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MedKoo Cat#: 207065 | Name: PEN-221

Description:

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

PEN-221 is discontinued for commercial reason.

Chemical Structure

PEN-221
PEN-221
CAS#1853254-97-3 (free base)

Theoretical Analysis

MedKoo Cat#: 207065

Name: PEN-221

CAS#: 1853254-97-3 (free base)

Chemical Formula: C83H109ClN14O20S4

Exact Mass: 1784.6514

Molecular Weight: 1786.55

Elemental Analysis: C, 55.80; H, 6.15; Cl, 1.98; N, 10.98; O, 17.91; S, 7.18

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
1853254-98-4 (diacetate) 2250036-35-0 (acetate) 1853254-97-3 (free base)
Synonym
PEN-221; PEN 221; PEN221; DM1-conjugate, DM1-Tyr3-octreotate; SSTR2-targeting protein/DM1 conjugate; maytansinoid conjugate;
IUPAC/Chemical Name
DPhe-cyclo[Cys-Tyr-DTrp-Lys-Thr-Cys]-Cys(DM1)-NH2
InChi Key
JVPMJFUBODFGNB-UFDFPQQFSA-N
InChi Code
InChI=1S/C83H109ClN14O20S4/c1-44-18-17-24-65(115-9)83(113)39-64(116-81(112)96-83)45(2)71-82(5,118-71)66(38-68(102)98(7)62-35-50(32-44)36-63(114-8)69(62)84)117-80(111)46(3)97(6)67(101)29-31-119-120-41-59(72(87)103)92-78(109)61-43-122-121-42-60(93-73(104)54(86)33-48-19-11-10-12-20-48)77(108)90-57(34-49-25-27-52(100)28-26-49)75(106)91-58(37-51-40-88-55-22-14-13-21-53(51)55)76(107)89-56(23-15-16-30-85)74(105)95-70(47(4)99)79(110)94-61/h10-14,17-22,24-28,35-36,40,45-47,54,56-61,64-66,70-71,88,99-100,113H,15-16,23,29-34,37-39,41-43,85-86H2,1-9H3,(H2,87,103)(H,89,107)(H,90,108)(H,91,106)(H,92,109)(H,93,104)(H,94,110)(H,95,105)(H,96,112)/b24-17+,44-18+/t45-,46+,47-,54-,56+,57+,58-,59+,60+,61+,64+,65-,66+,70+,71+,82+,83+/m1/s1
SMILES Code
O=C([C@H](CSSC[C@@H](C1=O)NC([C@H](N)CC2=CC=CC=C2)=O)NC([C@@]([H])(NC([C@@H](NC([C@@H](CC3=CNC4=C3C=CC=C4)NC([C@H](CC5=CC=C(O)C=C5)N1)=O)=O)CCCCN)=O)[C@H](O)C)=O)N[C@H](C(N)=O)CSSCCC(N(C)[C@@H](C)C(O[C@@H]6[C@](C)(O7)[C@@H]7[C@H](C)[C@](OC(N8)=O)([H])C[C@]8(O)[C@H](OC)/C=C/C=C(C)/CC9=CC(OC)=C(Cl)C(N(C)C(C6)=O)=C9)=O)=O
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
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
PEN-221 is a SSTR2-targeting protein/DM1 conjugate. PEN-221 is composed of a peptide analog of somatostatin that targets the somatostatin receptor 2 (SSTR2) and is conjugated, through a cleavable linker, to the microtubule-binding cytotoxic maytansinoid DM1 (mertansine), with potential anti-tumor activity. Upon administration, the peptide ligand moiety of PEN-221 targets and binds to SSTR2, which is overexpressed on certain tumor cell types. Binding stimulates SSTR2-mediated endocytosis of the agent; upon internalization, the DM1 moiety is released and binds to tubulin, thereby disrupting microtubule assembly/disassembly dynamics. This inhibits both cell division and the proliferation of SSTR2-expressing cancer cells. Compared to antibody-drug conjugates (ADCs), miniaturized drug conjugates are much smaller and can more easily penetrate and distribute in dense tumor tissue. (https://www.cancer.gov/publications/dictionaries/cancer-drug/def/sstr2-targeting-protein-dm1-conjugate-pen-221). Somatostatin receptor 2 (SSTR2) is frequently overexpressed on several types of solid tumors, including neuroendocrine tumors and small cell lung cancer. Peptide agonists of SSTR2 are rapidly internalized upon binding to the receptor and linking a toxic payload to an SSTR2 agonist is a potential method to kill SSTR2-expressing tumor cells.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,786.55 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
1: White BH, Whalen K, Kriksciukaite K, Alargova RG, Au Yeung T, Bazinet P, Brockman AH, Dupont M, Oller H, Lemelin CA, Lim Soo P, Moreau B, Perino S, Quinn JM, Sharma G, Shinde R, Sweryda-Krawiec B, Wooster R, Bilodeau MT. Discovery of an SSTR2-targeting maytansinoid conjugate (PEN-221) with potent activity in vitro and in vivo. J Med Chem. 2019 Feb 8. doi: 10.1021/acs.jmedchem.8b02036. [Epub ahead of print] PubMed PMID: 30735385.