorly understood in...
Related Content
Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.
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