B7-33

Last updated

B7-33
B7-33 structure.png
Identifiers
  • (4S)-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S,3S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S,3S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]acetyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoic acid
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C131H229N41O36S
Molar mass 2986.58 g·mol−1
3D model (JSmol)
  • CC[C@H](C)[C@@H](C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](C(C)C)N
  • InChI=1S/C131H229N41O36S/c1-21-68(14)100(125(205)150-72(18)106(186)169-101(69(15)22-2)127(207)167-90(59-174)108(188)148-57-96(181)152-84(44-50-209-20)115(195)165-93(62-177)122(202)172-103(73(19)178)128(208)162-88(54-74-55-146-76-34-25-24-33-75(74)76)118(198)166-91(60-175)120(200)155-78(35-26-28-45-132)111(191)154-81(39-32-49-145-131(141)142)113(193)164-92(61-176)121(201)159-85(104(136)184)51-63(4)5)170-116(196)82(40-42-94(134)179)153-105(185)71(17)149-109(189)80(38-31-48-144-130(139)140)157-124(204)99(67(12)13)168-119(199)87(53-65(8)9)161-114(194)83(41-43-97(182)183)156-110(190)77(37-30-47-143-129(137)138)151-95(180)56-147-107(187)89(58-173)163-117(197)86(52-64(6)7)160-112(192)79(36-27-29-46-133)158-126(206)102(70(16)23-3)171-123(203)98(135)66(10)11/h24-25,33-34,55,63-73,77-93,98-103,146,173-178H,21-23,26-32,35-54,56-62,132-133,135H2,1-20H3,(H2,134,179)(H2,136,184)(H,147,187)(H,148,188)(H,149,189)(H,150,205)(H,151,180)(H,152,181)(H,153,185)(H,154,191)(H,155,200)(H,156,190)(H,157,204)(H,158,206)(H,159,201)(H,160,192)(H,161,194)(H,162,208)(H,163,197)(H,164,193)(H,165,195)(H,166,198)(H,167,207)(H,168,199)(H,169,186)(H,170,196)(H,171,203)(H,172,202)(H,182,183)(H4,137,138,143)(H4,139,140,144)(H4,141,142,145)/t68-,69-,70-,71-,72-,73+,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,98-,99-,100-,101-,102-,103-/m0/s1
  • Key:UAGASAJLEJWQIF-GARFIVTISA-N

B7-33 is a synthetic 26-amino acid peptide with the sequence VIKLSGRELVRAQIAISGMSTWSKRSL or Val-Ile-Lys-Leu-Ser-Gly-Arg-Glu-Leu-Val-Arg-Ala-Gln-Ile-Ala-Ile-Ser-Gly-Met-Ser-Thr-Trp-Ser-Lys-Arg-Ser-Leu. It is an N-terminal truncated, C-terminal extended fragment from the B chain of human relaxin-2, and has similar anti-fibrotic effects to the full length peptide. It has been researched for conditions where excess fibrosis plays a role, such as cardiac fibrosis and pulmonary fibrosis. [1] [2] [3] [4] [5] [6] [7]

See also

References

  1. ↑ Hossain MA, Kocan M, Yao ST, Royce SG, Nair VB, Siwek C, et al. (June 2016). "A single-chain derivative of the relaxin hormone is a functionally selective agonist of the G protein-coupled receptor, RXFP1". Chemical Science. 7 (6): 3805–3819. doi:10.1039/c5sc04754d. PMC   6013806 . PMID   30155023.
  2. ↑ Praveen P, Kocan M, Valkovic A, Bathgate R, Hossain MA (May 2019). "Single chain peptide agonists of relaxin receptors". Molecular and Cellular Endocrinology. 487: 34–39. doi:10.1016/j.mce.2019.01.008. PMID   30641102.
  3. ↑ Devarakonda T, Mauro AG, Guzman G, Hovsepian S, Cain C, Das A, et al. (April 2020). "B7-33, a Functionally Selective Relaxin Receptor 1 Agonist, Attenuates Myocardial Infarction-Related Adverse Cardiac Remodeling in Mice". Journal of the American Heart Association. 9 (8) e015748. doi:10.1161/JAHA.119.015748. PMC   7428518 . PMID   32295457.
  4. ↑ Abboud C, Brochoire L, Drouet A, Hossain MA, Hleihel W, Gundlach AL, et al. (2021). "Analgesic effect of central relaxin receptor activation on persistent inflammatory pain in mice: behavioral and neurochemical data". Pain Reports. 6 (2): e937. doi:10.1097/PR9.0000000000000937. PMC   8213244 . PMID   34159282.
  5. ↑ Alam F, Gaspari TA, Kemp-Harper BK, Low E, Aw A, Ferens D, et al. (April 2023). "The single-chain relaxin mimetic, B7-33, maintains the cardioprotective effects of relaxin and more rapidly reduces left ventricular fibrosis compared to perindopril in an experimental model of cardiomyopathy". Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie. 160 114370. doi:10.1016/j.biopha.2023.114370. PMID   36753958.
  6. ↑ Praveen P, Wang C, Handley TN, Wu H, Samuel CS, Bathgate RA, et al. (April 2023). "A Lipidated Single-B-Chain Derivative of Relaxin Exhibits Improved In Vitro Serum Stability without Altering Activity". International Journal of Molecular Sciences. 24 (7): 6616. doi: 10.3390/ijms24076616 . PMC   10094921 . PMID   37047588.
  7. ↑ Handley TN, Praveen P, Tailhades J, Wu H, Bathgate RA, Hossain MA (August 2023). "Further Developments towards a Minimal Potent Derivative of Human Relaxin-2". International Journal of Molecular Sciences. 24 (16) 12670. doi: 10.3390/ijms241612670 . PMC   10454739 . PMID   37628851.
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