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MedKoo Cat#: 465640 | Name: TPP-CL2

Description:

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

TPP-CL2 is a component of the mitochondria-activatable luciferin (MAL) probe, designed for the non-invasive and longitudinal monitoring of mitochondrial membrane potential (ΔΨm). It is a caged luciferin triphenylphosphine ester that, upon reaction with an azido-triphenylphosphine reagent (azido-TPP), releases luciferin, generating a bioluminescent signal in the presence of luciferase. TPP-CL2 is specifically targeted to mitochondria via the triphenylphosphonium (TPP) moiety, ensuring high local concentrations in the mitochondrial matrix. This enables the MAL probe to detect small changes in ΔΨm with high sensitivity. Compared to earlier versions, TPP-CL2 has improved stability, reducing non-specific hydrolysis and background signal.

Chemical Structure

TPP-CL2
TPP-CL2
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 465640

Name: TPP-CL2

CAS#: unknown

Chemical Formula: C55H49BrN4O5P2S2

Exact Mass: 1050.1803

Molecular Weight: 1051.99

Elemental Analysis: C, 62.80; H, 4.70; Br, 7.60; N, 5.33; O, 7.60; P, 5.89; S, 6.10

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
TPP-CL2; TPPCL2; TPP CL2;
IUPAC/Chemical Name
(3-(4-((3-((2-(4-carboxy-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-yl)amino)propoxy)carbonyl)-3-(diphenylphosphanyl)benzamido)propyl)triphenylphosphonium bromide
InChi Key
ISCRYFABHDTVEE-UHFFFAOYSA-N
InChi Code
InChI=1S/C55H48N4O5P2S2.BrH/c60-51(57-33-17-35-66(43-22-10-3-11-23-43,44-24-12-4-13-25-44)45-26-14-5-15-27-45)39-28-30-46(49(36-39)65(41-18-6-1-7-19-41)42-20-8-2-9-21-42)55(63)64-34-16-32-56-40-29-31-47-50(37-40)68-53(58-47)52-59-48(38-67-52)54(61)62;/h1-15,18-31,36-37,48H,16-17,32-35,38H2,(H2-,56,57,59,60,61,62);1H
SMILES Code
O=C(NCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=C(C(OCCCNC5=CC=C6N=C(C7=NC(C(O)=O)CS7)SC6=C5)=O)C(P(C8=CC=CC=C8)C9=CC=CC=C9)=C4.[Br-]
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Applications: Mitochondrial Function Monitoring: The MAL probe using TPP-CL2 is a novel tool for assessing ΔΨm in vitro and in vivo, overcoming limitations of existing fluorescent probes such as autofluorescence, limited tissue penetration, and non-specific binding. Aging and Metabolic Studies: The MAL probe has been used to show that aging leads to mitochondrial depolarization and that nicotinamide riboside (NR) can reverse this effect in old mice. Cancer Research: The probe allows non-invasive imaging of mitochondrial activity in tumor models, demonstrating changes in ΔΨm following treatment with mitochondrial modulators like nigericin. Brown Adipose Tissue (BAT) Activation: The MAL probe has been applied to study mitochondrial depolarization in BAT upon stimulation with β3-adrenergic agonists, offering insights into metabolic regulation and obesity treatment strategies. Drug Development: Since ΔΨm is implicated in various diseases (cancer, neurodegenerative disorders, metabolic diseases), the probe facilitates drug screening and mechanistic studies of ΔΨm-modulating compounds. In summary, TPP-CL2 is a key component of a novel bioluminescent probe for highly sensitive, non-invasive monitoring of mitochondrial function, with broad applications in disease research and drug development.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,051.99 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.

Recalculate based on batch purity %
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
Bazhin AA, Sinisi R, De Marchi U, Hermant A, Sambiagio N, Maric T, Budin G, Goun EA. A bioluminescent probe for longitudinal monitoring of mitochondrial membrane potential. Nat Chem Biol. 2020 Dec;16(12):1385-1393. doi: 10.1038/s41589-020-0602-1. Epub 2020 Aug 10. PMID: 32778841.