Photoswitchable PAD inhibitor | CAS# 2226393-62-8 | PAD inhibitor

MedKoo Cat#: 574109 | Name: Photoswitchable PAD inhibitor

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Description:

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

Photoswitchable PAD inhibitor is a photoactivated protein arginine deiminase (PAD) inhibitor and a derivative of BB-Cl-amidine that contains an azobenzene photoswitch allowing optical control of PAD activity. Without photoactivation, it is a weak inhibitor of PAD2 and is less potent than BB-Cl-amidine in inhibiting citrulline production in vitro. It does not inhibit histone H3 citrullination in HEK293T cells overexpressing PAD2. However, it can rapidly be photoactivated with UV-A radiation to the more active cis-isomer, which is an irreversible, competitive inhibitor of histone H3 citrullination.

Chemical Structure

Photoswitchable PAD inhibitor

CAS#2226393-62-8

Theoretical Analysis

MedKoo Cat#: 574109

Name: Photoswitchable PAD inhibitor

CAS#: 2226393-62-8

Chemical Formula: C26H26ClN7O

Exact Mass: 487.1887

Molecular Weight: 487.99

Elemental Analysis: C, 63.99; H, 5.37; Cl, 7.26; N, 20.09; O, 3.28

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 500.00
5mg	USD 1,250.00

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Synonym

Photoswitchable PAD inhibitor

IUPAC/Chemical Name

N-[(1S)-1-(1H-benzimidazol-2-yl)-4-[(2-chloro-1-iminoethyl)amino]butyl]-4-(2-phenyldiazenyl)-benzamide

InChi Key

ZTBNXZDZQAHEDC-HIUQNGLMSA-N

InChi Code

InChI=1S/C26H26ClN7O/c27-17-24(28)29-16-6-11-23(25-30-21-9-4-5-10-22(21)31-25)32-26(35)18-12-14-20(15-13-18)34-33-19-7-2-1-3-8-19/h1-5,7-10,12-15,23H,6,11,16-17H2,(H2,28,29)(H,30,31)(H,32,35)/b34-33+/t23-/m0/s1

SMILES Code

O=C(N[C@@H](CCCNC(CCl)=N)C1=NC2=C(C=CC=C2)N1)C(C=C3)=CC=C3/N=N/C4=CC=CC=C4

Appearance

A crystalline solid

Purity

>70% (mixture of isomers)

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

>3 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:

Photoswitchable PAD inhibitor is a photoactivated protein arginine deiminase (PAD) inhibitor.

In vitro activity:

Herein, this study describes the development of the first photoswitchable PAD inhibitors. These compounds possess an azobenzene photoswitch to optically control PAD activity. Screening of a series of inhibitors structurally similar to BB-Cl-amidine afforded compounds 1 and 2 as the most promising candidates for the light-controlled inhibition of PAD2; the cis isomer of 1 is 10-fold more potent than its trans isomer, whereas the trans isomer of 2 is 45-fold more potent than the corresponding cis isomer. The altered inhibitory potency upon photoisomerization has been confirmed in a competitive activity-based protein profiling (ABPP) assay. Further investigations indicate that the trans isomer of 2 is an irreversible inhibitor, whereas the cis isomer acts as a competitive inhibitor. Reference: ACS Chem Biol. 2018 Apr 20;13(4):1057-1065. https://pubmed.ncbi.nlm.nih.gov/29517899/

In vivo activity:

TBD

	Solvent	mg/mL	mM	comments
Solubility
	Methanol	30.0	61.48

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 487.99 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:

Mondal S, Parelkar SS, Nagar M, Thompson PR. Photochemical Control of Protein Arginine Deiminase (PAD) Activity. ACS Chem Biol. 2018 Apr 20;13(4):1057-1065. doi: 10.1021/acschembio.8b00053. Epub 2018 Mar 16. PMID: 29517899; PMCID: PMC5910237.

In vitro protocol:

In vivo protocol:

TBD

1. Mondal, S., Parelkar, S.S., Nagar, M., et al. Photochemical control of protein arginine deiminase (PAD) activity. ACS Chem. Biol. 13(4), 1057-1065 (2018).